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

Details

Stereochemistry ABSOLUTE
Molecular Formula C14H9ClF3NO2
Molecular Weight 315.6754
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EFAVIRENZ

SMILES

C1CC1C#C[C@]2(c3cc(ccc3N=C(O)O2)Cl)C(F)(F)F

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 315.6754
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: Description was created based on several sources, including

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

Merck
202
Curator's Comment:: # Merck & Co

Approval Year

1998
113
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
7728
 4.0 nM [EC50]
Inhibitor
7728
 26.1 µM [IC50]
Modulator
780
 52.0 µM [IC50]
Inhibitor
7728
 20.0 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8043
SUSTIVA

Approved Use

SUSTIVA is a non-nucleoside reverse transcriptase inhibitor indicated in combination with other antiretroviral agents for the treatment of human immunodeficiency virus type 1 infection.

Launch Date

9.05904E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
12.9 μM
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020972s057,021360s045lbl.pdf
600 mg 1 times / day steady-state, oral
dose: 600 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
EFAVIRENZ plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
7.04 μg/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020972s057,021360s045lbl.pdf
300 mg 1 times / day steady-state, oral
dose: 300 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
EFAVIRENZ plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
184 μM × h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020972s057,021360s045lbl.pdf
600 mg 1 times / day steady-state, oral
dose: 600 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
EFAVIRENZ plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
257.56 μM × h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020972s057,021360s045lbl.pdf
300 mg 1 times / day steady-state, oral
dose: 300 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
EFAVIRENZ plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
40 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020972s057,021360s045lbl.pdf
600 mg 1 times / day steady-state, oral
dose: 600 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
EFAVIRENZ plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
0.5%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020972s057,021360s045lbl.pdf
600 mg 1 times / day steady-state, oral
dose: 600 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
EFAVIRENZ plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
3 g single, oral
Overdose
Dose: 3 g
Route: oral
Route: single
Dose: 3 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/23077707
unhealthy, 12 years
n = 1
Health Status: unhealthy
Condition: HIV infection
Age Group: 12 years
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/23077707
Sources:
https://pubmed.ncbi.nlm.nih.gov/23077707
600 mg 1 times / day multiple, oral
Recommended
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Co-administed with::
abacavir(300 mg q12h)
nelfinavir(1250 mg q12h)
Sources:
https://pubmed.ncbi.nlm.nih.gov/11418896
unhealthy, 33 years
n = 1
Health Status: unhealthy
Condition: HIV infection
Age Group: 33 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/11418896
Disc. AE: Mania...
AEs leading to
discontinuation/dose reduction:
Mania (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/11418896
25 mg/kg 1 times / day steady, oral
Highest studied dose
Dose: 25 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 25 mg/kg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/28483965
unhealthy, 33.9 months (range: 29.2–40.2 months)
n = 52
Health Status: unhealthy
Condition: HIV infection
Age Group: 33.9 months (range: 29.2–40.2 months)
Sex: M+F
Population Size: 52
Sources:
https://pubmed.ncbi.nlm.nih.gov/28483965
Sources:
https://pubmed.ncbi.nlm.nih.gov/28483965
800 mg 1 times / day steady, oral
Highest studied dose
Dose: 800 mg, 1 times / day
Route: oral
Route: steady
Dose: 800 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30792988
unhealthy, 37.3 years
n = 67
Health Status: unhealthy
Condition: tuberculosis
Age Group: 37.3 years
Sex: M+F
Population Size: 67
Sources:
https://pubmed.ncbi.nlm.nih.gov/30792988
Disc. AE: Hallucination, Dizziness...
AEs leading to
discontinuation/dose reduction:
Hallucination (1 patient)
Dizziness (1 patient)
Insomnia (1 patient)
Hepatotoxicity (1 patient)
Skin rash (1 patient)
Pruritus (1 patient)
Rash (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/30792988
AEs

