Calanolide A

Calanolide A

File: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
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
Molecular mass	370.44 g/mol
SMILES O=C/4Oc2c(c3OC(/C=C\c3c1O[C@@H]([C@@H](C)[C@H](O)c12)C)(C)C)\C(=C\4)CCC
InChI InChI=1S/C22H26O5/c1-6-7-13-10-15(23)26-21-16(13)20-14(8-9-22(4,5)27-20)19-17(21)18(24)11(2)12(3)25-19/h8-12,18,24H,6-7H2,1-5H3/t11-,12-,18+/m1/s1 Key:NIDRYBLTWYFCFV-FMTVUPSXSA-N

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. 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. 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 Sarawak MediChem in Lemont, Illinois.

Calanolide A is unique among NNRTIs in that it may bind two distinct sites in reverse transcriptase.

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