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Identification
NameEfavirenz
Accession NumberDB00625  (APRD00059, DB07709)
TypeSmall Molecule
GroupsApproved, Investigational
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.

Structure
Thumb
Synonyms
(-)-6-CHLORO-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one
(S)-6-chloro-4-(Cyclopropylethynyl)-1,4-dihydro-4-(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 Identifiers
  • DMP 266
  • L 743726
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Auro-efavirenztablet600 mgoralAuro Pharma Inc2014-03-03Not applicableCanada
Mylan-efavirenztablet600 mgoralMylan Pharmaceuticals Ulc2013-07-30Not applicableCanada
Sustivacapsule, gelatin coated50 mg/1oralBristol Myers Squibb Pharma Company1998-09-17Not applicableUs
Sustivatablet, film coated600 mg/1oralPhysicians Total Care, Inc.2012-10-11Not applicableUs
Sustivatablet, film coated600 mg/1oralBristol Myers Squibb Pharma Company2002-01-02Not applicableUs
Sustivacapsule, gelatin coated200 mg/1oralBristol Myers Squibb Pharma Company1998-09-17Not applicableUs
Sustiva 100mgcapsule100 mgoralBristol Myers Squibb Canada1999-03-252008-03-27Canada
Sustiva 200mgcapsule200 mgoralBristol Myers Squibb Canada1999-03-25Not applicableCanada
Sustiva 50mgcapsule50 mgoralBristol Myers Squibb Canada1999-03-25Not applicableCanada
Sustiva Tabletstablet600 mgoralBristol Myers Squibb Canada2002-11-05Not applicableCanada
Teva-efavirenztablet600 mgoralTeva Canada Limited2013-07-30Not applicableCanada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
E.FMcNeil & Argus
EfavirCipla
EfavirenzAspen Pharmacare
EfcureEmcure Pharmaceuticals
EffervenRanbaxy Laboratories
EstivaHetero
EvirenzAlkem Laboratories
StocrinMerck & Co.
ViranzAurobindo Pharma
Brand mixtures
NameLabellerIngredients
AtriplaBristol Myers Squibb & Gilead Sciences, Llc
SaltsNot Available
Categories
UNIIJE6H2O27P8
CAS number154598-52-4
WeightAverage: 315.675
Monoisotopic: 315.027390859
Chemical FormulaC14H9ClF3NO2
InChI KeyInChIKey=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)[C@]1(OC(=O)NC2=C1C=C(Cl)C=C2)C#CC1CC1
Taxonomy
DescriptionThis 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).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzoxazines
Sub ClassNot Available
Direct ParentBenzoxazines
Alternative Parents
Substituents
  • Benzoxazine
  • Benzenoid
  • Ynone
  • Aryl halide
  • Aryl chloride
  • Oxacycle
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organochloride
  • Organohalogen compound
  • Alkyl halide
  • Alkyl fluoride
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor use in combination treatment of HIV infection (AIDS)
PharmacodynamicsEfavirenz (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 actionSimilar 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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein binding99.5-99.75%
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.

Route of eliminationNearly all of the urinary excretion of the radiolabeled drug was in the form of metabolites.
