Oxolinic acid

261.23

261.23

238-750-8

L0A22B22FT

758177|110364

DTXSID1021089

CRYSTALS FROM DIMETHYLFORMAMIDE

J - Antiinfectives for systemic use

29349990

76.1

-0.2

White Crystalline Powder

1.3038 (rough estimate)

314-316 °C

473℃

>110°(230°F)

1.5500 (estimate)

Soluble in 0.5N NaOH with warming

2-8°C

9.24E-10mmHg at 25°C

LD50 in mice, rats (mg/kg): >6000, >2000 orally (Turner)

149.1 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]|147.8 Ų [M+H]+ [CCS Type: TW]|152.5 Ų [M+H]+ [CCS Type: TW, Method: calibrated with Waters Major Mix]|167.2 Ų [M+Na]+ [CCS Type: TW, Method: calibrated with Waters Major Mix]|150.35 Ų [M+H]+

3

22

22-24/25-60-36

JI5075000

Xn

Stable. Combustible.

P260, P261, P264, P270, P271, P273, P304+P312, P304+P340, P309+P311, P312, P314, P391, P405, P501

H332

|Warning|H302 (99.35%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 153 companies from 5 notifications to the ECHA C&L Inventory.|H332: Harmful if inhaled [Warning Acute toxicity, inhalation]|P260, P261, P264, P270, P271, P304+P312, P304+P340, P309+P311, P312, P314, P405, and P501

OXOLINIC ACID ANTAGONIZED HYPNOTIC ACTION OF SODIUM BARBITOL IN MICE & RATS. EFFECTS OF OXOLINIC ACID WERE ANTAGONIZED BY ALPHA-METHYLTYROSINE, PIMOZIDE, RESERPINE, & DIAZEPAM.

Anti-Infective Agents, Quinolone; Anti-Infective Agents, Urinary|DRUG HAS CHEMICAL STRUCTURE, MECHANISM OF ACTION, SPECTRUM OF ACTIVITY & POTENTIAL FOR TOXICITY THAT RESEMBLES NALIDIXIC ACID.|OXOLINIC ACID IS ALTERNATIVE FORM OF THERAPY FOR PENICILLIN-SENSITIVE OR CEPHALOSPORIN-SENSITIVE ADULT WHO HAS RECURRENT URINARY TRACT INFECTION CAUSED BY SUSCEPTIBLE ESCHERICHIA COLI OR PROTEUS MIRABILIS THAT IS NOT COMPLICATED BY BACTEREMIA.|...EXERTS IN VITRO ACTIVITY AGAINST MOST GRAM-NEGATIVE AEROBIC BACILLI THAT CAUSE BACTERIAL URINARY TRACT INFECTIONS. MAJORITY OF ESCHERICHIA COLI, KLEBSIELLA SP, ENTEROBACTER SP & PROTEUS SP ARE SUSCEPTIBLE. ... SALMONELLA, SHIGELLA & NEISSERIA (MENINGITIDIS, GONORRHEAE) ARE SUSCEPTIBLE...STAPHYLOCOCCUS AUREUS...|For more Therapeutic Uses (Complete) data for OXOLINIC ACID (6 total), please visit the HSDB record page.

PSEUDOMONAS AERUGINOSA & ACINETOBACTER CALCOACETICUS (VAR LIVOFFI & VAR ANITRATUS) ARE UNIFORMLY RESISTANT...|WHEN BACTERIAL RESISTANCE DEVELOPS...IT IS USUALLY RAPID. THEREFORE, IF FOLLOW-UP CULTURES INDICATE THAT URINE IS NOT STERILE WITHIN 48-72 HR, TREATMENT CAN PROBABLY BE CONSIDERED FAILURE SINCE ORGANISM BY THEN WILL HAVE DEVELOPED RESISTANCE. ... CROSS RESISTANCE TO NALIDIXIC ACID HAS BEEN REPORTED.|...HAS STIMULATORY EFFECT ON CNS, & SHOULD NOT BE PRESCRIBED FOR PT WITH KNOWN SEIZURE DISORDERS.|...HAS FAIRLY NARROW ANTIBACTERIAL SPECTRUM &, THEREFORE, BACTERIAL CULTURE & SENSITIVITY TESTS GENERALLY SHOULD BE PERFORMED PRIOR TO ITS USE.|For more Drug Warnings (Complete) data for OXOLINIC ACID (7 total), please visit the HSDB record page.

Substances capable of killing agents causing urinary tract infections or of preventing them from spreading. (See all compounds classified as Anti-Infective Agents, Urinary.)|Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)|Compounds that inhibit the activity of DNA TOPOISOMERASE II. Included in this category are a variety of ANTINEOPLASTIC AGENTS which target the eukaryotic form of topoisomerase II and ANTIBACTERIAL AGENTS which target the prokaryotic form of topoisomerase II. (See all compounds classified as Topoisomerase II Inhibitors.)

