Identification

Name
Efavirenz
Accession Number
DB00625
Description

Efavirenz (brand names Sustiva® and Stocrin®) is a non-nucleoside reverse transcriptase inhibitor (NNRTI) and is used as part of highly active antiretroviral therapy (HAART) for the treatment of a human immunodeficiency virus (HIV) type 1.

For HIV infection that has not previously been treated, efavirenz and lamivudine in combination with zidovudine or tenofovir is the preferred NNRTI-based regimen.

Efavirenz is also used in combination with other antiretroviral agents as part of an expanded postexposure prophylaxis regimen to prevent HIV transmission for those exposed to materials associated with a high risk for HIV transmission.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 315.675
Monoisotopic: 315.027390859
Chemical Formula
C14H9ClF3NO2
Synonyms
  • (S)-6-chloro-4-(Cyclopropylethynyl)-1,4-dihydro-(S)-6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one
  • (S)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one
  • 6-chloro-4-(2-cyclopropyl-1-ethynyl)-4-trifluoromethyl-(4S)-1,4-dihydro-2H-benzo[d][1,3]oxazin-2-one
  • Efavirenz
  • Éfavirenz
  • Efavirenzum
External IDs
  • DMP 266
  • L 743726

Pharmacology

Indication

For use in combination treatment of HIV infection (AIDS)

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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Pharmacodynamics

Efavirenz (dideoxyinosine, ddI) is an oral non-nucleoside reverse transcriptase inhibitor (NNRTI). It is a synthetic purine derivative and, similar to zidovudine, zalcitabine, and stavudine. Efavirenz was originally approved specifically for the treatment of HIV infections in patients who failed therapy with zidovudine. Currently, the CDC recommends that Efavirenz be given as part of a three-drug regimen that includes another nucleoside reverse transcriptase inhibitor (e.g., lamivudine, stavudine, zidovudine) and a protease inhibitor or efavirenz when treating HIV infection.

Mechanism of action

Similar to zidovudine, efavirenz inhibits the activity of viral RNA-directed DNA polymerase (i.e., reverse transcriptase). Antiviral activity of efavirenz is dependent on intracellular conversion to the active triphosphorylated form. The rate of efavirenz phosphorylation varies, depending on cell type. It is believed that inhibition of reverse transcriptase interferes with the generation of DNA copies of viral RNA, which, in turn, are necessary for synthesis of new virions. Intracellular enzymes subsequently eliminate the HIV particle that previously had been uncoated, and left unprotected, during entry into the host cell. Thus, reverse transcriptase inhibitors are virustatic and do not eliminate HIV from the body. Even though human DNA polymerase is less susceptible to the pharmacologic effects of triphosphorylated efavirenz, this action may nevertheless account for some of the drug's toxicity.

TargetActionsOrganism
AReverse transcriptase/RNaseH
inhibitor
Human immunodeficiency virus 1
Absorption
Not Available
Volume of distribution
Not Available
Protein binding

99.5-99.75%

Metabolism

Efavirenz is principally metabolized by the cytochrome P450 system to hydroxylated metabolites with subsequent glucuronidation of these hydroxylated metabolites. These metabolites are essentially inactive against HIV-1.

Hover over products below to view reaction partners

Route of elimination

Nearly all of the urinary excretion of the radiolabeled drug was in the form of metabolites.

