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Details

Stereochemistry ABSOLUTE
Molecular Formula C14H9ClF3NO2
Molecular Weight 315.675
Optical Activity ( - )
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=C1C=C(Cl)C=C2)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 No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

Unknown
123738
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:45:38 UTC 2023
Edited
by admin
on Fri Dec 15 15:45:38 UTC 2023
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  
USAN   INN  
Official Name English
L-743726
Code 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
DMP-266
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 [USAN]
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
(4S)-6-Chloro-4-(2-cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one
Systematic Name English
TELURA COMPONENT EFAVIRENZ
Brand Name English
Efavirenz [WHO-DD]
Common Name English
2H-3,1-Benzoxazin-2-one, 6-chloro-4-(2-cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-, (4S)-
Systematic 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
(-)-Efavirenz
Common Name English
Classification Tree Code System Code
NDF-RT N0000009948
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
LIVERTOX NBK548521
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
WHO-ATC J05AR11
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
NDF-RT N0000175460
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
EMA ASSESSMENT REPORTS SUSTIVA (AUTHORIZED: HIV INFECTIONS)
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
EMA ASSESSMENT REPORTS ATRIPLA (AUTHORIZED: HIV INFECTIONS)
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
NDF-RT N0000175463
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 6.4.2.3 (EFV/FTC/TEN)
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
WHO-VATC QJ05AR11
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
WHO-ATC J05AR06
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
WHO-VATC QJ05AR06
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 6.4.2.2
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
NCI_THESAURUS C97453
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
WHO-VATC QJ05AG03
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
WHO-ATC J05AG03
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
EMA ASSESSMENT REPORTS STOCRIN (AUTHORIZED: HIV INFECTIONS)
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
EMA ASSESSMENT REPORTS EFAVIRENZ TEVA (AUTHORIZED: HIV INFECTIONS)
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
Code System Code Type Description
NDF-RT
N0000182140
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
PRIMARY Cytochrome P450 2C19 Inhibitors [MoA]
DAILYMED
JE6H2O27P8
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
PRIMARY
ChEMBL
CHEMBL223228
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
PRIMARY
EPA CompTox
DTXSID9046029
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
PRIMARY
DRUG CENTRAL
989
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
EFAVIRENZ
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
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 Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
PRIMARY
PUBCHEM
64139
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
PRIMARY
MESH
C098320
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
PRIMARY
RS_ITEM_NUM
1234103
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
PRIMARY
RXCUI
195085
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
PRIMARY RxNorm
NDF-RT
N0000182141
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
PRIMARY Cytochrome P450 3A4 Inhibitors [MoA]
LACTMED
Efavirenz
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
PRIMARY
MERCK INDEX
m4839
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
PRIMARY Merck Index
HSDB
7163
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
PRIMARY
CHEBI
119486
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
PRIMARY
INN
7718
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
PRIMARY
FDA UNII
JE6H2O27P8
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
PRIMARY
NCI_THESAURUS
C29027
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
PRIMARY
SMS_ID
100000085266
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
PRIMARY
WIKIPEDIA
EFAVIRENZ
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
PRIMARY
USAN
II-77
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
PRIMARY
NDF-RT
N0000185504
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
PRIMARY Cytochrome P450 2C9 Inhibitors [MoA]
NDF-RT
N0000187064
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
PRIMARY Cytochrome P450 2B6 Inducers [MoA]
CAS
154598-52-4
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
PRIMARY
DRUG BANK
DB00625
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
PRIMARY
NDF-RT
N0000190118
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
PRIMARY Cytochrome P450 3A Inducers [MoA]
NSC
742403
Created by admin on Fri Dec 15 15:45:38 UTC 2023 , Edited by admin on Fri Dec 15 15:45:38 UTC 2023
PRIMARY
Related Record Type Details
CYTOCHROME P450 2B6
METABOLIC ENZYME -> SUBSTRATE
MRP-3
TRANSPORTER -> INHIBITOR
Structure of EFAVIRENZ
BASIS OF STRENGTH->SUBSTANCE
calculated on the anhydrous, solvent-free basis
ASSAY (HPLC)
USP
ATP-BINDING CASSETTE SUB-FAMILY G MEMBER 2
TRANSPORTER -> INHIBITOR
HUMAN IMMUNODEFICIENCY VIRUS TYPE 1
TARGET ORGANISM->INHIBITOR
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
HUMAN IMMUNODEFICIENCY VIRUS TYPE 1 POLYMERASE
TARGET -> INHIBITOR
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
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 EFAVIRENZ, (R)-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of DIHYDRO EFAVIRENZ, (E)-
IMPURITY -> PARENT
Structure of SG-275
IMPURITY -> PARENT
Structure of EFAVIRENZ PENT-3-ENE-1-YNE, (E)-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of (2S)-2-(5-CHLORO-2-((4-METHOXYPHENYL)METHYLAMINO)PHENYL)-4-CYCLOPROPYL-1,1,1-TRIFLUOROBUT-3-YN-2-OL
IMPURITY -> PARENT
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 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 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
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC IN HIV-INFECTED PATIENTS

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Biological Half-life PHARMACOKINETIC SINGLE DOSE

Biological Half-life PHARMACOKINETIC MULTIPLE DOSES

Tmax PHARMACOKINETIC SINGLE DOSE

ORAL ADMINISTRATION

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