Half life40-55 hours
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Human Immunodeficiency Virus
Pathways
PathwayCategorySMPDB ID
Efavirenz Action PathwayDrug actionSMP00740
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
Manufacturers
  • Bristol myers squibb co
  • Bristol myers squibb pharma co
Packagers
Dosage forms
FormRouteStrength
Tabletoral
Tablet, film coatedoral
Capsule, gelatin coatedoral200 mg/1
Capsule, gelatin coatedoral50 mg/1
Tablet, film coatedoral600 mg/1
Capsuleoral100 mg
Capsuleoral200 mg
Capsuleoral50 mg
Tabletoral600 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)
CA2101572 No2001-08-282013-07-29Canada
CA2279198 No2009-04-142018-02-02Canada
US5811423 No1992-08-072012-08-07Us
US5814639 Yes1996-03-292016-03-29Us
US5914331 Yes1998-01-022018-01-02Us
US5922695 Yes1998-01-252018-01-25Us
US5935946 Yes1998-01-252018-01-25Us
US5977089 Yes1998-01-252018-01-25Us
US6043230 Yes1998-01-252018-01-25Us
US6238695 Yes1999-10-062019-10-06Us
US6555133 Yes1999-10-062019-10-06Us
US6639071 Yes1998-08-142018-08-14Us
US6642245 Yes2001-05-042021-05-04Us
US6703396 Yes2001-09-092021-09-09Us
US6939964 Yes1998-07-202018-07-20Us
US8592397 No2004-01-132024-01-13Us
US8598185 No2008-05-012028-05-01Us
US8716264 No2004-01-132024-01-13Us
US9018192 No2006-06-132026-06-13Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point139-141 °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 RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
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 ]
External Links
ATC CodesJ05AG03J05AR06J05AR11
AHFS Codes
  • 08:18.08.16
PDB EntriesNot Available
FDA labelDownload (154 KB)
MSDSDownload (57.6 KB)
Interactions
Drug Interactions
Drug
AcenocoumarolThe serum concentration of Acenocoumarol can be decreased when it is combined with Efavirenz.
AmlodipineThe serum concentration of Amlodipine can be decreased when it is combined with Efavirenz.
AmodiaquineEfavirenz may increase the hepatotoxic activities of Amodiaquine.
AmrinoneThe serum concentration of Amrinone can be decreased when it is combined with Efavirenz.
AripiprazoleThe serum concentration of Aripiprazole can be decreased when it is combined with Efavirenz.
ArtemetherThe serum concentration of Artemether can be decreased when it is combined with Efavirenz.
AtazanavirThe serum concentration of Atazanavir can be decreased when it is combined with Efavirenz.
AtorvastatinThe serum concentration of Atorvastatin can be decreased when it is combined with Efavirenz.
AtovaquoneThe serum concentration of Atovaquone can be decreased when it is combined with Efavirenz.
AxitinibThe serum concentration of Axitinib can be decreased when it is combined with Efavirenz.
AzelastineEfavirenz may increase the central nervous system depressant (CNS depressant) activities of Azelastine.
BaclofenThe risk or severity of adverse effects can be increased when Baclofen is combined with Efavirenz.
BedaquilineThe serum concentration of Bedaquiline can be decreased when it is combined with Efavirenz.
BepridilThe serum concentration of Bepridil can be decreased when it is combined with Efavirenz.
BexaroteneThe serum concentration of Efavirenz can be decreased when it is combined with Bexarotene.
BoceprevirThe serum concentration of Boceprevir can be decreased when it is combined with Efavirenz.
BortezomibThe metabolism of Bortezomib can be decreased when combined with Efavirenz.
BosentanThe serum concentration of Efavirenz can be decreased when it is combined with Bosentan.
BosutinibThe serum concentration of Bosutinib can be decreased when it is combined with Efavirenz.
BrimonidineBrimonidine may increase the central nervous system depressant (CNS depressant) activities of Efavirenz.
BuprenorphineThe serum concentration of the active metabolites of Buprenorphine can be reduced when Buprenorphine is used in combination with Efavirenz resulting in a loss in efficacy.
BupropionThe serum concentration of Bupropion can be decreased when it is combined with Efavirenz.
CanagliflozinThe serum concentration of Canagliflozin can be decreased when it is combined with Efavirenz.
CarbamazepineThe serum concentration of Efavirenz can be decreased when it is combined with Carbamazepine.
CarvedilolThe serum concentration of Carvedilol can be increased when it is combined with Efavirenz.
CaspofunginThe serum concentration of Caspofungin can be decreased when it is combined with Efavirenz.
CilostazolThe serum concentration of Cilostazol can be increased when it is combined with Efavirenz.
CitalopramThe serum concentration of Citalopram can be increased when it is combined with Efavirenz.
ClarithromycinThe serum concentration of Clarithromycin can be decreased when it is combined with Efavirenz.
ClevidipineThe serum concentration of Clevidipine can be decreased when it is combined with Efavirenz.
ClopidogrelThe serum concentration of the active metabolites of Clopidogrel can be reduced when Clopidogrel is used in combination with Efavirenz resulting in a loss in efficacy.
CyclosporineThe serum concentration of Cyclosporine can be decreased when it is combined with Efavirenz.
DabrafenibThe serum concentration of Efavirenz can be decreased when it is combined with Dabrafenib.
DaclatasvirThe serum concentration of Daclatasvir can be decreased when it is combined with Efavirenz.
DarunavirThe serum concentration of Efavirenz can be increased when it is combined with Darunavir.
DeferasiroxThe serum concentration of Efavirenz can be decreased when it is combined with Deferasirox.
DelavirdineThe serum concentration of Efavirenz can be increased when it is combined with Delavirdine.
DicoumarolThe serum concentration of Dicoumarol can be decreased when it is combined with Efavirenz.
DienogestThe serum concentration of Dienogest can be decreased when it is combined with Efavirenz.
DiltiazemThe serum concentration of Diltiazem can be decreased when it is combined with Efavirenz.
DolutegravirThe serum concentration of Dolutegravir can be decreased when it is combined with Efavirenz.
DoxylamineDoxylamine may increase the central nervous system depressant (CNS depressant) activities of Efavirenz.
DronabinolThe serum concentration of Dronabinol can be increased when it is combined with Efavirenz.
DroperidolDroperidol may increase the central nervous system depressant (CNS depressant) activities of Efavirenz.
ElvitegravirThe serum concentration of Elvitegravir can be decreased when it is combined with Efavirenz.
EnzalutamideThe serum concentration of Enzalutamide can be decreased when it is combined with Efavirenz.
EthanolThe risk or severity of adverse effects can be increased when Efavirenz is combined with Ethanol.
EtonogestrelThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Efavirenz.
EtravirineThe serum concentration of Etravirine can be decreased when it is combined with Efavirenz.
EverolimusThe serum concentration of Everolimus can be decreased when it is combined with Efavirenz.
FelodipineThe serum concentration of Felodipine can be decreased when it is combined with Efavirenz.
FentanylThe serum concentration of Fentanyl can be decreased when it is combined with Efavirenz.
FlibanserinThe serum concentration of Flibanserin can be decreased when it is combined with Efavirenz.
FlunarizineThe serum concentration of Flunarizine can be decreased when it is combined with Efavirenz.
FlunisolideThe serum concentration of Flunisolide can be decreased when it is combined with Efavirenz.
FosamprenavirThe serum concentration of the active metabolites of Fosamprenavir can be reduced when Fosamprenavir is used in combination with Efavirenz resulting in a loss in efficacy.
FosphenytoinThe serum concentration of Efavirenz can be decreased when it is combined with Fosphenytoin.
GabapentinThe serum concentration of Gabapentin can be decreased when it is combined with Efavirenz.
Ginkgo bilobaThe serum concentration of Efavirenz can be decreased when it is combined with Ginkgo biloba.
HydrocodoneEfavirenz may increase the central nervous system depressant (CNS depressant) activities of Hydrocodone.
HydroxyzineHydroxyzine may increase the central nervous system depressant (CNS depressant) activities of Efavirenz.
IbrutinibThe serum concentration of Ibrutinib can be decreased when it is combined with Efavirenz.
IfosfamideThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Efavirenz resulting in a loss in efficacy.
IndinavirThe serum concentration of Indinavir can be decreased when it is combined with Efavirenz.
IsradipineThe serum concentration of Isradipine can be decreased when it is combined with Efavirenz.
