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85721-33-1 分子结构
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1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid

ChemBase编号:419
分子式:C17H18FN3O3
平均质量:331.3415232
单一同位素质量:331.13321967
SMILES和InChIs

SMILES:
Fc1c(N2CCNCC2)cc2n(C3CC3)cc(c(=O)c2c1)C(=O)O
Canonical SMILES:
Fc1cc2c(cc1N1CCNCC1)n(cc(c2=O)C(=O)O)C1CC1
InChI:
InChI=1S/C17H18FN3O3/c18-13-7-11-14(8-15(13)20-5-3-19-4-6-20)21(10-1-2-10)9-12(16(11)22)17(23)24/h7-10,19H,1-6H2,(H,23,24)
InChIKey:
MYSWGUAQZAJSOK-UHFFFAOYSA-N

引用这个纪录

CBID:419 http://www.chembase.cn/molecule-419.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-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid
IUPAC传统名
ciprofloxacin
1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid
商标名
Bacquinor
Baycip
Bernoflox
Ciflox
Cifloxin
Ciloxan
Ciprinol
Cipro
Cipro I.V.
Cipro XL
Cipro XR
Ciprobay
Ciprocinol
Ciprodar
Cipromycin
Ciproquinol
Ciproxan
Ciproxin
Flociprin
Floxin
Ocuflox
Proquin XR
Septicide
Velomonit
别名
西普乐
环丙沙星
Ciprofloxacin monohydrochloride
Ciprofloxacin hydrochloride
Ciprofloxacin HCl
Ciprofloxacin dihydrochloride
Ciprofloxacina
ciprofloxacin
Ciprofloxacin
Ciprofloxacin (Cipro)
Ciprobay
Ciprofloxacin
Cipro
Ciproxan
1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperzinyl)-3-quinolinecarboxylic acid HCl H2O
CIPROFLOXACIN HYDROCHLORIDE
Baycip
Belmacina
Catex
Ceprimax
Cetraxal
Ciflox
Cilox
Ciloxan
Ciprok
Ciproxin
Ciproxine
Cunesin
Estecina
Flociprin
Rigoran
Septocipro
Uniflox
Velmonit
1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic Acid
Bay q 3939
Ciflafin
Ciprine
Cipro IV
Ciprobay 100
Ciprofloxacillin
CAS号
85721-33-1
86393-32-0
MDL号
MFCD00185755
Beilstein号
3568352
PubChem SID
160963882
24850750
46504733
24860222
PubChem CID
2764

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 5.7555547  质子受体
质子供体 LogD (pH = 5.5) -1.1448648 
LogD (pH = 7.4) -0.8145325  Log P -0.81459606 
摩尔折射率 87.9394 cm3 极化性 32.267574 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 -0.57  LOG S -2.39 
溶解度 1.35e+00 g/l 

分子性质

分子性质

理化性质 安全信息 药理学性质 产品相关信息 生物活性(PubChem)
溶解度
1.1 mg/L expand 查看数据来源
dilute aqueous acid: soluble expand 查看数据来源
Hot DMSO expand 查看数据来源
Hot Methanol expand 查看数据来源
外观
White Powder expand 查看数据来源
熔点
253-255°C expand 查看数据来源
314-318°C expand 查看数据来源
密度
0.2-0.7 g/ml expand 查看数据来源
疏水性(logP)
2.3 expand 查看数据来源
保存条件
-20°C Freezer expand 查看数据来源
2-8°C expand 查看数据来源
RTECS编号
VB1993800 expand 查看数据来源
VB1994000 expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
德国WGK号
2 expand 查看数据来源
个人保护装置
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand 查看数据来源
作用靶点
Others expand 查看数据来源
相关基因信息
human ... CYP1A2(1544), KCNH1(3756)rat ... Gabra1(29705) expand 查看数据来源
生物活性机理
DNA gyrase (type II topoisomerase) and topoisomerase IV inhibitor expand 查看数据来源
纯度
≥98.0% (HPLC) expand 查看数据来源
级别
VETRANAL™, analytical standard expand 查看数据来源
成盐信息
Free Base expand 查看数据来源
质检报告
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
适用性
suitable for 1694 per US EPA expand 查看数据来源
应用领域
Broad spectrum antibacterial agent (used in treatment of Legionnaire's disease) expand 查看数据来源
Provides postexposure protection against exp. inhalation anthrax ( Bacillus anthracis ) expand 查看数据来源
Empirical Formula (Hill Notation)
C17H18FN3O3 expand 查看数据来源

