Nevirapine

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
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.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatHuman immunodeficiency virus type 1 (hiv-1) infection••••••••••••
Contraindications & Blackbox Warnings
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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.

TargetActionsOrganism
AReverse transcriptase/RNaseH
inhibitor
Human 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.

Hover over products below to view reaction partners

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
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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
PathwayCategory
Nevirapine Metabolism PathwayDrug metabolism
Nevirapine Action PathwayDrug 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.
DrugInteraction
AbametapirThe serum concentration of Nevirapine can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Nevirapine can be increased when combined with Abatacept.
AbirateroneThe metabolism of Nevirapine can be decreased when combined with Abiraterone.
AbrocitinibThe metabolism of Abrocitinib can be decreased when combined with Nevirapine.
AcalabrutinibThe 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

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Product Ingredients
IngredientUNIICASInChI Key
Nevirapine hemihydrateB7XF2TD73C220988-26-1KMTLSXAXTLQBKJ-UHFFFAOYSA-N
Product Images
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Nevirapine TevaTablet200 mgOralTeva B.V.2016-09-082023-03-21EU flag
Nevirapine TevaTablet200 mgOralTeva B.V.2016-09-082023-03-21EU flag
Nevirapine TevaTablet200 mgOralTeva B.V.2016-09-082023-03-21EU flag
Nevirapine TevaTablet200 mgOralTeva B.V.2016-09-082023-03-21EU flag
Nevirapine TevaTablet200 mgOralTeva B.V.2016-09-082023-03-21EU flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-nevirapineTablet200 mgOralApotex CorporationNot applicableNot applicableCanada flag
Apo-nevirapine XRTablet, extended release400 mgOralApotex Corporation2015-11-24Not applicableCanada flag
Auro-nevirapineTablet200 mgOralAuro Pharma Inc2010-12-29Not applicableCanada flag
Jamp NevirapineTablet200 mgOralJamp Pharma Corporation2013-06-03Not applicableCanada flag
Mylan-nevirapineTablet200 mgOralMylan Pharmaceuticals2012-06-20Not applicableCanada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Apo-zidovudine-lamivudine-nevirapineNevirapine (200 mg) + Lamivudine (150 mg) + Zidovudine (300 mg)TabletOralApotex CorporationNot applicableNot applicableCanada flag
Lamivudine, Nevirapine, and ZidovudineNevirapine (200 mg/1) + Lamivudine (150 mg/1) + Zidovudine (300 mg/1)Tablet, film coatedOralMicro Labs Limited2018-09-032019-12-17US flag
TREZAV® PEDNevirapine (50 mg) + Lamivudine (30 mg) + Zidovudine (60 mg)Tablet, solubleOralMylan Laboratories Limited2018-07-18Not applicableColombia flag
Zidovex LN (Lamivudine 150mg, Zidovudine 300mg, Nevirapine 200mg Tablets)Nevirapine (200 mg) + Lamivudine (150 mg) + Zidovudine (300 mg)TabletOralUNIMED SDN BHD2020-09-08Not applicableMalaysia flag
จีพีโอเวียร์ เอส 30Nevirapine (200 MG) + Lamivudine (150 MG) + Stavudine (30 MG)องค์การเภสัชกรรม2003-11-14Not applicableThailand flag

Categories

ATC Codes
J05AG01 — NevirapineJ05AR05 — Zidovudine, lamivudine and nevirapineJ05AR07 — Stavudine, lamivudine and nevirapine
Drug Categories
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
Human Metabolome Database
HMDB0014383
KEGG Drug
D00435
KEGG Compound
C07263
PubChem Compound
4463
PubChem Substance
46506789
ChemSpider
4308
BindingDB
1434
RxNav
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);">