ItraconazoleThe serum concentration of Itraconazole can be decreased when it is combined with Efavirenz.
KetoconazoleThe serum concentration of Ketoconazole can be decreased when it is combined with Efavirenz.
LamotrigineThe serum concentration of Lamotrigine can be decreased when it is combined with Efavirenz.
LercanidipineThe serum concentration of Lercanidipine can be decreased when it is combined with Efavirenz.
LevonorgestrelThe serum concentration of Levonorgestrel can be decreased when it is combined with Efavirenz.
LopinavirThe serum concentration of Lopinavir can be decreased when it is combined with Efavirenz.
LorazepamThe risk or severity of adverse effects can be increased when Lorazepam is combined with Efavirenz.
LovastatinThe serum concentration of Lovastatin can be decreased when it is combined with Efavirenz.
Magnesium SulfateMagnesium Sulfate may increase the central nervous system depressant (CNS depressant) activities of Efavirenz.
MaravirocThe serum concentration of Maraviroc can be decreased when it is combined with Efavirenz.
Medroxyprogesterone AcetateThe serum concentration of Medroxyprogesterone Acetate can be decreased when it is combined with Efavirenz.
MethadoneThe metabolism of Methadone can be increased when combined with Efavirenz.
MethotrimeprazineEfavirenz may increase the central nervous system depressant (CNS depressant) activities of Methotrimeprazine.
MetyrosineEfavirenz may increase the sedative activities of Metyrosine.
MifepristoneThe serum concentration of Efavirenz can be increased when it is combined with Mifepristone.
MinocyclineMinocycline may increase the central nervous system depressant (CNS depressant) activities of Efavirenz.
MirtazapineEfavirenz may increase the central nervous system depressant (CNS depressant) activities of Mirtazapine.
MitotaneThe serum concentration of Efavirenz can be decreased when it is combined with Mitotane.
NabiloneNabilone may increase the central nervous system depressant (CNS depressant) activities of Efavirenz.
NevirapineThe risk or severity of adverse effects can be increased when Efavirenz is combined with Nevirapine.
NicardipineThe serum concentration of Nicardipine can be decreased when it is combined with Efavirenz.
NifedipineThe serum concentration of Nifedipine can be decreased when it is combined with Efavirenz.
NimodipineThe serum concentration of Nimodipine can be decreased when it is combined with Efavirenz.
NisoldipineThe serum concentration of Nisoldipine can be decreased when it is combined with Efavirenz.
NitrendipineThe serum concentration of Nitrendipine can be decreased when it is combined with Efavirenz.
NorethisteroneThe serum concentration of Norethindrone can be decreased when it is combined with Efavirenz.
NorgestimateThe serum concentration of the active metabolites of Norgestimate can be reduced when Norgestimate is used in combination with Efavirenz resulting in a loss in efficacy.
OlaparibThe serum concentration of Olaparib can be decreased when it is combined with Efavirenz.
OrphenadrineEfavirenz may increase the central nervous system depressant (CNS depressant) activities of Orphenadrine.
PalbociclibThe serum concentration of Palbociclib can be decreased when it is combined with Efavirenz.
PantoprazoleThe metabolism of Pantoprazole can be decreased when combined with Efavirenz.
ParaldehydeEfavirenz may increase the central nervous system depressant (CNS depressant) activities of Paraldehyde.
ParoxetineThe risk or severity of adverse effects can be increased when Efavirenz is combined with Paroxetine.
PerampanelPerampanel may increase the central nervous system depressant (CNS depressant) activities of Efavirenz.
PerhexilineThe serum concentration of Perhexiline can be decreased when it is combined with Efavirenz.
PhenytoinThe serum concentration of Efavirenz can be decreased when it is combined with Phenytoin.
PosaconazoleThe serum concentration of Posaconazole can be decreased when it is combined with Efavirenz.
PramipexoleEfavirenz may increase the sedative activities of Pramipexole.
PravastatinThe serum concentration of Pravastatin can be decreased when it is combined with Efavirenz.
PrenylamineThe serum concentration of Prenylamine can be decreased when it is combined with Efavirenz.
ProguanilThe serum concentration of Proguanil can be decreased when it is combined with Efavirenz.
QuazepamThe serum concentration of Efavirenz can be increased when it is combined with Quazepam.
RanolazineThe serum concentration of Ranolazine can be decreased when it is combined with Efavirenz.
RifabutinThe serum concentration of Rifabutin can be decreased when it is combined with Efavirenz.
RifampicinThe serum concentration of Efavirenz can be decreased when it is combined with Rifampicin.
RilpivirineThe serum concentration of Rilpivirine can be increased when it is combined with Efavirenz.
RisedronateThe serum concentration of Risedronate can be decreased when it is combined with Efavirenz.
RitonavirThe risk or severity of adverse effects can be increased when Efavirenz is combined with Ritonavir.
RolapitantThe serum concentration of Rolapitant can be decreased when it is combined with Efavirenz.
RopiniroleEfavirenz may increase the sedative activities of Ropinirole.
RotigotineEfavirenz may increase the sedative activities of Rotigotine.
RufinamideThe risk or severity of adverse effects can be increased when Rufinamide is combined with Efavirenz.
SaquinavirThe risk or severity of adverse effects can be increased when Saquinavir is combined with Efavirenz.
SaxagliptinThe serum concentration of Saxagliptin can be decreased when it is combined with Efavirenz.
SertralineThe serum concentration of Sertraline can be decreased when it is combined with Efavirenz.
SildenafilThe metabolism of Sildenafil can be decreased when combined with Efavirenz.
SiltuximabThe serum concentration of Efavirenz can be decreased when it is combined with Siltuximab.
SimeprevirThe serum concentration of Simeprevir can be decreased when it is combined with Efavirenz.
SimvastatinThe serum concentration of Simvastatin can be decreased when it is combined with Efavirenz.
SirolimusThe serum concentration of Sirolimus can be decreased when it is combined with Efavirenz.
Sodium oxybateSodium oxybate may increase the central nervous system depressant (CNS depressant) activities of Efavirenz.
SonidegibThe serum concentration of Sonidegib can be decreased when it is combined with Efavirenz.
St. John's WortThe serum concentration of Efavirenz can be decreased when it is combined with St. John's Wort.
SuvorexantEfavirenz may increase the central nervous system depressant (CNS depressant) activities of Suvorexant.
TacrolimusThe serum concentration of Tacrolimus can be decreased when it is combined with Efavirenz.
TapentadolTapentadol may increase the central nervous system depressant (CNS depressant) activities of Efavirenz.
TelaprevirThe serum concentration of Telaprevir can be decreased when it is combined with Efavirenz.
ThalidomideEfavirenz may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
TiclopidineThe metabolism of Efavirenz can be decreased when combined with Ticlopidine.
TocilizumabThe serum concentration of Efavirenz can be decreased when it is combined with Tocilizumab.
TorasemideThe metabolism of Torasemide can be decreased when combined with Efavirenz.
UlipristalThe serum concentration of Ulipristal can be decreased when it is combined with Efavirenz.
VerapamilThe serum concentration of Verapamil can be decreased when it is combined with Efavirenz.
VoriconazoleThe serum concentration of Voriconazole can be decreased when it is combined with Efavirenz.
WarfarinThe serum concentration of Warfarin can be decreased when it is combined with Efavirenz.
ZolpidemEfavirenz may increase the central nervous system depressant (CNS depressant) activities of Zolpidem.
Food Interactions
  • Avoid excessive or chronic alcohol consumption.
  • Take without regard to meals.

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
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
Human
Pharmacological action
unknown
Actions
substrateinhibitorinducer
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  5. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitorinducer
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
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 imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
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 antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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Drug created on June 13, 2005 07:24 / Updated on May 25, 2016 03:19