基本情報
- CAS
14698-29-4- 標準SMILES
CCn1cc(C(=O)O)c(=O)c2cc3c(cc21)OCO3- InChIKey
KYGZCKSPAKDVKC-UHFFFAOYSA-N- 分子式
- C13H11NO5
- 平均分子量
- 261.23 g/mol
- 単同位体質量
- 261.06372245
概要
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.
名称と識別子
- 優先名称
- Oxolinic Acid
- IUPAC
- 5-ethyl-8-oxo-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid
- 現地名
- オキソリン酸
- 英語名
- Oxolinic acid
- 分子式
- C13H11NO5
- 分子量
- 261.23
名称と別名
oxolinic acid14698-29-4UtibidProdoxalOssianPietilAcido oxolinicoAcide oxoliniqueAcidum oxolinicumNSC-110364AqualinicW 4565
名称をさらに表示
1-エチル-6,7-(メチレンジオキシ)-4-オキソ-1,4-ジヒドロキノリン-3-カルボン酸ウロキソルオキソリン酸ウロトレートピチルウチビド5,8-ジヒドロ-5-エチル-8-オキソ-1,3-ジオキソロ[4,5-g]キノリン-7-カルボン酸ジオキサシンオッシアンオキソリニック酸ウルチビドプロドキソルウロ-アルバル1-エチル-1,4-ジヒドロ-6,7-メチレンビスオキシ-4-オキソ-3-キノリンカルボン酸5-エチル-5,8-ジヒドロ-8-オキソ-1,3-ジオキソロ[4,5-g]キノリン-7-カルボン酸ウリトレートオキソボイ1,4-ジヒドロ-1-エチル-4-オキソ-6,7-(メチレンジオキシ)キノリン-3-カルボン酸スターナニダンチンoxolinic5-ETHYL-8-OXO-5,8-DIHYDRO-[1,3]DIOXOLO[4,5-G]QUINOLINE-7-CARBOXYLIC ACIDw4565oxobois-0208uroxol
物性
構造計算による物性
- XLogP
- -0.2
- 極性表面積
- 76.1 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 6
- 回転可能結合数
- 2
- 重原子数
- 19
- 形式電荷
- 0
- 複雑度
- 446
実験および物理化学的性質
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]+
物理化学的性質
- 融点
- 314 · 314-316°C (dec.)
- 沸点
- 473 ℃ · 473℃
- 比重(密度)
- 1.3038 · 1.3038 (rough estimate)
- 屈折率
- 1.55 · 1.5500 (estimate)
- 闪点
- 110 ° · >110°(230°F)
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- 0.5 N · 加温により0.5N NaOHに可溶
- 外見
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
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]
危険有害性情報
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
毒性情報
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...
化学と産業
薬理情報
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.
関連反応
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化合物ノート
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