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    FLUMEQUINE

    First draft prepared by
    Dr L. Ritter
    Canadian Network of Toxicology Centres
    University of Guelph, Guelph, Ontario, Canada

    1.  EXPLANATION

         Flumequine is a first generation quinolone with anti-microbial
    activity against gram negative organisms and is used for the treatment
    of infections in animals. Flumequine had not been previously reviewed
    by the Committee.

    FIGURE 1

    2.  BIOLOGICAL DATA

    2.1  Biochemical aspects

    2.1.1  Absorption, distribution and excretion

         Studies with 14C-flumequine in dogs and rats indicated that
    flumequine is readily absorbed following oral administration. Peak
    plasma levels occurred in male dogs between 2 and 4 hours after
    dosing. Peak plasma levels were approximately 55-65 µg flumequine
    equivalents/ml of plasma after an oral dose of 25 mg/kg bw.
    Approximately one-half the concentration of total radioactivity for
    the first 12 hours following administration corresponded to unchanged
    drug. The disappearance of flumequine from the plasma appeared to
    follow multi-exponential kinetics with an initial half-life of about
    75 minutes and a terminal ß-phase half-life of 6.5 hours.

         In rats, peak plasma levels of about 70 µg/ml were produced
    approximately 2 hours after administration of the 25 mg/kg bw oral
    dose. Most of the radioactivity in plasma appeared to be unchanged
    drug. The plasma half-life for flumequine was 5.25 hours.

         Total recovery of the orally administered dose was achieved in
    the urine and faeces within 5 days after dosing in both species,
    indicating that very little residual flumequine and/or metabolites
    were retained in the tissues.

         There was a significant difference in the mode of drug excretion
    between dogs and rats. In dogs, 55-75% of the dose was excreted in the
    faeces compared to only 10-15% in rats. Less than 5% of the dose was
    present in the urine of dogs as unchanged drug while another 13-15%
    was excreted as a conjugate of flumequine. In rats, 20-36% of the dose
    was excreted in urine as unchanged drug and very little as a conjugate
    of flumequine. The concentrations of free flumequine in the 24-hour
    urine sample were about the same for both species.

         The concentrations of flumequine in the plasma and urine of dogs
    and monkeys during short-term toxicity studies were found to be
    consistent with findings in these studies (Riker Research Laboratories
    Inc., 1972a).

    2.1.2  Biotransformation

         In dogs, less than 5% of the dose was excreted in the urine as
    unchanged drug and 13-15% was excreted as an acid-labile urinary
    conjugate of flumequine (or a material fluorometrically similar to
    flumequine). In rats, 20-36% was excreted in the urine as unchanged
    drug and very little as an acid-labile conjugate (Riker Research
    Laboratories Inc., 1972b).

         Pre-treatment of rats with 100 mg flumequine/kg bw for 14 days
    significantly reduced the duration of hexobarbital sleep time. This
    indicates that treatment wth flumequine can increase liver microsomal
    drug-metabolizing activity in this species under these experimental
    conditions (Riker Research Laboratories Inc., 1972b).

    2.2.  Toxicological studies

    2.2.1  Acute toxicity studies

         The results of acute toxicity studies with flumequine are
    summarized in Table 1.

    2.2.2  Short-term toxicity studies

    2.2.2.1  Mice

         Flumequine was administered by gastric tube to 10 female Simonsen
    Swiss Webster mice at 500 mg/kg bw/day for 14 days. Observations were
    made daily with special attention directed to the occurrence of
    alopecia. No signs of alopecia or other toxicity were noted (Riker
    Research Laboratories Inc., 1972b).

    2.2.2.2  Rats

         Groups of 5 Simonsen Swiss Sprague-Dawley rats/sex/dose were
    orally administered (by gastric tube) 0, 125, 250, or 500 mg
    flumequine/kg bw/day for 14 days. No mortality occurred in the course
    of the study. Marked alopecia was observed in both sexes of the
    high-dose group after 3 to 5 days treatment, which persisted for the
    duration of the study (Riker Research Laboratories Inc., 1972b).

         Two groups of 5 Charles River CD rats/sex/dose and two groups of
    5 Carworth Farms CFN rats/sex/dose were orally administered (by
    gastric tube) 0 or 800 mg flumequine/kg bw/day for 14 days.
    Observations were made daily for signs of toxicity and mortality.
    Individual body weights were recorded daily. Clinical signs observed
    in treated rats included bloating, cyanosis, dehydration, reduced
    weight gain, and shedding. At necropsy, the only gross lesion reported
    for the treated Charles River CD rats was alopecia over the left flank
    area observed in one male. One male and 1 female Carworth Farms CFN
    rats receiving flumequine died during the study. Urine stained
    abdomen, red intestinal contents and meningeal haemorrhage were
    reported in the male which died on day 12. No gross lesions were seen
    in the female, which died on day 14. Gross lesions in the remaining
    Carworth Farms CFN rats treated for 14 days with flumequine included
    cachexia and paraphimosis in 1 male and urine stained abdomen in 1
    female (Wazeter  et al., 1971b).

        Table 1.  Acute toxicity studies1
                                                                                   

    Species          Sex             Route            LD50 (mg/kg bw)
                                                                                   

    Mouse            F               oral             2480 (2000-3075)
                     F               oral (fasted)    1630 (1190-2233)
                     F               i.v.             97 (90-104)
                     F               i.v.             90 (86-93)
                     F               i.v.             822 (718-944)

    Rat              M               oral (fasted)    2210 (1864-2625)
                     F               oral (fasted)    2450 (1992-3014)
                     F               oral (fasted)    1340 (971-1849)
                     F               oral (fasted)    1375 (1170-1620)
                     F               oral (fasted)    1753 (1520-2025)

    Rabbit           M               oral             > 2000

    Dog              2               i.v.             > 120
                                                                                   

    1     Riker Reserach Laboratories, 1972b.

    2     In this particular study, the test compound was administered
          as a 2% solution for two days per dose level; one male and one
          female each received 100 or 120 mg/kg bw, respectively.
          Although severe clonic-tonic convulsions, prostration,
          urination and defection were seen in all test animals, all
          dogs had returned to normal by the second day and were free of
          signs of toxicity for the balance of the fourteen-day
          observation period.
    
