EFAVIRENZ

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

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	MOL RATIO 1 MOL RATIO (average)

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

Approval Year

Substance Class	Chemical
Record UNII	JE6H2O27P8
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

EFAVIRENZ

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

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Classification Tree

Code System

Code

Reverse Transcriptase Inhibitors

NDF-RT

N0000009948

Antiviral: HIV

LIVERTOX

NBK548521

Antivirals for treatment of HIV infections, combinations

WHO-ATC

J05AR11

Analogs/Derivatives

NDF-RT

N0000175460

SEXUALLY TRANSMITTED DISEASES, VIRAL

EMA ASSESSMENT REPORTS

SUSTIVA (AUTHORIZED: HIV INFECTIONS)

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Code System

Code

Type

Description

NDF-RT

N0000182140

PRIMARY

Cytochrome P450 2C19 Inhibitors [MoA]

DAILYMED

JE6H2O27P8

PRIMARY

ChEMBL

CHEMBL223228

PRIMARY

EPA CompTox

DTXSID9046029

PRIMARY

DRUG CENTRAL

989

PRIMARY

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Related Record

Type

Details


					0UY97CSG1T

CYTOCHROME P450 2B6

METABOLIC ENZYME -> SUBSTRATE


					1YV0492L5Z

MRP-3

TRANSPORTER -> INHIBITOR


					JE6H2O27P8

EFAVIRENZ

BASIS OF STRENGTH->SUBSTANCE

Comments:

calculated on the anhydrous, solvent-free basis

Interaction Type:

ASSAY (HPLC)

Qualification:

USP

Amount:

RELATIONSHIP_AMOUNT [98 to 102] WEIGHT PERCENT (limits)


					76UB6O122H

ATP-BINDING CASSETTE SUB-FAMILY G MEMBER 2

TRANSPORTER -> INHIBITOR


					859A956UY8

HUMAN IMMUNODEFICIENCY VIRUS TYPE 1

TARGET ORGANISM->INHIBITOR

Amount:

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Related Record

Type

Details


					P8S49CKH6L

8-HYDROXYEFAVIRENZ

METABOLITE ACTIVE -> PARENT

Comments:

THE MAJOR OXIDATIVE METABOLITE OF EFAVIRENZ IN VIVO AND IN VITRO HUMAN LIVER MICROSOMAL PREPARATIONS IS 8-HYDROXYEFAVIRENZ

Interaction Type:

MAJOR

Amount:


					65K8P7K1J3

7-HYDROXYEFAVIRENZ

METABOLITE -> PARENT

Comments:

7-HYDROXYEFAVIRENZ REPRESENTS A MINOR PATHWAY

Interaction Type:

MINOR

Amount:

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Related Record

Type

Details


					GS9U39RG71

METHYL EFAVIRENZ

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

USP

Amount:

RELATIONSHIP_AMOUNT [<0.1] PERCENT PEAK AREA (limits)


					F86H88Z9IG

6-CHLORO-4-(3-METHYLBUT-3-EN-1-YNYL)-4-(TRIFLUOROMETHYL)-2H-3,1-BENZOXAZIN-2-ONE, (S)-

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

USP

Amount:

RELATIONSHIP_AMOUNT [<0.1] PERCENT PEAK AREA (limits)


					BVI6NU6S3C

EFAVIRENZ PENT-3-ENE-1-YNE, (Z)-

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

USP

Amount:

RELATIONSHIP_AMOUNT [<0.1] PERCENT PEAK AREA (limits)


					ZC619V1CML

6-CHLORO-2-CYCLOPROPYL-4-(TRIFLUOROMETHYL)QUINOLINE

IMPURITY -> PARENT

Amount:


					ZC619V1CML

6-CHLORO-2-CYCLOPROPYL-4-(TRIFLUOROMETHYL)QUINOLINE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

USP

Amount:

RELATIONSHIP_AMOUNT [<0.1] PERCENT PEAK AREA (limits)

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Type

Details


					JE6H2O27P8

EFAVIRENZ

ACTIVE MOIETY

Amount:

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Name	Property Type	Amount	Parameters
Tmax	PHARMACOKINETIC	[3 to 5] hours (average)	IN HIV-INFECTED PATIENTS ORAL ADMINISTRATION AT STEADY-STATE SINGLE DOSE

Biological Half-life	PHARMACOKINETIC	[52 to 76] hours (average)	SINGLE DOSE

Biological Half-life	PHARMACOKINETIC	[40 to 55] hours (average)	MULTIPLE DOSES

Tmax	PHARMACOKINETIC	5 hours (average)	SINGLE DOSE ORAL ADMINISTRATION IN UNINFECTED VOLUNTEERS