Rilpivirine hydrochloride , Human immunodeficiency virus type 1 reverse transcriptase inhibitor, CAS No.700361-47-3, Human immunodeficiency virus type 1 reverse transcriptase inhibitor

CAS: 700361-47-3 Cat. No.: R647297 Molecular Weight: 402.88 EC Number: 680-634-8 PubChem CID: 11711114

Synonyms

Rilpivirine HCl | Q27137040 | HCl, Rilpivirine | 700361-47-3 (HCl) | KZVVGZKAVZUACK-BJILWQEISA-N | 212WAX8KDD | SCHEMBL1831067 | EVIPLERA COMPONENT RILPIVIRINE HYDROCHLORIDE | RILPIVIRINE HYDROCHLORIDE [VANDF] | Edurant | Benzonitrile, 4-((4-((4-((1E)-2-c

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Rilpivirine (R278474) hydrochloride is a potent and specific diarylpyrimidine (DAPY) non-nucleoside reverse transcriptase inhibitor ( NNRTI ). Rilpivirine hydrochloride has high antiviral activity against wild-type HIV ( EC 50 =0.4 nM) and mutant viruses ( EC 50 =0.1-2.0 nM). Rilpivirine hydrochloride has a high genetic barrier to resistance development of HIV

In Vitro

R278474 is active against wild-type HIV-1 (EC 50 =0.4 nM) and all single and double mutants tested (EC 50 =0.1-2.0 nM). R278474 (10-5000 nM; 30 d) does not observe the sign of wild-type HIV-1 breakthrough at 1 μM within 30 days. R278474 inhibits 81% of clinical isolates (about 1200 recombinant clinical isolates) at a 50% inhibitory concentration (EC 50 ) less than 1 nM, and inhibits 94% at EC 50 less than 10 nM. TMC278 shows subnanomolar EC 50 s against wild-type HIV-1 group M isolates (0.07-1.01 nM). MCE has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

R278474 (10-160 mg/kg; p.o. for 1 month) does not produce abnormal effects in rat, apart from liver weight increase and species-specific thyroid hypertrophy, both at the higher dose levels . R278474 (i.v.) exhibits elimination half-life ranges from 4.4 h in rat to 31 h in dog, and exposure (AUC inf ) amounts to 3.1 μg?h/mL (4 mg/kg) in rat, 8.7 μg?h/mL (1.25 mg/kg) in dog, 1.4 μg?h/mL (1.25 mg/ kg) in monkey, and 44?μg h/mL (1.25 mg/kg) in rabbit . R278474 (p.o.) exhibits half-life ranges between 2.8 h in rat and 39 h in dog, and oral bioavailability of 32% and 31% in rat and dog . MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Form:Solid

IC50& Target:IC50: 20±10 μM (MMP), Ki: 1.5±0.27 nM (MMPs)

Specifications

Synonyms

Rilpivirine HCl | Q27137040 | HCl, Rilpivirine | 700361-47-3 (HCl) | KZVVGZKAVZUACK-BJILWQEISA-N | 212WAX8KDD | SCHEMBL1831067 | EVIPLERA COMPONENT RILPIVIRINE HYDROCHLORIDE | RILPIVIRINE HYDROCHLORIDE [VANDF] | Edurant | Benzonitrile, 4-((4-((4-((1E)-2-c

Biochemical and Physiological Mechanisms

Rilpivirine (R278474) hydrochloride is a potent and specific diarylpyrimidine (DAPY) non-nucleoside reverse transcriptase inhibitor ( NNRTI ). Rilpivirine hydrochloride has high antiviral activity against wild-type HIV ( EC 50 =0.4 nM) and mutant viruses

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Mechanism of action

Human immunodeficiency virus type 1 reverse transcriptase inhibitor

Names and Identifiers

• Canonical Smiles: CC1=CC(=CC(=C1NC2=NC(=NC=C2)NC3=CC=C(C=C3)C#N)C)/C=C/C#N.Cl
• IUPAC Name: 4-[[4-[4-[(E)-2-cyanoethenyl]-2,6-dimethylanilino]pyrimidin-2-yl]amino]benzonitrile;hydrochloride
• InChIKey: KZVVGZKAVZUACK-BJILWQEISA-N
• 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+
• Isomeric SMILES: CC1=CC(=CC(=C1NC2=NC(=NC=C2)NC3=CC=C(C=C3)C#N)C)/C=C/C#N.Cl
• PubChem CID: 11711114
• Molecular Weight: 402.88

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Benzonitriles

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Benzonitriles
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzonitriles
• Alternative Parents: m-Xylenes Styrenes Aniline and substituted anilines Aminopyrimidines and derivatives Imidolactams Heteroaromatic compounds Secondary amines Nitriles Azacyclic compounds Organopnictogen compounds Hydrochlorides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Benzonitrile - M-xylene - Xylene - Styrene - Aniline or substituted anilines - Aminopyrimidine - Pyrimidine - Imidolactam - Heteroaromatic compound - Organoheterocyclic compound - Azacycle - Secondary amine - Nitrile - Carbonitrile - Amine - Hydrocarbon derivative - Organonitrogen compound - Organopnictogen compound - Organic nitrogen compound - Hydrochloride - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as benzonitriles. These are organic compounds containing a benzene bearing a nitrile substituent.
• External Descriptors: hydrochloride

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 402.900 g/mol
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 402.136 Da
• Monoisotopic Mass: 402.136 Da
• Topological Polar Surface Area: 97.400 Ų
• Heavy Atom Count: 29
• Formal Charge: 0
• Complexity: 607.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 2

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