4,4-difluoro-N-[(1S)-3-[(1R,3S,5S)-3-{3-methyl-5-[(1,1,1,3,3,3-2H6)propan-2-yl]-4H-1,2,4-triazol-4-yl}-8-azabicyclo[3.2.1]octan-8-yl]-1-phenylpropyl]cyclohexane-1-carboxamide

• ChemBase ID: 172550
• Molecular Formular: C29H41F2N5O
• Molecular Mass: 513.6655464
• Monoisotopic Mass: 513.3279174
• SMILES: [C@@H]12N([C@@H](C[C@H](C1)n1c(nnc1C)C(C)C)CC2)CC[C@H](NC(=O)C1CCC(CC1)(F)F)c1ccccc1
• Canonical SMILES: O=C(C1CCC(CC1)(F)F)N[C@H](c1ccccc1)CCN1[C@@H]2CC[C@H]1C[C@@H](C2)n1c(C)nnc1C(C)C
• InChI: InChI=1S/C29H41F2N5O/c1-19(2)27-34-33-20(3)36(27)25-17-23-9-10-24(18-25)35(23)16-13-26(21-7-5-4-6-8-21)32-28(37)22-11-14-29(30,31)15-12-22/h4-8,19,22-26H,9-18H2,1-3H3,(H,32,37)/t23-,24+,25-,26-/m0/s1
• InChIKey: GSNHKUDZZFZSJB-QYOOZWMWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4,4-difluoro-N-[(1S)-3-[(1R,3S,5S)-3-{3-methyl-5-[(1,1,1,3,3,3-^2H₆)propan-2-yl]-4H-1,2,4-triazol-4-yl}-8-azabicyclo[3.2.1]octan-8-yl]-1-phenylpropyl]cyclohexane-1-carboxamide
• IUPAC Traditional name: 4,4-difluoro-N-[(1S)-3-[(1R,3S,5S)-3-{3-methyl-5-[(1,1,1,3,3,3-^2H₆)propan-2-yl]-1,2,4-triazol-4-yl}-8-azabicyclo[3.2.1]octan-8-yl]-1-phenylpropyl]cyclohexane-1-carboxamide
• Synonyms: 4,4-Difluoro-N-[(1S)-3-[(3-exo)-3-[3-methyl-5-(1-methylethyl-d6)-4H-1,2,4-triazol-4-yl]-8-azabicyclo[3.2.1]oct-8-yl]-1-phenylpropyl]cyclohexanecarboxamide; UK 427857-d6; Maraviroc-d6

Database IDs

• PubChem SID: 164228460
• PubChem CID: 71749908

CALCULATED PROPERTIES

• Acid pKa: 14.495693
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.27627262
• LogD (pH = 7.4): 1.6587688
• Log P: 3.6262107
• Molar Refractivity: 142.8808 cm^3
• Polarizability: 54.239895 Å^3
• Polar Surface Area: 63.05 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Brown Solid
• Melting Point: 79-81°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M193002

Potent, non-competitive CCR5 receptor antagonist; inhibits binding of HIV viral coat protein gp120. Antiviral.

REFERENCES

• Fumero, E., et al.: Clin. Microbiol. Infect., 9, 1077 (2003)
• Walker, D.K., et al.: Drug Metab. Dispos., 33, 587 (2003)
• Wood, A., et al.: Prog. Med. Chem., 43, 239 (2003)