NEVIRAPINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H14N4O
Molecular Weight	266.2984
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cc1ccnc2c1N=C(c3cccnc3N2C4CC4)O

InChI

InChIKey=NQDJXKOVJZTUJA-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Molecular Formula	C15H14N4O
Molecular Weight	266.2984
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.drugbank.ca/drugs/DB00238
Curator's Comment:: Description was created based on several sources, including https://www.drugs.com/pro/nevirapine.html

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. Nevirapine binds directly to reverse transcriptase (RT) and blocks the RNA-dependent and DNA-dependent DNA polymerase activities by causing a disruption of the enzyme's catalytic site. The activity of nevirapine does not compete with template or nucleoside triphosphates. Nevirapine is used for use in combination with other antiretroviral drugs in the ongoing treatment of HIV-1 infection.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
BXPC-3 2 Target ID: CHEMBL614530 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26086472	Inhibitor 7728	239.0 µM [EC50]
Human immunodeficiency virus 1 32 Target ID: CHEMBL378 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25240095	Inhibitor 7728	0.31 nM [EC50]
Human immunodeficiency virus type 1 reverse transcriptase 45 Target ID: CHEMBL247 Sources: http://www.drugbank.ca/drugs/DB00238	Inhibitor 7728	250.0 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
HIV-1 infection 140 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020933s022,020636s032lbl.pdf	Primary		Approved 8043	Viramune Approved Use VIRAMUNE is an NNRTI indicated for combination antiretroviral treatment of HIV-1 infection Launch Date 8.2036798E11

C_max

Value	Dose	Co-administered	Analyte	Population
2060 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/201152s013lbl.pdf	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:		NEVIRAPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
82000 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/201152s013lbl.pdf	400 mg 1 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	NEVIRAPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
96700 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/201152s013lbl.pdf	400 mg 1 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	NEVIRAPINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED
161000 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/201152s013lbl.pdf	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	NEVIRAPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
45 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/201152s013lbl.pdf	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:		NEVIRAPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
40% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/201152s013lbl.pdf	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:		NEVIRAPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
200 mg single, oral Overdose Dose: 200 mg Route: oral Route: single Dose: 200 mg Sources: https://pubmed.ncbi.nlm.nih.gov/17605042	unhealthy, 8-days-old n = 1 Health Status: unhealthy Age Group: 8-days-old Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/17605042	Other AEs: Neutropenia, Hyperlactatemia... Other AEs: Neutropenia (mild) Hyperlactatemia Sources: https://pubmed.ncbi.nlm.nih.gov/17605042
200 mg 2 times / day steady, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: steady Dose: 200 mg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/201152Orig1s000MedR.pdf Page: p. 56	unhealthy, >18 years n = 506 Health Status: unhealthy Age Group: >18 years Sex: M+F Population Size: 506 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/201152Orig1s000MedR.pdf Page: p. 56	Disc. AE: Rash, Stevens-Johnson syndrome... AEs leading to discontinuation/dose reduction: Rash (2%) Stevens-Johnson syndrome (1%) Transaminases increased (1%) ALT increased (1%) GGT increased (<1%) AST increased (<1%) Hepatic enzyme increased (<1%) Hepatitis (1%) Hepatotoxicity (1%) Hepatitis acute (<1%) Hepatitis toxic (<1%) Nausea (1%) Malaise (1%) Pyrexia (1%) Fatigue (1%) Vascular disorders (<1%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/201152Orig1s000MedR.pdf Page: p. 56
400 mg 1 times / day steady, oral Recommended Dose: 400 mg, 1 times / day Route: oral Route: steady Dose: 400 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/201152Orig1s000MedR.pdf Page: p. 56	unhealthy, >18 years n = 505 Health Status: unhealthy Age Group: >18 years Sex: M+F Population Size: 505 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/201152Orig1s000MedR.pdf Page: p. 56	Disc. AE: Rash, Drug rash with eosinophilia and systemic symptoms... AEs leading to discontinuation/dose reduction: Rash (2%) Drug rash with eosinophilia and systemic symptoms (<1%) Transaminases increased (1%) ALT increased (<1%) GGT increased (<1%) AST increased (<1%) Hepatic enzyme increased (<1%) Hepatitis (1%) Hepatotoxicity (<1%) Hepatitis acute (<1%) Hepatitis toxic (<1%) Nausea (<1%) Malaise (<1%) Pyrexia (<1%) Fatigue (<1%) Vascular disorders (<1%) Musculoskeletal and connective tissue disorders (<1%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/201152Orig1s000MedR.pdf Page: p. 56
800 mg 1 times / day multiple, oral Overdose Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020636s050,020933s040lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020636s050,020933s040lbl.pdf	Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020636s050,020933s040lbl.pdf
200 mg 1 times / day steady, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: steady Dose: 200 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020636s050,020933s040lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020636s050,020933s040lbl.pdf	Disc. AE: Hepatotoxicity, Reaction skin... AEs leading to discontinuation/dose reduction: Hepatotoxicity (grade 5) Reaction skin (severe) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020636s050,020933s040lbl.pdf

