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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 of NEVIRAPINE

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
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

Curator's Comment: Nevirapine (NVP) crosses well the BBB

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL614530
239.0 µM [EC50]
0.31 nM [EC50]
250.0 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Viramune

Approved Use

VIRAMUNE is an NNRTI indicated for combination antiretroviral treatment of HIV-1 infection

Launch Date

1995
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2060 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
161000 ng × h/mL
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
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
45 h
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
40%
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

Doses

DosePopulationAdverse events​
200 mg single, oral
Overdose
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
unhealthy, 8-days-old
Health Status: unhealthy
Age Group: 8-days-old
Sex: F
Sources:
Other AEs: Neutropenia, Hyperlactatemia...
Other AEs:
Neutropenia (mild)
Hyperlactatemia
Sources:
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:
unhealthy, >18 years
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Sources:
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:
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:
unhealthy, >18 years
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Sources:
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:
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:
unhealthy, adult
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:
unhealthy, adult
Disc. AE: Hepatotoxicity, Reaction skin...
AEs leading to
discontinuation/dose reduction:
Hepatotoxicity (grade 5)
Reaction skin (severe)
Sources:
AEs

AEs

AESignificanceDosePopulation
Hyperlactatemia
200 mg single, oral
Overdose
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
unhealthy, 8-days-old
Health Status: unhealthy
Age Group: 8-days-old
Sex: F
Sources:
Neutropenia mild
200 mg single, oral
Overdose
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
unhealthy, 8-days-old
Health Status: unhealthy
Age Group: 8-days-old
Sex: F
Sources:
ALT increased 1%
Disc. AE
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:
unhealthy, >18 years
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Sources:
Fatigue 1%
Disc. AE
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:
unhealthy, >18 years
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Sources:
Hepatitis 1%
Disc. AE
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:
unhealthy, >18 years
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Sources:
Hepatotoxicity 1%
Disc. AE
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:
unhealthy, >18 years
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Sources:
Malaise 1%
Disc. AE
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:
unhealthy, >18 years
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Sources:
Nausea 1%
Disc. AE
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:
unhealthy, >18 years
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Sources:
Pyrexia 1%
Disc. AE
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:
unhealthy, >18 years
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Sources:
Stevens-Johnson syndrome 1%
Disc. AE
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:
unhealthy, >18 years
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Sources:
Transaminases increased 1%
Disc. AE
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:
unhealthy, >18 years
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Sources:
Rash 2%
Disc. AE
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:
unhealthy, >18 years
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Sources:
AST increased <1%
Disc. AE
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:
unhealthy, >18 years
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Sources:
GGT increased <1%
Disc. AE
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:
unhealthy, >18 years
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Sources:
Hepatic enzyme increased <1%
Disc. AE
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:
unhealthy, >18 years
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Sources:
Hepatitis acute <1%
Disc. AE
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:
unhealthy, >18 years
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Sources:
Hepatitis toxic <1%
Disc. AE
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:
unhealthy, >18 years
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Sources:
Vascular disorders <1%
Disc. AE
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:
unhealthy, >18 years
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Sources:
Hepatitis 1%
Disc. AE
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:
unhealthy, >18 years
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Sources:
Transaminases increased 1%
Disc. AE
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:
unhealthy, >18 years
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Sources:
Rash 2%
Disc. AE
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:
unhealthy, >18 years
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Sources:
ALT increased <1%
Disc. AE
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:
unhealthy, >18 years
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Sources:
AST increased <1%
Disc. AE
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:
unhealthy, >18 years
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Sources:
Drug rash with eosinophilia and systemic symptoms <1%
Disc. AE
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:
unhealthy, >18 years
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Sources:
Fatigue <1%
Disc. AE
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:
unhealthy, >18 years
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Sources:
GGT increased <1%
Disc. AE
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:
unhealthy, >18 years
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Sources:
Hepatic enzyme increased <1%
Disc. AE
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:
unhealthy, >18 years
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Sources:
Hepatitis acute <1%
Disc. AE
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:
unhealthy, >18 years
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Sources:
Hepatitis toxic <1%
Disc. AE
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:
unhealthy, >18 years
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Sources:
Hepatotoxicity <1%
Disc. AE
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:
unhealthy, >18 years
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Sources:
Malaise <1%
Disc. AE
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:
unhealthy, >18 years
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Sources:
Musculoskeletal and connective tissue disorders <1%
Disc. AE
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:
unhealthy, >18 years
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Sources:
Nausea <1%
Disc. AE
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:
unhealthy, >18 years
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Sources:
Pyrexia <1%
Disc. AE
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:
unhealthy, >18 years
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Sources:
Vascular disorders <1%
Disc. AE
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:
unhealthy, >18 years
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Sources:
Hepatotoxicity grade 5
Disc. AE
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:
unhealthy, adult
Reaction skin severe
Disc. AE
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:
unhealthy, adult
PubMed