         Groups of 10 Charles River Sprague-Dawley rats/sex/dose were
    orally administered (by gastric tube) 0, 200, 400, or 800 mg
    flumequine/kg bw/day for 90 days. Observations were made daily for
    signs of toxicity and body weights were recorded weekly.

         No mortalities were reported. Body-weight gain was signif-icantly
    depressed in both sexes of the mid- and high-dose groups. Alopecia
    occurred in all treated rats, which appeared to be more severe in
    females than in males. Sporadic urinary incontinence occurred in most
    rats of the high-dose group and in a few females of the low-dose
    group. Salivation was noted in all rats of the mid- and high-dose
    groups, which was not reported in the low-dose or control groups.
    Pilomotor erection was seen sporadically in rats of the control, mid-,
    and high-dose groups.

         Haematological and clinical chemistry data revealed no
    treatment-related effects. However, urine of all treated rats showed
    a dose-related positive acetone (ketone) reaction. The authors
    suggested that this effect could have been due to the interference of
    the ketone test by the presence of flumequine metabolites in the
    urine.

         Relative kidney weights in both sexes and absolute kidney weights
    in males were increased significantly at the high-dose. The relative
    adrenal weights were significantly increased in both sexes at the mid
    and high doses. Relative weights of heart, brain, spleen and testes
    were also significantly increased in males of the high-dose group.
    Information on the microscopic examination of these organs was not
    available.

         Alopecia was the only gross abnormality observed at necropsy. A
    dose-related significant increase in relative liver weights occurred
    in all treated rats. Microscopic examination of liver revealed swollen
    and enlarged hepatocytes (30 to 90%) in rats of the high-dose group.
    Similar degenerative changes in hepatocytes were not observed in rats
    at the mid and low doses. The authors suggested that enlargement of
    the liver was due to stimulation of drug metabolizing enzymes by
    flumequine. A NOEL could not be determined in this study (Nelson  et
    al., 1972a).

    2.2.2.3  Guinea-pigs

         Groups of 5 female Hartley strain guinea-pigs were given oral
    doses of 0, 300, or 500 mg flumequine/kg bw/day by gavage for 14 days.
    Hair samples were plucked at initiation and termination of the study
    to examine any differences in hair growth patterns. Mortality was
    noted after 4 days in the high-dose group (2/5) with the remaining 3
    animals dying after 6 days. Two animals in the low-dose group died,
    one at day 12 and other one day after cessation of treatment. No
    alopecia was noted at any time during the study. No changes were seen
    microscopically in the hair samples taken at termination when compared
    with those taken at initiation of the study. Information on necropsy
    was not available (Riker Research Laboratories Inc., 1972b).

    2.2.2.4  Dogs - 90 Days

         Flumequine was given orally by gelatin capsule at 150 mg/kg bw
    twice daily for 21 days to 2 mongrel dogs, one male (8.3 kg) and 1
    female (5.0 kg). Prominent signs noted within 3 hours of
    administration included emesis, depression, ataxia, and mild
    hyperactivity. These signs were most severe between the 10th and 14th
    days after which they appeared to diminish. Both dogs became anorectic
    after the first week and, as a result, the male lost 0.6 kg and the
    female 0.8 kg during the study. No gross lesions were observed at
    necropsy in either dog (Riker Research Laboratories Inc., 1972b).

         Flumequine was administered orally (by gelatin capsule or tablet)
    to four groups (2/sex/group) of young adult purebred beagle dogs.
    Dosages administered were 0, 25, 50, or 100 mg flumequine/kg bw given
    twice daily for 90 days. Each dog was observed for signs of toxicity
    immediately following dosing and periodically throughout the day. Body
    weights were recorded at weekly intervals.

         There were no mortalities or consistent signs of toxicity at any
    dosage level. Flushing of the skin was the only clinical sign seen in
    treated dogs. This occurred very infrequently and in no specific
    pattern. Only minor fluctuations in body weight were observed during
    the study. None of the changes were considered significant or
    treatment-related.

         Haematologic and urinary parameters appeared to be unaffected by
    the administration of flumequine. Elevation of LDH values occurred in
    dogs at the low (1/4), mid (1/4), and high (3/4) doses on day 14. LDH
    values were normal on subsequent evaluations at days 42 and 90.

         Gross and microscopic examination of heart, liver, kidney and
    skeletal muscle at the end of the study revealed no treatment-related
    changes (Nelson  et al., 1972b).

    2.2.2.5  Dogs - 1 year

         Groups of four male and four female beagle dogs were given total
    daily oral doses of 0, 50, 100, or 200 mg flumequine/kg bw/day divided
    in half as twice daily doses. Emesis in the high-dose group resulted
    in this group receiving only a single 100 mg/kg bw dose for the first
    five days, after which the emesis subsided and the scheduled dosing of
    200 mg/kg/bw day divided into two 100 mg/kg bw doses was resumed.

         All dogs survived the one-year treatment period. A decrease in
    food consumption was noted in all treatment groups throughout the
    study. Declines in food consumption were reflected in weight loss over
    the first three weeks of the study. Weight loss did not appear to be
    entirely dose-dependent but due to the somewhat random distribution of
    affected animals within dose groups.