Half-life

40-55 hours

Clearance
Not Available
Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity
Not Available
Affected organisms
  • Human Immunodeficiency Virus
Pathways
PathwayCategory
Efavirenz Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 2B6CYP2B6*6Not AvailableG > T / A > GEffect Directly StudiedThe presence of this polymorphism in CYP2B6 is associated with reduction in efavirenz metabolism.Details

Interactions

Drug Interactions
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
AbacavirThe metabolism of Abacavir can be increased when combined with Efavirenz.
AbametapirThe serum concentration of Efavirenz can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Efavirenz can be increased when combined with Abatacept.
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Efavirenz.
AbirateroneThe serum concentration of Abiraterone can be increased when it is combined with Efavirenz.
AcalabrutinibThe metabolism of Acalabrutinib can be increased when combined with Efavirenz.
AcebutololThe risk or severity of QTc prolongation can be increased when Efavirenz is combined with Acebutolol.
AcenocoumarolThe metabolism of Acenocoumarol can be increased when combined with Efavirenz.
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Efavirenz.
AcetazolamideThe risk or severity of adverse effects can be increased when Efavirenz is combined with Acetazolamide.
Additional Data Available
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  • Evidence Level
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  • Action
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Food Interactions
  • Avoid excessive or chronic alcohol consumption.
  • Take with or without food. The absorption is unaffected by food.

Products

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Product Images
International/Other Brands
E.F. (McNeil & Argus) / Efavir (Cipla) / Efcure (Emcure Pharmaceuticals) / Efferven (Ranbaxy Laboratories) / Estiva (Hetero) / Evirenz (Alkem Laboratories) / Viranz (Aurobindo Pharma)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AtriplaTablet, film coated600 mg/1OralRemedy Repack2013-03-292014-03-29US flag
EfavirenzTablet, film coated600 mg/1OralMylan Laboratories Limited2016-02-17Not applicableUS flag
StocrinCapsule50 mgOralMerck Sharp & Dohme B.V.1999-05-28Not applicableEU flag
StocrinTablet, film coated600 mgOralMerck Sharp & Dohme B.V.1999-05-28Not applicableEU flag
StocrinTablet, film coated200 mgOralMerck Sharp & Dohme B.V.1999-05-28Not applicableEU flag
StocrinCapsule200 mgOralMerck Sharp & Dohme B.V.1999-05-28Not applicableEU flag
StocrinSolution30 mg/mlOralMerck Sharp & Dohme B.V.1999-05-28Not applicableEU flag
StocrinCapsule100 mgOralMerck Sharp & Dohme B.V.1999-05-28Not applicableEU flag
StocrinTablet, film coated50 mgOralMerck Sharp & Dohme B.V.1999-05-28Not applicableEU flag
StocrinCapsule200 mgOralMerck Sharp & Dohme B.V.1999-05-28Not applicableEU flag
Additional Data Available
  • Application Number
    Application Number
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    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code
    Available for Purchase

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Auro-efavirenzTabletOralAuro Pharma Inc2014-03-03Not applicableCanada flag
EfavirenzTablet600 mg/1OralREMEDYREPACK INC.2018-04-06Not applicableUS flag
EfavirenzCapsule50 mg/1OralAurobindo Pharma Limited2017-12-15Not applicableUS flag
EfavirenzCapsule50 mg/1OralRising Pharmaceuticals, Inc.2017-12-15Not applicableUS flag
EfavirenzCapsule200 mg/1OralAurobindo Pharma Limited2017-12-15Not applicableUS flag
EfavirenzTablet600 mg/1OralStrides Pharma Science Limited2018-03-29Not applicableUS flag
EfavirenzTablet, film coated600 mg/1OralCamber Pharmaceuticals, Inc.2018-04-27Not applicableUS flag
EfavirenzTablet, film coated600 mg/1OralREMEDYREPACK INC.2018-02-122020-05-11US flag
EfavirenzTablet, film coated600 mg/1OralAurobindo Pharma Limited2018-09-21Not applicableUS flag
EfavirenzTablet, film coated600 mg/1OralCipla USA Inc.2018-06-18Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code
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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Apo-efavirenz-emtricitabine-tenofovirEfavirenz (600 mg) + Emtricitabine (200 mg) + Tenofovir disoproxil fumarate (300 mg)TabletOralApotex Corporation2018-09-04Not applicableCanada flag
AtriplaEfavirenz (600 mg/1) + Emtricitabine (200 mg/1) + Tenofovir disoproxil fumarate (300 mg/1)Tablet, film coatedOralPhysicians Total Care, Inc.2012-10-16Not applicableUS flag
AtriplaEfavirenz (600 mg/1) + Emtricitabine (200 mg/1) + Tenofovir disoproxil fumarate (300 mg/1)Tablet, film coatedOralGilead Sciences, Llc2006-07-20Not applicableUS flag
AtriplaEfavirenz (600 mg/1) + Emtricitabine (200 mg/1) + Tenofovir disoproxil fumarate (300 mg/1)Tablet, film coatedOralAvera McKennan Hospital2015-03-062017-05-24US flag
AtriplaEfavirenz (600 mg/1) + Emtricitabine (200 mg/1) + Tenofovir disoproxil fumarate (300 mg/1)Tablet, film coatedOralREMEDYREPACK INC.2017-03-20Not applicableUS flag
AtriplaEfavirenz (600 mg/1) + Emtricitabine (200 mg/1) + Tenofovir disoproxil fumarate (300 mg/1)Tablet, film coatedOralDoh Central Pharmacy2009-07-01Not applicableUS flag
AtriplaEfavirenz (600 mg/1) + Emtricitabine (200 mg/1) + Tenofovir disoproxil fumarate (300 mg/1)Tablet, film coatedOralA-S Medication Solutions2006-07-202019-11-30US flag
AtriplaEfavirenz (600 mg/1) + Emtricitabine (200 mg/1) + Tenofovir disoproxil fumarate (300 mg/1)Tablet, film coatedOralA-S Medication Solutions2006-07-20Not applicableUS flag
AtriplaEfavirenz (600 mg/1) + Emtricitabine (200 mg/1) + Tenofovir disoproxil fumarate (300 mg/1)Tablet, film coatedOralLake Erie Medical Dba Quality Care Produts Llc2006-07-202014-12-31US flag
AtriplaEfavirenz (600 mg) + Emtricitabine (200 mg) + Tenofovir disoproxil fumarate (300 mg)TabletOralGilead Sciences, Llc2007-10-23Not applicableCanada flag

Categories

ATC Codes
J05AR06 — Emtricitabine, tenofovir disoproxil and efavirenzJ05AG03 — EfavirenzJ05AR11 — Lamivudine, tenofovir disoproxil and efavirenz
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzoxazines. These are organic compounds containing a benzene fused to an oxazine ring (a six-membered aliphatic ring with four carbon atoms, one oxygen atom, and one nitrogen atom).
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzoxazines
Sub Class
Not Available
Direct Parent
Benzoxazines
Alternative Parents
Ynones / Benzenoids / Aryl chlorides / Propargyl-type 1,3-dipolar organic compounds / Oxacyclic compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organofluorides / Organochlorides
show 2 more
Substituents
Alkyl fluoride / Alkyl halide / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenoid / Benzoxazine / Hydrocarbon derivative / Organic 1,3-dipolar compound
show 11 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organofluorine compound, organochlorine compound, cyclopropanes, acetylenic compound, benzoxazine (CHEBI:119486)

Chemical Identifiers

UNII
JE6H2O27P8
CAS number
154598-52-4
InChI Key
XPOQHMRABVBWPR-ZDUSSCGKSA-N
InChI
InChI=1S/C14H9ClF3NO2/c15-9-3-4-11-10(7-9)13(14(16,17)18,21-12(20)19-11)6-5-8-1-2-8/h3-4,7-8H,1-2H2,(H,19,20)/t13-/m0/s1
IUPAC Name
(4S)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one
SMILES
FC(F)(F)[[email protected]]1(OC(=O)NC2=C1C=C(Cl)C=C2)C#CC1CC1

References

Synthesis Reference

John Doney, "Amorphous efavirenz and the production thereof." U.S. Patent US20070026073, issued February 01, 2007.

US20070026073
General References
  1. Ren J, Bird LE, Chamberlain PP, Stewart-Jones GB, Stuart DI, Stammers DK: Structure of HIV-2 reverse transcriptase at 2.35-A resolution and the mechanism of resistance to non-nucleoside inhibitors. Proc Natl Acad Sci U S A. 2002 Oct 29;99(22):14410-5. Epub 2002 Oct 17. [PubMed:12386343]
  2. Robertson SM, Penzak SR, Lane J, Pau AK, Mican JM: A potentially significant interaction between efavirenz and phenytoin: a case report and review of the literature. Clin Infect Dis. 2005 Jul 15;41(2):e15-8. doi: 10.1086/431208. Epub 2005 Jun 7. [PubMed:15983905]
  3. Michaud V, Ogburn E, Thong N, Aregbe AO, Quigg TC, Flockhart DA, Desta Z: Induction of CYP2C19 and CYP3A activity following repeated administration of efavirenz in healthy volunteers. Clin Pharmacol Ther. 2012 Mar;91(3):475-82. doi: 10.1038/clpt.2011.249. Epub 2012 Feb 8. [PubMed:22318618]
  4. FDA Approved Drugs: Sustiva® oral capsules/tablets [Link]
Human Metabolome Database
HMDB0014763
KEGG Drug
D00896
KEGG Compound
C08088
PubChem Compound
64139
PubChem Substance
46506827
ChemSpider
57715
BindingDB
2483
RxNav
195085
ChEBI
119486
ChEMBL
CHEMBL223228
ZINC
ZINC000002020233
Therapeutic Targets Database
DAP000709
PharmGKB
PA449441
PDBe Ligand
EFZ
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Efavirenz
AHFS Codes
  • 08:18.08.16 — Nonnucleoside Reverse Transcriptase Inhibitors
PDB Entries
1fk9 / 1fko / 1ikv / 1ikw / 1jkh / 4b3o / 6bsg / 6bsh / 6bsi / 6bsj
FDA label
Download (154 KB)
MSDS
Download (57.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingOtherHuman Immunodeficiency Virus (HIV) Infections1
4CompletedNot AvailableHealthy Volunteers1
4CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
4CompletedBasic ScienceHuman Immunodeficiency Virus (HIV) Infections1
4CompletedDiagnosticCardiovascular Heart Disease / HIV-Associated Lipodystrophy Syndrome1
4CompletedDiagnosticHuman Immunodeficiency Virus (HIV) Infections / Lipodystrophies1
4CompletedOtherHealthy Volunteers1
4CompletedPreventionCentral Nervous System Diseases / Dementia / Human Immunodeficiency Virus (HIV) Infections1
4CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
4CompletedPreventionHuman Immunodeficiency Virus Type 1 (HIV-1) Infection1

Pharmacoeconomics

Manufacturers
  • Bristol myers squibb co
  • Bristol myers squibb pharma co
Packagers
  • Apotheca Inc.
  • Bristol-Myers Squibb Co.
  • Lake Erie Medical and Surgical Supply
  • Physicians Total Care Inc.
  • Remedy Repack
Dosage Forms
FormRouteStrength
Tablet, film coatedOral
Tablet, coatedOral400 mg
TabletOral600 mg
Tablet, film coatedOral245 mg
CapsuleOral100 mg/1
TabletOral600 mg/1
Tablet, coatedOral200 mg
TabletOral
Tablet, film coatedOral
Tablet, coatedOral0.6 g
CapsuleOral100 mg
CapsuleOral200 mg
CapsuleOral50 mg
SolutionOral30 mg/ml
Tablet, coatedOral50 mg
Tablet, film coatedOral200 mg
Tablet, film coatedOral50 mg
Tablet, film coatedOral600 mg
TabletOral200 MG
Tablet, coatedOral600 mg
CapsuleOral200 mg/1
CapsuleOral50 mg/1
Capsule, gelatin coatedOral200 mg/1
Capsule, gelatin coatedOral50 mg/1
SolutionOral30 MG
Tablet, film coatedOral600 mg/1
CapsuleOral
TabletOral
Tablet, film coatedOral300 mg
Prices
Unit descriptionCostUnit
Sustiva 600 mg tablet21.68USD tablet
Sustiva 200 mg capsule7.37USD capsule
Sustiva 100 mg capsule3.34USD capsule
Sustiva 50 mg capsule1.84USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5811423No1998-09-222012-08-07US flag
CA2279198No2009-04-142018-02-02Canada flag
CA2101572No2001-08-282013-07-29Canada flag
US5914331Yes1999-06-222018-01-02US flag
US6043230Yes2000-03-282018-01-25US flag
US5814639Yes1998-09-292017-03-29US flag
US6555133Yes2003-04-292019-10-06US flag
US6939964Yes2005-09-062018-07-20US flag
US6639071Yes2003-10-282018-08-14US flag
US6238695Yes2001-05-292019-10-06US flag
US6642245Yes2003-11-042021-05-04US flag
US6703396Yes2004-03-092021-09-09US flag
US5922695Yes1999-07-132018-01-25US flag
US5935946Yes1999-08-102018-01-25US flag
US5977089Yes1999-11-022018-01-25US flag
US8592397No2013-11-262024-01-13US flag
US8716264No2014-05-062024-01-13US flag
US9018192No2015-04-282026-06-13US flag
US8598185No2013-12-032028-05-01US flag
US9545414No2017-01-172026-06-13US flag
US9457036No2016-10-042024-01-13US flag
US9744181No2017-08-292024-01-13US flag
Additional Data Available
  • Filed On
    Filed On
    Available for Purchase

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)139-141 °CNot Available
logP4.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00855 mg/mLALOGPS
logP3.89ALOGPS
logP4.46ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)12.52ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.33 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity71.34 m3·mol-1ChemAxon
Polarizability26.81 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9964
Blood Brain Barrier+0.9182
Caco-2 permeable+0.5553
P-glycoprotein substrateNon-substrate0.7617
P-glycoprotein inhibitor INon-inhibitor0.7451
P-glycoprotein inhibitor IINon-inhibitor0.9557
Renal organic cation transporterNon-inhibitor0.9157
CYP450 2C9 substrateNon-substrate0.8033
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.6037
CYP450 1A2 substrateInhibitor0.6996
CYP450 2C9 inhibitorNon-inhibitor0.6975
CYP450 2D6 inhibitorNon-inhibitor0.8699
CYP450 2C19 inhibitorNon-inhibitor0.5291
CYP450 3A4 inhibitorNon-inhibitor0.7577
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6705
Ames testNon AMES toxic0.6991
CarcinogenicityNon-carcinogens0.8997
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5416 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9617
hERG inhibition (predictor II)Non-inhibitor0.9098
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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-03di-1059000000-f599b397bafd1974176e
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-014l-5090000000-b807e6fcee57f8b27cb6
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-014i-9040000000-260d9ba8c55987cd2b0e
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-014i-9010000000-459e48522e8275e941f8
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-014i-9000000000-531ef8f962aff7837863
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-014i-9000000000-9574533b450f3724a645
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-03dl-0098000000-f0d050ef36094b37e62d
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0fxx-0091000000-8ab690a60877e8476640
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0frx-0190000000-deeefb25f97b767955b2
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0giu-0390000000-7a682b484377bc11de1b
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-01b9-0790000000-a789e578dcf6568d7eb9
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-0930000000-a1dae29a53e6be48d87f
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014r-0910000000-70a86e64f2e50ce28b18
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00xu-0390000000-d7561e61b30a86d9a480
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0giu-1290000000-c402be3d2864520be5fb

Targets

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. Gazzard BG: Efavirenz in the management of HIV infection. Int J Clin Pract. 1999 Jan-Feb;53(1):60-4. [PubMed:10344069]
  2. Adkins JC, Noble S: Efavirenz. Drugs. 1998 Dec;56(6):1055-64; discussion 1065-6. [PubMed:9878993]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Michaud V, Ogburn E, Thong N, Aregbe AO, Quigg TC, Flockhart DA, Desta Z: Induction of CYP2C19 and CYP3A activity following repeated administration of efavirenz in healthy volunteers. Clin Pharmacol Ther. 2012 Mar;91(3):475-82. doi: 10.1038/clpt.2011.249. Epub 2012 Feb 8. [PubMed:22318618]
  2. Michaud V, Kreutz Y, Skaar T, Ogburn E, Thong N, Flockhart DA, Desta Z: Efavirenz-mediated induction of omeprazole metabolism is CYP2C19 genotype dependent. Pharmacogenomics J. 2014 Apr;14(2):151-9. doi: 10.1038/tpj.2013.17. Epub 2013 Apr 30. [PubMed:23629159]
  3. Xu C, Desta Z: In vitro analysis and quantitative prediction of efavirenz inhibition of eight cytochrome P450 (CYP) enzymes: major effects on CYPs 2B6, 2C8, 2C9 and 2C19. Drug Metab Pharmacokinet. 2013;28(4):362-71. Epub 2013 Feb 5. [PubMed:23385314]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
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. Xu C, Desta Z: In vitro analysis and quantitative prediction of efavirenz inhibition of eight cytochrome P450 (CYP) enzymes: major effects on CYPs 2B6, 2C8, 2C9 and 2C19. Drug Metab Pharmacokinet. 2013;28(4):362-71. Epub 2013 Feb 5. [PubMed:23385314]
  2. Efavirenz FDA label [File]
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. [PubMed:19515014]
  2. Hesse LM, von Moltke LL, Shader RI, Greenblatt DJ: Ritonavir, efavirenz, and nelfinavir inhibit CYP2B6 activity in vitro: potential drug interactions with bupropion. Drug Metab Dispos. 2001 Feb;29(2):100-2. [PubMed:11159797]
  3. Walsky RL, Astuccio AV, Obach RS: Evaluation of 227 drugs for in vitro inhibition of cytochrome P450 2B6. J Clin Pharmacol. 2006 Dec;46(12):1426-38. [PubMed:17101742]
  4. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
  5. Fahmi OA, Shebley M, Palamanda J, Sinz MW, Ramsden D, Einolf HJ, Chen L, Wang H: Evaluation of CYP2B6 Induction and Prediction of Clinical Drug-Drug Interactions: Considerations from the IQ Consortium Induction Working Group-An Industry Perspective. Drug Metab Dispos. 2016 Oct;44(10):1720-30. doi: 10.1124/dmd.116.071076. Epub 2016 Jul 15. [PubMed:27422672]
  6. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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. Lakhman SS, Ma Q, Morse GD: Pharmacogenomics of CYP3A: considerations for HIV treatment. Pharmacogenomics. 2009 Aug;10(8):1323-39. doi: 10.2217/pgs.09.53. [PubMed:19663676]
  2. Zhu M, Kaul S, Nandy P, Grasela DM, Pfister M: Model-based approach to characterize efavirenz autoinduction and concurrent enzyme induction with carbamazepine. Antimicrob Agents Chemother. 2009 Jun;53(6):2346-53. doi: 10.1128/AAC.01120-08. Epub 2009 Feb 17. [PubMed:19223624]
  3. Hariparsad N, Nallani SC, Sane RS, Buckley DJ, Buckley AR, Desai PB: Induction of CYP3A4 by efavirenz in primary human hepatocytes: comparison with rifampin and phenobarbital. J Clin Pharmacol. 2004 Nov;44(11):1273-81. doi: 10.1177/0091270004269142. [PubMed:15496645]
  4. Malaty LI, Kuper JJ: Drug interactions of HIV protease inhibitors. Drug Saf. 1999 Feb;20(2):147-69. doi: 10.2165/00002018-199920020-00005. [PubMed:10082072]
  5. FDA table of interactions [Link]
  6. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
  7. Efavirenz FDA label [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
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. Flockhart Table of Drug Interactions [Link]
  2. FDA table of interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
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. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Curator comments
The FDA label states that this enzyme inhibition occurs in vitro and is unlikely to occur at therapeutic concentrations.
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. Metzger IF, Dave N, Kreutz Y, Lu JBL, Galinsky RE, Desta Z: CYP2B6 Genotype-Dependent Inhibition of CYP1A2 and Induction of CYP2A6 by the Antiretroviral Drug Efavirenz in Healthy Volunteers. Clin Transl Sci. 2019 Jul 24. doi: 10.1111/cts.12671. [PubMed:31339646]
  2. Xu C, Desta Z: In vitro analysis and quantitative prediction of efavirenz inhibition of eight cytochrome P450 (CYP) enzymes: major effects on CYPs 2B6, 2C8, 2C9 and 2C19. Drug Metab Pharmacokinet. 2013;28(4):362-71. Epub 2013 Feb 5. [PubMed:23385314]
  3. Ogburn ET, Jones DR, Masters AR, Xu C, Guo Y, Desta Z: Efavirenz primary and secondary metabolism in vitro and in vivo: identification of novel metabolic pathways and cytochrome P450 2A6 as the principal catalyst of efavirenz 7-hydroxylation. Drug Metab Dispos. 2010 Jul;38(7):1218-29. doi: 10.1124/dmd.109.031393. Epub 2010 Mar 24. [PubMed:20335270]
  4. Efavirenz FDA label [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
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. [PubMed:11225565]
  2. Xu C, Desta Z: In vitro analysis and quantitative prediction of efavirenz inhibition of eight cytochrome P450 (CYP) enzymes: major effects on CYPs 2B6, 2C8, 2C9 and 2C19. Drug Metab Pharmacokinet. 2013;28(4):362-71. Epub 2013 Feb 5. [PubMed:23385314]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
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
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inducer
General Function
Steroid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name
UGT1A1
Uniprot ID
P22309
Uniprot Name
UDP-glucuronosyltransferase 1-1
Molecular Weight
59590.91 Da
References
  1. Interactions [Link]

