ETRAVIRINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H15BrN6O
Molecular Weight	435.277
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC(=CC(C)=C1OC2=C(Br)C(N)=NC(NC3=CC=C(C=C3)C#N)=N2)C#N

InChI

InChIKey=PYGWGZALEOIKDF-UHFFFAOYSA-N

InChI=1S/C20H15BrN6O/c1-11-7-14(10-23)8-12(2)17(11)28-19-16(21)18(24)26-20(27-19)25-15-5-3-13(9-22)4-6-15/h3-8H,1-2H3,(H3,24,25,26,27)

HIDE SMILES / InChI

Molecular Formula	C20H15BrN6O
Molecular Weight	435.277
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022187lbl.pdf
Curator's Comment: description was created based on several sources, including: https://www.drugs.com/ppa/etravirine.html | http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/000900/WC500034183.pdf | http://www.wikidoc.org/index.php/Etravirine

Etravirine (formerly known as TMC125) is an antiretroviral agent more specifically classified as a Non-Nucleoside Reverse Transcriptase Inhibitor. Etravirine exerts its effects via direct inhibition of the reverse transcriptase enzyme of human immunodeficiency virus type 1 (HIV-1). It directly binds reverse transcriptase and consequently blocks DNA-dependent and RNA-dependent polymerase activity. In combination with other antiretroviral agents, it is indicated for the treatment of human immunodeficiency virus type 1 (HIV-1) infection in antiretroviral treatment-experienced adult patients, who have evidence of viral replication and HIV-1 strains resistant to a non-nucleoside reverse transcriptase inhibitor (NNRTI) and other antiretroviral agents. The most common adverse events (incidence > 10%) of any intensity that occurred at a higher rate than placebo are rash and nausea. Etravirine should not be co-administered with the following antiretrovirals: Tipranavir/ritonavir, fosamprenavir/ritonavir, atazanavir/ritonavir; Protease inhibitors administered without ritonavir; NNRTIs.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
P-glycoprotein 1 54 Target ID: CHEMBL4302 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/000900/WC500034183.pdf	Inhibitor 8504		24.2 µM [IC50]
Human immunodeficiency virus type 1 reverse transcriptase 70 Target ID: CHEMBL247 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/000900/WC500034183.pdf	Inhibitor 8504		38.4 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
HIV-1 infection 156 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022187lbl.pdf	Primary		Approved 8583	INTELENCE Approved Use INTELENCE® Registered trademark of Tibotec Pharmaceuticals, in combination with other antiretroviral agents, is indicated for the treatment of human immunodeficiency virus type 1 (HIV-1) infection in antiretroviral treatment-experienced adult patients, who have evidence of viral replication and HIV-1 strains resistant to a non-nucleoside reverse transcriptase inhibitor (NNRTI) and other antiretroviral agents. This indication is based on Week 48 analyses from 2 randomized, double-blind, placebo-controlled trials of INTELENCE®. Both studies were conducted in clinically advanced, 3-class antiretroviral (NNRTI, N[t Launch Date 2008

C_max

Value	Dose	Co-administered	Analyte	Population
296.74 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022187lbl.pdf	200 mg 2 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered: DARUNAVIR	DARUNAVIR	ETRAVIRINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED

AUC

Value	Dose	Co-administered	Analyte	Population
4531.53 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022187lbl.pdf	200 mg 2 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered: DARUNAVIR	DARUNAVIR	ETRAVIRINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED

T_1/2

Value	Dose	Co-administered	Analyte	Population
41 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022187lbl.pdf	200 mg 2 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered: DARUNAVIR	DARUNAVIR	ETRAVIRINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED

F_unbound

Value	Dose	Co-administered	Analyte	Population
0.1% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022187lbl.pdf	200 mg 2 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered: DARUNAVIR	DARUNAVIR	ETRAVIRINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED

Doses

Dose	Population	Adverse events
800 mg 2 times / day multiple, oral Highest studied dose Dose: 800 mg, 2 times / day Route: oral Route: multiple Dose: 800 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17413684	unhealthy, 29–63 Health Status: unhealthy Age Group: 29–63 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/17413684	Sources: https://pubmed.ncbi.nlm.nih.gov/17413684
200 mg 2 times / day multiple, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/022187s009lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/022187s009lbl.pdf	Disc. AE: Reaction skin, Stevens-Johnson syndrome... AEs leading to discontinuation/dose reduction: Reaction skin (severe\|grade 4\|grade 5) Stevens-Johnson syndrome (severe\|grade 4\|grade 5) Hypersensitivity reaction (severe\|grade 4\|grade 5) Toxic epidermal necrolysis (severe\|grade 4\|grade 5) Erythema multiforme (severe\|grade 4\|grade 5) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/022187s009lbl.pdf
200 mg 2 times / day multiple, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/022187s009lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/022187s009lbl.pdf	Disc. AE: Rash... AEs leading to discontinuation/dose reduction: Rash (2.2%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/022187s009lbl.pdf

