Identification
- Summary
Nevirapine is a non-nucleoside reverse transcriptase inhibitor used as part of a management regimen for HIV-1 virus infection.
- Brand Names
- Viramune
- Generic Name
- Nevirapine
- DrugBank Accession Number
- DB00238
- Background
A potent, non-nucleoside reverse transcriptase inhibitor (NNRTI) used in combination with nucleoside analogues for treatment of Human Immunodeficiency Virus Type 1 (HIV-1) infection and AIDS. Structurally, nevirapine belongs to the dipyridodiazepinone chemical class.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Nevirapine (DB00238)
- Weight
- Average: 266.2979
Monoisotopic: 266.11676109 - Chemical Formula
- C15H14N4O
- Synonyms
- 11-cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido(3,2-b:2',3'-e)(1,4)diazepin-6-one
- NEV
- Nevirapina
- Nevirapine
- Nevirapine anhydrous
- Nevirapine, anhydrous
- NVP
- External IDs
- BIRG 0587
- BIRG-0587
- BIRG-587
- NSC-641530
Pharmacology
- Indication
For use in combination with other antiretroviral drugs in the ongoing treatment of HIV-1 infection.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Human immunodeficiency virus type 1 (hiv-1) infection •••••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
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.
- Mechanism of action
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.
Target Actions Organism AReverse transcriptase/RNaseH inhibitorHuman immunodeficiency virus 1 - Absorption
Nevirapine is readily absorbed (greater than 90%) after oral administration in healthy subjects and adults with HIV-1 infection. The absolute bioavailability in healthy adults following a single dose administration is 93 ± 9% (mean ± SD) for a 50 mg tablet and 91 ± 8% for an oral solution. Peak plasma nevirapine concentrations of 2 ± 0.4 mcg/mL (7.5 micromolar) were attained by 4 hours following a single 200 mg dose. Nevirapine tablets and suspension have been shown to be comparably bioavailable and interchangeable at doses up to 200 mg. When the oral tablet is given with a high-fat meal, the extent of absorption is compared to that of the fasted-state.
- Volume of distribution
- 1.21 ± 0.09 L/kg [apparent volume of distribution, healthy adults, IV] Nevirapine is capable of crossing the placenta and is found in breast milk.
- Protein binding
60% bound to plasma protein.
- Metabolism
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.
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- Route of 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.
- Half-life
45 hours
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Symptoms of overdose include edema, erythema nodosum, fatigue, fever, headache, insomnia, nausea, pulmonaryinfiltrates, rash, vertigo, vomiting, and weight decrease. The most common adverse reaction is rash.
- Pathways
Pathway Category Nevirapine Metabolism Pathway Drug metabolism Nevirapine Action Pathway Drug action - Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Nevirapine can be increased when it is combined with Abametapir. Abatacept The metabolism of Nevirapine can be increased when combined with Abatacept. Abiraterone The metabolism of Nevirapine can be decreased when combined with Abiraterone. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Nevirapine. Acalabrutinib The metabolism of Nevirapine can be decreased when combined with Acalabrutinib. - Food Interactions
- Avoid alcohol.
- Take with or without food. The absorption is unaffected by food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Nevirapine hemihydrate B7XF2TD73C 220988-26-1 KMTLSXAXTLQBKJ-UHFFFAOYSA-N - Product Images
