5573. Lopinavir
Nomenclature
CAS number: 192725-17-0
(αS)-N-[(1S,3S,4S)-4-[[(2,6-Dimethylphenoxy)acetyl]amino]-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]tetrahydro-α-(1-methylethyl)-2-oxo-1(2H)-pyrimidineacetamide; (αS)-tetrahydro-N-[(αS)-α-[(2S,3S)-2-hydroxy-4-phenyl-3-[2-(2,6-xylyloxy)acetamido]butyl]phenethyl]-α-isopropyl-2-oxo-1(2H)-pyrimidineacetamide; (2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5-[2S-(1-tetrahydropyrimid-2-onyl)-3-methylbutanoyl]amino-1,6-diphenylhexane; ABT-378; A-157378. C37H48N4O5; mol wt 628.80.
C 70.67%, H 7.69%, N 8.91%, O 12.72%.
Description and references
Peptidomimetic HIV protease inhibitor. Prepn: H. L. Sham et al., WO 9721685; idem et al., US 5914332 (1997, 1999 both to Abbott); E. J. Stoner et al., Org. Process Res. Dev. 3, 145 (1999). Protease inhibition and pharmacokinetics: H. L. Sham et al., Antimicrob. Agents Chemother. 42, 3218 (1998). In vitro metabolism study: G. N. Kumar et al., Drug Metab. Dispos. 27, 86 (1999). Pharmacokinetic enhancement by ritonavir: G. N. Kumar et al., ibid. 902. Clinical trial with ritonavir in HIV infection: S. Walmsley et al., N. Engl. J. Med. 346, 2039 (2002).
Properties
Colorless solid from ethyl acetate, mp 124-127°.Derivative
Mixture with ritonavir.Nomenclature
Kaletra (Abbott).Therapeutic Category
Antiretroviral.
Keywords
HIV Protease Inhibitor; Antiretroviral; Protease Inhibitors