4,4-difluoro-N-[(1S)-3-[(1R,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: 4379
• Molecular Formular: C29H41F2N5O
• Molecular Mass: 513.6655464
• Monoisotopic Mass: 513.3279174
• SMILES: FC1(F)CCC(C(=O)N[C@@H](CCN2[C@H]3CC(n4c(nnc4C)C(C)C)C[C@@H]2CC3)c2ccccc2)CC1
• Canonical SMILES: O=C(C1CCC(CC1)(F)F)N[C@H](c1ccccc1)CCN1[C@@H]2CC[C@H]1CC(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-HLMSNRGBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4,4-difluoro-N-[(1S)-3-[(1R,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: maraviroc
• Brand Name: Selzentry; Celsentri
• Synonyms: maraviroc; Maraviroc

Database IDs

• CAS Number: 376348-65-1
• PubChem SID: 46508040; 160967811
• PubChem CID: 3002977

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: 4.3
• LOG S: -4.68
• Solubility (Water): 1.06e-02 g/l

DETAILS

DrugBank - DB04835

• Drug Groups: approved; investigational
• Description: Maraviroc (brand-named Selzentry, or Celsentri outside the U.S.) is a chemokine receptor antagonist drug developed by the drug company Pfizer that is designed to act against HIV by interfering with the interaction between HIV and CCR5. It was originally labelled as UK-427857 during development but was assigned the Maraviroc name as it entered trials. It was approved for use by the FDA in August, 2007.
• Indication: For treatment-experienced adult patients infected with only CCR5-tropic HIV-1 detectable, who have evidence of viral replication and HIV-1 strains resistant to multiple antiretroviral agents.
• Pharmacology: Maraviroc is a chemokine receptor antagonist drug developed by the drug company Pfizer that is designed to act against HIV by interfering with the interaction between HIV and CCR5.
• Affected Organisms: Human Immunodeficiency Virus
• Biotransformation: In vitro studies indicate that CYP3A is the major enzyme responsible for maraviroc metabolism.
• Absorption: The absolute oral bioavailability of a 100 mg dose is 23% and is predicted to be 33% at 300 mg. Coadministration of a 300mg tablet with a high fat breakfast reduced maraviroc Cmax and AUC by 33% in healthy volunteers.
• Half Life: 14-18 hours
• Protein Binding: Approximately 76% bound to human plasma proteins, with moderate affinity for albumin and alpha-1 acid glycoprotein.
• Distribution: * 194 L
• External Links: Wikipedia; RxList; Drugs.com