PubMed

TitleDatePubMed
Activity of non-nucleoside reverse transcriptase inhibitors against HIV-2 and SIV.
1999 Aug 20
Synthesis and anti-HIV activity of 1,1,3-trioxo-2H,4H-thieno[3,4-e][1,2,4]thiadiazines (TTDs): a new family of HIV-1 specific non-nucleoside reverse transcriptase inhibitors.
1999 Dec
Expanded-spectrum nonnucleoside reverse transcriptase inhibitors inhibit clinically relevant mutant variants of human immunodeficiency virus type 1.
1999 Dec
N'-[2-(2-thiophene)ethyl]-N'-[2-(5-bromopyridyl)] thiourea as a potent inhibitor of NNI-resistant and multidrug-resistant human immunodeficiency virus-1.
1999 Dec 20
5-Alkyl-2-(alkylthio)-6-(2,6-dihalophenylmethyl)-3, 4-dihydropyrimidin-4(3H)-ones: novel potent and selective dihydro-alkoxy-benzyl-oxopyrimidine derivatives.
1999 Feb 25
N-[2-(1-cyclohexenyl)ethyl]-N'-[2-(5-bromopyridyl)]-thiourea and N'-[2-(1-cyclohexenyl)ethyl]-N'-[2-(5-chloropyridyl)]-thiourea as potent inhibitors of multidrug-resistant human immunodeficiency virus-1.
1999 Sep 20
Prevalence and characteristics of multinucleoside-resistant human immunodeficiency virus type 1 among European patients receiving combinations of nucleoside analogues.
2000 Aug
Human immunodeficiency virus type 1 reverse transcriptase dimer destabilization by 1-[Spiro[4"-amino-2",2" -dioxo-1",2" -oxathiole-5",3'-[2', 5'-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]]]-3-ethylthy mine.
2000 Feb 15
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
Structure-based design, synthesis, and biological evaluation of novel pyrrolyl aryl sulfones: HIV-1 non-nucleoside reverse transcriptase inhibitors active at nanomolar concentrations.
2000 May 4
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
The emerging roles of non-nucleoside reverse transcriptase inhibitors in antiretroviral therapy.
2001
Rwanda to receive cheaper anti-HIV drugs for chronic treatment and free viramune to prevent viral transmission from mother to child.
2001 Apr
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 Apr
Inhibitors of human immunodeficiency virus type 1 reverse transcriptase target distinct phases of early reverse transcription.
2001 Apr
Resolution of chronic parvovirus b19-induced anemia, by use of highly active antiretroviral therapy, in a patient with acquired immunodeficiency syndrome.
2001 Apr 1
Revised nevirapine insert.
2001 Feb
Indian company offers cheap anti-AIDS drugs.
2001 Feb 15
Nevirapine and postexposure prophylaxis for human immunodeficiency virus.
2001 Feb 21
Prevention of nevirapine-associated rash.
2001 Feb 3
Inhibition of human cytochrome P450 isoforms by nonnucleoside reverse transcriptase inhibitors.
2001 Jan
Pharmacokinetic of nevirapine in haemodialysis.
2001 Jan
Ritonavir-induced carbamazepine toxicity.
2001 Jan
Need for increased dose of warfarin in HIV patients taking nevirapine.
2001 Jan 26
Serious adverse events attributed to nevirapine regimens for postexposure prophylaxis after HIV exposures--worldwide, 1997-2000.
2001 Jan 5
Sequence-specific detection of individual DNA strands using engineered nanopores.
2001 Jul
Distribution of K103N and/or Y181C HIV-1 mutations by exposure to zidovudine and non-nucleoside reverse transcriptase inhibitors.
2001 Jul
Development of drug resistance in patients receiving combinations of zidovudine, didanosine and nevirapine.
2001 Jul 6
Severe lactic acidosis and thiamine administration in an HIV-infected patient on HAART.
2001 Jun
Saliva as an alternative body fluid for therapeutic drug monitoring of the nonnucleoside reverse transcription inhibitor nevirapine.
