Rac-Efavirenz

First approved in 1998

Details

Stereochemistry	RACEMIC
Molecular Formula	C14H9ClF3NO2
Molecular Weight	315.675
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

FC(F)(F)C1(OC(=O)NC2=CC=C(Cl)C=C12)C#CC3CC3

InChI

InChIKey=XPOQHMRABVBWPR-UHFFFAOYSA-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)

HIDE SMILES / InChI

Molecular Formula	C14H9ClF3NO2
Molecular Weight	315.675
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: http://www.drugbank.ca/drugs/DB00625
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

Approval Year

Targets

Primary Target	Pharmacology	Potency
Human immunodeficiency virus 1 34 Target ID: CHEMBL378 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19469474	Inhibitor 8504	4.0 nM [EC50]
Leishmania infantum 3 Target ID: CHEMBL612848 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27249967	Inhibitor 8504	26.1 µM [IC50]
Estrogen receptor alpha 134 Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20408889	Modulator 846	52.0 µM [IC50]
Human immunodeficiency virus type 1 reverse transcriptase 70 Target ID: CHEMBL247 Sources: http://www.drugbank.ca/drugs/DB00625	Inhibitor 8504	20.0 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
HIV-1 infection 156 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020972s038lbl.pdf	Primary		Approved 8583	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 1998

C_max

Value	Dose	Analyte	Population
1.6 μM DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020972s057,021360s045lbl.pdf	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	EFAVIRENZ plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
9.1 μM DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020972s057,021360s045lbl.pdf	1600 mg single, oral dose: 1600 mg route of administration: Oral experiment type: SINGLE co-administered:	EFAVIRENZ plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
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

AUC

Value	Dose	Co-administered	Analyte	Population
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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

F_unbound

Value	Dose	Co-administered	Analyte	Population
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

Dose	Population	Adverse 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 Health Status: unhealthy Age Group: 12 years Sex: M 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 Sources: https://pubmed.ncbi.nlm.nih.gov/11418896	unhealthy, 33 years Health Status: unhealthy Age Group: 33 years Sex: F 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) Health Status: unhealthy Age Group: 33.9 months (range: 29.2–40.2 months) Sex: M+F 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 Health Status: unhealthy Age Group: 37.3 years Sex: M+F 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

AE	Significance	Dose	Population
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 Sources: https://pubmed.ncbi.nlm.nih.gov/11418896	unhealthy, 33 years Health Status: unhealthy Age Group: 33 years Sex: F 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 Health Status: unhealthy Age Group: 37.3 years Sex: M+F 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 Health Status: unhealthy Age Group: 37.3 years Sex: M+F 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 Health Status: unhealthy Age Group: 37.3 years Sex: M+F 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 Health Status: unhealthy Age Group: 37.3 years Sex: M+F 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 Health Status: unhealthy Age Group: 37.3 years Sex: M+F 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 Health Status: unhealthy Age Group: 37.3 years Sex: M+F 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 Health Status: unhealthy Age Group: 37.3 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/30792988

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 1087 inhibitor 2252 substrate 1946	inhibitor 2438 substrate 1193	inhibitor 2507 substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
UGT 45 CYP2C19 2057 CYP1A2 2153 CYP2E1 1060 BCRP 910 MATE1 415 MRP2 499 MATE2-K 77 MRP1 116 OCT1 620 P-gp 1741 MRP3 246 OCT2 779	CYP2B6 776 CYP2C8 810 UGT1A3 470 UGT1A7 249 UGT2B4 278 UGT1A6 343 CYP2C19 1119 UGT1A8 323 CYP2E1 729 UGT1A1 479 UGT1A4 399 UGT1A10 331 UGT2B7 456 UGT2B17 237 UGT2B15 236 UGT1A9 423 CYP2A6 626 CYP1A2 1197 P-gp 2052 MRP1 113 MRP2 252	CYP2B6 669 UGT1A1 78 MRP1 74 MRP2 146 P-gp 301