         A dose-dependent incidence of convulsive episodes was observed in
    treated dogs. The convulsions were relatively severe, of short
    duration (15-30 seconds), and almost always followed by ataxia and
    tremors. Normal behaviour returned within about ten minutes after
    treatment. Other drug-related clinical signs observed included ataxia,
    hypoactivity, tremors, emesis (particularly early in the study),
    decreased food consumption, and body-weight loss. Less frequently
    observed treatment-related clinical signs included excessive
    salivation and mild gingivitis in five of eight high-dose dogs and in
    one mid-dose dog during the last six months of the study.

         Drug-related effects noted on physical examination included
    ataxia, a slow-knuckling response, and exaggerated knee and toe
    reflexes in one animal. Other effects appeared to be somewhat random,
    occurring in both control and treated animals.

         Treatment-related effects were not observed in haematology, serum
    chemistry, and urinalyses, organ weight data, or gross and microscopic
    pathology. The NOEL for this study was 50 mg/kg bw/day (Saunders &
    Case, 1976).

    2.2.2.6  Monkeys

         Flumequine was given orally by gelatin capsule twice daily at
    increasing dosage levels for 15.5 weeks to 3 female rhesus monkeys as
    follows: 100 mg/kg bw/day for 1 week, 200 mg/kg bw/day for 3 weeks,
    300 mg/kg bw/day for 8 weeks, 400 mg/kg bw/day for 1 week, 500 mg/kg
    bw/day for 1 week, and 600 mg/kg bw/day for 1.5 weeks. One monkey died
    accidentally on day 2 of drug administration. Clinical signs noted
    during the study included emesis, total anorexia, and transient hair
    loss. No gross lesions were observed at necropsy in either monkey. No
    microscopic abnormalities were noted in skin sections. Although
    specimens of the organ tissues were collected for microscopic
    examination, no further information was provided (Wazeter,  et al.,
    1971a).

    2.2.3  Long-term toxicity/carcinogenicity studies

    2.2.3.1  Mice

         In an 18-month study, flumequine was administered in the feed
    (concentrations not stated) to provide doses of 0, 400, or 800 mg/kg
    bw/day to groups of 93 Charles River CD-1/ ICR mice of each sex. The
    mice were observed daily for clinical signs of toxicity. Food
    consumption and body weights were recorded periodically. At the end of
    the study, animals were necropsied and subjected to a complete gross
    examination. Microscopic examination was conducted on tissues and
    gross lesions from all animals.

         A slight depression in body weight occurred in the high-dose
    group from the sixth week to termination of the study. There were no
    differences in food consumption in male or female mice of the treated
    and control groups throughout the study. Survival rates were
    comparable in treated and control groups. Clinical observations showed
    no adverse effects attributable to the administration of flumequine.
    Information was not available on haematology, clinical chemistry,
    urinalysis, or organ weights.

         Incidences of liver tumours seen grossly at necropsy, which are
    summarized in Table 2, were dose-related and more prevalent in males
    than in females.

         The liver tumours were classified histologically into hepatoma,
    hepatoma with atypica, and hepatocellular carcinoma. The first two,
    hepatoma and hepatoma with atypica, were considered benign, and
    hepatocellular carcinoma was considered malignant in this study. A
    definite dose-response was apparent and the higher incidence of both
    benign and malignant liver tumours in males, observed grossly, was
    confirmed by histopathological analysis. Dose-related toxic changes in
    hepatocytes occurred in the low-dose males and in the high-dose males
    and females. These included cytoplasmic degenerative changes,
    vacuolation, fatty infiltration, and the presence of lymphocytes and
    neutrophils. The incidence of hepatic toxic changes paralleled the
    liver tumour incidence. Chi-square analysis of the number of
    tumour-bearing animals indicated significant increases (p < 0.05) for
    the low- and high-dose males considering all tumours and benign
    tumours. The number of high-dose males with both benign and malignant
    liver tumours was also statistically significant. In females, the only
    significant increases occurred in the high-dose group for numbers of
    animals with any type or benign only tumours. No other tissue changes
    were considered significant or treatment-related. A NOEL could not be
    determined in this study (Sibinski  et al., 1977a).

         A special 18-month dietary study of flumequine was conducted to
    correlate the length of drug administration with the development of
    toxic and neoplastic liver changes observed in the Sibinski  et al.
    (1977a) study. Five groups of male Charles River (CD-1/ICR) mice
    comprised the study. The substance was administered via dietary
    admixture. Group A (60 males) served as controls and received no
    treatment. Group B (100) males received flumequine at 800 mg/kg bw/day
    for 18 months; interim necropsies of 10 mice each were done at 3, 6,
    9, and 12 months to follow the development of the liver tumorigenic
    response. Group C (80) males received flumequine at 800 mg/kg bw/day
    for the first 6 weeks of the study; for the next 6 weeks they were off
    drug; the following 6 weeks they were back on the same dose of drug
    and then off drug for the rest of the study. Necropsies of 10 mice
    each were done at 12, 18, and 24 weeks. Group D (60) males received
    flumequine at 800 mg/kg bw/day for the first 6 weeks of the study,
    then fed control diet for the rest of the study. At the end of the
    6-week period, 10 mice were necropsied. Group E (50) males received a
    formulation of flumequine at 800 mg/kg bw/day that contained less
    than 0.001% of dimethylformamide (DMF) for 18 months. Group E was
    added to evaluate whether the 0.3% DMF present in the lot administered
    in the previous 18-month study had a role in the carcinogenic
    response. The analytical specification for DMF is < 0.5%. Interim
    necropsies were performed on 5 mice after 6 weeks and on 10 mice after
    12 months of drug treatment.

