4-{[4-({4-[(1E)-2-cyanoeth-1-en-1-yl]-2,6-dimethylphenyl}amino)pyrimidin-2-yl]amino}benzonitrile

• ChemBase ID: 6200
• Molecular Formular: C22H18N6
• Molecular Mass: 366.41852
• Monoisotopic Mass: 366.15929461
• SMILES: c1(c(c(cc(c1)/C=C/C#N)C)Nc1ccnc(n1)Nc1ccc(cc1)C#N)C
• Canonical SMILES: N#C/C=C/c1cc(C)c(c(c1)C)Nc1ccnc(n1)Nc1ccc(cc1)C#N
• InChI: InChI=1S/C22H18N6/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)/b4-3+
• InChIKey: YIBOMRUWOWDFLG-ONEGZZNKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[4-({4-[(1E)-2-cyanoeth-1-en-1-yl]-2,6-dimethylphenyl}amino)pyrimidin-2-yl]amino}benzonitrile
• IUPAC Traditional name: rilpivirine
• Synonyms: 4-{[4-({4-[(E)-2-cyanoethenyl]-2,6-dimethylphenyl}amino)pyrimidin-2-yl]amino}benzonitrile; R278474; TMC278; 4-[[4-[[4-[(1E)-2-Cyanoethenyl]-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]benzonitrile; R 278474; TMC 278; Rilpivirine

Database IDs

• CAS Number: 500287-72-9
• PubChem SID: 99445063; 160969625
• PubChem CID: 6451164

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.92605
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 5.3170266
• LogD (pH = 7.4): 5.4708285
• Log P: 5.4732256
• Molar Refractivity: 111.7394 cm^3
• Polarizability: 40.55384 Å^3
• Polar Surface Area: 97.42 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 3.8
• LOG S: -4.5
• Solubility (Water): 1.16e-02 g/l

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: N/ABright Yellow Solid
• Melting Point: 241-243°C

Safety Information

• Storage Condition: Refrigerator

Pharmacology Properties

• Target: Reverse Transcriptase

Product Information

• Salt Data: Free Base

DETAILS

DrugBank - DB08592

Drug information: experimental

Toronto Research Chemicals - R509800

A novel non-nucleoside reverse transcriptase inhibitor. Rilpivirine seems to be well tolerated with less CNS disturbance than Efavirenz, and has non-teratogenic potential. An anti-HIV agent.

REFERENCES

• Sun, et al.: J. Med. Chem., 41, 4648 (1998)
• Kashiwada, et al.: Bioorg. Med. Chem. Lett., 11, 183 (1998)