NEVIRAPINE

First approved in 1996

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H14N4O
Molecular Weight	266.2979
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=C2NC(=O)C3=CC=CN=C3N(C4CC4)C2=NC=C1

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	266.2979
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 8504	239.0 µM [EC50]
Human immunodeficiency virus 1 34 Target ID: CHEMBL378 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25240095	Inhibitor 8504	0.31 nM [EC50]
Human immunodeficiency virus type 1 reverse transcriptase 70 Target ID: CHEMBL247 Sources: http://www.drugbank.ca/drugs/DB00238	Inhibitor 8504	250.0 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
HIV-1 infection 156 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020933s022,020636s032lbl.pdf	Primary		Approved 8583	Viramune Approved Use VIRAMUNE is an NNRTI indicated for combination antiretroviral treatment of HIV-1 infection Launch Date 1995

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
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
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

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 Health Status: unhealthy Age Group: 8-days-old Sex: F 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	unhealthy, >18 years Health Status: unhealthy Age Group: >18 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/201152Orig1s000MedR.pdf	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
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	unhealthy, >18 years Health Status: unhealthy Age Group: >18 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/201152Orig1s000MedR.pdf	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
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
eMolecules	766252	https://www.emolecules.com/cgi-bin/more?vid=766252
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

PubMed

Title	Date	PubMed
Mismatched double-stranded RNA (polyI-polyC(12)U) is synergistic with multiple anti-HIV drugs and is active against drug-sensitive and drug-resistant HIV-1 in vitro.	2001-09	11448730
Antiviral drugs: current state of the art.	2001-08	11418355
Development of drug resistance in patients receiving combinations of zidovudine, didanosine and nevirapine.	2001-07-06	11426071
Hepatotoxicity in HIV-1-infected patients receiving nevirapine-containing antiretroviral therapy.	2001-07-06	11426070
The steady-state pharmacokinetics of efavirenz and nevirapine when used in combination in human immunodeficiency virus type 1-infected persons.	2001-07-01	11398107
Sequence-specific detection of individual DNA strands using engineered nanopores.	2001-07	11433274
Distribution of K103N and/or Y181C HIV-1 mutations by exposure to zidovudine and non-nucleoside reverse transcriptase inhibitors.	2001-07	11418520
South Africa in crisis on HIV/AIDS treatment.	2001-06-29	11441877
Phenotypic hypersusceptibility to non-nucleoside reverse transcriptase inhibitors in treatment-experienced HIV-infected patients: impact on virological response to efavirenz-based therapy.	2001-06-15	11416714
High exposure to nevirapine in plasma is associated with an improved virological response in HIV-1-infected individuals.	2001-06-15	11416710
Analysis of human immunodeficiency virus type 1 drug resistance in children receiving nucleoside analogue reverse-transcriptase inhibitors plus nevirapine, nelfinavir, or ritonavir (Pediatric AIDS Clinical Trials Group 377).	2001-06-15	11372025
2-Amino-6-arylsulfonylbenzonitriles as non-nucleoside reverse transcriptase inhibitors of HIV-1.	2001-06-07	11384233
The effect of nevirapine in combination with nelfinavir in heavily pretreated HIV-1-infected patients: a prospective, open-label, controlled, randomized study.	2001-06-01	11404533
Limits of deep salvage antiretroviral therapy with nelfinavir plus either efavirenz or nevirapine, in highly pre-treated patients with HIV disease.	2001-06	11397623
Severe lactic acidosis and thiamine administration in an HIV-infected patient on HAART.	2001-06	11368826
Saliva as an alternative body fluid for therapeutic drug monitoring of the nonnucleoside reverse transcription inhibitor nevirapine.	2001-06	11360034
New developments in anti-HIV chemotherapy.	2001-05-12	11347962
HIV in body fluids during primary HIV infection: implications for pathogenesis, treatment and public health.	2001-05-04	11399956
An in vivo model for HIV resistance development.	2001-05-01	11375059
