Sparfloxacin

HCID 60464CAS 110871-86-8

기본 정보

표준 SMILES
C[C@@H]1CN(c2c(F)c(N)c3c(=O)c(C(=O)O)cn(C4CC4)c3c2F)C[C@H](C)N1
InChIKey
DZZWHBIBMUVIIW-DTORHVGOSA-N
분자식
C19H22F2N4O3
평균 분자량
392.4 g/mol
단동위원소 질량
392.165997

개요

Sparfloxacin is a quinolone, a quinolinemonocarboxylic acid, a N-arylpiperazine, a quinolone antibiotic and a fluoroquinolone antibiotic.

이름 및 식별자

우선 이름
Sparfloxacin
IUPAC
5-amino-1-cyclopropyl-7-[(3R,5S)-3,5-dimethylpiperazin-1-yl]-6,8-difluoro-4-oxoquinoline-3-carboxylic acid

이름 및 동의어

sparfloxacin110871-86-8ZagamEsparfloxacinoSparfloxacineSparaAT-4140CI-978SparfloxacinumSPFXDTXSID9023590CHEBI:9212
이름 더 보기
Q90AGA787L5-Amino-1-cyclopropyl-7-(cis-3,5-dimethyl-1-piperazinyl)-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidNSC-7596415-amino-1-cyclopropyl-7-[(3R,5S)-3,5-dimethylpiperazin-1-yl]-6,8-difluoro-4-oxoquinoline-3-carboxylic acidcis-5-Amino-1-cyclopropyl-7-(3,5-dimethyl-1-piperazinyl)-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidDTXCID508201543-Quinolinecarboxylic acid, 5-amino-1-cyclopropyl-7-(3,5-dimethyl-1-piperazinyl)-6,8-difluoro-1,4-dihydro-4-oxo-, cis-5-amino-1-cyclopropyl-7-((3R,5S)-3,5-dimethylpiperazin-1-yl)-6,8-difluoro-4-oxoquinoline-3-carboxylic acid

데이터베이스 식별자

CAS
110871-86-8
PubChem CID
60464
DTXSID
DTXSID9023590
ChEMBL
CHEMBL850
ChEBI
CHEBI:9212
UNII
Q90AGA787L
EC Number
629-019-8
Nikkaji
J324.247A

물성

구조 계산 물성

XLogP
0.1
극성 표면적
98.9 Ų
수소 결합 공여자 수
3
수소 결합 수용자 수
9
회전 가능 결합 수
3
무거운 원자 수
28

실험 및 물리화학적 성질

Drugs · 3건

Pharmaceuticals -> Listed in ZINC15

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

Pharmaceuticals -> Antibiotics

LogP2.5
Solubility · 2건

Practically insoluble

1.13e-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

Physical DescriptionSolid
Collision Cross Section · 2건

190.2 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID9023590]

216.1 Ų [M+K]+

안전 및 규제

GHS 분류

GHS Classification · 4건

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, 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 CategoriesSkin Irrit. 2 (100%)

독성 정보

Drug Induced Liver Injury · 4건

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

Sparfloxacin

DILI Positive

DOI:10.1016/j.drudis.2019.09.022

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

화학 및 산업

약리 정보

ATC Code · 2건

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

Protein BindingLow plasma protein binding in serum at about 45%.
Pharmacodynamics · 1건

Sparfloxacin is a synthetic fluoroquinolone broad-spectrum antimicrobial agent in the same class as ofloxacin and norfloxacin. Sparfloxacin has in vitro activity against a wide range of gram-negative and gram-positive microorganisms. Sparfloxacin exerts its antibacterial activity by inhibiting DNA gyrase, a bacterial topoisomerase. DNA gyrase is an essential enzyme which controls DNA topology and assists in DNA replication, repair, deactivation, and transcription. Quinolones differ in chemical structure and mode of action from (beta)-lactam antibiotics. Quinolones may, therefore, be active against bacteria resistant to (beta)-lactam antibiotics. Although cross-resistance has been observed between sparfloxacin and other fluoroquinolones, some microorganisms resistant to other fluoroquinolones may be susceptible to sparfloxacin. In vitro tests show that the combination of sparfloxacin and rifampin is antagonistic against Staphylococcus aureus.

Mechanism of ActionThe bactericidal action of sparfloxacin 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-LifeMean terminal elimination half-life of 20 hours (range 16-30 hours). Prolonged in patients with renal impairment (creatinine clearance <50 mL/min).
Metabolism/MetabolitesHepatic. Metabolized primarily by phase II glucuronidation to form a glucuronide conjugate. Metabolism does not utilize or interfere with the cytochrome P450 enzyme system.

관련 반응

1건

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