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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
75
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
7197
HIV Infections
 20.0 nM [EC50]
Inhibitor
7197
HIV Infections
 4.0 nM [EC50]
Inhibitor
7197
 26.1 µM [IC50]
Modulator
720
 52.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Human immunodeficiency virus type 1 reverse transcriptase
Human immunodeficiency virus 1
Approved
7777
SUSTIVA
PubMed

PubMed

TitleDatePubMed
Synthesis and evaluation of benzoxazinones as HIV-1 reverse transcriptase inhibitors. Analogs of Efavirenz (SUSTIVA).
1999 Nov 15
A novel genotype encoding a single amino acid insertion and five other substitutions between residues 64 and 74 of the HIV-1 reverse transcriptase confers high-level cross-resistance to nucleoside reverse transcriptase inhibitors. Abacavir CNA2007 International Study Group.
1999 Oct 1
Synthesis and evaluation of analogs of Efavirenz (SUSTIVA) as HIV-1 reverse transcriptase inhibitors.
1999 Oct 4
Long-term exposure of HIV type 1-infected cell cultures to combinations of the novel quinoxaline GW420867X with lamivudine, abacavir, and a variety of nonnucleoside reverse transcriptase inhibitors.
2000 Apr 10
Mutational analysis of trp-229 of human immunodeficiency virus type 1 reverse transcriptase (RT) identifies this amino acid residue as a prime target for the rational design of new non-nucleoside RT inhibitors.
2000 May
The tolerability of efavirenz after nevirapine-related adverse events.
2000 Sep
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
Smaller amounts of antiretroviral drugs are needed when combined with an active ribozyme against HIV-1.
2001 Apr
Amino acid deletion at codon 67 and Thr-to-Gly change at codon 69 of human immunodeficiency virus type 1 reverse transcriptase confer novel drug resistance profiles.
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
Determination of serum levels of thirteen human immunodeficiency virus-suppressing drugs by high-performance liquid chromatography.
2001 Apr 13
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
Antiviral drugs: current state of the art.
2001 Aug
Solution structures and reactivities of the mixed aggregates derived from n-butyllithium and vicinal amino alkoxides.
2001 Aug 22
Antiretroviral therapy for previously treated patients.
2001 Aug 9
Efavirenz plasma levels can predict treatment failure and central nervous system side effects in HIV-1-infected patients.
2001 Jan 5
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
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
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
4,1-Benzoxazepinone analogues of efavirenz (Sustiva) as HIV-1 reverse transcriptase inhibitors.
2001 Jun 4
Use of MM-PBSA in reproducing the binding free energies to HIV-1 RT of TIBO derivatives and predicting the binding mode to HIV-1 RT of efavirenz by docking and MM-PBSA.
2001 Jun 6
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
Anti-AIDS drugs available 'at cost'.
2001 Mar 15
Sequencing antiretroviral drugs.
2001 Mar 30
Efavirenz-induced acute eosinophilic hepatitis.
2001 May
Efavirenz-induced photoallergic dermatitis in HIV.
2001 May 25
[Drug interactions with antiretroviral agents].
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
New developments in anti-HIV chemotherapy.
2001 Nov
Thiosugars. VIII. Preparation of new 4'-thio-L-lyxo pyrimidine nucleoside analogues.
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
Switching from protease inhibitors to the non-nuke efavirenz.
2001 Spring
Patents

Patents

8378143
2
JP4676536B2
25
JP4708329B2
13
JP4738172B2
26

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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