AEs

AESignificanceDosePopulation
Mania 1 patient
Disc. AE
600 mg 1 times / day multiple, oral
Recommended
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Co-administed with::
abacavir(300 mg q12h)
nelfinavir(1250 mg q12h)
Sources:
https://pubmed.ncbi.nlm.nih.gov/11418896
unhealthy, 33 years
n = 1
Health Status: unhealthy
Condition: HIV infection
Age Group: 33 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/11418896
Dizziness 1 patient
Disc. AE
800 mg 1 times / day steady, oral
Highest studied dose
Dose: 800 mg, 1 times / day
Route: oral
Route: steady
Dose: 800 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30792988
unhealthy, 37.3 years
n = 67
Health Status: unhealthy
Condition: tuberculosis
Age Group: 37.3 years
Sex: M+F
Population Size: 67
Sources:
https://pubmed.ncbi.nlm.nih.gov/30792988
Hallucination 1 patient
Disc. AE
800 mg 1 times / day steady, oral
Highest studied dose
Dose: 800 mg, 1 times / day
Route: oral
Route: steady
Dose: 800 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30792988
unhealthy, 37.3 years
n = 67
Health Status: unhealthy
Condition: tuberculosis
Age Group: 37.3 years
Sex: M+F
Population Size: 67
Sources:
https://pubmed.ncbi.nlm.nih.gov/30792988
Hepatotoxicity 1 patient
Disc. AE
800 mg 1 times / day steady, oral
Highest studied dose
Dose: 800 mg, 1 times / day
Route: oral
Route: steady
Dose: 800 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30792988
unhealthy, 37.3 years
n = 67
Health Status: unhealthy
Condition: tuberculosis
Age Group: 37.3 years
Sex: M+F
Population Size: 67
Sources:
https://pubmed.ncbi.nlm.nih.gov/30792988
Insomnia 1 patient
Disc. AE
800 mg 1 times / day steady, oral
Highest studied dose
Dose: 800 mg, 1 times / day
Route: oral
Route: steady
Dose: 800 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30792988
unhealthy, 37.3 years
n = 67
Health Status: unhealthy
Condition: tuberculosis
Age Group: 37.3 years
Sex: M+F
Population Size: 67
Sources:
https://pubmed.ncbi.nlm.nih.gov/30792988
Pruritus 1 patient
Disc. AE
800 mg 1 times / day steady, oral
Highest studied dose
Dose: 800 mg, 1 times / day
Route: oral
Route: steady
Dose: 800 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30792988
unhealthy, 37.3 years
n = 67
Health Status: unhealthy
Condition: tuberculosis
Age Group: 37.3 years
Sex: M+F
Population Size: 67
Sources:
https://pubmed.ncbi.nlm.nih.gov/30792988
Rash 1 patient
Disc. AE
800 mg 1 times / day steady, oral
Highest studied dose
Dose: 800 mg, 1 times / day
Route: oral
Route: steady
Dose: 800 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30792988
unhealthy, 37.3 years
n = 67
Health Status: unhealthy
Condition: tuberculosis
Age Group: 37.3 years
Sex: M+F
Population Size: 67
Sources:
https://pubmed.ncbi.nlm.nih.gov/30792988
Skin rash 1 patient
Disc. AE
800 mg 1 times / day steady, oral
Highest studied dose
Dose: 800 mg, 1 times / day
Route: oral
Route: steady
Dose: 800 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30792988
unhealthy, 37.3 years
n = 67
Health Status: unhealthy
Condition: tuberculosis
Age Group: 37.3 years
Sex: M+F
Population Size: 67
Sources:
https://pubmed.ncbi.nlm.nih.gov/30792988
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:119486
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:119486
ChemicalBook
CB7181559
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7181559
MolPort
MolPort-003-983-924
https://www.molport.com/shop/molecule-link/MolPort-003-983-924
ZINC
ZINC000002020233
http://zinc15.docking.org/substances/ZINC000002020233
eMolecules
2735350
https://www.emolecules.com/cgi-bin/more?vid=2735350
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
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
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
[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
Antiretroviral rounds. When success is a pain.
2001 Aug
Antiretrovirals: simultaneous determination of five protease inhibitors and three nonnucleoside transcriptase inhibitors in human plasma by a rapid high-performance liquid chromatography--mass spectrometry assay.
2001 Aug
Antiviral drugs: current state of the art.
2001 Aug
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
Structure-based design, synthesis, and biological evaluation of conformationally restricted novel 2-alkylthio-6-[1-(2,6-difluorophenyl)alkyl]-3,4-dihydro-5-alkylpyrimidin-4(3H)-ones as non-nucleoside inhibitors of HIV-1 reverse transcriptase.
2001 Aug 2
Antiretroviral therapy for previously treated patients.
2001 Aug 9
Nelfinavir, efavirenz, or both after the failure of nucleoside treatment of HIV infection.
2001 Aug 9
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
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
New developments in anti-HIV chemotherapy.
2001 Jan-Feb
Predictors of protease inhibitor-associated adverse events.
2001 Jul
Manic syndrome associated with efavirenz overdose.
2001 Jul 15
Synthesis and evaluation of novel quinolinones as HIV-1 reverse transcriptase inhibitors.
2001 Jul 23
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
Efavirenz plasma concentrations and efficiency.
2001 Jun 15
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
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
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
The pharmacokinetics of methadone in HIV-positive patients receiving the non-nucleoside reverse transcriptase inhibitor efavirenz.
2001 Mar
Anti-AIDS drugs available 'at cost'.
2001 Mar 15
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
Synthesis and evaluation of efavirenz (Sustiva) analogues as HIV-1 reverse transcriptase inhibitors: replacement of the cyclopropylacetylene side chain.
2001 May 7
[Apropos of atypical melancholia with Sustiva (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-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
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
Evolution of anti-HIV drug candidates. Part 3: Diarylpyrimidine (DAPY) analogues.
2001 Sep 3
Patents