AEs

AE	Significance	Dose	Population
Erythema multiforme	severe\|grade 4\|grade 5 Disc. AE	200 mg 2 times / day multiple, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/022187s009lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/022187s009lbl.pdf
Hypersensitivity reaction	severe\|grade 4\|grade 5 Disc. AE	200 mg 2 times / day multiple, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/022187s009lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/022187s009lbl.pdf
Reaction skin	severe\|grade 4\|grade 5 Disc. AE	200 mg 2 times / day multiple, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/022187s009lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/022187s009lbl.pdf
Stevens-Johnson syndrome	severe\|grade 4\|grade 5 Disc. AE	200 mg 2 times / day multiple, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/022187s009lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/022187s009lbl.pdf
Toxic epidermal necrolysis	severe\|grade 4\|grade 5 Disc. AE	200 mg 2 times / day multiple, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/022187s009lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/022187s009lbl.pdf
Rash	2.2% Disc. AE	200 mg 2 times / day multiple, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/022187s009lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/022187s009lbl.pdf

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:63589	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:63589
ChemicalBook	CB51509336	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB51509336
eMolecules	31592739	https://www.emolecules.com/cgi-bin/more?vid=31592739
MolPort	MolPort-009-194-145	https://www.molport.com/shop/molecule-link/MolPort-009-194-145
Selleck Chemicals	etravirine-tmc125	http://www.selleckchem.com/products/etravirine-tmc125.html
ZINC	ZINC000000602632	http://zinc15.docking.org/substances/ZINC000000602632

PubMed

Title	Date	PubMed
TMC125 shows promise.	2002 Feb	11892632
TMC125 exerts similar initial antiviral potency as a five-drug, triple class antiretroviral regimen.	2003 Dec 5	14685056
A series of diaryltriazines and diarylpyrimidines are highly potent nonnucleoside reverse transcriptase inhibitors with possible applications as microbicides.	2004 Oct	15388420
New non-nucleoside reverse transcriptase inhibitors (NNRTIs) in development for the treatment of HIV infections.	2004 Oct	15351347
Gateways to clinical trials.	2005 Jan-Feb	15834459
Next-generation HIV-1 non-nucleoside reverse transcriptase inhibitors.	2006 Feb	16499282
Optimization of diarylamines as non-nucleoside inhibitors of HIV-1 reverse transcriptase.	2006 Feb	16298131
Pharmacokinetics of darunavir/ritonavir and TMC125 alone and coadministered in HIV-negative volunteers.	2007	17713162
Prevalence of etravirine (TMC-125) resistance mutations in HIV-infected patients with prior experience of non-nucleoside reverse transcriptase inhibitors.	2007 Dec	17913723
Gateways to clinical trials.	2007 Jan-Feb	17344945
FDA accepts NDA for priority review of TMC125.	2007 Oct	17992720
Highlights of the 15th Conference on Retroviruses and Opportunistic Infections. Advances in antiretroviral therapy.	2008 Apr-May	18441381
Hemorrhagic cardiomyopathy in male mice treated with an NNRTI: the role of vitamin K.	2008 Feb	18367644
The incidence of multidrug and full class resistance in HIV-1 infected patients is decreasing over time (2001-2006) in Portugal.	2008 Feb 1	18241328
[New drugs for HIV infection].	2008 Mar	18416392
Pharmacokinetic and pharmacodynamic study of the concomitant administration of methadone and TMC125 in HIV-negative volunteers.	2008 Mar	18195053
Adverse cutaneous reactions associated with the newest antiretroviral drugs in patients with human immunodeficiency virus infection.	2008 Nov	18653488

Patents

Sample Use Guides

In Vivo Use Guide

200 mg (two 100 mg tablets) taken twice daily following a meal

Route of Administration: Oral

In Vitro Use Guide

TMC125, was highly active against wild-type HIV-1 (50% effective concentration [EC50] = 1.4 to 4.8 nM) and showed some activity against HIV-2 (EC50 = 3.5 microM). TMC125 also inhibited a series of HIV-1 group M subtypes and circulating recombinant forms and a group O virus.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:13:38 GMT 2025` Edited by `admin` on `Mon Mar 31 18:13:38 GMT 2025`
Record UNII	0C50HW4FO1
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

INTELENCE

Preferred Name

English

ETRAVIRINE

Official Name

English

ETRAVIRINE [JAN]

Common Name

English

etravirine [INN]

Common Name

English

TMC 125

Code

English

ETRAVIRINE [MI]

Common Name

English

ETRAVIRINE [MART.]

Common Name

English

ETRAVIRINE [VANDF]

Common Name

English

Etravirine [WHO-DD]

Common Name

English

R165335

Code

English

BENZONITRILE, 4-((6-AMINO-5-BROMO-2-((4-CYANOPHENYL)AMINO)-4-PYRIMIDINYL)OXY)-3,5-DIMETHYL-

Systematic Name

English

4-[[6-Amino-5-bromo-2-[(4-cyanophenyl)amino]-4-pyrimidinyl]oxy]-3,5-dimethyl-benzonitrile

Systematic Name

English

TMC125

Code

English

ETRAVIRINE [USAN]

Common Name

English

TMC-125

Code

English

ETRAVIRINE [EMA EPAR]

Common Name

English

ETRAVIRINE [ORANGE BOOK]

Common Name

English

R-165335

Code

English

Classification Tree Code System Code

EMA ASSESSMENT REPORTS

INTELENCE (AUTHORIZED: HIV INFECTIONS)