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
MATE2-K 77	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/30114293/	likely
CYP2E1 1146	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20972biopharm_review.pdf#page=13 Page: 13.0	no
MRP1 232	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/20660679/	no
MRP2 625	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/20660679/	no
P-gp 1932	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/20660679/	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20972biopharm_review.pdf#page=13 Page: 13.0	yes [IC50 1 uM]	8-OH efavirenz 2
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020972s057,021360s045lbl.pdf#page=25 \| https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20972biopharm_review.pdf#page=13 Page: 25, (ClinP) 13	yes [IC50 10 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20972biopharm_review.pdf#page=13 Page: 13.0	yes [IC50 10 uM]	8-OH efavirenz 2
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20972biopharm_review.pdf#page=13 Page: 13.0	yes [IC50 13 uM]	8-OH efavirenz 2
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020972s057,021360s045lbl.pdf#page=25 Page: 25.0	yes [IC50 160 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20972biopharm_review.pdf#page=13 Page: 13.0	yes [IC50 17 uM]
OCT1 656	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/30114293/	yes [IC50 2.3 uM]
UGT 70	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20972biopharm_review.pdf#page=13 Page: 13.0	yes [IC50 250 uM]	M4 4
MATE1 416	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/30114293/	yes [IC50 3.85 uM]
BCRP 985	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/30114293/	yes [IC50 31.5 uM]
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/30114293/	yes [IC50 33.3 uM]
UGT 70	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20972biopharm_review.pdf#page=13 Page: 13.0	yes [IC50 390 uM]
MRP2 625	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/30114293/	yes [IC50 4.9 uM]
OCT2 782	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/30114293/	yes [IC50 5.66 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20972biopharm_review.pdf#page=13 Page: 13.0	yes [IC50 6 uM]	8-OH efavirenz 2
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020972s057,021360s045lbl.pdf#page=25 \| https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20972biopharm_review.pdf#page=13 Page: 25, (ClinP) 13	yes [IC50 8.5 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020972s057,021360s045lbl.pdf#page=25 Page: 25.0	yes [Ki 82 uM]
CYP2B6 1160	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020972s057,021360s045lbl.pdf#page=25 Page: 24, 25	yes
CYP3A4 2633	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020972s057,021360s045lbl.pdf#page=25 \| https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20972biopharm_review.pdf#page=10 Page: 24, 25, (ClinP) 10	yes
MRP1 232	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/17172311/	yes
MRP3 326	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/17172311/	yes
UGT1A1 303	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/27704562/	yes		yes (co-administration study) Comment: Efavirenz decreased Raltegravir AUCinf by 14% and Cmax by 9%. Sources: https://pubmed.ncbi.nlm.nih.gov/27704562/

Drug as victim

Target	Modality	Activity	Metabolite
CYP2B6 776	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020972s057,021360s045lbl.pdf#page=24 Page: 24.0	major
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020972s057,021360s045lbl.pdf#page=24 \| https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20972biopharm_review.pdf#page=12 Page: 24, (ClinP) 12	major
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25391641/	minor
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25391641/	minor
CYP2C19 1119	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20972biopharm_review.pdf#page=12 Page: 12.0	no
CYP2C8 810	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20972biopharm_review.pdf#page=12 Page: 12.0	no
CYP2C9 1193	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20972biopharm_review.pdf#page=12 Page: 12.0	no
CYP2D6 1388	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20972biopharm_review.pdf#page=12 Page: 12.0	no
CYP2E1 729	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20972biopharm_review.pdf#page=12 Page: 12.0	no
MRP1 113	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20660679/	no
MRP2 252	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20660679/	no
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20660679/	no
UGT1A4 399	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21319958/	no	7-OH efavirenz 2
UGT2B7 456	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21319958/	yes [Km 22.7 uM]
UGT1A1 479	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21319958/	yes	7-OH efavirenz 2
UGT1A1 479	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21319958/	yes	8,14-diOH efavirenz 2
UGT1A1 479	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21319958/	yes	8-OH efavirenz 2
UGT1A10 331	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21319958/	yes	7-OH efavirenz 2
UGT1A10 331	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21319958/	yes	8,14-diOH efavirenz 2
UGT1A10 331	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21319958/	yes	8-OH efavirenz 2
UGT1A3 470	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21319958/	yes	7-OH efavirenz 2
UGT1A3 470	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21319958/	yes	8,14-diOH efavirenz 2
UGT1A3 470	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21319958/	yes	8-OH efavirenz 2
UGT1A4 399	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21319958/	yes	8,14-diOH efavirenz 2
UGT1A4 399	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21319958/	yes	8-OH efavirenz 2
UGT1A6 343	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21319958/	yes	7-OH efavirenz 2
UGT1A6 343	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21319958/	yes	8,14-diOH efavirenz 2
UGT1A6 343	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21319958/	yes	8-OH efavirenz 2
UGT1A7 249	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21319958/	yes	7-OH efavirenz 2
UGT1A7 249	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21319958/	yes	8,14-diOH efavirenz 2
UGT1A7 249	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21319958/	yes	8-OH efavirenz 2
UGT1A8 323	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21319958/	yes	7-OH efavirenz 2
UGT1A8 323	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21319958/	yes	8,14-diOH efavirenz 2
UGT1A8 323	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21319958/	yes	8-OH efavirenz 2
UGT1A9 423	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21319958/	yes	7-OH efavirenz 2
UGT1A9 423	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21319958/	yes	8,14-diOH efavirenz 2
UGT1A9 423	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21319958/	yes	8-OH efavirenz 2
UGT2B15 236	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21319958/	yes	7-OH efavirenz 2
UGT2B15 236	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21319958/	yes	8,14-diOH efavirenz 2
UGT2B15 236	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21319958/	yes	8-OH efavirenz 2
UGT2B17 237	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21319958/	yes	7-OH efavirenz 2
UGT2B17 237	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21319958/	yes	8,14-diOH efavirenz 2
UGT2B17 237	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21319958/	yes	8-OH efavirenz 2
UGT2B4 278	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21319958/	yes	7-OH efavirenz 2
UGT2B4 278	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21319958/	yes	8,14-diOH efavirenz 2
UGT2B4 278	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21319958/	yes	8-OH efavirenz 2
UGT2B7 456	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21319958/	yes	7-OH efavirenz 2
UGT2B7 456	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21319958/	yes	8,14-diOH efavirenz 2
UGT2B7 456	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21319958/	yes	8-OH efavirenz 2

