Nevirapine

Summary

Nevirapine (CHEMBL57) is an approved small-molecule antiviral drug (ATC J05AG01); indicated across 6 conditions including hiv infectious disease and viral infectious disease.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: J05AG01
• Indications: 6 conditions
• Clinical trials: 135
• Chemistry: 266.3 Da · C15H14N4O

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL57
Name	Nevirapine
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	4463
ChEBI	CHEBI:63613
ATC	J05AG01
Molecular formula	C15H14N4O
Molecular weight	266.3
InChIKey	NQDJXKOVJZTUJA-UHFFFAOYSA-N

SMILES: CC1=C2C(=NC=C1)N(C3=C(C=CC=N3)C(=O)N2)C4CC4

IUPAC name: 2-cyclopropyl-7-methyl-2,4,9,15-tetrazatricyclo[9.4.0.03,8]pentadeca-1(11),3,5,7,12,14-hexaen-10-one

ChEBI definition: A dipyridodiazepine that is 5,11-dihydro-6H-dipyrido[3,2-b:2’,3’-e][1,4]diazepine which is substituted by methyl, oxo, and cyclopropyl groups at positions 4, 6, and 11, respectively. A non-nucleoside reverse transcriptase inhibitor with activity against HIV-1, it is used in combination with other antiretrovirals for the treatment of HIV infection.

Pharmacological roles (ChEBI): antiviral drug, HIV-1 reverse transcriptase inhibitor.

Also known as: BIRG 0587, BIRG-0587, BIRG0587, Nevirapina, Nevirapine, Nevirapine anhydrous, Nevirapine teva, anhydrous, Nevirapinum anhydrous, NSC-641530, Viramune, Viramune xr

Parent form; salt/anhydrous children: CHEMBL4649102

Patent coverage: 9,522 distinct patent families (36,739 SureChEMBL compound mentions), from 4 matched compound structure(s). One matched structure accounts for 36,178 (98%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 8 (assay-derived). Sample: Prelamin-A/C, Adenosine receptor A1, DNA polymerase beta, cGMP-inhibited 3’,5’-cyclic phosphodiesterase 3A, Adenosine receptor A2a, Adenosine receptor A3, Aldehyde dehydrogenase 1A1, Mitogen-activated protein kinase 1.

Bioactivity

ChEMBL activities: 5 potent at pChembl ≥ 5 of 9 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
LMNA	7.45	Potency	35.5	nM	CHEMBL_ACT_3645206
ADORA3	5.99	AC50	1020	nM	CHEMBL_ACT_25134738
MAPK1	5.45	Potency	3548	nM	CHEMBL_ACT_4729916
PDE3A	5.35	AC50	4500	nM	CHEMBL_ACT_25191235
MAPK1	5.05	Potency	8912	nM	CHEMBL_ACT_4741621

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

6 indications (3 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
HIV infectious disease	4	MONDO:0005109	EFO:0000764
viral infectious disease	4	MONDO:0005108	EFO:0000763
AIDS	3	MONDO:0012268	EFO:0000765
tuberculosis	3	MONDO:0018076	MONDO:0018076

2 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 135.