2001 Jun
The effect of nevirapine in combination with nelfinavir in heavily pretreated HIV-1-infected patients: a prospective, open-label, controlled, randomized study.
2001 Jun 1
South Africa in crisis on HIV/AIDS treatment.
2001 Jun 29
Indinavir, nevirapine, stavudine, and lamivudine for human immunodeficiency virus-infected, amprenavir-experienced subjects: AIDS Clinical Trials Group protocol 373.
2001 Mar 1
Sequencing antiretroviral drugs.
2001 Mar 30
[Cutaneous adverse events related to simultaneous nevirapine treatment and pneumococcal vaccination in HIV-infected patients].
2001 Mar 31
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 Sep
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
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
  • Download
Name Type Language
NEVIRAPINE
EMA EPAR   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   VANDF   WHO-DD  
INN   USAN  
Official Name English
NEVIRAPINE, ANHYDROUS
EP  
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)
Created by admin on Mon Mar 31 17:59:54 GMT 2025 , Edited by admin on Mon Mar 31 17:59:54 GMT 2025
NCI_THESAURUS C97453
Created by admin on Mon Mar 31 17:59:54 GMT 2025 , Edited by admin on Mon Mar 31 17:59:54 GMT 2025
WHO-ATC J05AR05
Created by admin on Mon Mar 31 17:59:54 GMT 2025 , Edited by admin on Mon Mar 31 17:59:54 GMT 2025
WHO-VATC QJ05AG01
Created by admin on Mon Mar 31 17:59:54 GMT 2025 , Edited by admin on Mon Mar 31 17:59:54 GMT 2025
NDF-RT N0000175463
Created by admin on Mon Mar 31 17:59:54 GMT 2025 , Edited by admin on Mon Mar 31 17:59:54 GMT 2025
EMA ASSESSMENT REPORTS VIRAMUNE (AUTHORIZED: HIV INFECTIONS)
Created by admin on Mon Mar 31 17:59:54 GMT 2025 , Edited by admin on Mon Mar 31 17:59:54 GMT 2025
LIVERTOX NBK548895
Created by admin on Mon Mar 31 17:59:54 GMT 2025 , Edited by admin on Mon Mar 31 17:59:54 GMT 2025
WHO-ESSENTIAL MEDICINES LIST 6.4.2.2
Created by admin on Mon Mar 31 17:59:54 GMT 2025 , Edited by admin on Mon Mar 31 17:59:54 GMT 2025
WHO-VATC QJ05AR07
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NDF-RT N0000009948
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NDF-RT N0000175460
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WHO-ESSENTIAL MEDICINES LIST 6.4.2.3 (LAM/NEV/STA)
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WHO-ATC J05AG01
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FDA ORPHAN DRUG 293409
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WHO-ESSENTIAL MEDICINES LIST 6.4.2.3 (LAM/NEV/ZID)
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WHO-VATC QJ05AR05
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WHO-ATC J05AR07
Created by admin on Mon Mar 31 17:59:54 GMT 2025 , Edited by admin on Mon Mar 31 17:59:54 GMT 2025
Code System Code Type Description
EVMPD
SUB09214MIG
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PRIMARY
NDF-RT
N0000190118
Created by admin on Mon Mar 31 17:59:54 GMT 2025 , Edited by admin on Mon Mar 31 17:59:54 GMT 2025
PRIMARY Cytochrome P450 3A Inducers [MoA]
EPA CompTox
DTXSID7031797
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PRIMARY
RXCUI
53654
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PRIMARY RxNorm
LACTMED
Nevirapine
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PRIMARY
EVMPD
SUB25191
Created by admin on Mon Mar 31 17:59:54 GMT 2025 , Edited by admin on Mon Mar 31 17:59:54 GMT 2025
PRIMARY
RS_ITEM_NUM
1460703
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PRIMARY
