Calanolide A

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Calanolide A
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
Identifiers
CAS number 142632-32-4
ATC code  ?
PubChem 64972
Chemical data
Formula C22H26O5 
Mol. mass 370.44 g/mol
Pharmacokinetic data
Bioavailability  ?
Protein binding >97%
Metabolism Hepatic (mostly CYP3A4-mediated)
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

?
Legal status
Routes  ?

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.[1] 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.[2]

[edit] Further reading

[edit] References

  1. ^ 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. 
  2. ^ 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. 
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Antivirals used against HIV (HAART) (primarily J05)
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°DHHS preferred first-line agent. †Undergoing clinical trials, not FDA approved. ‡Formerly or rarely used agent. §Development terminated.