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Nevirapine Teva Tablet 200 mg Oral Teva B.V. 2016-09-08 2023-03-21 EU 
Nevirapine Teva Tablet 200 mg Oral Teva B.V. 2016-09-08 2023-03-21 EU Nevirapine Teva Tablet 200 mg Oral Teva B.V. 2016-09-08 2023-03-21 EU Nevirapine Teva Tablet 200 mg Oral Teva B.V. 2016-09-08 2023-03-21 EU Nevirapine Teva Tablet 200 mg Oral Teva B.V. 2016-09-08 2023-03-21 EU - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo-nevirapine Tablet 200 mg Oral Apotex Corporation Not applicable Not applicable Canada 
Apo-nevirapine XR Tablet, extended release 400 mg Oral Apotex Corporation 2015-11-24 Not applicable Canada Auro-nevirapine Tablet 200 mg Oral Auro Pharma Inc 2010-12-29 Not applicable Canada Jamp Nevirapine Tablet 200 mg Oral Jamp Pharma Corporation 2013-06-03 Not applicable Canada Mylan-nevirapine Tablet 200 mg Oral Mylan Pharmaceuticals 2012-06-20 Not applicable Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Apo-zidovudine-lamivudine-nevirapine Nevirapine (200 mg) + Lamivudine (150 mg) + Zidovudine (300 mg) Tablet Oral Apotex Corporation Not applicable Not applicable Canada Lamivudine, Nevirapine, and Zidovudine Nevirapine (200 mg/1) + Lamivudine (150 mg/1) + Zidovudine (300 mg/1) Tablet, film coated Oral Micro Labs Limited 2018-09-03 2019-12-17 US 
TREZAV® PED Nevirapine (50 mg) + Lamivudine (30 mg) + Zidovudine (60 mg) Tablet, soluble Oral Mylan Laboratories Limited 2018-07-18 Not applicable Colombia 
Zidovex LN (Lamivudine 150mg, Zidovudine 300mg, Nevirapine 200mg Tablets) Nevirapine (200 mg) + Lamivudine (150 mg) + Zidovudine (300 mg) Tablet Oral UNIMED SDN BHD 2020-09-08 Not applicable Malaysia 
จีพีโอเวียร์ เอส 30 Nevirapine (200 MG) + Lamivudine (150 MG) + Stavudine (30 MG) องค์การเภสัชกรรม 2003-11-14 Not applicable Thailand 
Categories
- ATC Codes
- J05AG01 — Nevirapine
- J05AG — Non-nucleoside reverse transcriptase inhibitors
- J05A — DIRECT ACTING ANTIVIRALS
- J05 — ANTIVIRALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- J05AR — Antivirals for treatment of HIV infections, combinations
- J05A — DIRECT ACTING ANTIVIRALS
- J05 — ANTIVIRALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- Drug Categories
- Anti-HIV Agents
- Anti-Infective Agents
- Anti-Retroviral Agents
- Antiinfectives for Systemic Use
- Antiviral Agents
- Antivirals for Systemic Use
- Antivirals used in combination for the treatment of HIV infections
- Cytochrome P-450 CYP1A2 Inhibitors
- Cytochrome P-450 CYP1A2 Inhibitors (weak)
- Cytochrome P-450 CYP2A6 Substrates
- Cytochrome P-450 CYP2B6 Inducers
- Cytochrome P-450 CYP2B6 Inducers (strong)
- Cytochrome P-450 CYP2B6 Substrates
- Cytochrome P-450 CYP2C9 Inducers
- Cytochrome P-450 CYP2C9 Inducers (strength unknown)
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (weak)
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (weak)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Substrates
- Cytochrome P-450 CYP3A7 Substrates
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Direct Acting Antivirals
- Enzyme Inhibitors
- Hepatotoxic Agents
- Human Immunodeficiency Virus 1 Non-Nucleoside Analog Reverse Transcriptase Inhibitor
- Inducers of Drug Clearance
- Non-Nucleoside Reverse Transcriptase Inhibitors
- Nonnucleoside Reverse Transcriptase Inhibitors
- Nucleic Acid Synthesis Inhibitors
- OCT1 inhibitors
- Pyridines
- Reverse Transcriptase Inhibitors
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as alkyldiarylamines. These are tertiary alkylarylamines having two aryl and one alkyl groups attached to the amino group.
