Rilpivirine hydrochlorideProduct ingredient for Rilpivirine

Name
Rilpivirine hydrochloride
Drug Entry
Rilpivirine

Rilpivirine is non-nucleoside reverse transcriptase inhibitor (NNRTI) which is used for the treatment of HIV-1 infections in treatment-naive patients.1 It is a diarylpyrimidine derivative.2 The internal conformational flexibility of rilpivirine and the plasticity of it interacting binding site gives it a very high potency and reduces the chance of resistance compared to other NNRTI's.3 Rilpivirine was developed by Tilbotec, Inc. and FDA approved on May 20, 2011.6 On November 21, 2017, Rilpivirine, in combination with dolutegravir, was approved as part of the first complete treatment regimen with only two drugs for the treatment of adults with HIV-1 named Juluca.7 Rilpivirine in combination with cabotegravir was granted FDA approval on 21 January 2021.10

Accession Number
DBSALT000152
Structure
Thumb
Synonyms
Rilpivirine HCl / Rilpivirine hydrochlorid
External IDs
TMC278 hydrochloride
UNII
212WAX8KDD
CAS Number
700361-47-3
Weight
Average: 402.879
Monoisotopic: 402.135972345
Chemical Formula
C22H19ClN6
InChI Key
KZVVGZKAVZUACK-BJILWQEISA-N
InChI
InChI=1S/C22H18N6.ClH/c1-15-12-18(4-3-10-23)13-16(2)21(15)27-20-9-11-25-22(28-20)26-19-7-5-17(14-24)6-8-19;/h3-9,11-13H,1-2H3,(H2,25,26,27,28);1H/b4-3+;
IUPAC Name
4-{[4-({4-[(1E)-2-cyanoeth-1-en-1-yl]-2,6-dimethylphenyl}amino)pyrimidin-2-yl]amino}benzonitrile hydrochloride
SMILES
Cl.CC1=CC(\C=C\C#N)=CC(C)=C1NC1=CC=NC(NC2=CC=C(C=C2)C#N)=N1
PubChem Compound
11711114
ChemSpider
9885836
ChEBI
68602
ChEMBL
CHEMBL1628504
Wikipedia
Rilpivirine
Predicted Properties
PropertyValueSource
Water Solubility0.0116 mg/mLALOGPS
logP3.8ALOGPS
logP5.47ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)11.43ChemAxon
pKa (Strongest Basic)4.44ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area97.42 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity111.74 m3·mol-1ChemAxon
Polarizability40.78 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon