Trademarks: Isentress
Molecular Formula: C20H21FN6O5
CAS Registry Number: 518048-05-0
CAS Name: N-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-2-{2-[(5-methyl-1,3,4-oxadiazol-2-yl)formamido]propan-2-yl}-6-oxo-1,6-dihydropyrimidine-4-carboxamide
Molecular Weight: 444.416
SMILES: N1C(=O)C(O)=C(N=C1C(C)C)NC(=O)C1=NN=C(C)O1)C(=O)NCC1=CC=C(F)C=C1
InChI Key: CZFFBEXEKNGXKS-UHFFFAOYSA-N
InChI: InChI=1S/C20H21FN6O5/c1-10-25-26-17(32-10)16(30)24-20(2,3)19-23-13(14(28)18(31)27(19)4)15(29)22-9-11-5-7-12(21)8-6-11/h5-8,28H,9H2,1-4H3,(H,22,29)(H,24,30)
Activity: AIDS Medicines, Anti-HIV Agents, Anti-infective Therapy; Integrase Inhibitors; Highly Active Antiretroviral Therapy; HAART Therapy
Status: Launched 2007
Originator: Merck
Raltegravir synthesis: J Med Chem 2008, 51(18), 5843-5855 (see Ref. 2 for reaction mechanism, which involves stepwise radical pair rearrangement. It is a good read)
Raltegravir synthesis: WO2006060712A2 (The synthesis can be divided into two steps)
References:
1. Summa, V.; et. al. Discovery of Raltegravir, a Potent, Selective Orally Bioavailable HIV-Integrase Inhibitor for the Treatment of HIV-AIDS Infection. J Med Chem 2008, 51(18), 5843-5855.
2. Pye, P. J. Dr.; et. al. A Polar Radical Pair Pathway To Assemble the Pyrimidinone Core of the HIV Integrase Inhibitor Raltegravir Potassium. Angew Chem Int Ed 2008, 47(22),4134-4136.
3. Belyk, K. M.; et. al. Potassium salt of an hiv integrase inhibitor. WO2006060712A2