        Table 2.     Incidence of liver tumours and toxic changes in the liver in
                 18-month oral carcinogenicity study of flumequine in mice
                                                                                               

                           Control                Low dose                 High dose
                                                  (400 mg/kg bw/day)       (800 mg/kg bw/day)
                                                                                               

                        Males        Females      Males       Females      Males        Females
                                                                                               

    Number of           n=70a        n=64a        n=75a       n=69a        n=78a        n=69a
    mice with           n            n            n           n            n            n
    liver tumours       (%)          (%)          (%)         (%)          (%)          (%)

    Any type            6            0            28b         0            69b          9b
                        (9)          (37)                     (88)         (13)

    Benign              6            0            25b         0            36b          7b
    onlyc               (9)          (33)                     (46)         (10)

    Benign &            0            0            0           0            30b          0
    malignantd                                                             (38)

    Only                0            0            3           0            3            2
    malignante                                    (4)                      (4)          (3)
    ---------------------------------------------------------------------------------------------

    Toxic                            0            32b         1            78b          39b
    changes in                                    (43)                     (100)        (57)
    liver
                                                                                               

    a      Number of animals that had gross and microscopic tissue
           examination.
    b      Significant difference from control (p <0.05) (Chi-square).
    c      Hepatoma and/or hepatoma with atypica.
    d      Hepatoma with or without atypica and hepatocellular carcinoma
           in the same animal.
    e      Hepatocellular carcinoma.
    
         The mice were observed daily for clinical signs of toxicity with
    the exception of week-ends and holidays, during which only live/dead
    checks were made. Daily observations were replaced with live/dead
    checks during the last third of the study. For the first 18 weeks of
    the study, body weights and food consumption were recorded weekly;
    thereafter, they were recorded on a monthly basis. Liver tumours and
    toxic changes in the liver were classified histologically as described
    in the previous Sibinski  et al. 1977a study.

         Mice in Group B and Group E had lower mean body weights from
    weeks 18 to 78 and higher mortality rates as compared to Group A
    controls. Group E showed a 15% higher food intake from week 18 to
    termination. Incidence of swollen abdomen was more prevalent in the
    treated groups than in the control group. Information was not
    available on haematology, clinical chemistry, urinalysis, or organ
    weights.

         Interim necropsies of Group B mice revealed a time-dependent
    development of liver tumours following flumequine administration. At
    3 months, 0/10 mice had liver tumours, but all 10 mice had evidence of
    toxic changes in the liver. The number of mice with liver tumours at
    6, 9 and 12 months was 1/10, 3/10, and 9 (2 malignant)/ 10,
    respectively. Interim necropsies of Group E mice at week 6 revealed
    toxic changes in the liver of all 5 mice. At 12 months, 6/10 mice had
    liver tumours.

         Table 3 shows the incidence of liver tumours and toxic changes in
    the liver of all mice necropsied at the end of the study. An increase
    in the incidence of liver tumours, both benign and malignant, was
    statistically significant for mice in Groups B and E. Two mice in
    Group B had metastatic lung lesions of hepatocellular carcinoma
    origin. A large percentage of mice in Group B (81%) and Group E (97%)
    had toxic changes in the liver as compared to Group A controls (0%).

         Toxic changes in the liver which were reversible and no longer
    evident at the end of the study, as shown in Table 3, occurred in
    Groups C and D. No liver tumours were found in animals killed for
    interim necropsies. Although the percent of animals with any type of
    liver tumour was increased nearly 2-fold compared to controls in
    Groups C and D, the increase was not statistically significant.

         Results from Group E indicated that the presence of DMF as a
    contaminant in flumequine did not influence the development of toxic
    and neoplastic liver changes in mice in response to oral flumequine
    exposure (Sibinski  et al., 1979).

    2.2.3.2  Rats

         Groups of 60 Carworth CFN (Wistar derived) rats/sex/dose were
    orally administered flumequine via dietary admixture (concentrations
    nolt stated), to provide daily doses of 0, 200, 400, or 800 mg
    flumequine/kg bw/day. The rats were observed daily for clinical signs
    of toxicity. Food consumption and body weights were recorded
    periodically. At the end of the study, animals were necropsied and
    subjected to complete gross examinations. Microscopic examinations
    were conducted on the tissues and gross lesions from all animals.

        Table 3.    Incidence of liver tumours and toxic changes in the liver at the
                end of the special 18-month toxicity study of flumequine in male
                mice
                                                                                   

                        Group A      Group B      Group C     Group D      Group E

    Number of           n=60a        n=58a        n=49a      n=48a         n=35a
    mice with           n            n            n          n             n
    liver tumours       (%)          (%)          (%)        (%)           (%)
                                                                                   

    Any type            7            39b          11         10            29b
                        (12)         (67)         (22)       (21)          (83)

    Benign onlyc        5            26b          8          7             15b
                        (8)          (45)         (16)       (15)          (43)

    Benign &            1            12b          2          1             11b
    malignantd          (2)          (21)         (4)        (2)           (31)

    Malignant           1            1            1          2             3
    onlye               (2)          (2)          (2)        (4)           (9)
    --------------------------------------------------------------------------------

    Toxic               0            47b          0          0             34b
    changes in liver                 (81)                                  (97)
                                                                                   

    a     Number of animals that had gross and microscopic examination.
    b     Significant difference from control (p <0.05) (Chi-square).
    c     Hepatoma and/or hepatoma with atypica.
    d     Hepatoma with or without atypica and hepatocellular carcinoma
          in the same animal.
    e     Hepatocellular carcinoma.
    
         Dose-related decreases in mean body weight and food consumption
    occurred in rats of flumequine treated groups. Mortality at 400 and
    800 mg/kg bw/day was significantly reduced. Results of haematology,
    clinical chemistry, and urinalysis were comparable in treated and
    control groups.

         Significant increases in the mean relative weights of the
    pituitary gland, liver, heart, and brain occurred in males in the mid-
    and high-dose groups. A similar effect was observed in the mean organ
    weights of the liver, heart, and brain of females in the high-dose
    group.

         Microscopically, benign chromophobe adenoma was noted in the
    pituitary gland of males at the mid- and the high-doses, but the
    incidence was not greater than in controls. Livers showed scattered
    foci of swollen hepatocytes due to mild degenerative changes. A few of
    these cells also had fatty changes with fat droplets in their
    cytoplasm. Spermatogenesis was absent in many of the males at the mid
    and high doses; this effect was not analyzed statistically.

