Gatifloxacin

HCID 5379CAS 112811-59-3

기본 정보

표준 SMILES
COc1c(N2CCNC(C)C2)c(F)cc2c(=O)c(C(=O)O)cn(C3CC3)c12
InChIKey
XUBOMFCQGDBHNK-UHFFFAOYSA-N
분자식
C19H22FN3O4
평균 분자량
375.4 g/mol
단동위원소 질량
375.1594344

개요

Gatifloxacin is a monocarboxylic acid that is 4-oxo-1,4-dihydroquinoline-3-carboxylic acid which is substituted on the nitrogen by a cyclopropyl group and at positions 6, 7, and 8 by fluoro, 3-methylpiperazin-1-yl, and methoxy groups, respectively. Gatifloxacin is an antibiotic of the fourth-generation fluoroquinolone family, that like other members of that family, inhibits the bacterial topoisomerase type-II enzymes. It has a role as an antimicrobial agent, an antiinfective agent and an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor. It is a quinolone, a quinolinemonocarboxylic acid, an organofluorine compound, a N-arylpiperazine and a quinolone antibiotic.

이름 및 식별자

우선 이름
Gatifloxacin
IUPAC
1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid

이름 및 동의어

Gatifloxacin112811-59-3TequinGatifloZymarAM-1155GatifloxacineZymaxidZymergatifloxacin anhydrousAM 11553-Quinolinecarboxylic acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-
이름 더 보기
gatifloxacinoDTXSID50457041-Cyclopropyl-1,4-dihydro-6-fluoro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acidgatifloxacinumPD-1354321-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acidNSC-758701CHEBI:5280

데이터베이스 식별자

CAS
112811-59-3
PubChem CID
5379
DTXSID
DTXSID5045704
ChEMBL
CHEMBL31
ChEBI
CHEBI:5280
UNII
81485Y3A9A
EC Number
664-293-2
Nikkaji
J523.172H

물성

구조 계산 물성

XLogP
-0.7
극성 표면적
82.1 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
8
회전 가능 결합 수
4
무거운 원자 수
27

실험 및 물리화학적 성질

Drugs · 2건

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Anti infectives for systemic use -> Antibacterials for systemic use

LogP2.6
Solubility6.31e-01 g/L
Human Drugs · 3건

Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Quinolones; Fluoroquinolones

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Melting Point · 2건

182-185 °C

182 - 185 °C

Physical DescriptionSolid

안전 및 규제

GHS 분류

GHS Classification · 4건

Warning

H302 (97.5%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Hazard Classes and CategoriesAcute Tox. 4 (97.5%)

독성 정보

Treatment · 1건

In the event of acute oral overdose, the stomach should be emptied by inducing vomiting or by gastric lavage. The patient should be carefully observed (including ECG monitoring) and given symptomatic and supportive treatment. Adequate hydration should be maintained. (L1712)

Health EffectsAntibiotic resistance
Exposure RoutesOphthalmic. Well absorbed from the gastrointestinal tract after oral administration with absolute bioavailability of gatifloxacin is 96%
Toxicity SummaryThe bactericidal action of Gatifloxacin results from inhibition of the enzymes topoisomerase II (DNA gyrase) and topoisomerase IV, which are required for bacterial DNA replication, transcription, repair, and recombination.
Signs and SymptomsThe most common side effects from antibiotics are diarrhea, nausea, vomiting. Fungal infections of the mouth, digestive tract and vagina can also occur with antibiotics
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

화학 및 산업

약리 정보

ATC Code · 4건

S - Sensory organs

J - Antiinfectives for systemic use

QS - Sensory organs

QJ - Antiinfectives for systemic use

Protein Binding20%
Pharmacodynamics · 1건

Gatifloxacin is a synthetic broad-spectrum 8-methoxyfluoroquinolone antibacterial agent for oral or intravenous administration. is bactericidal and its mode of action depends on blocking of bacterial DNA replication by binding itself to an enzyme called DNA gyrase, which allows the untwisting required to replicate one DNA double helix into two. Notably the drug has 100 times higher affinity for bacterial DNA gyrase than for mammalian. Gatifloxacin is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria. It should be used only to treat or prevent infections that are proven or strongly suspected to be caused by bacteria.

Mechanism of ActionThe bactericidal action of Gatifloxacin results from inhibition of the enzymes topoisomerase II (DNA gyrase) and topoisomerase IV, which are required for bacterial DNA replication, transcription, repair, and recombination.
Biological Half-Life7-14 hours
Metabolism/Metabolites · 2건

Gatifloxacin undergoes limited biotransformation in humans with less than 1% of the dose excreted in the urine as ethylenediamine and methylethylenediamine metabolites

Gatifloxacin undergoes limited biotransformation in humans with less than 1% of the dose excreted in the urine as ethylenediamine and methylethylenediamine metabolites Half Life: 7-14 hours

용도 및 제조

Uses · 2건

Use (kg) in USA (2002): 7250

For the treatment of bronchitis, sinusitis, community-acquired pneumonia, and skin infections (abscesses, wounds) caused by S. pneumoniae, H. influenzae, S. aureus, M. pneumoniae, C. pneumoniae, L. pneumophila, S. pyogenes

관련 반응

29건

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