Calanolide A

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Calanolide A
File:Calanolide A.svg
Pharmacokinetic data
Protein binding>97%
MetabolismHepatic (mostly CYP3A4-mediated)
Identifiers
CAS Number
PubChem CID
E number{{#property:P628}}
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Chemical and physical data
FormulaC22H26O5
Molar mass370.44 g/mol

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]

Further reading

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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