(+)-[10 R,11 S,12 S]-10,11- trans-dihydro-
2 H,6 H-benzo[1,2- b:3,4- b':5,6- b'']tripyran-2-one
Pregnancy cat. ?
Legal status ?
Protein binding >97%
Hepatic (mostly CYP3A4-mediated)
ATC code None
C 22 H 26 O 5
Mol. mass 370.44 g/mol
Calanolide A is a new, experimental non-nucleoside reverse transcriptase inhibitor (NNRTI) first acquired from trees in Calophyllum lanigerum Malaysia. The U.S. National Cancer Institute tested calanolide A as a possible cancer treatment, but had no effect. It was later found to have potent anti- HIV activity. Since the plant source is relatively rare, a total synthesis was developed in 1996. The form in current use is formulated for oral administration and produced by [1 ] Sarawak MediChem in Lemont, Illinois.
Calanolide A is unique among NNRTIs in that it may bind two distinct sites in
reverse transcriptase. [2 ]
Further reading [ edit ]
References [ edit ]
^ Flavin MT, Rizzo JD, Khilevich A, et al. (1996). "Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (±)-calanolide A and its enantiomers". J Med Chem 39 (6): 1303–13. doi: 10.1021/jm950797i. PMID 8632437.
^ Currens MJ, Mariner JM, McMahon JB, Boyd MR (1996). "Kinetic analysis of inhibition of human immunodeficiency virus type-1 reverse transcriptase by calanolide A". J Pharmacol Exp Ther 279 (2): 652–61. PMID 8930168.