4,4-difluoro-N-[(1S)-3-[(1R,3S,5S)-3-[3-methyl-5-(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: 128214
• Molecular Formular: C29H41F2N5O
• Molecular Mass: 513.6655464
• Monoisotopic Mass: 513.3279174
• SMILES: Cc1nnc(n1[C@@H]1C[C@H]2CC[C@@H](C1)N2CC[C@H](NC(=O)C1CCC(F)(F)CC1)c1ccccc1)C(C)C
• 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-(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-isopropyl-5-methyl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-phenylpropyl]cyclohexane-1-carboxamide
• Brand Name: Selzentry
• Synonyms: 4,4-Difluoro-N-[(1S)-3-[(3-exo)-3-[3-methyl-5-(1-methylethyl)-4H-1,2,4-triazol-4-yl]-8-azabicyclo[3.2.1]oct-8-yl]-1-phenylpropyl]cyclohexanecarboxamide; UK-427857; Maraviroc; Maraviroc

Database IDs

• CAS Number: 376348-65-1
• MDL Number: MFCD13188530
• PubChem SID: 162222523
• PubChem CID: 3002977
• ATC CODE: J05AX09
• CHEMBL: 1201187
• Chemspider ID: 20078004
• DrugBank ID: DB04835
• IUPHAR ligand ID: 803
• Unique Ingredient Identifier: MD6P741W8A
• Wikipedia Title: Maraviroc
• Medline Plus: a607076

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: 54.23912 Å^3
• Polar Surface Area: 63.05 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >30 mg/mL
• Apperance: white powder
• Optical Rotation: [α]-15/D

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 1
• Risk Statements: 48/22
• Safety Statements: 22-36
• Storage Temperature: room temp

Pharmacology Properties

• Admin Routes: Oral
• Bioavailability: 23%
• Half Life: 16 h
• Metabolism: Liver
• Legal Status: POM (UK); Rx-only (US)
• Pregnancy Category: B (US); B1 (Australia)
• US Licence: Maraviroc
• EU Licence: Celsentri

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C29H41F2N5O

DETAILS

Sigma Aldrich - PZ0002

Legal Information
Sold for research purposes under agreement from Pfizer Inc.
Biochem/physiol Actions
Maraviroc is a CCR5 chemokine receptor antagonist, and antiretroviral entry inhibitor. Maraviroc inhibits HIV entry by blocking interaction of viral coat protein gp120 with the receptor.