Phase distribution

Phase	Trials
PHASE3	31
Not specified	26
PHASE4	25
PHASE1	25
PHASE2	21
PHASE1/PHASE2	5
PHASE2/PHASE3	1
EARLY_PHASE1	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00127972	PHASE4	COMPLETED	2NN & CHARM Long-Term Follow-up Study
NCT00144157	PHASE4	COMPLETED	Open Label Study of NVP+CBV Treatment in Women Who Have Received sdNVP for the pMTCT of HIV
NCT00144248	PHASE4	COMPLETED	A Pharmacokinetic Study to Assess Nevirapine [Viramune] Levels in HIV Infected Patients With Impaired Hepatic Functions
NCT00144261	PHASE4	COMPLETED	An Open-label, Non-randomized, Single-arm Study to Investigate the Mechanism(s) by Which Nevirapine Increases Plasma HDL in HIV+ Subjects
NCT00192660	PHASE4	COMPLETED	HIV Infection And Metabolic Abnormalities Protocol 1 (HAMA001)
NCT00273988	PHASE4	COMPLETED	Pharmacokinetic Study of Interaction Between Nevirapine and Methadone in HIV-1 Infected, Opioid-dependent Adults
NCT00274001	PHASE4	COMPLETED	Quality of Life and Changes in Metabolism of Lipids and Glucose After Switching to a Nevirapine-based Regimen in HIV+ Patients
NCT00355719	PHASE4	COMPLETED	Study to Evaluate the Influence of Nevirapine to Atazanavir in Steady State Equilibrium in HIV Patients
NCT00405171	PHASE4	COMPLETED	Efavirenz to Nevirapine Switch and Low-Density Lipoprotein (LDL)-Dyslipidemia
NCT00415090	PHASE4	COMPLETED	Study to Evaluate the Replacement of Reverse Transcriptase Nucleoside/Nucleotide Inhibitors by Nevirapine in Patients on Triple Treatment With Analogues Only
NCT00455585	PHASE4	COMPLETED	Comparison of Plasma Drug Levels of Triomune 40 With Those of the Originator Products
NCT00540137	PHASE4	COMPLETED	The CogNaive Study: Assessing Changes in Neurocognitive Function in Treatment Naïve HIV-1 Positive Subjects
NCT00620438	PHASE4	UNKNOWN	Drug Interaction Between Coartem® and Nevirapine, Efavirenz or Rifampicin in HIV Positive Ugandan Patients
NCT00661349	PHASE4	TERMINATED	Trial About Hepatic Security of Antiretroviral Treatment Based on Kaletra Versus Nevirapine in Co-infected HIV/HCV Patients
NCT00703898	PHASE4	COMPLETED	Durability of Nevirapine-Based Antiretroviral Regimen
NCT00704249	PHASE4	COMPLETED	VENICE Study Nevirapine Full Dose/Dose Escalation
NCT01025830	PHASE4	COMPLETED	Triomune Bioequivalence With Innovators
NCT01637558	PHASE4	COMPLETED	Optimal Dosing of 1st Line Antituberculosis and Antiretroviral Drugs in Children (a Pharmacokinetic Study)
NCT01772940	PHASE4	COMPLETED	Nevirapine vs Ritonavir-boosted Lopinavir in ART Naive HIV-infected Adults in a Resource Limited Setting
NCT02181946	PHASE4	COMPLETED	Effects of Nevirapine on the Steady State Pharmacokinetics of Fluconazole in HIV Positive Patients
NCT02184078	PHASE4	COMPLETED	Study to Determine the Effects of Nevirapine (VIRAMUNE®) on the Steady State Pharmacokinetics of Rifabutin (MYCOBUTIN®) in HIV+ Patients
NCT02184299	PHASE4	COMPLETED	Study of Nevirapine and Prednisone to Determine the Safety and Effectiveness in Preventing Nevirapine Associated Rash in Human Immunodeficiency Virus (HIV) Infected Patients
NCT02431975	PHASE4	COMPLETED	Latency and Early Neonatal Provision of Antiretroviral Drugs Clinical Trial
NCT02712801	PHASE4	COMPLETED	Antiretroviral Regime for Viral Eradication in Newborns
NCT03088410	PHASE4	COMPLETED	Study of HIV-Infected and Uninfected Pregnant Woman/Child Dyads in Gaborone, Botswana
NCT02369406	PHASE2/PHASE3	ACTIVE_NOT_RECRUITING	Early Infant HIV Treatment in Botswana
NCT00000869	PHASE3	COMPLETED	A Study of Nevirapine for the Prevention of HIV Transmission From Mothers to Their Babies
NCT00000942	PHASE3	COMPLETED	A Study of Nevirapine to Prevent HIV Transmission From Mothers to Their Babies
NCT00001135	PHASE3	COMPLETED	A Study of Nevirapine to Prevent HIV Transmission From Mothers to Their Infants
NCT00002166	PHASE3	COMPLETED	An Open-Label, Non-Randomized Trial to Evaluate the Tolerability and Safety of Viramune (Nevirapine) in Adult and Pediatric Patients With Progressive HIV Disease
NCT00002368	PHASE3	COMPLETED	The Safety and Effectiveness of Nevirapine Plus Lamivudine Plus Other Anti-HIV Drugs
NCT00004581	PHASE3	COMPLETED	A Study to Compare Two Anti-HIV Drug Combinations in HIV-Infected Patients Who Have Previously Received Anti-HIV Treatment
NCT00006396	PHASE3	COMPLETED	Effectiveness of AZT and Nevirapine in Preventing HIV Transmission From Ugandan Mothers to Their Newborns
NCT00013520	PHASE3	COMPLETED	Comparison of Three Different Initial Treatments Without Protease Inhibitors for HIV Infection
NCT00017719	PHASE3	COMPLETED	Combination Treatment With and Without Protease Inhibitors for Women Who Begin Therapy for HIV Infection During Pregnancy
NCT00021671	PHASE3	COMPLETED	Antibiotics to Reduce Chorioamnionitis-Related Perinatal HIV Transmission
NCT00061321	PHASE3	COMPLETED	Daily Nevirapine to Prevent Mother to Infant Transmission of HIV
NCT00074399	PHASE3	COMPLETED	Nevirapine (NVP) Use to Prevent Mother-to-Child Transmission of HIV
NCT00074412	PHASE3	COMPLETED	Using Nevirapine to Prevent Mother-to-Child HIV Transmission During Breastfeeding
NCT00074581	PHASE3	COMPLETED	Preventing Sexual Transmission of HIV With Anti-HIV Drugs

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline, but PharmGKB curates 66 clinical and 208 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).