AFTER INGESTION OF OXOLINIC ACID, 5-ETHYL-5,8-DIHYDRO-8 -OXO-1,3-DIOXOLO-[4,5-G]QUINOLINE-7-CARBOXYLIC ACID, BY HUMAN SUBJECTS, URINE CONTAINED SMALL QUANTITY OF BIOLOGICALLY-INACTIVE & UNIDENTIFIED OXOLINIC ACID COMPLEX, BUT NO UNCHANGED OXOLINIC ACID.|OF ORAL DOSE OF ANTIBACTERIAL, (14)C-OXOLINIC ACID, THERE WAS EXCRETED IN 24-HR URINE & FECES RESPECTIVELY, 27 & 41% BY RAT, 19 & 14% BY DOG, 49 & 37% BY RABBIT, & 35 & 10% BY MAN. BLOOD LEVELS OF (14)C PEAKED AFTER 4 HR IN DOG & MAN, & AFTER 6 HR IN RAT & RABBIT.|AFTER ORAL ADMIN...RAPIDLY ABSORBED FROM GI TRACT. PEAK SERUM CONCN OF BIOLOGICALLY ACTIVE UNCONJUGATED DRUG ARE ATTAINED IN 2-4 HR & RANGE FROM 1.8-3.6 UG/ML. LOWER SERUM LEVELS...OCCUR DURING 1ST 3 DAYS OF DOSING, SUGGESTING SLOW DISTRIBUTION... PROTEIN BINDING OF DRUG IS ABOUT 77-81%.|750 MG ADMIN TWICE/DAY FOR 7 DAYS STUDIED IN 10 HEALTHY WOMEN. WHEN TAKEN WITH FOOD, EXCRETION RETARDED BY 6 HR BUT 48 HR RECOVERY NOT DECR.|For more Absorption, Distribution and Excretion (Complete) data for OXOLINIC ACID (6 total), please visit the HSDB record page.

YIELDS 1-ETHYL-1,4-DIHYDRO-7-HYDROXY-6-METHOXY-6-OXOQUINOLINE-3-CARBOXYLIC ACID IN RAT, RABBIT, DOG; YIELDS OXOLINOYL-BETA-D-GLUCURONIC ACID IN RAT, RABBIT, DOG; CREW, MC, MELGAR, MD, HAYNES, LJ, GALA, RL, & DICARLO, FJ, XENOBIOTICA, 1, 193 (1971). /FROM TABLE/|MAJOR URINARY METABOLITE WAS GLUCURONIDE OF OXOLINIC ACID...THIS COMPD WAS BIOLOGICALLY ACTIVE WHEREAS ALMOST ALL DRUG GLUCURONIDES ARE BIOLOGICALLY INERT...

AFTER REPEATED DOSING, BIPHASIC EXCRETION PATTERN HAS BEEN OBSERVED. INITIAL PHASE IS RAPID WITH T/2 OF ABOUT 1.5 HR, & IS FOLLOWED BY SLOW PHASE WITH T/2 OF ABOUT 15 HR. URINARY CONCN OF UNCONJUGATED DRUG RANGE FROM 15-155 UG/ML IN PT WITH NORMAL RENAL FUNCTION.

...INTERFERENCE WITH DEOXYRIBONUCLEIC ACID (DNA) SYNTH. OXOLINIC ACID, HOWEVER, HAS DEMONSTRATED 10-FOLD GREATER /THAN NALIDIXIC ACID/ ABILITY TO INHIBIT DNA REPLICATION, WHICH IS PARALLELED BY ITS GREATER IN VITRO ACTIVITY FOR ENTEROBACTERIACEAE.

CNS TOXICITY HAS INCL INSOMNIA (MOST FREQUENT), RESTLESSNESS, DIZZINESS, HEADACHE, DROWSINESS, & VISUAL DISTURBANCES. ... GI REACTIONS INCL NAUSEA (MOST FREQUENT), VOMITING, ABDOMINAL DISCOMFORT & DIARRHEA.|LESS FREQUENT...REACTIONS INCL FEVER, SKIN ERUPTIONS, PHOTOSENSITIVITY, PALPITATIONS, DYSPNEA & SENSE OF CHEST TIGHTNESS. TRANSIENT ELEVATIONS OF SERUM BILIRUBIN, SGOT & ALKALINE PHOSPHATASE, AS WELL AS LEUKOPENIA & HEMOLYTIC ANEMIA HAVE ALSO BEEN DESCRIBED.|OCCASIONAL REACTIONS INCL ANOREXIA...CONSTIPATION, WEAKNESS...PRURITUS... RARELY, DRUG MAY CAUSE SWELLING OF EXTREMITIES, URTICARIA, SORENESS OF MOUTH & GUMS, METALLIC TASTE...

Acid, Oxolinic

Veterinary Drug -> ANTIMICROBIAL_AGENT; -> JECFA Functional Classes

Veterinary Drug -> ANTIMICROBIAL_AGENT;