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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
INTELENCE

Cmax

ValueDoseCo-administeredAnalytePopulation
296.74 ng/mL
200 mg 2 times / day steady-state, oral
ETRAVIRINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
4531.53 ng × h/mL
200 mg 2 times / day steady-state, oral
ETRAVIRINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
41 h
200 mg 2 times / day steady-state, oral
ETRAVIRINE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
0.1%
200 mg 2 times / day steady-state, oral
ETRAVIRINE plasma
Homo sapiens

Doses

AEs

PubMed

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
Record UNII
0C50HW4FO1
Record Status Validated (UNII)
Record Version