基本情報
- CAS
147059-72-1- 標準SMILES
NC1[C@H]2CN(c3nc4c(cc3F)c(=O)c(C(=O)O)cn4-c3ccc(F)cc3F)C[C@@H]12- InChIKey
WVPSKSLAZQPAKQ-SOSAQKQKSA-N- 分子式
- C20H15F3N4O3
- 平均分子量
- 416.4 g/mol
- 単同位体質量
- 416.10962484
概要
Trovafloxacin is a 1,8-naphthyridine derivative that is 4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid bearing additional 2,4-difluorophenyl, fluoro and 6-amino-3-azabicyclo[3.1.0]hex-3-yl substituents at positions 1, 6 and 7 respectively. A broad-spectrum antibiotic that was withdrawn from the market due to risk of liver failure. It has a role as an antimicrobial agent, an antibacterial drug, a hepatotoxic agent, a topoisomerase IV inhibitor and a DNA synthesis inhibitor. It is a monocarboxylic acid, an amino acid, an azabicycloalkane, a difluorobenzene, a primary amino compound, a tertiary amino compound, a 1,8-naphthyridine derivative, a quinolone antibiotic and a fluoroquinolone antibiotic. It is a conjugate base of a trovafloxacin(1+).
名称と識別子
- 優先名称
- 1,8-Naphthyridine-3-carboxylic acid, 7-(1alpha,5alpha,6alpha)-6-amino-3-azabicyclo3.1.0hex-3-yl-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-
- IUPAC
- 7-[(1R,5S)-6-amino-3-azabicyclo[3.1.0]hexan-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid
- 現地名
- トロバフロキサシン
- 英語名
- TROVAFLOXACIN
- 分子式
- C20H15F3N4O3
- 分子量
- 416.35
名称と別名
1,8-Naphthyridine-3-carboxylic acid, 7-[(1alpha,5alpha,6alpha)-6-amino-3-azabicyclo[3.1.0]hex-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-Naphthyridine-3-carboxylic acid, 7-(1alpha,5alpha,6alpha)-6-amino-3-azabicyclo3.1.0hex-3-yl-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-Naphthyridine-3-carboxylic acid, 7-((1alpha,5alpha,6alpha)-6-amino-3-azabicyclo(3.1.0)hex-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-RefChem:4179231,8-Naphthyridine-3-carboxylic acid, 7-[(1.alpha.,5.alpha.,6.alpha.)-6-amino-3-azabicyclo[3.1.0]hex-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-Naphthyridine-3-carboxylic acid, 7-(1.alpha.,5.alpha.,6.alpha.)-6-amino-3-azabicyclo3.1.0hex-3-yl-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-Trovafloxacin147059-72-1TVFXTrovafloxacin [INN]trovafloxacinetrovafloxacino
名称をさらに表示
トロバフロキサシン7-[(1α,5α)-6α-アミノ-3-アザビシクロ[3.1.0]ヘキサン-3-イル]-1-(2,4-ジフルオロフェニル)-6-フルオロ-1,4-ジヒドロ-4-オキソ-1,8-ナフチリジン-3-カルボン酸
物性
構造計算による物性
- XLogP
- 0.3
- 極性表面積
- 99.8 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 10
- 回転可能結合数
- 3
- 重原子数
- 30
- 形式電荷
- 0
- 複雑度
- 770
実験および物理化学的性質
Drugs
Pharmaceuticals -> Anti infectives for systemic use -> Antibacterials for systemic use
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antibiotics
LogP3.7
Solubility7.04e-02 g/L
Human DrugsPharmaceuticals
Physical DescriptionSolid
Dissociation Constants
5.9
8.11
物理化学的性質
- 融点
- 195 oC · >195oC (dec.)
- 沸点
- 630.5 · 630.5±55.0 °C(Predicted)
- 比重(密度)
- 1.612 · 1.612±0.06 g/cm3(Predicted)
- 貯蔵温度
- -20 °C · -20°C Freezer, Under inert atmosphere
- 溶解性
- アセトニトリル（微量）、DMSO（微量）
- 酸解離定数(Pka)
- 5.8 · 5.80±0.70(Predicted)
- 外見
- 個体
- 色
- ペールベージュからライトベージュ
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。
危険有害性情報
Regulatory Information
1,8-Naphthyridine-3-carboxylic acid, 7-(1.alpha.,5.alpha.,6.alpha.)-6-amino-3-azabicyclo3.1.0hex-3-yl-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-: Does not have an individual approval but may be used under an appropriate group standard
安全データ
- 注意喚起語
- 警告
- 危険有害性情報
- コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード H302
化学と産業
薬理情報
Protein BindingThe mean plasma protein bound fraction is approximately 76%, and is concentration-independent.
Pharmacodynamics
Trovafloxacin is a broad spectrum antibiotic that inhibits DNA supercoiling in various bacteria by blocking the activity of DNA gyrase and topoisomerase IV. It is not used widely due to the risk of hepatotoxicity. It tends to have better gram-positive bacterial coverage and less gram-negative coverage than the previous fluoroquinolones. Mechanism of action of fluoroquinolones including trovafloxacin is different from that of penicillins, cephalosporins, aminoglycosides, macrolides, and tetracyclines. Therefore fluoroquinolones may be active against pathogens that are resistant to these antibiotics. There is no cross-resistance between trovafloxacin and the mentioned classes of antibiotics. The overall results obtained from in vitro synergy studies, testing combinations of trovafloxacin with beta-lactams and aminoglycosides, indicate that synergy is strain specific and not commonly encountered. This agrees with results obtained previously with other fluoroquinolones. Resistance to trovafloxacin in vitro develops slowly via multiple-step mutation in a manner similar to other fluoroquinolones. Resistance to trovafloxacin in vitro occurs at a general frequency of between 1x10<sup>-7</sup> to 10<sup>-10</sup>. Although cross-resistance has been observed between trovafloxacin and some other fluoroquinolones, some microorganisms resistant to other fluoroquinolones may be susceptible to trovafloxacin.
Mechanism of Action
Trovafloxacin is a fluoronaphthyridone related to the fluoroquinolones with in vitro activity against a wide range of gram-negative and gram-positive aerobic and anaerobic microorganisms. The bactericidal action of trovafloxacin results from inhibition of DNA gyrase and topoisomerase IV. DNA gyrase is an essential enzyme that is involved in the replication, transcription, and repair of bacterial DNA. Topoisomerase IV is an enzyme known to play a key role in the partitioning of the chromosomal DNA during bacterial cell division.
Biological Half-LifeFollowing oral administration, half-life ranged from 9.1 hours to 12.2 hours over the dosage range of 100 to 200 mg tablets. Following intravenous infusion, half-life ranged from 9.4 to 12.7 hours over a dosage range of 100 to 300 mg.
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