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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

Description

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

Targets

Primary TargetPharmacologyConditionPotency
24.2 µM [IC50]
38.4 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
INTELENCE
PubMed

PubMed

TitleDatePubMed
Prevalence and risk factors for etravirine resistance among patients failing on non-nucleoside reverse transcriptase inhibitors.
2008
Etravirine for the treatment of HIV infection.
2008 Aug
How developing world concerns need to be part of drug development plans: a case study of four emerging antiretrovirals.
2008 Jul
FDA notifications. FDA grants accelerated approval for etravirine.
2008 Mar
New drugs: Etravirine, sinecatechins, and desvenlafaxine succinate.
2008 May-Jun
Adverse cutaneous reactions associated with the newest antiretroviral drugs in patients with human immunodeficiency virus infection.
2008 Nov
Prevalence of etravirine-associated mutations in clinical samples with resistance to nevirapine and efavirenz.
2008 Nov
Shifting paradigms: the resistance profile of etravirine.
2008 Oct
A survey of the syntheses of active pharmaceutical ingredients for antiretroviral drug combinations critical to access in emerging nations.
2008 Sep
Evolution of genetic diversity and drug resistance mutations in HIV-1 among untreated patients from Mali between 2005 and 2006.
2008 Sep
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.
Name Type Language
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
INTELENCE
Brand Name English
ETRAVIRINE [VANDF]
Common Name English
R165335
Code English
ETRAVIRINE [WHO-DD]
Common Name 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 Oct 21 19:49:07 UTC 2019 , Edited by admin on Mon Oct 21 19:49:07 UTC 2019
NCI_THESAURUS C97453
Created by admin on Mon Oct 21 19:49:07 UTC 2019 , Edited by admin on Mon Oct 21 19:49:07 UTC 2019
WHO-VATC QJ05AG04
Created by admin on Mon Oct 21 19:49:07 UTC 2019 , Edited by admin on Mon Oct 21 19:49:07 UTC 2019
NDF-RT N0000175463
Created by admin on Mon Oct 21 19:49:07 UTC 2019 , Edited by admin on Mon Oct 21 19:49:07 UTC 2019
NDF-RT N0000009948
Created by admin on Mon Oct 21 19:49:07 UTC 2019 , Edited by admin on Mon Oct 21 19:49:07 UTC 2019
LIVERTOX 390
Created by admin on Mon Oct 21 19:49:07 UTC 2019 , Edited by admin on Mon Oct 21 19:49:07 UTC 2019
WHO-ATC J05AG04
Created by admin on Mon Oct 21 19:49:07 UTC 2019 , Edited by admin on Mon Oct 21 19:49:07 UTC 2019
NDF-RT N0000175460
Created by admin on Mon Oct 21 19:49:07 UTC 2019 , Edited by admin on Mon Oct 21 19:49:07 UTC 2019
Code System Code Type Description
PUBCHEM
193962
Created by admin on Mon Oct 21 19:49:07 UTC 2019 , Edited by admin on Mon Oct 21 19:49:07 UTC 2019
PRIMARY
EPA CompTox
269055-15-4
Created by admin on Mon Oct 21 19:49:07 UTC 2019 , Edited by admin on Mon Oct 21 19:49:07 UTC 2019
PRIMARY
MERCK INDEX
M5205
Created by admin on Mon Oct 21 19:49:07 UTC 2019 , Edited by admin on Mon Oct 21 19:49:07 UTC 2019
PRIMARY Merck Index
WIKIPEDIA
ETRAVIRINE
Created by admin on Mon Oct 21 19:49:07 UTC 2019 , Edited by admin on Mon Oct 21 19:49:07 UTC 2019
PRIMARY
CAS
269055-15-4
Created by admin on Mon Oct 21 19:49:07 UTC 2019 , Edited by admin on Mon Oct 21 19:49:07 UTC 2019
PRIMARY
INN
8303
Created by admin on Mon Oct 21 19:49:07 UTC 2019 , Edited by admin on Mon Oct 21 19:49:07 UTC 2019
PRIMARY
ChEMBL
CHEMBL308954
Created by admin on Mon Oct 21 19:49:07 UTC 2019 , Edited by admin on Mon Oct 21 19:49:07 UTC 2019
PRIMARY
MESH
C451734
Created by admin on Mon Oct 21 19:49:07 UTC 2019 , Edited by admin on Mon Oct 21 19:49:07 UTC 2019
PRIMARY
NCI_THESAURUS
C73195
Created by admin on Mon Oct 21 19:49:07 UTC 2019 , Edited by admin on Mon Oct 21 19:49:07 UTC 2019
PRIMARY
LactMed
269055-15-4
Created by admin on Mon Oct 21 19:49:07 UTC 2019 , Edited by admin on Mon Oct 21 19:49:07 UTC 2019
PRIMARY
EVMPD
SUB25650
Created by admin on Mon Oct 21 19:49:07 UTC 2019 , Edited by admin on Mon Oct 21 19:49:07 UTC 2019
PRIMARY
RXCUI
475969
Created by admin on Mon Oct 21 19:49:07 UTC 2019 , Edited by admin on Mon Oct 21 19:49:07 UTC 2019
PRIMARY RxNorm
DRUG BANK
DB06414
Created by admin on Mon Oct 21 19:49:07 UTC 2019 , Edited by admin on Mon Oct 21 19:49:07 UTC 2019
PRIMARY