Patents

08378143
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 Fri Jun 25 21:38:46 UTC 2021
Edited
by admin
on Fri Jun 25 21:38:46 UTC 2021
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
EFAVIRENZ [USP MONOGRAPH]
Common 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
NSC-742403
Code 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 Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
LIVERTOX 341
Created by admin on Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
WHO-ATC J05AR11
Created by admin on Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
NDF-RT N0000175460
Created by admin on Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
EMA ASSESSMENT REPORTS SUSTIVA (AUTHORIZED: HIV INFECTIONS)
Created by admin on Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
EMA ASSESSMENT REPORTS ATRIPLA (AUTHORIZED: HIV INFECTIONS)
Created by admin on Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
NDF-RT N0000175463
Created by admin on Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 6.4.2.3 (EFV/FTC/TEN)
Created by admin on Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
WHO-VATC QJ05AR11
Created by admin on Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
WHO-ATC J05AR06
Created by admin on Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
WHO-VATC QJ05AR06
Created by admin on Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 6.4.2.2
Created by admin on Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
NCI_THESAURUS C97453
Created by admin on Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
WHO-VATC QJ05AG03
Created by admin on Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
WHO-ATC J05AG03
Created by admin on Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
EMA ASSESSMENT REPORTS STOCRIN (AUTHORIZED: HIV INFECTIONS)
Created by admin on Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
EMA ASSESSMENT REPORTS EFAVIRENZ TEVA (AUTHORIZED: HIV INFECTIONS)
Created by admin on Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
Code System Code Type Description
NDF-RT
N0000182140
Created by admin on Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
PRIMARY Cytochrome P450 2C19 Inhibitors [MoA]
ChEMBL
CHEMBL223228
Created by admin on Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
PRIMARY
USP_CATALOG
1234103
Created by admin on Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
PRIMARY USP-RS
EPA CompTox
154598-52-4
Created by admin on Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
PRIMARY
DRUG CENTRAL
989
Created by admin on Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
EFAVIRENZ
Created by admin on Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
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 Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
PRIMARY
PUBCHEM
64139
Created by admin on Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
PRIMARY
MESH
C098320
Created by admin on Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
PRIMARY
RXCUI
195085
Created by admin on Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
PRIMARY RxNorm
NDF-RT
N0000182141
Created by admin on Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
PRIMARY Cytochrome P450 3A4 Inhibitors [MoA]
LACTMED
Efavirenz
Created by admin on Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
PRIMARY
MERCK INDEX
M4839
Created by admin on Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
PRIMARY Merck Index
HSDB
7163
Created by admin on Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
PRIMARY
INN
7718
Created by admin on Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
PRIMARY
FDA UNII
JE6H2O27P8
Created by admin on Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
PRIMARY
NCI_THESAURUS
C29027
Created by admin on Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
PRIMARY
WIKIPEDIA
EFAVIRENZ
Created by admin on Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
PRIMARY
NDF-RT
N0000185504
Created by admin on Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
PRIMARY Cytochrome P450 2C9 Inhibitors [MoA]
NDF-RT
N0000187064
Created by admin on Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
PRIMARY Cytochrome P450 2B6 Inducers [MoA]
CAS
154598-52-4
Created by admin on Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
PRIMARY
DRUG BANK
DB00625
Created by admin on Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
PRIMARY
NDF-RT
N0000190118
Created by admin on Fri Jun 25 21:38:46 UTC 2021 , Edited by admin on Fri Jun 25 21:38:46 UTC 2021
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-2
TRANSPORTER -> INHIBITOR
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
MRP-3
TRANSPORTER -> INHIBITOR
CYTOCHROME P450 2B6
METABOLIC ENZYME -> SUBSTRATE
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
Related Record Type Details
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 METHYL (4-CHLORO-2-((2S)-4-CYCLOPROPYL-1,1,1-TRIFLUORO-2-HYDROXYBUT-3-YN-1-YL)PHENYL)CARBAMATE
IMPURITY -> PARENT
Structure of EFAVIRENZ, (R)-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of DIHYDRO EFAVIRENZ, (E)-
IMPURITY -> PARENT
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 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
Structure of SG-275
IMPURITY -> PARENT
Related Record Type Details
Structure of EFAVIRENZ
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC IN HIV-INFECTED PATIENTS

ORAL ADMINISTRATION

AT STEADY-STATE

SINGLE DOSE

Biological Half-life PHARMACOKINETIC SINGLE DOSE

Biological Half-life PHARMACOKINETIC MULTIPLE DOSES

Tmax PHARMACOKINETIC SINGLE DOSE

ORAL ADMINISTRATION

IN UNINFECTED VOLUNTEERS

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