详细说明

详细说明

MP Biomedicals MP Biomedicals DrugBank DrugBank Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals -  02199020 external link
Hydrochloride
Anti-bacterial Agent
DrugBank -  DB00537 external link
Item Information
Drug Groups approved; investigational
Description A broad-spectrum antimicrobial carboxyfluoroquinoline. [PubChem]
Indication For the treatment of the following infections caused by susceptible organisms: urinary tract infections, acute uncomplicated cystitis, chronic bacterial prostatitis, lower respiratory tract infections, acute sinusitis, skin and skin structure infections, bone and joint infections, complicated intra-abdominal infections (used in combination with metronidazole), infectious diarrhea, typhoid fever (enteric fever), uncomplicated cervical and urethral gonorrhea, and inhalational anthrax (post-exposure).
Pharmacology Ciprofloxacin is a broad-spectrum antiinfective agent of the fluoroquinolone class. Ciprofloxacin has in vitro activity against a wide range of gram-negative and gram-positive microorganisms. The mechanism of action of quinolones, including ciprofloxacin, is different from that of other antimicrobial agents such as beta-lactams, macrolides, tetracyclines, or aminoglycosides; therefore, organisms resistant to these drugs may be susceptible to ciprofloxacin. There is no known cross-resistance between ciprofloxacin and other classes of antimicrobials. Notably the drug has 100 times higher affinity for bacterial DNA gyrase than for mammalian.
Toxicity The major adverse effect seen with use of is gastrointestinal irritation, common with many antibiotics.
Affected Organisms
Enteric bacteria and other eubacteria
Biotransformation Hepatic. Four metabolites have been identified in human urine which together account for approximately 15% of an oral dose. The metabolites have antimicrobial activity, but are less active than unchanged ciprofloxacin.
Absorption Rapidly and well absorbed from the gastrointestinal tract after oral administration. The absolute bioavailability is approximately 70% with no substantial loss by first pass metabolism.
Half Life 4 hours
Protein Binding 20 to 40%
Elimination Approximately 40 to 50% of an orally administered dose is excreted in the urine as unchanged drug.
Clearance * Renal cl=300 mL/min
References
Drusano GL, Standiford HC, Plaisance K, Forrest A, Leslie J, Caldwell J: Absolute oral bioavailability of ciprofloxacin. Antimicrob Agents Chemother. 1986 Sep;30(3):444-6. [Pubmed]
Hilliard JJ, Krause HM, Bernstein JI, Fernandez JA, Nguyen V, Ohemeng KA, Barrett JF: A comparison of active site binding of 4-quinolones and novel flavone gyrase inhibitors to DNA gyrase. Adv Exp Med Biol. 1995;390:59-69. [Pubmed]
Spivey JM, Cummings DM, Pierson NR: Failure of prostatitis treatment secondary to probable ciprofloxacin-sucralfate drug interaction. Pharmacotherapy. 1996 Mar-Apr;16(2):314-6. [Pubmed]
Brouwers JR: Drug interactions with quinolone antibacterials. Drug Saf. 1992 Jul-Aug;7(4):268-81. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Sigma Aldrich -  17850 external link
Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Sigma Aldrich -  33434 external link
法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC
Toronto Research Chemicals -  C482500 external link
Fluorinated quinolone antibacterial.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Hilliard JJ, Krause HM, Bernstein JI, Fernandez JA, Nguyen V, Ohemeng KA, Barrett JF: A comparison of active site binding of 4-quinolones and novel flavone gyrase inhibitors to DNA gyrase. Adv Exp Med Biol. 1995;390:59-69. Pubmed
  • Spivey JM, Cummings DM, Pierson NR: Failure of prostatitis treatment secondary to probable ciprofloxacin-sucralfate drug interaction. Pharmacotherapy. 1996 Mar-Apr;16(2):314-6. Pubmed
  • Drusano GL, Standiford HC, Plaisance K, Forrest A, Leslie J, Caldwell J: Absolute oral bioavailability of ciprofloxacin. Antimicrob Agents Chemother. 1986 Sep;30(3):444-6. Pubmed
  • Brouwers JR: Drug interactions with quinolone antibacterials. Drug Saf. 1992 Jul-Aug;7(4):268-81. Pubmed
  • Hoffken, G., et al.: Antimicrob. Ag. Chemother., 27, 375 (1985)
  • Scully, B.E., et al.: Lancet, 1, 819 (1986)
  • Ger. Pat., 1983, Bayer, 3 142 854; CA, 99, 53790h, (synth, pharmacol)
  • Chin, N.X. et al., Antimicrob. Agents Chemother., 1984, 25, 319, (pharmacol)
  • Curr. Clin. Pract. Ser., (Eds. Neu, H.C. et al), Excerpta Medica, 1986, (book)
  • Ball, P., J. Antimicrob. Chemother., Suppl. D, 1986, 18, 187, (tox)
  • Ciprofloxacin Product Information Monograph, M. Dekker, 1988, (book)
  • Campoli-Richards, D.M. et al., Drugs, 1988, 35, 373, (rev)
  • Vance-Bryan, K. et al., Clin. Pharmacokinet., 1990, 19, 434, (rev, pharmacokinet)
  • New Gener. Quinolones, 1990, (Eds. Siporin, C. et al), M. Dekker (see Infect. Dis. Ther. v5 1990), 1990, (book)
  • Textbook of Adverse Drug Reactions, 4th edn., (ed. Davies, D.M.), Oxford University Press, 1991, (tox)
  • Mehta, A.C. et al., J. Clin. Pharm. Ther., 1992, 17, 117, (hplc)
  • Friedlander, A.M. et al., J. Infect. Dis., 1993, 167, 1239-1243, (use)
  • Wiseman, L.R. et al., Drugs Aging, 1994, 4, 145, (rev)
  • Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 5748, (synonyms)
  • Davis, R. et al., Drugs, 1996, 51, 1019, (rev, pharmacol)
  • Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 185
  • Hay, A.M. et al., Synthesis, 1999, 1979-1985, (synth, uv, pmr)
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专利

专利

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