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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 of ETRAVIRINE

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
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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
296.74 ng/mL
200 mg 2 times / day steady-state, oral
dose: 200 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: DARUNAVIR
ETRAVIRINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
4531.53 ng × h/mL
200 mg 2 times / day steady-state, oral
dose: 200 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: DARUNAVIR
ETRAVIRINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
41 h
200 mg 2 times / day steady-state, oral
dose: 200 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: DARUNAVIR
ETRAVIRINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
0.1%
200 mg 2 times / day steady-state, oral
dose: 200 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: DARUNAVIR
ETRAVIRINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
Doses

Doses

DosePopulationAdverse 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:
unhealthy, 29–63
Health Status: unhealthy
Age Group: 29–63
Sex: M+F
Sources:
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:
unhealthy
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:
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:
unhealthy
Disc. AE: Rash...
AEs leading to
discontinuation/dose reduction:
Rash (2.2%)
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
PubMed

PubMed

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

Sample Use Guides

200 mg (two 100 mg tablets) taken twice daily following a meal
Route of Administration: Oral
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
  • Download
Name Type Language
INTELENCE
Preferred Name English
ETRAVIRINE
DASH   EMA EPAR   INN   JAN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN   INN  
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)
Created by admin on Mon Mar 31 18:13:38 GMT 2025 , Edited by admin on Mon Mar 31 18:13:38 GMT 2025
NCI_THESAURUS C97453
Created by admin on Mon Mar 31 18:13:38 GMT 2025 , Edited by admin on Mon Mar 31 18:13:38 GMT 2025
WHO-VATC QJ05AG04
Created by admin on Mon Mar 31 18:13:38 GMT 2025 , Edited by admin on Mon Mar 31 18:13:38 GMT 2025
NDF-RT N0000175463
Created by admin on Mon Mar 31 18:13:38 GMT 2025 , Edited by admin on Mon Mar 31 18:13:38 GMT 2025
NDF-RT N0000009948
Created by admin on Mon Mar 31 18:13:38 GMT 2025 , Edited by admin on Mon Mar 31 18:13:38 GMT 2025
LIVERTOX NBK548290
Created by admin on Mon Mar 31 18:13:38 GMT 2025 , Edited by admin on Mon Mar 31 18:13:38 GMT 2025
WHO-ATC J05AG04
Created by admin on Mon Mar 31 18:13:38 GMT 2025 , Edited by admin on Mon Mar 31 18:13:38 GMT 2025
NDF-RT N0000175460
Created by admin on Mon Mar 31 18:13:38 GMT 2025 , Edited by admin on Mon Mar 31 18:13:38 GMT 2025
Code System Code Type Description
PUBCHEM
193962
Created by admin on Mon Mar 31 18:13:38 GMT 2025 , Edited by admin on Mon Mar 31 18:13:38 GMT 2025
PRIMARY
EPA CompTox
DTXSID30181412
Created by admin on Mon Mar 31 18:13:38 GMT 2025 , Edited by admin on Mon Mar 31 18:13:38 GMT 2025
PRIMARY
MERCK INDEX
m5205
Created by admin on Mon Mar 31 18:13:38 GMT 2025 , Edited by admin on Mon Mar 31 18:13:38 GMT 2025
PRIMARY Merck Index
WIKIPEDIA
ETRAVIRINE
Created by admin on Mon Mar 31 18:13:38 GMT 2025 , Edited by admin on Mon Mar 31 18:13:38 GMT 2025
PRIMARY
CAS
269055-15-4
Created by admin on Mon Mar 31 18:13:38 GMT 2025 , Edited by admin on Mon Mar 31 18:13:38 GMT 2025
PRIMARY
INN
8303
Created by admin on Mon Mar 31 18:13:38 GMT 2025 , Edited by admin on Mon Mar 31 18:13:38 GMT 2025
PRIMARY
ChEMBL
CHEMBL308954
Created by admin on Mon Mar 31 18:13:38 GMT 2025 , Edited by admin on Mon Mar 31 18:13:38 GMT 2025
PRIMARY
MESH
C451734
Created by admin on Mon Mar 31 18:13:38 GMT 2025 , Edited by admin on Mon Mar 31 18:13:38 GMT 2025
PRIMARY
USAN
RR-30
Created by admin on Mon Mar 31 18:13:38 GMT 2025 , Edited by admin on Mon Mar 31 18:13:38 GMT 2025
PRIMARY
DAILYMED
0C50HW4FO1
Created by admin on Mon Mar 31 18:13:38 GMT 2025 , Edited by admin on Mon Mar 31 18:13:38 GMT 2025
PRIMARY
NCI_THESAURUS
C73195
Created by admin on Mon Mar 31 18:13:38 GMT 2025 , Edited by admin on Mon Mar 31 18:13:38 GMT 2025
PRIMARY
SMS_ID
100000089817
Created by admin on Mon Mar 31 18:13:38 GMT 2025 , Edited by admin on Mon Mar 31 18:13:38 GMT 2025
PRIMARY
EVMPD
SUB25650
Created by admin on Mon Mar 31 18:13:38 GMT 2025 , Edited by admin on Mon Mar 31 18:13:38 GMT 2025
PRIMARY
FDA UNII
0C50HW4FO1
Created by admin on Mon Mar 31 18:13:38 GMT 2025 , Edited by admin on Mon Mar 31 18:13:38 GMT 2025
PRIMARY
RS_ITEM_NUM
1266824
Created by admin on Mon Mar 31 18:13:38 GMT 2025 , Edited by admin on Mon Mar 31 18:13:38 GMT 2025
PRIMARY
LACTMED
Etravirine
Created by admin on Mon Mar 31 18:13:38 GMT 2025 , Edited by admin on Mon Mar 31 18:13:38 GMT 2025
PRIMARY
RXCUI
475969
Created by admin on Mon Mar 31 18:13:38 GMT 2025 , Edited by admin on Mon Mar 31 18:13:38 GMT 2025
PRIMARY RxNorm
CHEBI
63589
Created by admin on Mon Mar 31 18:13:38 GMT 2025 , Edited by admin on Mon Mar 31 18:13:38 GMT 2025
PRIMARY
DRUG CENTRAL
1115
Created by admin on Mon Mar 31 18:13:38 GMT 2025 , Edited by admin on Mon Mar 31 18:13:38 GMT 2025
PRIMARY
DRUG BANK
DB06414
Created by admin on Mon Mar 31 18:13:38 GMT 2025 , Edited by admin on Mon Mar 31 18:13:38 GMT 2025
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> INDUCER
BINDER->LIGAND
BINDING
METABOLIC ENZYME -> INHIBITOR
ANTAGONIST
IC50
EXCRETED UNCHANGED
AMOUNT EXCRETED
FECAL
TRANSPORTER -> INHIBITOR
WEAK
IC50
TRANSPORTER -> SUBSTRATE
EXCRETED UNCHANGED
No unchanged drug was recovered in the urine.
URINE
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
IMPURITY -> PARENT
IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC SINGLE DOSE

ORAL ADMINISTRATION

Volume of Distribution PHARMACOKINETIC
Tmax PHARMACOKINETIC ORAL ADMINISTRATION

SINGLE DOSE