Calanolide A

Calanolide A
	File:Calanolide A.svg
Pharmacokinetic data
Protein binding	>97%
Metabolism	Hepatic (mostly CYP3A4-mediated)
Identifiers
	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;
CAS Number	142632-32-4;
PubChem CID	64972;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C22H26O5
Molar mass	370.44 g/mol

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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]

References

↑ 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.
↑ 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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[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.

[1]

[2]

v t e Antivirals used against HIV (HAART) (primarily J05)
Nucleoside & Nucleotide Reverse Transcriptase Inhibitors (NRTI)	Abacavir (ABC)° • Emtricitabine° • Lamivudine (3TC)° • Tenofovir° • Didanosine • Zidovudine (AZT) • Apricitabine^† • Stampidine^† • Elvucitabine^† • Racivir^† • Amdoxovir^† • Stavudine^‡ • Zalcitabine^‡
Non-Nucleoside Reverse Transcriptase Inhibitors (NNRTI)	Efavirenz° • Nevirapine • Etravirine • Rilpivirine^† • Loviride^‡ • Delavirdine^‡
Protease Inhibitors (PI)	Atazanavir° • Fosamprenavir° • Lopinavir° • Darunavir • Nelfinavir • Ritonavir • Saquinavir • Tipranavir • Amprenavir^‡ • Indinavir^‡
Entry/fusion inhibitors	Enfuvirtide • Maraviroc • Vicriviroc^† • PRO 140^† • Ibalizumab^†
Integrase inhibitors	Raltegravir • Elvitegravir^†
Maturation inhibitors	Bevirimat^† • Vivecon™^†
Combined formulations	Combivir • Atripla • Trizivir • Truvada • Kaletra • Epzicom
Other & experimental agents	Foscarnet • Hydroxyurea • Synergistic enhancers • Epigallocatechin gallate • Portmanteau inhibitors • Globoidnan A • Griffithsin • Diarylpyrimidines • Calanolide A • Cyanovirin-N • Miltefosine
°DHHS preferred first-line agent. ^†Undergoing clinical trials, not FDA approved. ^‡Formerly or rarely used agent.

Calanolide A

Further reading

References

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