AEs

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:63613	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:63613
ChemicalBook	CB9743074	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9743074
MolPort	MolPort-002-507-817	https://www.molport.com/shop/molecule-link/MolPort-002-507-817
MolPort	MolPort-046-594-170	https://www.molport.com/shop/molecule-link/MolPort-046-594-170
Selleck Chemicals	Nevirapine(Viramune)	http://www.selleckchem.com/products/Nevirapine(Viramune).html
ZINC	ZINC000000004778	http://zinc15.docking.org/substances/ZINC000000004778
eMolecules	766252	https://www.emolecules.com/cgi-bin/more?vid=766252

PubMed

Title	Date	PubMed
A novel genotype encoding a single amino acid insertion and five other substitutions between residues 64 and 74 of the HIV-1 reverse transcriptase confers high-level cross-resistance to nucleoside reverse transcriptase inhibitors. Abacavir CNA2007 International Study Group.	1999 Oct 1	10843527
Didanosine-induced hepatitis.	2000 Aug	10950090
Prevalence and characteristics of multinucleoside-resistant human immunodeficiency virus type 1 among European patients receiving combinations of nucleoside analogues.	2000 Aug	10898683
Increasing cerebrospinal fluid chemokine concentrations despite undetectable cerebrospinal fluid HIV RNA in HIV-1-infected patients receiving antiretroviral therapy.	2000 Dec 15	11141242
Drug resistance and drug combination features of the human immunodeficiency virus inhibitor, BCH-10652 [(+/-)-2'-deoxy-3'-oxa-4'-thiocytidine, dOTC].	2000 Jul	10950391
Presence of 2',5'-Bis-O-(tert-butyldimethylsilyl)-3'-spiro-5"-(4"-amino-1",2"-oxath iole-2",2"-dioxide) (TSAO)-resistant virus strains in TSAO-inexperienced HIV patients.	2000 Jun 10	10875608
Non-nucleoside HIV-1 reverse transcriptase inhibitors: synthesis and biological evaluation of novel quinoxalinylethylpyridylthioureas as potent antiviral agents.	2000 Mar	10819438
Inhibition of clinically relevant mutant variants of HIV-1 by quinazolinone non-nucleoside reverse transcriptase inhibitors.	2000 May 18	10821714
Synthesis and antiviral activity of 4-benzyl pyridinone derivatives as potent and selective non-nucleoside human immunodeficiency virus type 1 reverse transcriptase inhibitors.	2000 Oct 19	11052800
Piperidinylethyl, phenoxyethyl and fluoroethyl bromopyridyl thiourea compounds with potent anti-HIV activity.	2000 Sep	11142631
Computer-assisted design, synthesis and biological evaluation of novel pyrrolyl heteroaryl sulfones targeted at HIV-1 reverse transcriptase as non-nucleoside inhibitors.	2000 Sep	11026542
The tolerability of efavirenz after nevirapine-related adverse events.	2000 Sep	11017835
Stereochemistry of halopyridyl and thiazolyl thiourea compounds is a major determinant of their potency as nonnucleoside inhibitors of HIV-1 reverse transcriptase.	2000 Sep 18	10999473
The emerging roles of non-nucleoside reverse transcriptase inhibitors in antiretroviral therapy.	2001	11217868
Rwanda to receive cheaper anti-HIV drugs for chronic treatment and free viramune to prevent viral transmission from mother to child.	2001 Apr	11436238
Long-term safety and efficacy of nevirapine, stavudine and lamivudine in a real-world setting.	2001 Apr 13	11371699
High prevalence of genotypic and phenotypic HIV-1 drug-resistant strains among patients receiving antiretroviral therapy in Abidjan, Côte d'Ivoire.	2001 Apr 15	11391173
Long-term follow-up of antiretroviral-naive HIV-positive patients treated with nevirapine.	2001 Apr 15	11391166
Revised nevirapine insert.	2001 Feb	11224936
