4-({6-amino-5-bromo-2-[(4-cyanophenyl)amino]pyrimidin-4-yl}oxy)-3,5-dimethylbenzonitrile

• ChemBase ID: 4843
• Molecular Formular: C20H15BrN6O
• Molecular Mass: 435.2767
• Monoisotopic Mass: 434.04907113
• SMILES: c1(Oc2nc(Nc3ccc(cc3)C#N)nc(N)c2Br)c(C)cc(cc1C)C#N
• Canonical SMILES: N#Cc1ccc(cc1)Nc1nc(N)c(c(n1)Oc1c(C)cc(cc1C)C#N)Br
• InChI: 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)
• InChIKey: PYGWGZALEOIKDF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-({6-amino-5-bromo-2-[(4-cyanophenyl)amino]pyrimidin-4-yl}oxy)-3,5-dimethylbenzonitrile
• IUPAC Traditional name: intelence; etravirine
• Synonyms: 4-({6-AMINO-5-BROMO-2-[(4-CYANOPHENYL)AMINO]PYRIMIDIN-4-YL}OXY)-3,5-DIMETHYLBENZONITRILE; 4-[[6-Amino-5-bromo-2-[(4-cyanophenyl)amino]-4-pyrimidinyl]oxy]-3,5-dimethyl-benzonitrile; Intelence; R 165335; TMC 125; Etravirine; Etravirine (TMC125)

Database IDs

• CAS Number: 269055-15-4
• PubChem SID: 160968275; 99443662
• PubChem CID: 193962

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.491134
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 5.5185337
• LogD (pH = 7.4): 5.536277
• Log P: 5.5365114
• Molar Refractivity: 111.8711 cm^3
• Polarizability: 40.72325 Å^3
• Polar Surface Area: 120.64 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 3.67
• LOG S: -4.41
• Solubility (Water): 1.69e-02 g/l

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White to Off-White Solid
• Melting Point: 265°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

Pharmacology Properties

• Target: Reverse Transcriptase

Product Information

• Salt Data: Free Base

DETAILS

DrugBank - DB07191

Drug information: experimental

Toronto Research Chemicals - E937000

A novel HIV reverse transcriptase inhibitor useful in treatment of HIV infection.

REFERENCES

• Scholler-Gyure, M., et al.: J. Clin. Pharmacol., 48, 322 (2008)
• Thakur, A., et al.: Eur. J. Med. Chem., 43, 471 (2008)