         No carcinogenic effect attributable to flumequine was observed
    either during or at the end of 2 years of its administration. The
    benign and malignant tumours observed in all groups were considered
    spontaneous in nature and there was no significant increase in tumour
    incidence in treated groups as compared to controls. The NOEL was 200
    mg/kg bw/day (Sibinski  et al., 1977b).

    2.2.4  Reproduction studies

    2.2.4.1  Rats

         A fertility and general reproductive performance (Segment I)
    study with flumequine was conducted in Charles River Sprague-Dawley
    rats. Groups of 11 or 12 males weighing 140-160 g were treated, by
    gavage, with doses of 0, 100, 200, 400, or 800 mg flumequine/kg bw/day
    for at least 80 days before breeding and throughout the breeding
    period. Females weighing 150-215 g were treated with a gavage dose of
    flumequine for at least 21 days prior to breeding and throughout
    gestation and lactation. The females were divided into 8 groups each
    having 20 or 21 animals. Dose schedules varied by group as follows:

    Group I               Control

    Group II              800 mg/kg bw/day (19/21 animals died in the
                          second week of treatment).

    Group III             400 mg/kg bw/day until breeding, bred to males of
                          the 400 mg/kg bw/day group, then dosed at 200
                          mg/kg bw twice daily throughout gestation and
                          lactation.

    Group IV              200 mg/kg bw/day until breeding, bred to males of
                          the 200 mg/kg bw/day group, then dosed at 100
                          mg/kg bw twice daily throughout gestation and
                          lactation.

    Group V               100 mg/kg bw/day until breeding, bred to males of
                          the 200 mg/kg bw/day group, then dosed at 50
                          mg/kg bw twice daily throughout gestation and
                          lactation.

    Group VI              Control, bred to males of the 800 mg/kg bw/day
                          group.

    Group VII             200 mg/kg bw/day, bred to males of the 400 mg/kg
                          bw/day group, dosing stopped on the 15th day of
                          gestation.

    Group VIII            100 mg/kg bw/day, bred to males of the 200 mg/kg
                          bw/day group, dosing stopped on the 15th day of
                          gestation.

         Group II females had 4 deaths in the first week and 15 deaths in
    the second week of flumequine treatment. The mean body weight was
    significantly lower than that of controls. Prominent signs of toxicity
    included alopecia, prostration, and respiratory depression. The
    remaining 2 females were sacrificed after 3 weeks of dosing. Necropsy
    results were not available.

         Group III females had significantly lower mean body weight,
    longer mean gestation period, smaller mean litter size, and a larger
    number of dead pups than did the controls. Group IV females showed a
    similar pattern of changes as Group III females in pregnancy rate,
    length of gestation, litter size and pup survival, but the changes
    were not statistically significant. The mean pup weights of Group III
    and Group IV were significantly lower when compared to the controls.

         No significant changes in reproduction parameters were noted with
    females of Groups V, VI, VII and VIII. However, the pups from females
    treated with flumequine (100, 200, or 400 mg/kg bw/day) throughout
    gestation and lactation had significant lower mean body weight at
    birth and at weaning. A NOEL could not be determined in this study
    (Gortner & Case, 1974a).

    2.2.5  Special studies on embryotoxicity/teratogenicity

    2.2.5.1  Mice

         Groups of 18 or 22 pregnant Charles River CD-1 mice were given
    doses of 0, 50, 100, 200, or 400 mg flumequine/kg bw/day by gavage
    from the sixth through fifteenth days of gestation. Observations were
    made daily for signs of toxicity and body weights were recorded on
    days 6, 9, 12, 15, and 17 of pregnancy. Ovaries, uteri, and their
    contents were collected from animals at termination on day 17 to
    determine the number of viable fetuses, number of resorption sites,
    fetal weights, and gross fetal abnormalities.

         Mean maternal body weights at 200 and 400 mg/kg bw/day were
    significantly reduced from the twelfth day of gestation throughout the
    rest of pregnancy. No change in the number of viable fetuses or
    resorption sites was observed in any treatment group. A slight

    reduction in mean fetal weight was noted at 400 mg/kg bw/day, but the
    change was not significant when compared with the control value. Cleft
    palate was seen grossly in 3% (6/227) of fetuses from the high-dose
    group. Internal examination of 72 of the fetuses revealed that 9 (13%)
    had cleft plate. Of these, 4 had been detected on gross examination.
    There was one fetus each with cleft palate at the 50 and 100 mg/kg
    bw/day level but none at the 200 mg/kg dose level. Incomplete
    ossification of sternebra and skull bones were noted in the great
    majority of the fetuses in all groups including the controls. The
    authors suggested that the incomplete ossification was the result of
    removing the fetuses one day earlier than the 18-day gestation period
    known to be required for this strain of mice. The NOEL in this study
    was 400 mg/kg bw/day (Gortner & Case, 1974b).

         Groups of 32 or 35 pregnant OFI-IOPS mice were orally
    administered (by gastric tube) doses of 0, 100, 200, or 400 mg
    flumequine/kg bw/day from the second to fifteenth days of gestation.
    Incomplete ossification, invaginated trachea, dilatation of the renal
    pelvis, and cleft palate were observed in fetuses at the mid and high
    doses. These observations were interpreted as evidence of fetotoxic,
    not teratogenic, responses to exposure to flumequine. The NOEL in this
    study was 100 mg/kg bw/day (Ecole Nationale Vétérinaire de Lyon,
    1974).