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. [PubMed:15814459]
  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. [PubMed:16336266]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Transporter activity
Specific Function
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name
ABCB11
Uniprot ID
O95342
Uniprot Name
Bile salt export pump
Molecular Weight
146405.83 Da
References
  1. Pedersen JM, Matsson P, Bergstrom CA, Hoogstraate J, Noren A, LeCluyse EL, Artursson P: Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43. doi: 10.1093/toxsci/kft197. Epub 2013 Sep 6. [PubMed:24014644]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
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. [PubMed:25914645]
  2. Arimany-Nardi C, Minuesa G, Keller T, Erkizia I, Koepsell H, Martinez-Picado J, Pastor-Anglada M: Role of Human Organic Cation Transporter 1 (hOCT1) Polymorphisms in Lamivudine (3TC) Uptake and Drug-Drug Interactions. Front Pharmacol. 2016 Jun 24;7:175. doi: 10.3389/fphar.2016.00175. eCollection 2016. [PubMed:27445813]
  3. Ceckova M, Reznicek J, Deutsch B, Fromm MF, Staud F: Efavirenz reduces renal excretion of lamivudine in rats by inhibiting organic cation transporters (OCT, Oct) and multidrug and toxin extrusion proteins (MATE, Mate). PLoS One. 2018 Aug 16;13(8):e0202706. doi: 10.1371/journal.pone.0202706. eCollection 2018. [PubMed:30114293]

Drug created on June 13, 2005 07:24 / Updated on November 29, 2020 03:54

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