기본 정보
- CAS
14698-29-4- 표준 SMILES
CCn1cc(C(=O)O)c(=O)c2cc3c(cc21)OCO3- InChIKey
KYGZCKSPAKDVKC-UHFFFAOYSA-N- 분자식
- C13H11NO5
- 평균 분자량
- 261.23 g/mol
- 단동위원소 질량
- 261.06372245
개요
Oxolinic acid is a quinolinemonocarboxylic acid having the carboxy group at position 7 as well as oxo and ethyl groups at positions 4 and 1 respectively and a dioxolo ring fused at the 5- and 6-positions. A synthetic antibiotic, it is used in veterinary medicine for the treatment of bacterial infections in cattle, pigs and poultry. It has a role as an enzyme inhibitor, an antimicrobial agent, an antiinfective agent, an antifungal agent and an antibacterial drug. It is a quinolinemonocarboxylic acid, an organic heterotricyclic compound, an aromatic carboxylic acid, an oxacycle and a quinolone antibiotic. It is a conjugate acid of an oxolinate.
이름 및 식별자
- 우선 이름
- Oxolinic Acid
- IUPAC
- 5-ethyl-8-oxo-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid
- 현지명
- 옥솔린산
- 영어명
- Oxolinic acid
- 분자식
- C13H11NO5
- 분자량
- 261.23
이름 및 동의어
oxolinic acid14698-29-4UtibidProdoxalOssianPietilAcido oxolinicoAcide oxoliniqueAcidum oxolinicumNSC-110364AqualinicW 4565
이름 더 보기
옥솔린산oxolinic5-ETHYL-8-OXO-5,8-DIHYDRO-[1,3]DIOXOLO[4,5-G]QUINOLINE-7-CARBOXYLIC ACIDw4565oxobois-0208uroxolstarner
5-ethyl-8-oxo-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid1-Ethyl-6,7-methylenedioxy-4-quinolone-3-carboxylic acid5-Ethyl-8-oxo-5,8-dihydro[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acidDTXSID10210891-Ethyl-1,4-dihydro-6,7-methylenedioxy-4-oxo-3-quinolinecarboxylic acid5-Ethyl-5,8-dihydro-8-oxo-1,3-dioxolo(4,5-g)quinoline-7-carboxylic acidL0A22B22FTCHEBI:138856
데이터베이스 식별자
- CAS
14698-29-4- PubChem CID
- 4628
- DTXSID
DTXSID1021089- ChEMBL
CHEMBL416755- ChEBI
CHEBI:138856- UNII
- L0A22B22FT
물성
구조 계산 물성
- XLogP
- -0.2
- 극성 표면적
- 76.1 Ų
- 수소 결합 공여자 수
- 1
- 수소 결합 수용자 수
- 6
- 회전 가능 결합 수
- 2
- 무거운 원자 수
- 19
- 형식 전하
- 0
- 복잡도
- 446
실험 및 물리화학적 성질
Drugs
Pharmaceuticals -> Antibiotics (Quinolones)
Pharmaceuticals -> Antibiotics
LogP1.01
Color/FormCRYSTALS FROM DIMETHYLFORMAMIDE
Melting Point314-316 °C
Collision Cross Section
152.6 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID1021089]
147.8 Ų [M+H]+ [CCS Type: TW]
167.2 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]
149.1 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
150.35 Ų [M+H]+
물리화학적 성질
- 녹는점
- 314 · 314-316°C (dec.)
- 끓는 점
- 473 ℃ · 473℃
- 밀도
- 1.3038 · 1.3038 (rough estimate)
- 굴절률
- 1.55 · 1.5500 (estimate)
- 인화점
- 110 ° · >110°(230°F)
- 저장 조건
- 2 · 2-8°C
- 용해도
- 0.5 N · 가온과 함께 0.5N NaOH에 용해됨
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
GHS 분류
GHS Classification
Warning
H302 (98.9%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 93 reports by companies from 5 notifications to the ECHA C&L Inventory.
Warning
H332: Harmful if inhaled [Warning Acute toxicity, inhalation]
유해성 정보
Regulatory InformationOxolinic acid: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - 1,3-Dioxolo[4,5-g]quinoline-7-carboxylic acid, 5-ethyl-5,8-dihydro-8-oxo-: Environment tier I assessment
Hazard Classes and Categories
Acute Tox. 4 (98.9%)
Acute toxicity (Inhalation: Dusts and mists) - Category 4
독성 정보
InteractionsOXOLINIC ACID ANTAGONIZED HYPNOTIC ACTION OF SODIUM BARBITOL IN MICE & RATS. EFFECTS OF OXOLINIC ACID WERE ANTAGONIZED BY ALPHA-METHYLTYROSINE, PIMOZIDE, RESERPINE, & DIAZEPAM.
Human Toxicity Excerpts
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...
화학 및 산업
약리 정보
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Mechanism of Action
...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.
Biological Half-Life
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.
Metabolism/Metabolites
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...
MeSH Pharmacological Classification
Substances capable of killing agents causing urinary tract infections or of preventing them from spreading.
Substances that inhibit the growth or reproduction of BACTERIA.
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.
Absorption, Distribution and Excretion
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.
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4건
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