- Kingdom
- Organic compounds
- Super Class
- Organic nitrogen compounds
- Class
- Organonitrogen compounds
- Sub Class
- Amines
- Direct Parent
- Alkyldiarylamines
- Alternative Parents
- Pyridodiazepines / Methylpyridines / 1,4-diazepines / Imidolactams / Vinylogous amides / Heteroaromatic compounds / Secondary carboxylic acid amides / Lactams / Azacyclic compounds / Organopnictogen compounds show 3 more
- Substituents
- Alkyldiarylamine / Aromatic heteropolycyclic compound / Azacycle / Carboxamide group / Carboxylic acid derivative / Heteroaromatic compound / Hydrocarbon derivative / Imidolactam / Lactam / Methylpyridine show 10 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- dipyridodiazepine (CHEBI:63613)
- Affected organisms
- Human Immunodeficiency Virus
Chemical Identifiers
- UNII
- 99DK7FVK1H
- CAS number
- 129618-40-2
- InChI Key
- NQDJXKOVJZTUJA-UHFFFAOYSA-N
- 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)
- IUPAC Name
- 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
- SMILES
- CC1=C2NC(=O)C3=C(N=CC=C3)N(C3CC3)C2=NC=C1
References
- Synthesis Reference
- US5366972
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014383
- KEGG Drug
- D00435
- KEGG Compound
- C07263
- PubChem Compound
- 4463
- PubChem Substance
- 46506789
- ChemSpider
- 4308
- BindingDB
- 1434
- 53654
- ChEBI
- 63613
- ChEMBL
- CHEMBL57
- ZINC
- ZINC000000004778
- Therapeutic Targets Database
- DAP000184
- PharmGKB
- PA450616
- PDBe Ligand
- NVP
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Nevirapine
- PDB Entries
- 1fkp / 1jlb / 1jlf / 1lw0 / 1lwc / 1lwe / 1lwf / 1s1u / 1s1x / 1vrt … show 15 more
- FDA label
- Download (423 KB)
- MSDS
- Download (57 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Not Available Human Immunodeficiency Virus (HIV) Infections 2 4 Completed Diagnostic Cardiovascular Disease (CVD) / HIV Lipodystrophy Syndrome 1 4 Completed Diagnostic Human Immunodeficiency Virus (HIV) Infections / Quality of Life (QOL) 1 4 Completed Prevention Antiretroviral Therapy / High Cholesterol / Human Immunodeficiency Virus (HIV) Infections 1 4 Completed Prevention Central Nervous System Disorder / Dementia / Human Immunodeficiency Virus (HIV) Infections 1
Pharmacoeconomics
- Manufacturers
- Boehringer ingelheim pharmaceuticals inc
- Packagers
- Boehringer Ingelheim Ltd.
- Dept Health Central Pharmacy
- Kaiser Foundation Hospital
- Lake Erie Medical and Surgical Supply
- Murfreesboro Pharmaceutical Nursing Supply
- PD-Rx Pharmaceuticals Inc.
- Physicians Total Care Inc.
- Remedy Repack
- Roxane Labs
- Dosage Forms
Form Route Strength Tablet, coated Oral Tablet, film coated Oral Tablet Oral 200.000 mg Tablet Oral Tablet, extended release Oral Suspension Oral 1 g Suspension Oral 50 mg/5mL Tablet, coated Oral 200 mg/1 Tablet, extended release Oral 100 mg/1 Tablet Oral 100 mg/1 Tablet Oral 400 mg/1 Suspension Oral Tablet Oral 200.0 mg Tablet, soluble Oral Tablet Oral 200 mg/1 Tablet, extended release Oral 100 MG Tablet, extended release Oral 400 mg/1 Tablet, extended release Oral 50 MG Tablet, extended release Oral 400 mg Tablet Oral Tablet, coated Oral 200 mg Tablet Oral 200 mg - Prices
Unit description Cost Unit Viramune 200 mg tablet 9.3USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5366972 No 1994-11-22 2012-05-22 US CA2030056 No 1995-10-17 2010-11-15 Canada US8460704 No 2013-06-11 2029-03-12 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 196.06 Not Available water solubility 0.7046 mg/L Not Available logP 2.5 Not Available Caco2 permeability -4.52 ADME Research, USCD - Predicted Properties
