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129618-40-2 分子结构
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2-cyclopropyl-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-10-one

ChemBase编号:123
分子式:C15H14N4O
平均质量:266.29786
单一同位素质量:266.11676109
SMILES和InChIs

SMILES:
O=c1[nH]c2c(n(C3CC3)c3ncccc13)nccc2C
Canonical SMILES:
Cc1ccnc2c1[nH]c(=O)c1c(n2C2CC2)nccc1
InChI:
InChI=1S/C15H14N4O/c1-9-6-8-17-14-12(9)18-15(20)11-3-2-7-16-13(11)19(14)10-4-5-10/h2-3,6-8,10H,4-5H2,1H3,(H,18,20)
InChIKey:
NQDJXKOVJZTUJA-UHFFFAOYSA-N

引用这个纪录

CBID:123 http://www.chembase.cn/molecule-123.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
2-cyclopropyl-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-10-one
2-cyclopropyl-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-one
2-cyclopropyl-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-one
2-cyclopropyl-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,11,13-hexaen-10-one
IUPAC传统名
nevirapine
@nevirapine
2-cyclopropyl-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-one
商标名
Viramune
别名
NEV
NVP
Nevirapine
11-CYCLOPROPYL-5,11-DIHYDRO-4-METHYL-6H-DIPYRIDO[3,2-B:2',3'-E][1,4]DIAZEPIN-6-ONE
11-cyclopropyl-4-methyl-5H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6(11H)-one
11-Cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido[3,2-b:2′,3′-e][1,4]diazepin-6-one
Nevirapine
11-Cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido[3,2-b:2’,3’-e][1,4]diazepin-6-one
2-cyclopropyl-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-10-one
NSC 641530
Nevarapine
Viramune
BI-RG 587
CAS号
129618-40-2
MDL号
MFCD00866928
PubChem SID
46506789
160963586
PubChem CID
4463

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 10.371185  质子受体
质子供体 LogD (pH = 5.5) 2.3533716 
LogD (pH = 7.4) 2.480226  Log P 2.4880428 
摩尔折射率 77.482 cm3 极化性 28.112658 Å3
极化表面积 58.12 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P 1.75  LOG S -3.41 
溶解度 1.05e-01 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
0.7046 mg/L expand 查看数据来源
Chloroform expand 查看数据来源
DMSO: ≥22 mg/mL expand 查看数据来源
Methanol expand 查看数据来源
外观
Off-white to Pale Yellow Solid expand 查看数据来源
white to tan powder expand 查看数据来源
熔点
247-249°C expand 查看数据来源
疏水性(logP)
2.5 expand 查看数据来源
2.65 expand 查看数据来源
保存条件
-20°C expand 查看数据来源
-20°C Freezer 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
德国WGK号
2 expand 查看数据来源
保存温度
room temp expand 查看数据来源
生物活性机理
Non-nucleoside reverse transcriptase inhibitor (NNRTI) expand 查看数据来源
纯度
≥98% (HPLC) expand 查看数据来源
95% 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
应用领域
Used to treat HIV-1 infection and AIDS expand 查看数据来源
Virucide expand 查看数据来源
Empirical Formula (Hill Notation)
C15H14N4O expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank -  DB00238 external link
Item Information
Drug Groups approved
Description A potent, non-nucleoside reverse transcriptase inhibitor used in combination with nucleoside analogues for treatment of HIV infection and AIDS. [PubChem]
Indication For use in combination with other antiretroviral drugs in the ongoing treatment of HIV-1 infection.
Pharmacology Nevirapine is a non-nucleoside reverse transcriptase inhibitor (nNRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). HIV-2 RT and eukaryotic DNA polymerases (such as human DNA polymerases alpha, beta, or sigma) are not inhibited by nevirapine. Nevirapine is, in general, only prescribed after the immune system has declined and infections have become evident. It is always taken with at least one other HIV medication such as Retrovir or Videx. The virus can develop resistance to nevirapine if the drug is taken alone, although even if used properly, nevirapine is effective for only a limited time.
Toxicity Symptoms of overdose include edema, erythema nodosum, fatigue, fever, headache, insomnia, nausea, pulmonaryinfiltrates, rash, vertigo, vomiting, and weight decrease.
Affected Organisms
Human Immunodeficiency Virus
Biotransformation Hepatic. In vivo studies in humans and in vitro studies with human liver microsomes have shown that nevirapine is extensively biotransformed via cytochrome P450 3A4 metabolism to several hydroxylated metabolites.
Absorption 90% (absolute bioavailability 93 ± 9%)
Half Life 45 hours
Protein Binding 60%
Elimination Thus cytochrome P450 metabolism, glucuronide conjugation, and urinary excretion of glucuronidated metabolites represent the primary route of nevirapine biotransformation and elimination in humans. Only a small fraction (<5%) of the radioactivity in urine (representing <3% of the total dose) was made up of parent compound; therefore, renal excretion plays a minor role in elimination of the parent compound.
Distribution * 1.21 ± 0.09 L/kg
External Links
Wikipedia
RxList
Drugs.com
DrugBank -  DB08311 external link
Drug information: experimental
Selleck Chemicals -  S1742 external link
Research Area: Infection
Biological Activity:
Nevirapine(Viramune) is a non-nucleoside reverse transcriptase inhibitor (NNRTI) used to treat HIV-1 infection and AIDS.[1] Nevirapine is not effective against HIV-2, as the pocket of the HIV-2 reverse transcriptase has a different structure, which confers intrinsic resistance to the NNRTI class. [1]
Sigma Aldrich -  SML0097 external link
Biochem/physiol Actions
Nevirapine is an allosteric, non-nucleoside inhibitor of HIV reverse transcriptase (NNRTI). The Ki for inhibition of wild-type RT by Nevirapine is 200 nM.
Toronto Research Chemicals -  N391275 external link
A potent (IC50=84nM) and selective non-nucleoside inhibitor of HIV-1 reverse transcriptase. Antiviral.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • http://en.wikipedia.org/wiki/Nevirapine
  • Hargrave, K.D., et al.: J. Med. Chem., 34, 2231 (1991)
  • Cheeseman, S.H., et al.: Antimicrob. Agents Chemother., 37, 178 (1991)
  • Guay, L.A., et al.: Lancet, 354, 795 (1991)
  • Merluzzi, V.J. et al., Science (Washington, D.C.), 1990, 250, 1411, (pharmacol)
  • Eur. Pat., 1991, Boehringer Ingelheim, 429 987; CA, 115, 114559n, (synth, pharmacol)
  • Cohen, K.A. et al., J. Biol. Chem., 1991, 266, 14670, (pharmacol)
  • Koup, R.A. et al., J. Infect. Dis., 1991, 163, 966, (pharmacol)
  • Hargrave, K.D. et al., J. Med. Chem., 1991, 34, 2231, (synth, pharmacol)
  • Grob, P.M. et al., AIDS Res. Hum. Retroviruses, 1992, 8, 145, (pharmacol, rev)
  • Merluzzi, V.J. et al., Adv. Exp. Med. Biol., 1992, 312, 89, (rev)
  • Mui, P.W. et al., J. Med. Chem., 1992, 35, 201, (cryst struct)
  • Skoog, M.T. et al., Med. Res. Rev., 1992, 12, 27, (rev)
  • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1393
  • Grozinger, K.G. et al., J. Het. Chem., 1995, 32, 259, (synth)
  • Pedersen, O.S. et al., Synthesis, 2000, 479-495, (rev)
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专利

专利

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