Stevens-Johnson syndrome caused by the antiretroviral drug nevirapine.	2001 Feb	11174414
Ritonavir, efavirenz, and nelfinavir inhibit CYP2B6 activity in vitro: potential drug interactions with bupropion.	2001 Feb	11159797
SJ-3366, a unique and highly potent nonnucleoside reverse transcriptase inhibitor of human immunodeficiency virus type 1 (HIV-1) that also inhibits HIV-2.	2001 Feb	11158731
Galactorrhoea, hyperprolactinaemia, and protease inhibitors.	2001 Feb 10	11273090
South Africa's AIDS activists say new neviripine programme is not enough.	2001 Feb 10	11273077
Indian company offers cheap anti-AIDS drugs.	2001 Feb 15	11236967
Drug interaction between St John's wort and nevirapine.	2001 Feb 16	11273226
Nevirapine and postexposure prophylaxis for human immunodeficiency virus.	2001 Feb 21	11180728
Anti-HIV activity of aromatic and heterocyclic thiazolyl thiourea compounds.	2001 Feb 26	11229762
Further views by the Erice working group on mother-to-child transmission of HIV type 1.	2001 Jan	11227325
Inhibition of human cytochrome P450 isoforms by nonnucleoside reverse transcriptase inhibitors.	2001 Jan	11225565
Pharmacokinetic of nevirapine in haemodialysis.	2001 Jan	11209031
Ritonavir-induced carbamazepine toxicity.	2001 Jan	11197575
Sex differences in nevirapine rash.	2001 Jan	11118391
Estimation of binding affinities for HEPT and nevirapine analogues with HIV-1 reverse transcriptase via Monte Carlo simulations.	2001 Jan 18	11170624
Efficacy, tolerance, and pharmacokinetics of the combination of stavudine, nevirapine, nelfinavir, and saquinavir as salvage regimen after ritonavir or indinavir failure.	2001 Jan 20	11177388
Nevirapine should not be prescribed for needlestick injuries.	2001 Jan 20	11159560
From the Centers for Disease Control and Prevention. Serious adverse events attributed to nevirapine regimens for postexposure prophylaxis after HIV exposures--worldwide, 1997-2000.	2001 Jan 24-31	11263401
Need for increased dose of warfarin in HIV patients taking nevirapine.	2001 Jan 26	11216940
Sequence-specific detection of individual DNA strands using engineered nanopores.	2001 Jul	11433274
Distribution of K103N and/or Y181C HIV-1 mutations by exposure to zidovudine and non-nucleoside reverse transcriptase inhibitors.	2001 Jul	11418520
The steady-state pharmacokinetics of efavirenz and nevirapine when used in combination in human immunodeficiency virus type 1-infected persons.	2001 Jul 1	11398107
Limits of deep salvage antiretroviral therapy with nelfinavir plus either efavirenz or nevirapine, in highly pre-treated patients with HIV disease.	2001 Jun	11397623
Phenotypic hypersusceptibility to non-nucleoside reverse transcriptase inhibitors in treatment-experienced HIV-infected patients: impact on virological response to efavirenz-based therapy.	2001 Jun 15	11416714
South Africa in crisis on HIV/AIDS treatment.	2001 Jun 29	11441877
[Nevirapine and clinical withdrawal syndrome].	2001 Mar	11387833
Pharmacokinetics of ritonavir and nevirapine in peritoneal dialysis.	2001 Mar	11239054
International perspectives on antiretroviral resistance. Nonnucleoside reverse transcriptase inhibitor resistance.	2001 Mar 1	11264999
Indinavir, nevirapine, stavudine, and lamivudine for human immunodeficiency virus-infected, amprenavir-experienced subjects: AIDS Clinical Trials Group protocol 373.	2001 Mar 1	11181147
Efficiency comparisons of rank and permutation tests based on summary statistics computed from repeated measures data.	2001 Mar 15	11241572
Prophylaxis with a nevirapine-containing triple regimen after exposure to HIV-1.	2001 Mar 3	11247556