Property Value Source Water Solubility 0.105 mg/mL ALOGPS logP 1.75 ALOGPS logP 2.49 Chemaxon logS -3.4 ALOGPS pKa (Strongest Acidic) 14.98 Chemaxon pKa (Strongest Basic) 3.28 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 58.12 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 77.48 m3·mol-1 Chemaxon Polarizability 27.8 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9958 Blood Brain Barrier + 0.9756 Caco-2 permeable + 0.8867 P-glycoprotein substrate Non-substrate 0.5606 P-glycoprotein inhibitor I Non-inhibitor 0.6488 P-glycoprotein inhibitor II Non-inhibitor 0.8514 Renal organic cation transporter Non-inhibitor 0.7124 CYP450 2C9 substrate Non-substrate 0.6179 CYP450 2D6 substrate Substrate 0.8919 CYP450 3A4 substrate Substrate 0.6413 CYP450 1A2 substrate Inhibitor 0.6175 CYP450 2C9 inhibitor Non-inhibitor 0.8009 CYP450 2D6 inhibitor Non-inhibitor 0.9451 CYP450 2C19 inhibitor Non-inhibitor 0.7971 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5443 Ames test AMES toxic 0.5952 Carcinogenicity Non-carcinogens 0.9383 Biodegradation Not ready biodegradable 0.964 Rat acute toxicity 2.6729 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9827 hERG inhibition (predictor II) Non-inhibitor 0.8321
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 166.3653361 predictedDarkChem Lite v0.1.0 [M-H]- 166.4877361 predictedDarkChem Lite v0.1.0 [M-H]- 166.5629361 predictedDarkChem Lite v0.1.0 [M-H]- 168.27943 predictedDeepCCS 1.0 (2019) [M+H]+ 167.0910361 predictedDarkChem Lite v0.1.0 [M+H]+ 167.0887361 predictedDarkChem Lite v0.1.0 [M+H]+ 167.2134361 predictedDarkChem Lite v0.1.0 [M+H]+ 170.63744 predictedDeepCCS 1.0 (2019) [M+Na]+ 166.5001361 predictedDarkChem Lite v0.1.0 [M+Na]+ 166.8277361 predictedDarkChem Lite v0.1.0 [M+Na]+ 176.73059 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- Kind
- Protein
- Organism
- Human immunodeficiency virus 1
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Rna-dna hybrid ribonuclease activity
- Specific Function
- Not Available
- Gene Name
- pol
- Uniprot ID
- Q72547
- Uniprot Name
- Reverse transcriptase/RNaseH
- Molecular Weight
- 65223.615 Da
References
- Ambrose Z, Herman BD, Sheen CW, Zelina S, Moore KL, Tachedjian G, Nissley DV, Sluis-Cremer N: The human immunodeficiency virus type 1 nonnucleoside reverse transcriptase inhibitor resistance mutation I132M confers hypersensitivity to nucleoside analogs. J Virol. 2009 Apr;83(8):3826-33. doi: 10.1128/JVI.01968-08. Epub 2009 Feb 4. [Article]
- Nikolenko GN, Delviks-Frankenberry KA, Pathak VK: A novel molecular mechanism of dual resistance to nucleoside and nonnucleoside reverse transcriptase inhibitors. J Virol. 2010 May;84(10):5238-49. doi: 10.1128/JVI.01545-09. Epub 2010 Mar 10. [Article]
- Ghosn J, Chaix ML, Delaugerre C: HIV-1 resistance to first- and second-generation non-nucleoside reverse transcriptase inhibitors. AIDS Rev. 2009 Jul-Sep;11(3):165-73. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- von Moltke LL, Greenblatt DJ, Granda BW, Giancarlo GM, Duan SX, Daily JP, Harmatz JS, Shader RI: Inhibition of human cytochrome P450 isoforms by nonnucleoside reverse transcriptase inhibitors. J Clin Pharmacol. 2001 Jan;41(1):85-91. doi: 10.1177/00912700122009728. [Article]
- Heil SG, van der Ende ME, Schenk PW, van der Heiden I, Lindemans J, Burger D, van Schaik RH: Associations between ABCB1, CYP2A6, CYP2B6, CYP2D6, and CYP3A5 alleles in relation to efavirenz and nevirapine pharmacokinetics in HIV-infected individuals. Ther Drug Monit. 2012 Apr;34(2):153-9. doi: 10.1097/FTD.0b013e31824868f3. [Article]
- Wen B, Chen Y, Fitch WL: Metabolic activation of nevirapine in human liver microsomes: dehydrogenation and inactivation of cytochrome P450 3A4. Drug Metab Dispos. 2009 Jul;37(7):1557-62. doi: 10.1124/dmd.108.024851. Epub 2009 Apr 13. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58293.76 Da
References
- von Moltke LL, Greenblatt DJ, Granda BW, Giancarlo GM, Duan SX, Daily JP, Harmatz JS, Shader RI: Inhibition of human cytochrome P450 isoforms by nonnucleoside reverse transcriptase inhibitors. J Clin Pharmacol. 2001 Jan;41(1):85-91. doi: 10.1177/00912700122009728. [Article]
- Mhandire D, Lacerda M, Castel S, Mhandire K, Zhou D, Swart M, Shamu T, Smith P, Musingwini T, Wiesner L, Stray-Pedersen B, Dandara C: Effects of CYP2B6 and CYP1A2 Genetic Variation on Nevirapine Plasma Concentration and Pharmacodynamics as Measured by CD4 Cell Count in Zimbabwean HIV-Infected Patients. OMICS. 2015 Sep;19(9):553-62. doi: 10.1089/omi.2015.0104. [Article]
- Nevirapine [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Oxygen binding
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP3A7
- Uniprot ID
- P24462
- Uniprot Name
- Cytochrome P450 3A7
- Molecular Weight
- 57525.03 Da
References
