U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C14H9ClF3NO2
Molecular Weight 315.675
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EFAVIRENZ

SMILES

FC(F)(F)[C@]1(OC(=O)NC2=CC=C(Cl)C=C12)C#CC3CC3

InChI

InChIKey=XPOQHMRABVBWPR-ZDUSSCGKSA-N
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

HIDE SMILES / InChI

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.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Four new antiretroviral medications will soon offer more options to HIV patients.
1998 Jul-Aug
Antiretroviral therapy in pregnancy: a focus on safety.
2001
A single amino acid change at Leu-188 in the reverse transcriptase of HIV-2 and SIV renders them sensitive to non-nucleoside reverse transcriptase inhibitors.
2001
Efavirenz: a pharmacoeconomic review of its use in HIV infection.
2001
An open-label randomized trial to evaluate different therapeutic strategies of combination therapy in HIV-1 infection: design, rationale, and methods of the initio trial.
2001 Apr
Performance of a quadruple combination including nelfinavir plus efavirenz in naive subjects with high baseline viral load and in patients failing protease inhibitor-containing regimens.
2001 Apr 1
Persistent dyslipidemia in HIV-infected individuals switched from a protease inhibitor-containing to an efavirenz-containing regimen.
2001 Apr 1
High prevalence of genotypic and phenotypic HIV-1 drug-resistant strains among patients receiving antiretroviral therapy in Abidjan, Côte d'Ivoire.
2001 Apr 15
A pilot study of the use of mycophenolate mofetil as a component of therapy for multidrug-resistant HIV-1 infection.
2001 Apr 15
[Results of the AIDS-In-Europe Study. Non-nucleoside reverse transcriptase inhibitor does not equal non-nucleoside reverse transcriptase inhibitor].
2001 Apr 2
[Positive change from protease inhibitor to non-nucleoside reverse transcriptase inhibitor efavirenz. Improved virus control thanks to protease inhibitor switch].
2001 Apr 2
Efavirenz as a substitute for protease inhibitors in HIV-1-infected patients with undetectable plasma viral load on HAART: a median follow-up of 64 weeks.
2001 Aug 15
Non-nucleoside reverse transcriptase inhibitor failure impairs HIV-RNA responses to efavirenz-containing salvage antiretroviral therapy.
2001 Aug 17
Solution structures and reactivities of the mixed aggregates derived from n-butyllithium and vicinal amino alkoxides.
2001 Aug 22
Nelfinavir, efavirenz, or both after the failure of nucleoside treatment of HIV infection.
2001 Aug 9
Quinoxalinylethylpyridylthioureas (QXPTs) as potent non-nucleoside HIV-1 reverse transcriptase (RT) inhibitors. Further SAR studies and identification of a novel orally bioavailable hydrazine-based antiviral agent.
2001 Feb 1
Protease-sparing regimen in a real-life practice with naïve patients: an equal opportunity approach?
2001 Jan-Feb
Eruptive cheilitis: a new adverse effect in reactive HIV-positive patients subjected to high activity antiretroviral therapy (HAART). Presentation of six clinical cases.
2001 Jan-Feb
Predictors of protease inhibitor-associated adverse events.
2001 Jul
Gynecomastia without lipodystrophy syndrome in HIV-infected men treated with efavirenz.
2001 Jul 27
