5749. Maraviroc
Nomenclature
CAS number: 376348-65-1
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; N-[(1S)-3-[3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-exo-8-azabicyclo[3.2.1]oct-8-yl]-1-phenylpropyl]-4,4-difluorocyclohexanecarboxamide; UK-427857; Celsentri (Pfizer); Selzentry (Pfizer). C29H41F2N5O; mol wt 513.67.
C 67.81%, H 8.05%, F 7.40%, N 13.63%, O 3.11%.
Description and references
CCR5 chemokine receptor antagonist; inhibits HIV entry by blocking interaction of viral coat protein gp120 with the receptor. Prepn: M. Perros et al., WO 0190106; eidem, US 6667314 (2001, 2003 both to Pfizer); D. A. Price et al., Tetrahedron Lett. 46, 5005 (2005). Overview of structure identification and development: A. Wood, D. Armour, Prog. Med. Chem. 43, 239-271 (2005). Pharmacokinetics and metabolism in humans and animals: D. K. Walker et al., Drug Metab. Dispos. 33, 587 (2005). Clinical evaluation in HIV-1 infected patients: G. F"atkenheuer et al., Nat. Med. 11, 1170 (2005). Review: N. A. Meanwell, J. F. Kadow, Curr. Opin. Investig. Drugs 8, 669-681 (2007).
Properties
White solid from toluene/hexane (2:1), mp 197-198°. pKa 7.3. Moderate lipophilicity, logD 2.1.Therapeutic Category
Antiretroviral.
Keywords
Antiretroviral; Entry Inhibitors