EFAVIRENZ

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 Search

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

Targets

Primary Target	Pharmacology	Condition	Potency
Human immunodeficiency virus type 1 reverse transcriptase 45	Inhibitor 7197	HIV Infections	20.0 nM [EC50]
Human immunodeficiency virus 1 30	Inhibitor 7197	HIV Infections	4.0 nM [EC50]
Leishmania infantum 2	Inhibitor 7197		26.1 µM [IC50]
Estrogen receptor alpha 112	Modulator 720		52.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
HIV Infections 125	Primary	Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1	Approved 7777	SUSTIVA

PubMed

Title	Date	PubMed
Four new antiretroviral medications will soon offer more options to HIV patients.	1998 Jul-Aug	11365545
Antiretroviral therapy in pregnancy: a focus on safety.	2001	11522121
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	11402860
Efavirenz: a pharmacoeconomic review of its use in HIV infection.	2001	11383758
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	11306154
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	11317086
Persistent dyslipidemia in HIV-infected individuals switched from a protease inhibitor-containing to an efavirenz-containing regimen.	2001 Apr 1	11317084
High prevalence of genotypic and phenotypic HIV-1 drug-resistant strains among patients receiving antiretroviral therapy in Abidjan, Côte d'Ivoire.	2001 Apr 15	11391173
A pilot study of the use of mycophenolate mofetil as a component of therapy for multidrug-resistant HIV-1 infection.	2001 Apr 15	11391161
[Results of the AIDS-In-Europe Study. Non-nucleoside reverse transcriptase inhibitor does not equal non-nucleoside reverse transcriptase inhibitor].	2001 Apr 2	11373776
[Positive change from protease inhibitor to non-nucleoside reverse transcriptase inhibitor efavirenz. Improved virus control thanks to protease inhibitor switch].	2001 Apr 2	11373775
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	11511822
Non-nucleoside reverse transcriptase inhibitor failure impairs HIV-RNA responses to efavirenz-containing salvage antiretroviral therapy.	2001 Aug 17	11504994
Solution structures and reactivities of the mixed aggregates derived from n-butyllithium and vicinal amino alkoxides.	2001 Aug 22	11506560
Nelfinavir, efavirenz, or both after the failure of nucleoside treatment of HIV infection.	2001 Aug 9	11496850
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	11462972
Protease-sparing regimen in a real-life practice with naïve patients: an equal opportunity approach?	2001 Jan-Feb	11590510
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	11488127
Predictors of protease inhibitor-associated adverse events.	2001 Jul	11478584
Gynecomastia without lipodystrophy syndrome in HIV-infected men treated with efavirenz.	2001 Jul 27	11504970
Management of sudden psychiatric disorders related to efavirenz.	2001 Jul 6	11426084
Metformin in an HIV-infected patient with protease inhibitor-induced diabetic ketoacidosis.	2001 Jul-Aug	11485138
Limits of deep salvage antiretroviral therapy with nelfinavir plus either efavirenz or nevirapine, in highly pre-treated patients with HIV disease.	2001 Jun	11397623
[Vertical trasmission of human immunodeficiency virus (HIV) and other sexually transmitted infections (STI)].	2001 Jun	11395690
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	11416714
4,1-Benzoxazepinone analogues of efavirenz (Sustiva) as HIV-1 reverse transcriptase inhibitors.	2001 Jun 4	11378361
2-Amino-6-arylsulfonylbenzonitriles as non-nucleoside reverse transcriptase inhibitors of HIV-1.	2001 Jun 7	11384233
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	11384232
Synthesis and biological activities of potential metabolites of the non-nucleoside reverse transcriptase inhibitor efavirenz.	2001 Mar 12	11266155
Anti-AIDS drugs available 'at cost'.	2001 Mar 15	11268163
Competition prompts drug companies to cut antiretroviral drug prices.	2001 Mar 17	11265962
Sequencing antiretroviral drugs.	2001 Mar 30	11316990
Efavirenz-induced acute eosinophilic hepatitis.	2001 May	11434632
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	11275435
Pulmonary hypersensitivity reaction induced by efavirenz.	2001 May 12	11377607
Efavirenz-induced photoallergic dermatitis in HIV.	2001 May 25	11400003
[Apropos of atypical melancholia with Sustiva (efavirenz)].	2001 May-Jun	11488260
[Drug interactions with antiretroviral agents].	2001 May-Jun	11475806
Evidence of hypertriglyceridemia in managing HIV patients on efavirenz.	2001 May-Jun	11387809
Other issues: penetration into sanctuary sites, immune reconstitution and NNRTI sequencing.	2001 Nov	11589825
Factors affecting adherence and convenience in antiretroviral therapy.	2001 Nov	11589824
Comparison of NNRTIs in antiretroviral-experienced patients.	2001 Nov	11589823
Comparison of NNRTIs in antiretroviral-naïve patients.	2001 Nov	11589822
The role of NNRTIs in antiretroviral combination therapy: an introduction.	2001 Nov	11589821
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	11572864
Thiosugars. VIII. Preparation of new 4'-thio-L-lyxo pyrimidine nucleoside analogues.	2001 Sep	11580190
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	11448730
Efavirenz-induced psychosis.	2001 Sep 28	11579266
Response to first protease inhibitor- and efavirenz-containing antiretroviral combination therapy. The Swiss HIV Cohort Study.	2001 Sep 28	11579241
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	11575933

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

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