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129618-40-2 molecular structure
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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 ID: 123
Molecular Formular: C15H14N4O
Molecular Mass: 266.29786
Monoisotopic Mass: 266.11676109
SMILES and 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

Cite this record

CBID:123 http://www.chembase.cn/molecule-123.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
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 Traditional name
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
Brand Name
Viramune
Synonyms
NEV
NVP
Nevirapine
11-CYCLOPROPYL-5,11-DIHYDRO-4-METHYL-6H-DIPYRIDO[3,2-B:2',3'-E][1,4]DIAZEPIN-6-ONE
Viramune
BI-RG 587
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
CAS Number
129618-40-2
MDL Number
MFCD00866928
PubChem SID
160963586
46506789
PubChem CID
4463

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 10.371185  H Acceptors
H Donor LogD (pH = 5.5) 2.3533716 
LogD (pH = 7.4) 2.480226  Log P 2.4880428 
Molar Refractivity 77.482 cm3 Polarizability 28.112658 Å3
Polar Surface Area 58.12 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 1.75  LOG S -3.41 
Solubility (Water) 1.05e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
0.7046 mg/L expand Show data source
Chloroform expand Show data source
DMSO: ≥22 mg/mL expand Show data source
Methanol expand Show data source
Apperance
Off-white to Pale Yellow Solid expand Show data source
white to tan powder expand Show data source
Melting Point
247-249°C expand Show data source
Hydrophobicity(logP)
2.5 expand Show data source
2.65 expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
Storage Temperature
room temp expand Show data source
Mechanism of Action
Non-nucleoside reverse transcriptase inhibitor (NNRTI) expand Show data source
Purity
≥98% (HPLC) expand Show data source
95% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Application(s)
Used to treat HIV-1 infection and AIDS expand Show data source
Virucide expand Show data source
Empirical Formula (Hill Notation)
C15H14N4O expand Show data source

DETAILS

DETAILS

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.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
  • • 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)
  • •  http://en.wikipedia.org/wiki/Nevirapine
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PATENTS

PATENTS

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INTERNET

INTERNET

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