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119914-60-2 分子结构
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1-cyclopropyl-6-fluoro-5-methyl-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

ChemBase编号:249
分子式:C19H22FN3O3
平均质量:359.3946832
单一同位素质量:359.1645198
SMILES和InChIs

SMILES:
Fc1c(N2CC(NCC2)C)cc2n(C3CC3)cc(c(=O)c2c1C)C(=O)O
Canonical SMILES:
CC1NCCN(C1)c1cc2c(c(c1F)C)c(=O)c(cn2C1CC1)C(=O)O
InChI:
InChI=1S/C19H22FN3O3/c1-10-8-22(6-5-21-10)15-7-14-16(11(2)17(15)20)18(24)13(19(25)26)9-23(14)12-3-4-12/h7,9-10,12,21H,3-6,8H2,1-2H3,(H,25,26)
InChIKey:
AIJTTZAVMXIJGM-UHFFFAOYSA-N

引用这个纪录

CBID:249 http://www.chembase.cn/molecule-249.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
1-cyclopropyl-6-fluoro-5-methyl-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
IUPAC传统名
grepafloxacin hydrochloride
商标名
Raxar
别名
Grepafloxacin
CAS号
119914-60-2
PubChem SID
160963712
46507253
PubChem CID
72474

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 DB00365 external link
PubChem 72474 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 5.876593  质子受体
质子供体 LogD (pH = 5.5) -0.26560268 
LogD (pH = 7.4) 0.12430624  Log P 0.118112005 
摩尔折射率 97.3994 cm3 极化性 35.853886 Å3
极化表面积 72.88 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P -0.12  LOG S -2.76 
溶解度 6.32e-01 g/l 

分子性质

分子性质

理化性质 生物活性(PubChem)
疏水性(logP)
2.9 expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank
DrugBank -  DB00365 external link
Item Information
Drug Groups approved; withdrawn
Description Grepafloxacin hydrochloride (Raxar®, Glaxo Wellcome) is an oral broad-spectrum quinoline antibacterial agent used to treat bacterial infections. Grepafloxacin was withdrawn in the United States due to its side effect of lengthening the QT interval on the electrocardiogram, leading to cardiac events and sudden death. [Wikipedia]
Indication For treatment of adults with mild to moderate infections caused by susceptible strains of Haemophilus influenzae, Streptococcus pneumoniae, or Moraxella catarrhalis.
Pharmacology Grepafloxacin has in vitro activity against a wide range of gram-positive and gram-negative aerobic microorganisms, as well as some atypical microorganisms.
Toxicity Withdrawn from the US market in 1999 due to associations with QTc prolongation and adverse cardiovascular events.
Affected Organisms
Enteric bacteria and other eubacteria
Biotransformation Primarily hepatic via CYP1A2 and CYP3A4. The major metabolite is a glucuronide conjugate; minor metabolites include sulfate conjugates and oxidative metabolites. The oxidative metabolites are formed mainly by the cytochrome P450 enzyme CYP1A2, while the cytochrome P450 enzyme CYP3A4 plays a minor role. The nonconjugated metabolites have little antimicrobial activity compared with the parent drug, and the conjugated metabolites have no antimicrobial activity
Absorption Rapidly and extensively absorbed following oral administration. The absolute bioavailability is approximately 70%.
Half Life 15 ± 3 hours
Protein Binding 50%
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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