- Torimoto N, Ishii I, Toyama K, Hata M, Tanaka K, Shimomura H, Nakamura H, Ariyoshi N, Ohmori S, Kitada M: Helices F-G are important for the substrate specificities of CYP3A7. Drug Metab Dispos. 2007 Mar;35(3):484-92. doi: 10.1124/dmd.106.011304. Epub 2006 Dec 18. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInducer
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
- Fichtenbaum CJ, Gerber JG: Interactions between antiretroviral drugs and drugs used for the therapy of the metabolic complications encountered during HIV infection. Clin Pharmacokinet. 2002;41(14):1195-211. doi: 10.2165/00003088-200241140-00004. [Article]
- Mouly S, Rizzo-Padoin N, Simoneau G, Verstuyft C, Aymard G, Salvat C, Mahe I, Bergmann JF: Effect of widely used combinations of antiretroviral therapy on liver CYP3A4 activity in HIV-infected patients. Br J Clin Pharmacol. 2006 Aug;62(2):200-9. doi: 10.1111/j.1365-2125.2006.02637.x. [Article]
- Indiana University - Department of Medicine Clinical Pharmacology [Link]
- Lexicomp database [Link]
- Viramune (Nevirapine) FDA Label [Link]
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInducer
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2B6
- Uniprot ID
- P20813
- Uniprot Name
- Cytochrome P450 2B6
- Molecular Weight
- 56277.81 Da
References
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
- Paganotti GM, Russo G, Sobze MS, Mayaka GB, Muthoga CW, Tawe L, Martinelli A, Romano R, Vullo V: CYP2B6 poor metaboliser alleles involved in efavirenz and nevirapine metabolism: CYP2B6*9 and CYP2B6*18 distribution in HIV-exposed subjects from Dschang, Western Cameroon. Infect Genet Evol. 2015 Oct;35:122-6. doi: 10.1016/j.meegid.2015.08.003. Epub 2015 Aug 4. [Article]
- Hedrich WD, Hassan HE, Wang H: Insights into CYP2B6-mediated drug-drug interactions. Acta Pharm Sin B. 2016 Sep;6(5):413-425. doi: 10.1016/j.apsb.2016.07.016. Epub 2016 Aug 9. [Article]
- Viramune (Nevirapine) FDA Label [Link]
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Oxygen binding
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- Curator comments
- There are limited data on the literature supporting this enzyme action, with the exception of some case reports.
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- Liedtke MD, Rathbun RC: Warfarin-antiretroviral interactions. Ann Pharmacother. 2009 Feb;43(2):322-8. doi: 10.1345/aph.1L497. Epub 2009 Feb 5. [Article]
- Stolbach A, Paziana K, Heverling H, Pham P: A Review of the Toxicity of HIV Medications II: Interactions with Drugs and Complementary and Alternative Medicine Products. J Med Toxicol. 2015 Sep;11(3):326-41. doi: 10.1007/s13181-015-0465-0. [Article]
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
- Gene Name
- CYP2A6
- Uniprot ID
- P11509
- Uniprot Name
- Cytochrome P450 2A6
- Molecular Weight
- 56501.005 Da
References
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
- Wen B, Chen Y, Fitch WL: Metabolic activation of nevirapine in human liver microsomes: dehydrogenation and inactivation of cytochrome P450 3A4. Drug Metab Dispos. 2009 Jul;37(7):1557-62. doi: 10.1124/dmd.108.024851. Epub 2009 Apr 13. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- Bocedi A, Notaril S, Narciso P, Bolli A, Fasano M, Ascenzi P: Binding of anti-HIV drugs to human serum albumin. IUBMB Life. 2004 Oct;56(10):609-14. [Article]
- Bocedi A, Notari S, Menegatti E, Fanali G, Fasano M, Ascenzi P: Allosteric modulation of anti-HIV drug and ferric heme binding to human serum albumin. FEBS J. 2005 Dec;272(24):6287-96. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- Inhibition data supported only by 1 in vitro study.
- General Function
- Secondary active organic cation transmembrane transporter activity
- Specific Function
- Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
- Gene Name
- SLC22A1
- Uniprot ID
- O15245
- Uniprot Name
- Solute carrier family 22 member 1
- Molecular Weight
- 61153.345 Da
References
- Moss DM, Liptrott NJ, Siccardi M, Owen A: Interactions of antiretroviral drugs with the SLC22A1 (OCT1) drug transporter. Front Pharmacol. 2015 Apr 10;6:78. doi: 10.3389/fphar.2015.00078. eCollection 2015. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:54