Calanolide A

Drugbox
IUPAC_name = (+)- [10"R",11"S",12"S"] -10,11-"trans"-dihydro-
12-hydroxy-6,6,10,11-tetramethyl-4-propyl-
2"H",6"H"-benzo [1,2-"b":3,4-"b"':5,6-"b""] tripyran-2-one

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CAS_number = 142632-32-4
ATC_prefix =
ATC_suffix =
PubChem = 64972
DrugBank =
C=22|H=26|O=5
molecular_weight = 370.44 g/mol
bioavailability =
protein_bound = >97%
metabolism = Hepatic (mostly CYP3A4-mediated)
elimination_half-life =
excretion =
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pregnancy_US =
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Calanolide A is a new, experimental non-nucleoside reverse transcriptase inhibitor (NNRTI) first acquired from "Calophylum lanigerum" trees in 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. [cite journal |author=Flavin MT, Rizzo JD, Khilevich A, "et al" |title=Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (±)-calanolide A and its enantiomers |journal=J Med Chem |volume=39 |issue=6 |pages=1303–13 |year=1996 |pmid=8632437 |doi=10.1021/jm950797i] The form in current use is formulated for oral administration and produced by Sarawak MediChem in Lemont, Illinois.

Calanolide A is unique among NNRTIs in that it may bind two distinct sites in reverse transcriptase. [cite journal |author=Currens MJ, Mariner JM, McMahon JB, Boyd MR |title=Kinetic analysis of inhibition of human immunodeficiency virus type-1 reverse transcriptase by calanolide A |journal=J Pharmacol Exp Ther |volume=279 |issue=2 |pages=652–61 |year=1996 |pmid=8930168 |doi=]

Further reading

*http://www.natural-medicinal-herbs.com/herbs/calanolide-a.htm
*http://news.mongabay.com/2005/0913-AIDS.html
*http://www.aidsmap.com/cms1032372.asp

References