    2.2.5.2  Rats

         Groups of 23 or 27 pregnant COBS rats were dosed orally (by
    gavage) with 0, 100, 200, or 400 mg flumequine/kg bw/day from the
    sixth through fifteenth days of gestation. Observations were made
    daily for signs of toxicity and body weights were recorded on days 6,
    9, 12, 15, and 20 of pregnancy. Ovaries, uteri and their contents were
    collected from animals at termination on day 20 to determine the
    number of corpora lutea, number of resorption sites, number of viable
    fetuses, fetal weights and fetal abnormalities.

         There was a dose-related reduction of mean body weight in the
    treated dams and the difference from controls was significant at 400
    mg/kg bw/day. The mean fetal weights of the mid- and high-dose groups
    were significantly lower as compared to controls. Dose-related
    incomplete ossification of sternebra, vertebrae, and skull bones were
    also noted in fetuses of the mid- and high-dose groups. No
    drug-related visceral or skeletal malformations were found and there
    was no embryotoxic effect noted in this study. The NOEL in this study
    was 100 mg/kg bw/day (Nelson & Owen, 1972a).

    2.2.5.3  Rabbits

         Groups of 15 or 21 pregnant New Zealand white rabbits were orally
    administered (by gastric tube) doses of 0, 100, 200, or 400 mg
    flumequine/kg bw/day from sixth through eighteenth days of gestation.

    Observations were made daily for signs of toxicity and body weights
    were recorded on days 0, 6, 14, 21, and 29 of pregnancy. On day 29 the
    animals were killed and uterine disposition of young, resorption
    sites, and number of corpora lutea were evaluated. Viable young were
    weighed, sexed, and examined internally and externally for
    abnormalities.

         There was a slight, but not significant reduction of mean body
    weights of dams and pups in the mid- and high-dose groups. Examination
    of the stained skeletons of the pups revealed no increase of
    incomplete ossification of bones in any dose group. No drug-related
    visceral or skeletal teratologic changes, or embryotoxic effects were
    noted in this study. The NOEL in this study was 400 mg/kg bw/day
    (Nelson & Owen, 1972b).

    2.2.6  Special studies on genotoxicity

         The results of  in vitro and  in vivo genotoxicity studies of
    flumequine are summarized in Table 4.

    2.3  Observations in humans

         No information was available.

        Table 4. Results of genotoxicity studies on flumequine
                                                                                   

    Test             Test object       Concentration  Results   References
                                                                                   

     In vitro

    Ames test (1)     S. typhimurium   0.01-1000     negative   Rohlfing &
                     TA1515, 1537,     µg/disc                  Winandy, 1977
                     1538, 98, 100

    HGPRT test (1)   Mouse L5178Y      0-200 µg/ml    negative  Kennelly  et al.,
                     lymphoma cells                             1985

    Gene mutation    Chinese hamster   0-200 µg/ml    negative  Kirkland  et al.,
    assay (1)        ovary cells                                1985

     In vivo

    Chromosome       Rat bone marrow   1000 mg/kg     negative  Marshall  et al.,
    aberration assay                   bw po                    1987
                                                                                   

    (1)  With and without rat liver S-9 fraction.
    
    3.  COMMENTS

         Information from a range of studies on flumequine was available
    for assessment, including data on pharmacokinetics, acute toxicity,
    short-term and long-term toxicity, reproductive and developmental
    toxicity, and genotoxicity.

         Studies with 14C-labelled flumequine in dogs and rats indicated
    that flumequine is readily absorbed following oral administration.
    Most of the radioactivity in plasma appeared to be unchanged drug. The
    plasma half-life for flumequine was 5.25 hours in the rat. There were
    some differences in the pattern of drug excretion between dogs and
    rats. In dogs, 55-75% of the dose was excreted in the faeces, while in
    rats, only 10-15% was excreted by this route. Less than 5% of the dose
    was present in the urine of dogs as unchanged drug and 13-15% as a
    conjugate of flumequine. In rats, 20-36% was eliminated in urine as
    unchanged drug and very little as a conjugate of flumequine.

         Single oral doses of flumequine were slightly toxic (LD50 =
    1630-2210 mg/kg bw) in rats, mice, and rabbits.

         The most common findings in rats dosed with 800 mg/kg bw/day by
    gastric tube for 14 days included bloating, cyanosis, dehydration,
    reduced weight gain, and alopecia. In a 90-day study in rats, animals
    receiving doses of 0, 200, 400, or 800 mg/kg bw/day by gastric
    intubation showed a dose-dependent significant increase in relative
    liver weights. Guinea-pigs were given repeated gavage administration
    of 300 or 500 mg/kg bw/day for 14 days, and two of six animals died at
    the 300 mg dose. All animals receiving 500 mg/kg bw/day died after six
    days of treatment.

         Repeated oral administration of flumequine to dogs at 300 mg/kg
    bw/day for 21 days resulted in emesis, depression, ataxia, and mild
    hyperactivity, but there was no mortality or consistent signs of
    toxicity at 200 mg/kg bw given in divided doses. In a one-year study
    in dogs given total daily oral doses up to 200 mg/kg bw/day, the most
    prominent effects were neuro-logical signs. The NOEL was 50 mg/kg
    bw/day.

         In an 18-month carcinogenicity study in mice, flumequine was
    administered in the feed at 0, 400, or 800 mg/kg bw/day. The only
    clinical signs were a slight depression in body weight which occurred
    in the high-dose group from the sixth week to termination of the
    study. The incidence of benign and malignant liver tumours combined
    was dose-related with 9, 37 and 88% in the control, low-dose, and
    high-dose males affected, respectively, and 0, 0, and 13% in the
    control, low-dose, and high-dose females affected, respectively.

    Dose-related toxic changes in the hepatocytes, which paralleled the
    liver tumour incidence, occurred in the low-dose males and in the
    high-dose males and females. The incidence of hepatotoxicity was
    statistically significant in both male treatment groups and in the
    high-dose female group. A NOEL could not be determined in this study.