Patents

Sample Use Guides

In Vivo Use Guide

The recommended dose for Nevirapine is one 200 mg tablet daily for the first 14 days, followed by one 200 mg tablet twice daily, in combination with other antiretroviral agents.

Route of Administration: Oral

In Vitro Use Guide

The IC50 value for inhibition by nevirapine against immunodeficiency virus type 1 (HIV) nucleoside reverse transcriptase (RT) in removal assay was 3 uM

Substance Class	Chemical Created by `admin` on `Fri Jun 25 20:56:11 UTC 2021` Edited by `admin` on `Fri Jun 25 20:56:11 UTC 2021`
Record UNII	99DK7FVK1H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NEVIRAPINE

Official Name

English

NEVIRAPINE ANHYDROUS [USP-RS]

Common Name

English

VIRAMUNE

Brand Name

English

NEVIRAPINE [MI]

Common Name

English

NEVIRAPINE, ANHYDROUS [EP]

Common Name

English

NEVIRAPINE [EP MONOGRAPH]

Common Name

English

NEVIRAPINE [USP]

Common Name

English

NEVIRAPINE TEVA

Brand Name

English

NEVIRAPINUM ANHYDROUS [WHO-IP LATIN]

Common Name

English

NSC-641530

Code

English

NEVIRAPINE [MART.]

Common Name

English

NEVIRAPINE [INN]

Common Name

English

NEVIRAPINE ANHYDROUS [WHO-IP]

Common Name

English

NEVIRAPINE, ANHYDROUS

Common Name

English

BIRG-0587

Code

English

NEVIRAPINE [EMA EPAR]

Common Name

English

NEVIRAPINE [VANDF]

Common Name

English

BIRG 0587

Code

English

NEVIRAPINE [JAN]

Common Name

English

11-CYCLOPROPYL-5,11-DIHYDRO-4-METHYL-6H-DIPYRIDO(3,2-B:2',3'-E)(1,4)DIAZEPIN-6-ONE

Systematic Name

English

NEVIRAPINE [USP MONOGRAPH]

Common Name

English

6H-DIPYRIDO(3,2-B:2',3'-E)(1,4)DIAZEPIN-6-ONE, 11-CYCLOPROPYL-5,11-DIHYDRO-4-METHYL-

Systematic Name

English

NEVIRAPINE [WHO-DD]

Common Name

English

NEVIRAPINE [HSDB]

Common Name

English

NEVIRAPINE [USAN]

Common Name

English

NEVIRAPINE [ORANGE BOOK]

Common Name

English

Classification Tree Code System Code

EMA ASSESSMENT REPORTS

NEVIRAPINE TEVA (AUTHORIZED: HIV INFECTIONS)