Finafloxacin
기본 정보
- CAS
209342-40-5- 표준 SMILES
N#Cc1c(N2C[C@@H]3NCCO[C@H]3C2)c(F)cc2c(=O)c(C(=O)O)cn(C3CC3)c12- InChIKey
FYMHQCNFKNMJAV-HOTGVXAUSA-N- 분자식
- C20H19FN4O4
- 평균 분자량
- 398.4 g/mol
- 단동위원소 질량
- 398.13903331
개요
Finafloxacin is a quinolone that is 4-oxo-1,4-dihydroquinoline-3-carboxylic acid which is substituted at positions 1, 6, 7 and 8 by cyclopropyl, fluoro, hexahydropyrrolo[3,4-b][1,4]oxazin-6-yl and cyano groups respectively; an antibiotic used for treatment of acute otitis externa (swimmer's ear) caused by the bacteria Pseudomonas aeruginosa and Staphylococcus aureus. It has a role as an antimicrobial agent and an antibacterial drug. It is a nitrile, a quinolone, a monocarboxylic acid, an organofluorine compound, a secondary amino compound, a tertiary amino compound and a member of cyclopropanes.
이름 및 식별자
- 우선 이름
- Finafloxacin
- IUPAC
- 7-[(4aS,7aS)-3,4,4a,5,7,7a-hexahydro-2H-pyrrolo[3,4-b][1,4]oxazin-6-yl]-8-cyano-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid
- 영어명
- 3-Quinolinecarboxylic acid, 8-cyano-1-cyclopropyl-6-fluoro-7-[(4aS,7aS)-hexahydropyrrolo[3,4-b]-1,4-oxazin-6(2H)-yl]-1,4-dihydro-4-oxo-
- 분자식
- C20H19FN4O4
- 분자량
- 398.39
이름 및 동의어
Finafloxacin209342-40-5XtorofinafloxacinefinafloxacinoD26OSN9Q4RAL-60371CHEBI:85176DTXSID101750967-[(4aS,7aS)-3,4,4a,5,7,7a-hexahydro-2H-pyrrolo[3,4-b][1,4]oxazin-6-yl]-8-cyano-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid3-Quinolinecarboxylic acid, 8-cyano-1-cyclopropyl-6-fluoro-7-[(4aS,7aS)-hexahydropyrrolo[3,4-b]-1,4-oxazin-6(2H)-yl]-1,4-dihydro-4-oxo-finafloxacinum
이름 더 보기
100827Finafloxacin OticValine Impurity 71Finafloxacin (Xtoro)Finafloxacin >=95% (HPLC)Finafloxacin (BAY35-3377)BAY35-3377,finafloxacin hydrochloride8-Cyano-1-cyclopropyl-6-fluoro-7-[(4aS,7aS)-hexahydropyrrolo[3,4-b][1,4]oxazin-6(2H)-yl]-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid8-cyano-1-cyclopropyl-6-fluoro-7-((4aS,7aS)-hexahydropyrrolo[3,4-b][1,4]oxazin-6(2H)-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
3-Quinolinecarboxylic acid, 8-cyano-1-cyclopropyl-6-fluoro-7-((4aS,7aS)-hexahydropyrrolo(3,4-b)-1,4-oxazin-6(2H)-yl)-1,4-dihydro-4-oxo-7-((4aS,7aS)-3,4,4a,5,7,7a-hexahydro-2H-pyrrolo(3,4-b)(1,4)oxazin-6-yl)-8-cyano-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acidRefChem:56697DTXCID5097587111-147-67-((4aS,7aS)-octahydropyrrolo(3,4-b)morpholin-6-yl)-8-cyano-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid8-Cyano-1-cyclopropyl-6-fluoro-7-((4aS,7aS)-hexahydropyrrolo(3,4-b)-1,4-oxazin-6(2H)-yl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidFinafloxacin [INN]
물성
구조 계산 물성
- XLogP
- -0.7
- 극성 표면적
- 106 Ų
- 수소 결합 공여자 수
- 2
- 수소 결합 수용자 수
- 9
- 회전 가능 결합 수
- 3
- 무거운 원자 수
- 29
- 형식 전하
- 0
- 복잡도
- 806
실험 및 물리화학적 성질
Drugs
Pharmaceuticals -> Anti infectives for systemic use -> Antibacterials for systemic use
Pharmaceuticals -> Listed in ZINC15
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
물리화학적 성질
- 끓는 점
- 686.2 · 686.2±55.0 °C(Predicted)
- 밀도
- 1.57 · 1.57±0.1 g/cm3(Predicted)
- 저장 조건
- -20 °C · -20°C
- 용해도
- 6.4 mg/mL · DMSO : 6.4 mg/mL (16.06 mM)
- 물리적 상태
- 가루
- 산도 계수 (pKa)
- 6.38 · 6.38±0.50(Predicted)
- 색상
- 흰색에서 베이지색
- InChIKey
- FYMHQCNFKNMJAV-HOTGVXAUSA-N
- SMILES
- Fc1cc2c([n](cc([c]2=O)C(=O)O)C5CC5)c(c1N3C[C@@H]4NCCO[C@H]4C3)C#N
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
GHS 분류
GHS Classification
Danger
H340 (100%): May cause genetic defects [Danger Germ cell mutagenicity]
P203, P280, P318, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
유해성 정보
Hazard Classes and CategoriesMuta. 1B (100%)
안전 데이터
- wgk
- WGK 3
- Hazard Classifications
- Muta. 1BRepr. 2
- 스토리지 클래스
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
화학 및 산업
약리 정보
Mechanism of ActionFinafloxacin is a fluoroquinolone antibiotic, which selectively inhibit bacterial type II topoisomerase enzymes, DNA gyrase and topoisomerase IV, which are required for bacterial DNA replication, transcription, repair and recombination.
FDA Pharmacological Classification
D26OSN9Q4R
FINAFLOXACIN
Established Pharmacologic Class [EPC] - Quinolone Antimicrobial
Chemical Structure [CS] - Quinolones
Finafloxacin is a Quinolone Antimicrobial.
FINAFLOXACIN
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.
응용 분야
개요Finafloxacin, an antimicrobial agent of the 8-cyano subclass of fluoroquinolones, was approved by the US FDA in December 2014 for treatment of acute otitis externa, commonly known as swimmer’s ear, caused by susceptible strains of Pseudomonas aeruginosa and Staphylococcus aureus. Finafloxacin was developed by MerLion Pharmaceuticals in partnership with Bayer Health Care Pharmaceuticals, and the drug was licensed by Mer- Lion to Alcon (a division of Novartis) for development and commercialization for ear infections in North America. In contrast to other marketed fluoroquinolones, which display reduced activity in slightly acidic environments, finafloxacin exhibits increased antibacterial activity at pH 5–6, with minimum inhibitory concentration values that are 4- to 8-fold lower than at neutral pH. It is highly selective for bacterial type II topoisomerases, which are involved in bacterial DNA replication, transcription, repair, and recombination, and has broad spectrum antibacterial activity against Gram-positive and Gram-negative strains, including ciprofloxacin-resistant strains.
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2건
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