         A further 18-month dietary study in mice of flumequine was
    conducted to investigate the relationship of duration of drug
    administration with the development of toxic and neoplastic liver
    lesions. Interim necropsies of males receiving 800 mg/kg bw/day
    revealed a time-dependent development of liver tumours following
    flumequine administration. At 3 months, 0/10 mice had liver tumours,
    but the same 10 mice all had evidence of toxic changes in the liver.
    The number of mice with liver tumours at 6, 9, and 12 months was 1/10,
    3/10, and 9/10, respectively. Of these, malignant tumours were
    observed in two animals from the 12-month sacrifice. Tumours observed
    in all other animals were benign.

         In a two-year carcinogenicity study in rats dosed with flumequine
    at 0, 200, 400, or 800 mg/kg bw/day, no carcinogenic effects were
    observed. Dose-related decreases in mean body weight and food
    consumption occurred. Spermatogenesis was absent in many males in the
    mid- and high-dose groups, in addition to significant increases in the
    mean relative weight of the pituitary gland, liver, heart, and brain.
    A similar effect was observed in the mean weights of the liver, heart,
    and brain of females in the high-dose group. At the high dose the
    liver showed foci of swollen hepatocytes due to mild degenerative
    changes and a few cells also had fatty changes. The NOEL was 200 mg/kg
    bw/day.

         There was evidence of compound-related tumorigenic effects in the
    liver of mice. The Committee noted that the tumorigenic activity of
    flumequine was most pronounced in the liver of male mice, which are
    known to be sensitive to liver tumour induction. As the compound was
    negative in a range of mutagenicity studies, the mechanism of this
    tumorigenesis is unclear.

         A fertility and general reproductive performance study on
    flumequine was conducted in rats. In an unconventional protocol,
    groups of male and female rats were treated with gavage doses of
    flumequine at 0, 100, 200, 400, or 800 mg/kg bw/day. Virtually all
    females in the high-dose group died within two weeks of initiation of
    treatment. Because of reduced body weight of pups at all doses, a NOEL
    could not be determined, but the Committee noted that there were no
    effects on fertility or reproductive performance of the dams.

         In a teratogenicity study, groups of mice were given gavage doses
    of 0, 50, 100, 200, or 400 mg flumequine/kg bw/day from the sixth
    through fifteenth days of gestation. Incomplete ossification of
    sternebra and skull bones were noted in many of the fetuses in all
    groups including the controls. The NOEL was 400 mg/kg bw/day in this
    study.

         In another teratogenicity study, groups of mice received doses of
    0, 100, 200, or 400 mg flumequine/kg bw/day by gastric tube from the
    second to fifteenth days of gestation. Increased frequency in cleft
    palate was considered to be indicative of fetotoxicity and
    compound-related in the mid- and high-dose groups. The NOEL was 100
    mg/kg bw/day.

         In a teratology study, groups of rats were dosed orally with 0,
    100, 200, or 400 mg flumequine/kg bw/day from the sixth through
    fifteenth days of gestation. There was a significant reduction of mean
    body weight at 400 mg/kg bw/day. In the mid- and high-dose groups,
    there was a significant reduction in mean fetal weights and incomplete
    ossification of sternebra, vertebrae, and skull bones. No drug-related
    visceral or skeletal malformation were observed and no embryotoxic
    effects were observed in this study. The NOEL was 100 mg/kg bw/day.

         In a rabbit teratology study, animals were dosed by gavage with
    0, 100, 200, or 400 mg flumequine/kg bw/day from the sixth through
    eighteenth days of gestation. No drug-related visceral or skeletal
    teratogenic changes or embryotoxic effects were noted in this study.
    The NOEL was 400 mg/kg bw/day.

         The Committee recognized the association of quinolone exposure
    and arthropathy and concluded that data to evaluate this hazard were
    not adequate for flumequine.

         Genotoxicity studies in an  in vitro bacterial and mammalian
    gene mutation assay and in an  in vivo mammalian chromosome
    aberration assay were negative.

         No data were available that would permit the Committee to
    evaluate the microbiological hazard of flumequine residues in food.

    4.  EVALUATION

         The Committee was unable to establish an ADI for this compound
    due to the absence of the information outlined below. Before reviewing
    flumequine again the Committee would wish to see:

         A.   Further data from mice which would identify NOELs for
              hepatotoxicity.

         B.   Information regarding the tumorigenic mechanism of
              flumequine.

         C.   Further data relating to whether the compound induces
              arthropathy.

         D.   Information regarding the microbiological safety of
              flumequine residues.

         E.   Appropriate residue data.

    5.  REFERENCES

    ECOLE NATIONALE VÉTÉRINAIRE DE LYON (1974). Rapport d'expérimentation
    concernant la recherche des risques d'effets tératogčnes chez la
    souris des substances EU802 (flumequine) et EU805. Unpublished report
    from Ecole Nationale Vétérinaire de Lyon, France. Submitted to WHO by
    Sanofi Santé Nutrition Animale, Libourne Cedex, France.

    GORTNER, E.G. & CASE, M.T. (1974a). General reproductive study in rats
    on R-802 (flumequine). Unpublished report from Riker Laboratories
    Inc., St. Paul, MN, USA. Submitted to WHO by Sanofi Santé Nutrition
    Animale, Libourne Cedex, France.

    GORTNER, E.G. & CASE, M.T. (1974b). Mouse teratology study of R-802
    (flumequine). Unpublished report from Riker Laboratories Inc., St.
    Paul, MN, USA. Submitted to WHO by Sanofi Santé Nutrition Animale,
    Libourne Cedex, France.

    KENNELLY, J.C., CAMPBELL, J. & SINCLAIR, P. (1985). Study to determine
    the ability of MBR 10995 to induce mutations to 6-thioguanine
    resistance in mouse lymphoma L5178Y cells using a fluctuation test.
    Unpublished report from Microtest Research Ltd., Heslington, York, UK.
    Submitted to WHO by Sanofi Santé Nutrition Animale, Libourne Cedex,
    France.

