Calanolide A

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Calanolide A
Calanolide A.svg
Systematic (IUPAC) name
(+)-[10R,11S,12S]-10,11-trans-dihydro-
12-hydroxy-6,6,10,11-tetramethyl-4-propyl-
2H,6H-benzo[1,2-b:3,4-b':5,6-b'']tripyran-2-one
Clinical data
Legal status
?
Pharmacokinetic data
Protein binding >97%
Metabolism Hepatic (mostly CYP3A4-mediated)
Identifiers
CAS number 142632-32-4
ATC code None
PubChem CID 64972
ChemSpider 58497
ChEMBL CHEMBL267447
Chemical data
Formula C22H26O5 
Mol. mass 370.44 g/mol

Calanolide A is an experimental non-nucleoside reverse transcriptase inhibitor (NNRTI) first acquired from the Calophyllum lanigerum, variety austrocoriaceum, trees in the Malaysian state of Sarawak by botanist John Burley in 1987.[1] 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. On return trip to Malaysia, it was found that all of the austrocoriaceum variety tree species of Calophyllum lanigerum had been cut down most likely for fuel and building material in the swamp forest near Lundu where the first tree samples were taken; however, a few existing species were eventually located in the Singapore Botanic Garden.[2] Since the plant source is relatively rare, a total synthesis was developed in 1996.[3] 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.[4]

Further reading[edit]

References[edit]

  1. ^ Wilson EO (2005–2006). 16. In Allen JL. "What Is Nature Worth? There's a powerful economic argument for preserving our living natural environment: The biosphere promotes the long-term material prosperity and health of the human race to a degree that is almost incalculable. But moral reasons, too, should compel us to take responsibility for the natural world.". Environment Annual Editions 24: 107–116. 
  2. ^ Wilson EO (2005–2006). 16. In Allen JL. "What Is Nature Worth? There's a powerful economic argument for preserving our living natural environment: The biosphere promotes the long-term material prosperity and health of the human race to a degree that is almost incalculable. But moral reasons, too, should compel us to take responsibility for the natural world.". Environment Annual Editions 24: 107–116. 
  3. ^ 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. 
  4. ^ 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.