10242. Raltegravir

Nomenclature

CAS number: 518048-05-0
N-[(4-Fluorophenyl)methyl]-1,6-dihydro-5-hydroxy-1-methyl-2-[1-methyl-1-[[(5-methyl-1,3,4-oxadiazol-2-yl)carbonyl]amino]ethyl]-6-oxo-4-pyrimidinecarboxamide; N-(4-fluorobenzyl)-5-hydroxy-1-methyl-2-[1-methyl-1-[[(5-methyl-1,3,4-oxadiazol-2-yl)carbonyl]amino]ethyl]-6-oxo-1,6-dihydropyrimidine-4-carboxamide.
C20H21FN6O5; mol wt 444.42.
C 54.05%, H 4.76%, F 4.27%, N 18.91%, O 18.00%.

Description and references

HIV-1 integrase strand transfer inhibitor. Prepn: B. Crescenzi et al., WO 03035077; eidem, US 7169780 (2003, 2007 both to IRBM); of the crystalline potassium salt: K. M. Belyk et al., US 060122205 (2006 to Merck & Co.). HPLC/MS/MS determn in plasma: S. A. Merschman et al., J. Chromatogr. B 857, 15 (2007) DOI PubMed. Metabolism and disposition: K. Kassahun et al., Drug Metab. Dispos. 35, 1657 (2007) DOI PubMed. Clinical evaluation in treatment-experienced patients: B. Grinsztejn et al., Lancet 369, 1261 (2007) DOI PubMed.

Chemical structure

Properties

Sol in organic solvents such as acetonitrile, chloroform, DMSO, methylene chloride, THF. Limited soly in water, ethanol.

Derivative

Monopotassium salt.

Nomenclature

CAS number: 871038-72-1
MK-0518; Isentress (Merck & Co.).
C20H20FKN6O5; mol wt 482.51.
C 49.78%, H 4.18%, F 3.94%, K 8.10%, N 17.42%, O 16.58%.

Properties

White to off-white powder. Sol in water; slightly sol in methanol; very slightly sol in ethanol, acetonitrile. Insol in isopropanol.

Therapeutic Category

Antiretroviral.

Keywords

HIV Integrase Inhibitor; Antiretroviral; Integrase Inhibitors