Jaundice and hepatocellular damage associated with nevirapine therapy.	2001-05	11374701
High prevalence of genotypic and phenotypic HIV-1 drug-resistant strains among patients receiving antiretroviral therapy in Abidjan, Côte d'Ivoire.	2001-04-15	11391173
Long-term follow-up of antiretroviral-naive HIV-positive patients treated with nevirapine.	2001-04-15	11391166
Long-term safety and efficacy of nevirapine, stavudine and lamivudine in a real-world setting.	2001-04-13	11371699
Determination of serum levels of thirteen human immunodeficiency virus-suppressing drugs by high-performance liquid chromatography.	2001-04-13	11355843
[Highly active antiretroviral therapy with nevirapine. Therapy compliance determines success].	2001-04-02	11373787
[Results of the AIDS-In-Europe Study. Non-nucleoside reverse transcriptase inhibitor does not equal non-nucleoside reverse transcriptase inhibitor].	2001-04-02	11373776
Resolution of chronic parvovirus b19-induced anemia, by use of highly active antiretroviral therapy, in a patient with acquired immunodeficiency syndrome.	2001-04-01	11264051
Rwanda to receive cheaper anti-HIV drugs for chronic treatment and free viramune to prevent viral transmission from mother to child.	2001-04	11436238
Amino acid deletion at codon 67 and Thr-to-Gly change at codon 69 of human immunodeficiency virus type 1 reverse transcriptase confer novel drug resistance profiles.	2001-04	11264389
Inhibitors of human immunodeficiency virus type 1 reverse transcriptase target distinct phases of early reverse transcription.	2001-04	11238836
[Cutaneous adverse events related to simultaneous nevirapine treatment and pneumococcal vaccination in HIV-infected patients].	2001-03-31	11333714
Sequencing antiretroviral drugs.	2001-03-30	11316990
From the Centers for Disease Control and Prevention. Serious adverse events attributed to nevirapine regimens for postexposure prophylaxis after HIV exposures--worldwide, 1997-2000.	2001-03-27	11263401
Efficiency comparisons of rank and permutation tests based on summary statistics computed from repeated measures data.	2001-03-15	11241572
Prophylaxis with a nevirapine-containing triple regimen after exposure to HIV-1.	2001-03-03	11247556
International perspectives on antiretroviral resistance. Nonnucleoside reverse transcriptase inhibitor resistance.	2001-03-01	11264999
[Nevirapine and clinical withdrawal syndrome].	2001-03	11387833
Pharmacokinetics of ritonavir and nevirapine in peritoneal dialysis.	2001-03	11239054
Anti-HIV activity of aromatic and heterocyclic thiazolyl thiourea compounds.	2001-02-26	11229762
Simple and rapid determination of nevirapine in human serum by reversed-phase high-performance liquid chromatography.	2001-02-25	11236094
Drug interaction between St John's wort and nevirapine.	2001-02-16	11273226
Indian company offers cheap anti-AIDS drugs.	2001-02-15	11236967
Galactorrhoea, hyperprolactinaemia, and protease inhibitors.	2001-02-10	11273090
South Africa's AIDS activists say new neviripine programme is not enough.	2001-02-10	11273077
South Africa cuts agreement for one AIDS drug but ignores another.	2001-02	11302027
Revised nevirapine insert.	2001-02	11224936
Further views by the Erice working group on mother-to-child transmission of HIV type 1.	2001-01	11227325
Inhibition of human cytochrome P450 isoforms by nonnucleoside reverse transcriptase inhibitors.	2001-01	11225565
A single amino acid change at Leu-188 in the reverse transcriptase of HIV-2 and SIV renders them sensitive to non-nucleoside reverse transcriptase inhibitors.	2001	11402860
The emerging roles of non-nucleoside reverse transcriptase inhibitors in antiretroviral therapy.	2001	11217868

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 `Mon Mar 31 17:59:54 GMT 2025` Edited by `admin` on `Mon Mar 31 17:59:54 GMT 2025`
Record UNII	99DK7FVK1H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NEVIRAPINE

Official Name

English

NEVIRAPINE, ANHYDROUS

Preferred Name

English

NEVIRAPINE ANHYDROUS [USP-RS]

Common Name

English

VIRAMUNE

Brand Name

English

NEVIRAPINE [MI]

Common Name

English

NEVIRAPINE [EP MONOGRAPH]

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 [WHO-DD]

Common Name

English

NEVIRAPINE ANHYDROUS [WHO-IP]

Common Name

English

BIRG-0587

Code

English

NEVIRAPINE [EMA EPAR]

Common Name

English

NEVIRAPINE [VANDF]

Common Name

English

NEVIRAPINE [USP IMPURITY]

Common Name

English

BIRG0587

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 [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)