    KIRKLAND, D.J., GARNER, J.V., RUTTER, A., BIDGOOD, J. & ARNOLD, W.
    (1985). Study to evaluate the chromosome damaging potential of
    MBR-10995-R-802 (flumequine) by its effects on cultured Chinese
    hamster ovary (CHO) cells using an  in vitro cytogenetics assay.
    Unpublished report from Microtest Research Ltd., Heslington, York, UK.
    Submitted to WHO by Sanofi Santé Nutrition Animale, Libourne Cedex,
    France.

    MARSHALL, R.R., HULME, L., BIDGOOD, J., RUTTER, A., McENANEY, S.,
    TAYLOR, M., FEASBY, T., BARKER, L., KENNELLY, J.C. & COLE, H. (1987).
    Study to evaluate the chromosome damaging potential of MBR 10995
    (flumequine) by its effects on the bone marrow cells of treated rats.
    Unpublished report from Microtest Research Ltd., Heslington, York, UK.
    Submitted to WHO by Sanofi Santé Nutrition Animale, Libourne Cedex,
    France.

    NELSON, R.A. & OWEN, G. (1972a). Effect of R-802 (flumequine) on
    pregnancy of the albino rat. Unpublished report from Riker
    Laboratories Inc., St. Paul, MN, USA. Submitted to WHO by Sanofi Santé
    Nutrition Animale, Libourne Cedex, France.

    NELSON, R.A. & OWEN, G. (1972b). Effect of R-802 (flumequine) on the
    pregnancy of the New Zealand white rabbit. Unpublished report from
    Riker Laboratories Inc., St. Paul, MN, USA. Submitted to WHO by Sanofi
    Santé Nutrition Animale, Libourne Cedex, France.

    NELSON, R.A., CASE, M.T. & HAMILTON, R.R. (1972a). Ninety (90) day
    subacute oral toxicity of flumequine in Charles River rats.
    Unpublished report from Riker Laboratories, Inc., St. Paul, MN, USA.
    Submitted to WHO by Sanofi Santé Nutrition Animale, Libourne Cedex,
    France.

    NELSON, R.A., CASE, M.T., GLICK, P.R., & STEFFEN, G.R. (1972b). Ninety
    (90) day subacute oral toxicity of flumequine in beagle dogs.
    Unpublished report from Riker Laboratories, Inc. St. Paul, MN, USA.
    Submitted to WHO by Sanofi Santé Nutrition Animale, Libourne Cedex,
    France.

    RIKER RESEARCH LABORATORIES (1972a). Metabolic studies of R-802
    (flumequine). Unpublished report from Riker Research Laboratories
    Inc., St. Paul, MN, USA. Submitted by Sanofi Santé Nutrition Animale,
    Libourne Cedex, France.

    RIKER RESEARCH LABORATORIES (1972b). Range-finding studies of R-802
    (flumequine) in mice, rats, guinea-pigs, and dogs. Unpublished report
    from Riker Research Laboratories Inc., St. Paul, MN, USA. Submitted by
    Sanofi Santé Nutrition Animale, Libourne Cedex, France.

    ROHLFING, S.R. & WINANDY, R.M. (1977). Mutagenicity study with MBR
    10995 (flumequine). Unpublished report from Riker Laboratories, Inc.,
    St. Paul, MN, USA. Submitted to WHO by Sanofi Santé Nutrition Animale,
    Libourne Cedex, France.

    SAUNDERS, D.R. & CASE, M.T. (1976). One-year oral toxicity study of
    R-802 in dogs. Unpublished report from Riker Laboratories, Inc., St.
    Paul, MN, USA. Submitted to WHO by Sanofi Santé Nutrition Animale,
    Libourne Codex, France.

    SIBINSKI, L.J., STEFFEN, G.R. & CASE, M.T. (1977a). Eighteen (18)
    month oral carcinogenicity study of R-802 (flumequine) in mice.
    Unpublished report from Riker Laboratories, Inc., St. Paul, MN, USA.
    Submitted to WHO by Sanofi Santé Nutrition Animale, Libourne Cedex,
    France.

    SIBINSKI, L.J., STEFFEN, G.R. & CASE, M.T. (1977b). Two-year oral
    toxicity-carcinogenicity study of R-802 (flumequine) in rats.
    Unpublished report from Riker Laboratories, Inc., St. Paul MN, USA.
    Submitted to WHO by Sanofi Santé Nutrition Animale, Libourne Cedex,
    France.

    SIBINSKI, L.J., STEFFEN, G.R. & CASE, M.T. (1979). Special 18-month
    toxicity study of R-802 (flumequine) in male mice. Unpublished report
    from Riker Laboratories, Inc., St. Paul, MN, USA. Submitted to WHO by
    Sanofi Santé Nutrition Animale, Libourne Cedex, France.

    WAZETER, F.X., GOLDENTHAL, E.I., GEIL, R.G., COOKSON, K.M. & HOWELL,
    D.G. (1971a). Subacute rang-finding study of S-10995 (flumequine) in
    monkeys. Unpublished report from International Research and
    Development Corp., Mattawan, MI, USA. Submitted to WHO by Sanofi Santé
    Nutrition Animale, Libourne Cedex, France.

    WAZETER, F.X., GOLDENTHAL, E.I., GEIL, R.G. & HOWELL, D.G. (1971b).
    Fourteen-day oral toxicity study of flumequine in rats. Unpublished
    report from International Research and Development Corp., Mattawan,
    MI, USA. Submitted to WHO by Sanofi Santé Nutrition Animale, Libourne
    Cedex, France.


    See Also:
       Toxicological Abbreviations
       Flumequine (JECFA Food Additives Series 51)
       Flumequine (WHO Food Additives Series 53)
       Flumequine (WHO Food Additives Series 39)
       FLUMEQUINE (JECFA Evaluation)