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
FormRouteStrength
Tablet, coatedOral
Tablet, film coatedOral
TabletOral200.000 mg
TabletOral
Tablet, extended releaseOral
SuspensionOral1 g
SuspensionOral50 mg/5mL
Tablet, coatedOral200 mg/1
Tablet, extended releaseOral100 mg/1
TabletOral100 mg/1
TabletOral400 mg/1
SuspensionOral
TabletOral200.0 mg
Tablet, solubleOral
TabletOral200 mg/1
Tablet, extended releaseOral100 MG
Tablet, extended releaseOral400 mg/1
Tablet, extended releaseOral50 MG
Tablet, extended releaseOral400 mg
TabletOral
Tablet, coatedOral200 mg
TabletOral200 mg
Prices
Unit descriptionCostUnit
Viramune 200 mg tablet9.3USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5366972No1994-11-222012-05-22US flag
CA2030056No1995-10-172010-11-15Canada flag
US8460704No2013-06-112029-03-12US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)196.06Not Available
water solubility0.7046 mg/LNot Available
logP2.5Not Available
Caco2 permeability-4.52ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.105 mg/mLALOGPS
logP1.75ALOGPS
logP2.49Chemaxon
logS-3.4ALOGPS
pKa (Strongest Acidic)14.98Chemaxon
pKa (Strongest Basic)3.28Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area58.12 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity77.48 m3·mol-1Chemaxon
Polarizability27.8 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9958
Blood Brain Barrier+0.9756
Caco-2 permeable+0.8867
P-glycoprotein substrateNon-substrate0.5606
P-glycoprotein inhibitor INon-inhibitor0.6488
P-glycoprotein inhibitor IINon-inhibitor0.8514
Renal organic cation transporterNon-inhibitor0.7124
CYP450 2C9 substrateNon-substrate0.6179
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateSubstrate0.6413
CYP450 1A2 substrateInhibitor0.6175
CYP450 2C9 inhibitorNon-inhibitor0.8009
CYP450 2D6 inhibitorNon-inhibitor0.9451
CYP450 2C19 inhibitorNon-inhibitor0.7971
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5443
Ames testAMES toxic0.5952
CarcinogenicityNon-carcinogens0.9383
BiodegradationNot ready biodegradable0.964
Rat acute toxicity2.6729 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9827
hERG inhibition (predictor II)Non-inhibitor0.8321
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-01s9-0890000000-c2ef64541073a1c774c3
MS/MS Spectrum - , positiveLC-MS/MSsplash10-016r-1390000000-cbb2d729a2b310bf5dd0
MS/MS Spectrum - , positiveLC-MS/MSsplash10-016r-0290000000-64af72aec31bfd168e68
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004i-3980000000-98e328d2867c43716973
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0090000000-10bdb19b71518c59c569
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0090000000-d351f6ef3474d3056c8f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0090000000-9bcc7b0fbd855bbc51fd
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0090000000-5f0a3978624cbd981066
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0490000000-f0c614e221a23c83d0ca
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a59-1980000000-e10e618e222fc59ed8e8
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-166.3653361
predicted
DarkChem Lite v0.1.0
[M-H]-166.4877361
predicted
DarkChem Lite v0.1.0
[M-H]-166.5629361
predicted
DarkChem Lite v0.1.0
[M-H]-168.27943
predicted
DeepCCS 1.0 (2019)
[M+H]+167.0910361
predicted
DarkChem Lite v0.1.0
[M+H]+167.0887361
predicted
DarkChem Lite v0.1.0
[M+H]+167.2134361
predicted
DarkChem Lite v0.1.0
[M+H]+170.63744
predicted
DeepCCS 1.0 (2019)
[M+Na]+166.5001361
predicted
DarkChem Lite v0.1.0
[M+Na]+166.8277361
predicted
DarkChem Lite v0.1.0
[M+Na]+176.73059
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
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
  1. 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]
  2. 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]
  3. 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
Substrate
Inhibitor
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
  1. 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]
  2. 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]
  3. 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
  1. 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]
  2. 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]
  3. 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
  1. 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
Substrate
Inducer
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
  1. 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]
  2. 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]
  3. 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]
  4. Indiana University - Department of Medicine Clinical Pharmacology [Link]
  5. Lexicomp database [Link]
  6. Viramune (Nevirapine) FDA Label [Link]
  7. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inducer
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
  1. 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]
  2. 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]
  3. 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]
  4. Viramune (Nevirapine) FDA Label [Link]
  5. 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
  1. 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]
  2. Flockhart Table of Drug Interactions [Link]
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
  1. 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]
  2. 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]
  3. 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
  1. 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]
  2. 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
  1. 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]
  2. 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
  1. 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