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147059-72-1 分子结构
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7-[(1R,5S)-6-amino-3-azabicyclo[3.1.0]hexan-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

ChemBase编号:567
分子式:C20H15F3N4O3
平均质量:416.3533096
单一同位素质量:416.10962502
SMILES和InChIs

SMILES:
Fc1c(N2C[C@H]3[C@H](C3N)C2)nc2n(cc(c(=O)c2c1)C(=O)O)c1c(F)cc(F)cc1
Canonical SMILES:
NC1[C@@H]2[C@H]1CN(C2)c1nc2c(cc1F)c(=O)c(cn2c1ccc(cc1F)F)C(=O)O
InChI:
InChI=1S/C20H15F3N4O3/c21-8-1-2-15(13(22)3-8)27-7-12(20(29)30)17(28)9-4-14(23)19(25-18(9)27)26-5-10-11(6-26)16(10)24/h1-4,7,10-11,16H,5-6,24H2,(H,29,30)/t10-,11+,16?
InChIKey:
WVPSKSLAZQPAKQ-SOSAQKQKSA-N

引用这个纪录

CBID:567 http://www.chembase.cn/molecule-567.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
7-[(1R,5S)-6-amino-3-azabicyclo[3.1.0]hexan-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
IUPAC传统名
trovafloxacin
商标名
Trovan
别名
TVFX
Trovafloxacin mesylate
Trovafloxacin
CAS号
147059-72-1
PubChem SID
46508751
160964030
PubChem CID
62959

数据来源

数据来源

所有数据来源 商品来源 非商品来源
数据来源 数据ID
DrugBank DB00685 external link
PubChem 62959 external link
数据来源 数据ID 价格

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 5.4131193  质子受体
质子供体 LogD (pH = 5.5) -0.057143982 
LogD (pH = 7.4) 0.13973176  Log P 0.13645041 
摩尔折射率 101.0404 cm3 极化性 36.818485 Å3
极化表面积 99.76 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P 0.86  LOG S -3.77 
溶解度 7.04e-02 g/l 

分子性质

分子性质

理化性质 生物活性(PubChem)
溶解度
12.3 mg/L expand 查看数据来源
疏水性(logP)
3.7 expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank
DrugBank -  DB00685 external link
Item Information
Drug Groups approved
Description Trovafloxacin (sold as Trovan by Pfizer) is a broad spectrum antibiotic that inhibits the uncoiling of supercoiled DNA in various bacteria by blocking the activity of DNA gyrase and topoisomerase IV. It was withdrawn from the market due to the risk of hepatotoxicity. It had better gram-positive bacterial coverage and less gram-negative coverage than the previous fluoroquinolones. [Wikipedia]
Indication For treatment of infections caused by susceptible strains of the designated microorganisms in uncomplicated urethral gonorrhea in males and endocervical and rectal gonorrhea in females caused by Neisseria gonorrhoeae as well as non gonoccocal urethritis and cervicitis due to Chlamydia trachomatis.
Pharmacology 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 1x10-7 to 10-10. Although cross-resistance has been observed between trovafloxacin and some other fluoroquinolones, some microorganisms resistant to other fluoroquinolones may be susceptible to trovafloxacin.
Toxicity Symptoms of overdose include convulsions, decreased activity, diarrhea, sleepiness, tremors, and/or vomiting.
Affected Organisms
Enteric bacteria and other eubacteria
Biotransformation Metabolism Trovafloxacin is metabolized by conjugation (the role of cytochrome P450 oxidative metabolism of trovafloxacin is minimal). The major metabolites include the ester glucuronide, which appears in the urine (13% of the administered dose); and the N -acetyl metabolite, which appears in the feces and serum (9% and 2.5% of the administered dose, respectively). Other minor metabolites include diacid, hydroxycarboxylic acid, and sulfamate, which have been identified in both the feces and the urine in small amounts (< 4% of the administered dose).
Absorption Well-absorbed from the gastrointestinal tract after oral administration and does not depend on concomitant food intake. The absolute bioavailability is approximately 88%.
Half Life Following 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.
Protein Binding The mean plasma protein bound fraction is approximately 76%, and is concentration-independent.
Elimination Approximately 50% of an oral dose is excreted unchanged (43% in the feces and 6% in the urine).
External Links
Wikipedia
RxList
Drugs.com

参考文献

参考文献

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专利

专利

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