Management of sudden psychiatric disorders related to efavirenz.
2001 Jul 6
Metformin in an HIV-infected patient with protease inhibitor-induced diabetic ketoacidosis.
2001 Jul-Aug
Limits of deep salvage antiretroviral therapy with nelfinavir plus either efavirenz or nevirapine, in highly pre-treated patients with HIV disease.
2001 Jun
[Vertical trasmission of human immunodeficiency virus (HIV) and other sexually transmitted infections (STI)].
2001 Jun
Phenotypic hypersusceptibility to non-nucleoside reverse transcriptase inhibitors in treatment-experienced HIV-infected patients: impact on virological response to efavirenz-based therapy.
2001 Jun 15
4,1-Benzoxazepinone analogues of efavirenz (Sustiva) as HIV-1 reverse transcriptase inhibitors.
2001 Jun 4
2-Amino-6-arylsulfonylbenzonitriles as non-nucleoside reverse transcriptase inhibitors of HIV-1.
2001 Jun 7
Identification of a putative binding site for [2',5'-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)thymine (TSAO) derivatives at the p51-p66 interface of HIV-1 reverse transcriptase.
2001 Jun 7
Synthesis and biological activities of potential metabolites of the non-nucleoside reverse transcriptase inhibitor efavirenz.
2001 Mar 12
Anti-AIDS drugs available 'at cost'.
2001 Mar 15
Competition prompts drug companies to cut antiretroviral drug prices.
2001 Mar 17
Sequencing antiretroviral drugs.
2001 Mar 30
Efavirenz-induced acute eosinophilic hepatitis.
2001 May
Development and validation of a reverse-phase HPLC method for analysis of efavirenz and its related substances in the drug substance and in a capsule formulation.
2001 May
Pulmonary hypersensitivity reaction induced by efavirenz.
2001 May 12
Efavirenz-induced photoallergic dermatitis in HIV.
2001 May 25
[Apropos of atypical melancholia with Sustiva (efavirenz)].
2001 May-Jun
[Drug interactions with antiretroviral agents].
2001 May-Jun
Evidence of hypertriglyceridemia in managing HIV patients on efavirenz.
2001 May-Jun
Other issues: penetration into sanctuary sites, immune reconstitution and NNRTI sequencing.
2001 Nov
Factors affecting adherence and convenience in antiretroviral therapy.
2001 Nov
Comparison of NNRTIs in antiretroviral-experienced patients.
2001 Nov
Comparison of NNRTIs in antiretroviral-naïve patients.
2001 Nov
The role of NNRTIs in antiretroviral combination therapy: an introduction.
2001 Nov
The stereoselective targeting of a specific enzyme-substrate complex is the molecular mechanism for the synergic inhibition of HIV-1 reverse transcriptase by (R)-(-)-PPO464: a novel generation of nonnucleoside inhibitors.
2001 Nov 30
Thiosugars. VIII. Preparation of new 4'-thio-L-lyxo pyrimidine nucleoside analogues.
2001 Sep
Mismatched double-stranded RNA (polyI-polyC(12)U) is synergistic with multiple anti-HIV drugs and is active against drug-sensitive and drug-resistant HIV-1 in vitro.
2001 Sep
Efavirenz-induced psychosis.
2001 Sep 28
Response to first protease inhibitor- and efavirenz-containing antiretroviral combination therapy. The Swiss HIV Cohort Study.
2001 Sep 28
Structural mechanisms of drug resistance for mutations at codons 181 and 188 in HIV-1 reverse transcriptase and the improved resilience of second generation non-nucleoside inhibitors.
2001 Sep 28
Patents

Sample Use Guides

In Vivo Use Guide
SUSTIVA should be taken orally once daily on an empty stomach, preferably at bedtime. • Recommended adult dose: 600 mg. • With voriconazole, increase voriconazole maintenance dose to 400 mg every 12 hours and decrease SUSTIVA dose to 300 mg once daily using the capsule formulation.
Route of Administration: Oral
In Vitro Use Guide
10 pM efavirenz completely inhibited 0.5 U HIV RT.
Name Type Language
EFAVIRENZ
EMA EPAR   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USP-RS   VANDF   WHO-DD   WHO-IP  
INN  
Official Name English
SUSTIVA
Brand Name English
(S)-6-CHLORO-4-(CYCLOPROPYLETHYNYL)-1,4-DIHYDRO-4-(TRIFLUOROMETHYL)-2H-3,1-BENZOXAZIN-2-ONE
Systematic Name English
EFAVIRENZ [EMA EPAR]
Common Name English
EFAVIRENZ [MI]
Common Name English
EFAVIRENZ [VANDF]
Common Name English
EFAVIRENZ [ORANGE BOOK]
Common Name English
EFAVIRENZ [WHO-IP]
Common Name English
EFAVIRENZ [WHO-DD]
Common Name English
EFAVIRENZUM [WHO-IP LATIN]
Common Name English
EFAVIRENZ [HSDB]
Common Name English
EFAVIRENZ [JAN]
Common Name English
VIRADAY
Brand Name English
EFAVIRENZ [INN]
Common Name English
TELURA COMPONENT EFAVIRENZ
Common Name English
STOCRIN
Brand Name English
EFAVIRENZ [USP-RS]
Common Name English
EFAVIRENZ TEVA
Brand Name English
EFV
Common Name English
EFAVIRENZ [MART.]
Common Name English
EFAVIRENZ COMPONENT OF ATRIPLA
Common Name English
ATRIPLA COMPONENT EFAVIRENZ
Common Name English
Classification Tree Code System Code
NDF-RT N0000009948
Created by admin on Mon Oct 21 19:49:24 UTC 2019 , Edited by admin on Mon Oct 21 19:49:24 UTC 2019
LIVERTOX 341
Created by admin on Mon Oct 21 19:49:24 UTC 2019 , Edited by admin on Mon Oct 21 19:49:24 UTC 2019
WHO-ATC J05AR11
Created by admin on Mon Oct 21 19:49:24 UTC 2019 , Edited by admin on Mon Oct 21 19:49:24 UTC 2019
NDF-RT N0000175460
Created by admin on Mon Oct 21 19:49:24 UTC 2019 , Edited by admin on Mon Oct 21 19:49:24 UTC 2019
EMA ASSESSMENT REPORTS SUSTIVA (AUTHORIZED: HIV INFECTIONS)
Created by admin on Mon Oct 21 19:49:24 UTC 2019 , Edited by admin on Mon Oct 21 19:49:24 UTC 2019
EMA ASSESSMENT REPORTS ATRIPLA (AUTHORIZED: HIV INFECTIONS)
Created by admin on Mon Oct 21 19:49:24 UTC 2019 , Edited by admin on Mon Oct 21 19:49:24 UTC 2019
NDF-RT N0000175463
Created by admin on Mon Oct 21 19:49:24 UTC 2019 , Edited by admin on Mon Oct 21 19:49:24 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 6.4.2.3 (EFV/FTC/TEN)
Created by admin on Mon Oct 21 19:49:24 UTC 2019 , Edited by admin on Mon Oct 21 19:49:24 UTC 2019
WHO-VATC QJ05AR11
Created by admin on Mon Oct 21 19:49:24 UTC 2019 , Edited by admin on Mon Oct 21 19:49:24 UTC 2019
WHO-ATC J05AR06
Created by admin on Mon Oct 21 19:49:24 UTC 2019 , Edited by admin on Mon Oct 21 19:49:24 UTC 2019
WHO-VATC QJ05AR06
Created by admin on Mon Oct 21 19:49:24 UTC 2019 , Edited by admin on Mon Oct 21 19:49:24 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 6.4.2.2
Created by admin on Mon Oct 21 19:49:24 UTC 2019 , Edited by admin on Mon Oct 21 19:49:24 UTC 2019
NCI_THESAURUS C97453
Created by admin on Mon Oct 21 19:49:24 UTC 2019 , Edited by admin on Mon Oct 21 19:49:24 UTC 2019
WHO-VATC QJ05AG03
Created by admin on Mon Oct 21 19:49:24 UTC 2019 , Edited by admin on Mon Oct 21 19:49:24 UTC 2019
WHO-ATC J05AG03
Created by admin on Mon Oct 21 19:49:24 UTC 2019 , Edited by admin on Mon Oct 21 19:49:24 UTC 2019
EMA ASSESSMENT REPORTS STOCRIN (AUTHORIZED: HIV INFECTIONS)
Created by admin on Mon Oct 21 19:49:24 UTC 2019 , Edited by admin on Mon Oct 21 19:49:24 UTC 2019
EMA ASSESSMENT REPORTS EFAVIRENZ TEVA (AUTHORIZED: HIV INFECTIONS)
Created by admin on Mon Oct 21 19:49:24 UTC 2019 , Edited by admin on Mon Oct 21 19:49:24 UTC 2019
Code System Code Type Description
NDF-RT
N0000182140
Created by admin on Mon Oct 21 19:49:24 UTC 2019 , Edited by admin on Mon Oct 21 19:49:24 UTC 2019
PRIMARY Cytochrome P450 2C19 Inhibitors [MoA]
ChEMBL
CHEMBL223228
Created by admin on Mon Oct 21 19:49:24 UTC 2019 , Edited by admin on Mon Oct 21 19:49:24 UTC 2019
PRIMARY
EPA CompTox
154598-52-4
Created by admin on Mon Oct 21 19:49:24 UTC 2019 , Edited by admin on Mon Oct 21 19:49:24 UTC 2019
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
EFAVIRENZ
Created by admin on Mon Oct 21 19:49:24 UTC 2019 , Edited by admin on Mon Oct 21 19:49:24 UTC 2019
PRIMARY Description: White to slightly pink powder.Solubility: Practically insoluble in water, freely soluble in methanol.Category. Antiretroviral (Non-nucleoside Reverse Transcriptase Inhibitor).Storage. Efavirenz should be kept in a well-closed container, protected from light.Additional information: Efavirenz may exhibit polymorphism.Requirements: Definition: Efavirenz contains not less than 97.0% and not more than 103.0% of C14H9ClF3NO2, calculated with reference to thedried substance.Manufacture: The production method is validated to ensure that the substance is the (4S)-enantiomer.
EVMPD
SUB06463MIG
Created by admin on Mon Oct 21 19:49:24 UTC 2019 , Edited by admin on Mon Oct 21 19:49:24 UTC 2019
PRIMARY
PUBCHEM
64139
Created by admin on Mon Oct 21 19:49:24 UTC 2019 , Edited by admin on Mon Oct 21 19:49:24 UTC 2019
PRIMARY
MESH
C098320
Created by admin on Mon Oct 21 19:49:24 UTC 2019 , Edited by admin on Mon Oct 21 19:49:24 UTC 2019
PRIMARY
RXCUI
195085
Created by admin on Mon Oct 21 19:49:24 UTC 2019 , Edited by admin on Mon Oct 21 19:49:24 UTC 2019
PRIMARY RxNorm
NDF-RT
N0000182141
Created by admin on Mon Oct 21 19:49:24 UTC 2019 , Edited by admin on Mon Oct 21 19:49:24 UTC 2019
PRIMARY Cytochrome P450 3A4 Inhibitors [MoA]
MERCK INDEX
M4839
Created by admin on Mon Oct 21 19:49:24 UTC 2019 , Edited by admin on Mon Oct 21 19:49:24 UTC 2019
PRIMARY Merck Index
HSDB
154598-52-4
Created by admin on Mon Oct 21 19:49:24 UTC 2019 , Edited by admin on Mon Oct 21 19:49:24 UTC 2019
PRIMARY
INN
7718
Created by admin on Mon Oct 21 19:49:24 UTC 2019 , Edited by admin on Mon Oct 21 19:49:24 UTC 2019
PRIMARY
NCI_THESAURUS
C29027
Created by admin on Mon Oct 21 19:49:24 UTC 2019 , Edited by admin on Mon Oct 21 19:49:24 UTC 2019
PRIMARY
WIKIPEDIA
EFAVIRENZ
Created by admin on Mon Oct 21 19:49:24 UTC 2019 , Edited by admin on Mon Oct 21 19:49:24 UTC 2019
PRIMARY
NDF-RT
N0000185504
Created by admin on Mon Oct 21 19:49:24 UTC 2019 , Edited by admin on Mon Oct 21 19:49:24 UTC 2019
PRIMARY Cytochrome P450 2C9 Inhibitors [MoA]
NDF-RT
N0000187064
Created by admin on Mon Oct 21 19:49:24 UTC 2019 , Edited by admin on Mon Oct 21 19:49:24 UTC 2019
PRIMARY Cytochrome P450 2B6 Inducers [MoA]
CAS
154598-52-4
Created by admin on Mon Oct 21 19:49:24 UTC 2019 , Edited by admin on Mon Oct 21 19:49:24 UTC 2019
PRIMARY
DRUG BANK
DB00625
Created by admin on Mon Oct 21 19:49:24 UTC 2019 , Edited by admin on Mon Oct 21 19:49:24 UTC 2019
PRIMARY
NDF-RT
N0000190118
Created by admin on Mon Oct 21 19:49:24 UTC 2019 , Edited by admin on Mon Oct 21 19:49:24 UTC 2019
PRIMARY Cytochrome P450 3A Inducers [MoA]