CHEBI
63613
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PRIMARY
INN
6815
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PRIMARY
WIKIPEDIA
NEVIRAPINE
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PRIMARY
ChEMBL
CHEMBL57
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PRIMARY
SMS_ID
100000085470
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PRIMARY
DAILYMED
99DK7FVK1H
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PRIMARY
MESH
D019829
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PRIMARY
MERCK INDEX
m7845
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PRIMARY Merck Index
NSC
641530
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PRIMARY
CAS
129618-40-2
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PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
NEVIRAPINE
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PRIMARY Description: A white to almost white powder. Solubility: Practically insoluble in water, sparingly to slightly soluble in dichloromethane R, slightly soluble in methanol R. Category: Antiretroviral (Non-Nucleoside Reverse Transcriptase Inhibitor). Storage: Nevirapine should be kept in a well-closed container. Labelling: The designation on the container should state whether the substance is the hemihydrate or is in the anhydrous form. Definition: Nevirapine contains not less than 98.0% and not more than 102.0% of nevirapine (C15H14N4O), calculated with reference to the anhydrous substance.
DRUG BANK
DB00238
Created by admin on Mon Mar 31 17:59:54 GMT 2025 , Edited by admin on Mon Mar 31 17:59:54 GMT 2025
PRIMARY
DRUG CENTRAL
1904
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PRIMARY
USAN
DD-19
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PRIMARY
NCI_THESAURUS
C29277
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PRIMARY
PUBCHEM
4463
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PRIMARY
HSDB
7164
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PRIMARY
NDF-RT
N0000187064
Created by admin on Mon Mar 31 17:59:54 GMT 2025 , Edited by admin on Mon Mar 31 17:59:54 GMT 2025
PRIMARY Cytochrome P450 2B6 Inducers [MoA]
FDA UNII
99DK7FVK1H
Created by admin on Mon Mar 31 17:59:54 GMT 2025 , Edited by admin on Mon Mar 31 17:59:54 GMT 2025
PRIMARY
Related Record Type Details
SOLVATE->ANHYDROUS
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
BASIS OF STRENGTH->SUBSTANCE
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
SUBSTANCE->BASIS OF STRENGTH
TARGET ORGANISM->INHIBITOR
IC50 values (50% inhibitory concentration) ranged from 10-100 nM against laboratory and clinical isolates of HIV-1.
IC50
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> INHIBITOR
Related Record Type Details
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
This reactive intermediate was catalyzed primarily by CYP3A and possibly by CYP2D6, CYP2C19, and CYP2A6
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
Related Record Type Details
IMPURITY -> PARENT
IMPURITY -> PARENT
Amount NOT SPECIFIED
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
The test is not valid unless the resolution between nevirapine and nevirapine impurity B RS is not less than 5. In the chromatogram obtained with solution (3) the peak due to impurity (B) is eluted at a relative retention of about 0.7 with reference to nevirapine (retention time about 7.6 minutes).
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
Amount NOT SPECIFIED
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC