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

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

1998
74
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
7468
HIV Infections
 20.0 nM [EC50]
Inhibitor
7468
HIV Infections
 4.0 nM [EC50]
Inhibitor
7468
 26.1 µM [IC50]
Modulator
769
 52.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Human immunodeficiency virus type 1 reverse transcriptase
Human immunodeficiency virus 1
Approved
7883
SUSTIVA
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
Efavirenz: a pharmacoeconomic review of its use in HIV infection.
2001
The emerging roles of non-nucleoside reverse transcriptase inhibitors in antiretroviral therapy.
2001
Retinal toxicity due to Efavirenz.
2001 Apr
Smaller amounts of antiretroviral drugs are needed when combined with an active ribozyme against HIV-1.
2001 Apr
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
Determination of serum levels of thirteen human immunodeficiency virus-suppressing drugs by high-performance liquid chromatography.
2001 Apr 13
[Progress in HIV therapy. Effective and simple therapy with efavirenz].
2001 Apr 2
Antiretroviral rounds. When success is a pain.
2001 Aug
Antiviral drugs: current state of the art.
2001 Aug
Preliminary data of a prospective study on neuropsychiatric side effects after initiation of efavirenz.
2001 Aug 1
Non-nucleoside reverse transcriptase inhibitor failure impairs HIV-RNA responses to efavirenz-containing salvage antiretroviral therapy.
2001 Aug 17
Antiretroviral therapy for previously treated patients.
2001 Aug 9
Trifluoromethyl-containing 3-alkoxymethyl- and 3-aryloxymethyl-2-pyridinones are potent inhibitors of HIV-1 non-nucleoside reverse transcriptase.
2001 Feb 12
Dynamics of seminal plasma HIV-1 decline after antiretroviral treatment.
2001 Feb 16
Protease-sparing regimen in a real-life practice with naïve patients: an equal opportunity approach?
2001 Jan-Feb
New developments in anti-HIV chemotherapy.
2001 Jan-Feb
Predictors of protease inhibitor-associated adverse events.
2001 Jul
The steady-state pharmacokinetics of efavirenz and nevirapine when used in combination in human immunodeficiency virus type 1-infected persons.
2001 Jul 1
Manic syndrome associated with efavirenz overdose.
2001 Jul 15
Gynecomastia without lipodystrophy syndrome in HIV-infected men treated with efavirenz.
2001 Jul 27
Metformin in an HIV-infected patient with protease inhibitor-induced diabetic ketoacidosis.
2001 Jul-Aug
In vitro anti-HIV-1 synergy between non-nucleoside reverse transcriptase inhibitors nevirapine and efavirenz.
2001 Jun
Efavirenz plasma concentrations and efficiency.
2001 Jun 15
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
International perspectives on antiretroviral resistance. Nonnucleoside reverse transcriptase inhibitor resistance.
2001 Mar 1
Synthesis and biological activities of potential metabolites of the non-nucleoside reverse transcriptase inhibitor efavirenz.
2001 Mar 12
Competition prompts drug companies to cut antiretroviral drug prices.
2001 Mar 17
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
Synthesis and evaluation of efavirenz (Sustiva) analogues as HIV-1 reverse transcriptase inhibitors: replacement of the cyclopropylacetylene side chain.
2001 May 7
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
Comparison of NNRTIs in antiretroviral-experienced patients.
2001 Nov
Comparison of NNRTIs in antiretroviral-naïve patients.
2001 Nov
New developments in anti-HIV chemotherapy.
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
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
Evolution of anti-HIV drug candidates. Part 3: Diarylpyrimidine (DAPY) analogues.
2001 Sep 3
Comparison of initial combination antiretroviral therapy with a single protease inhibitor, ritonavir and saquinavir, or efavirenz.
2001 Sep 7
Switching from protease inhibitors to the non-nuke efavirenz.
2001 Spring
Patents

Patents

8378143
2
JP4676536B2
24
JP4708329B2
13
JP4738172B2
25

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.
Substance Class Chemical
Created
by admin
on Mon Oct 21 19:49:24 UTC 2019
Edited
by admin
on Mon Oct 21 19:49:24 UTC 2019
Record UNII
JE6H2O27P8
Record Status Validated (UNII)
Record Version
  • Download
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]
Related Record Type Details
HUMAN IMMUNODEFICIENCY VIRUS TYPE 1
INHIBITOR->TARGET ORGANISM
ATP-BINDING CASSETTE SUB-FAMILY G MEMBER 2
TRANSPORTER -> INHIBITOR
Structure of EFAVIRENZ
BASIS OF STRENGTH->SUBSTANCE
calculated on the anhydrous, solvent-free basis
ASSAY (HPLC)
USP
MRP-3
TRANSPORTER -> INHIBITOR
CYTOCHROME P450 2B6
METABOLIC ENZYME -> SUBSTRATE
MRP-2
TRANSPORTER -> INHIBITOR
Related Record Type Details
Structure of 8-HYDROXYEFAVIRENZ
METABOLITE ACTIVE -> PARENT
THE MAJOR OXIDATIVE METABOLITE OF EFAVIRENZ IN VIVO AND IN VITRO HUMAN LIVER MICROSOMAL PREPARATIONS IS 8-HYDROXYEFAVIRENZ
MAJOR
Structure of 7-HYDROXYEFAVIRENZ
METABOLITE -> PARENT
7-HYDROXYEFAVIRENZ REPRESENTS A MINOR PATHWAY
MINOR
Structure of 8,14-DIHYDROXYEFAVIRENZ
METABOLITE -> PARENT
Related Record Type Details
Structure of SG-275
IMPURITY -> PARENT
Structure of METHYL EFAVIRENZ
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of 6-CHLORO-4-(3-METHYLBUT-3-EN-1-YNYL)-4-(TRIFLUOROMETHYL)-2H-3,1-BENZOXAZIN-2-ONE, (S)-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of EFAVIRENZ PENT-3-ENE-1-YNE, (Z)-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of 6-CHLORO-2-CYCLOPROPYL-4-(TRIFLUOROMETHYL)QUINOLINE
IMPURITY -> PARENT
Structure of 6-CHLORO-2-CYCLOPROPYL-4-(TRIFLUOROMETHYL)QUINOLINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of N-(4-CHLORO-2-(4-CYCLOPROPYL-1,1,1-TRIFLUORO-2-HYDROXYBUT-3-YN-2-YL)PHENYL)-4-METHOXYBENZAMIDE, (S)-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of EFAVIRENZ, (R)-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of DIHYDRO EFAVIRENZ, (E)-
IMPURITY -> PARENT
Structure of ETHYL 5-CHLORO-2-CYCLOBUTENYL-3-(TRIFLUOROMETHYL)-1H-INDOLE-1-CARBOXYLATE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of EFAVIRENZ PENT-3-ENE-1-YNE, (E)-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of N-(4-METHOXYBENZYL)EFAVIRENZ
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of METHYL (4-CHLORO-2-((2S)-4-CYCLOPROPYL-1,1,1-TRIFLUORO-2-HYDROXYBUT-3-YN-1-YL)PHENYL)CARBAMATE
IMPURITY -> PARENT
Structure of EFAVIRENZ AMINO ALCOHOL ETHYL CARBAMATE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of EFAVIRENZ AMINOALCOHOL
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of 6-CHLORO-4-(PENT-1-YNYL)-4-(TRIFLUOROMETHYL)-2H-3,1-BENZOXAZIN-2-ONE, (S)-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of DIHYDRO EFAVIRENZ, (E)-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of EFAVIRENZ AMINO ALCOHOL BIS(ETHOXYCARBONYL)
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of EFAVIRENZ AMINOALCOHOL
IMPURITY -> PARENT
Structure of EFAVIRENZ AMINO ALCOHOL METHYL CARBAMATE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
Structure of EFAVIRENZ
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