Calanolide A

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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
Chemical data
Formula C22H26O5
Molar mass 370.44 g/mol[[Script error: No such module "String".]]
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Calanolide A is a new, experimental non-nucleoside reverse transcriptase inhibitor (NNRTI) first acquired from Calophyllum 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

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Antiviral drugs: antiretroviral drugs used against HIV (primarily J05)
Entry/fusion inhibitors
(Discovery & development)
Reverse transcriptase
inhibitors (RTIs)
(1st gen) Efavirenz°# · Nevirapine#  · Loviride◊ · Delavirdine◊ ·
(2nd gen) diarylpyrimidines (Etravirine, Rilpivirine†)  · Lersivirine†
Integrase inhibitors
Raltegravir · Elvitegravir† · Globoidnan A (experimental)  · MK-2048†  · GSK-572†
Maturation inhibitors
Bevirimat† · Vivecon†
Protease Inhibitors (PI)
(Discovery and development)
Combined formulations
Experimental agents
TRIM5alpha (gene)
Other
Failed agents
°DHHS preferred first-line agent. ◊Formerly or rarely used agent.


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  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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