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:119486	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:119486
ChemicalBook	CB7181559	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7181559
eMolecules	2735350	https://www.emolecules.com/cgi-bin/more?vid=2735350
MolPort	MolPort-003-983-924	https://www.molport.com/shop/molecule-link/MolPort-003-983-924
ZINC	ZINC000002020233	http://zinc15.docking.org/substances/ZINC000002020233

PubMed

Title	Date	PubMed
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.	2001-11-30	11572864
Other issues: penetration into sanctuary sites, immune reconstitution and NNRTI sequencing.	2001-11	11589825
Factors affecting adherence and convenience in antiretroviral therapy.	2001-11	11589824
Comparison of NNRTIs in antiretroviral-experienced patients.	2001-11	11589823
Comparison of NNRTIs in antiretroviral-naïve patients.	2001-11	11589822
The role of NNRTIs in antiretroviral combination therapy: an introduction.	2001-11	11589821
New developments in anti-HIV chemotherapy.	2001-11	11562282
Protease-sparing regimen in a real-life practice with naïve patients: an equal opportunity approach?	2001-10-09	11590510
Efavirenz-induced psychosis.	2001-09-28	11579266
Response to first protease inhibitor- and efavirenz-containing antiretroviral combination therapy. The Swiss HIV Cohort Study.	2001-09-28	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.	2001-09-28	11575933
Comparison of initial combination antiretroviral therapy with a single protease inhibitor, ritonavir and saquinavir, or efavirenz.	2001-09-07	11546943
Evolution of anti-HIV drug candidates. Part 3: Diarylpyrimidine (DAPY) analogues.	2001-09-03	11527705
Thiosugars. VIII. Preparation of new 4'-thio-L-lyxo pyrimidine nucleoside analogues.	2001-09	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.	2001-09	11448730
Solution structures and reactivities of the mixed aggregates derived from n-butyllithium and vicinal amino alkoxides.	2001-08-22	11506560
Non-nucleoside reverse transcriptase inhibitor failure impairs HIV-RNA responses to efavirenz-containing salvage antiretroviral therapy.	2001-08-17	11504994
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.	2001-08-15	11511822
Antiretroviral therapy for previously treated patients.	2001-08-09	11496858
Nelfinavir, efavirenz, or both after the failure of nucleoside treatment of HIV infection.	2001-08-09	11496850
[Apropos of atypical melancholia with Sustiva (efavirenz)].	2001-08-08	11488260
Eruptive cheilitis: a new adverse effect in reactive HIV-positive patients subjected to high activity antiretroviral therapy (HAART). Presentation of six clinical cases.	2001-08-08	11488127
Metformin in an HIV-infected patient with protease inhibitor-induced diabetic ketoacidosis.	2001-08-04	11485138
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.	2001-08-02	11472208
Preliminary data of a prospective study on neuropsychiatric side effects after initiation of efavirenz.	2001-08-01	11468421
Antiretroviral rounds. When success is a pain.	2001-08	11547461
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.	2001-08	11477320
Antiviral drugs: current state of the art.	2001-08	11418355
[Drug interactions with antiretroviral agents].	2001-07-31	11475806
Gynecomastia without lipodystrophy syndrome in HIV-infected men treated with efavirenz.	2001-07-27	11504970
Synthesis and evaluation of novel quinolinones as HIV-1 reverse transcriptase inhibitors.	2001-07-23	11459666
Manic syndrome associated with efavirenz overdose.	2001-07-15	11418896
Management of sudden psychiatric disorders related to efavirenz.	2001-07-06	11426084
The steady-state pharmacokinetics of efavirenz and nevirapine when used in combination in human immunodeficiency virus type 1-infected persons.	2001-07-01	11398107
Predictors of protease inhibitor-associated adverse events.	2001-07	11478584
Efavirenz plasma concentrations and efficiency.	2001-06-15	11416729
Phenotypic hypersusceptibility to non-nucleoside reverse transcriptase inhibitors in treatment-experienced HIV-infected patients: impact on virological response to efavirenz-based therapy.	2001-06-15	11416714
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.	2001-06-06	11457384
In vitro anti-HIV-1 synergy between non-nucleoside reverse transcriptase inhibitors nevirapine and efavirenz.	2001-06	11491419
Limits of deep salvage antiretroviral therapy with nelfinavir plus either efavirenz or nevirapine, in highly pre-treated patients with HIV disease.	2001-06	11397623
[Vertical trasmission of human immunodeficiency virus (HIV) and other sexually transmitted infections (STI)].	2001-06	11395690
Efavirenz-induced photoallergic dermatitis in HIV.	2001-05-25	11400003
High-performance liquid chromatographic method for the determination of HIV-1 non-nucleoside reverse transcriptase inhibitor efavirenz in plasma of patients during highly active antiretroviral therapy.	2001-05-05	11393699
Efavirenz-induced acute eosinophilic hepatitis.	2001-05	11434632
High prevalence of genotypic and phenotypic HIV-1 drug-resistant strains among patients receiving antiretroviral therapy in Abidjan, Côte d'Ivoire.	2001-04-15	11391173
A pilot study of the use of mycophenolate mofetil as a component of therapy for multidrug-resistant HIV-1 infection.	2001-04-15	11391161
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.	2001-02-01	11462972
Switching from protease inhibitors to the non-nuke efavirenz.	2001	11570089
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

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.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 17:39:54 GMT 2025` Edited by `admin` on `Wed Apr 02 17:39:54 GMT 2025`
Record UNII	YXP9JDK7R7
Record Status	`Validated (UNII)`
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Name

Type

Language

Rac-Efavirenz

Common Name

English

L-741211

Preferred Name

English

2H-3,1-Benzoxazin-2-one, 6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-

Systematic Name

English

2H-3,1-Benzoxazin-2-one, 6-chloro-4-(2-cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-

Systematic Name

English

(±)-Efavirenz

Common Name

English

Efavirenz Racemic

Common Name

English

6-Chloro-4-(2-cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one

Systematic Name

English

Code System Code Type Description

FDA UNII

YXP9JDK7R7

Created by admin on Wed Apr 02 17:39:54 GMT 2025 , Edited by admin on Wed Apr 02 17:39:54 GMT 2025

PRIMARY

EPA CompTox

DTXSID00861416

Created by admin on Wed Apr 02 17:39:54 GMT 2025 , Edited by admin on Wed Apr 02 17:39:54 GMT 2025

PRIMARY

CAS

177530-93-7

Created by admin on Wed Apr 02 17:39:54 GMT 2025 , Edited by admin on Wed Apr 02 17:39:54 GMT 2025

PRIMARY

PUBCHEM

3203

Created by admin on Wed Apr 02 17:39:54 GMT 2025 , Edited by admin on Wed Apr 02 17:39:54 GMT 2025

PRIMARY

Details

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DescriptionSources: http://www.drugbank.ca/drugs/DB00625Curator's Comment: Description was created based on several sources, including

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Conditions

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T1/2

Funbound

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Overview

OverviewOther

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Drug as victim

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PubMed

Patents

Sample Use Guides

Description
Sources: http://www.drugbank.ca/drugs/DB00625
Curator's Comment: Description was created based on several sources, including

C_max

T_1/2

F_unbound

Drug as perpetrator