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Wikipedia

Calanolide A

From Wikipedia, the free encyclopedia

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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	none
PubChem	64972
ChemSpider	58497
Chemical data
Formula	C₂₂H₂₆O₅
Mol. mass	370.44 g/mol
SMILES	eMolecules & PubChem
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 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]

References

^ Flavin MT, Rizzo JD, Khilevich A, et al. (1996). [Expression error: Missing operand for > "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). [Expression error: Missing operand for > "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.

Antiviral drugs: antiretroviral drugs used against HIV (primarily J05)

Entry/fusion inhibitors
(Discovery & development)

gp41 (Enfuvirtide) · CCR5 (Maraviroc, Vicriviroc^†, PRO 140^†) · CD4 (Ibalizumab^†)

Reverse transcriptase
inhibitors (RTIs)

Nucleoside & Nucleotide (NRTI)	Nucleoside analogues/NARTIs: Abacavir (ABC)°^# · Emtricitabine (FTC)°^# · Lamivudine (3TC)°^# · Didanosine (ddI)^# · Zidovudine (AZT)^# · Apricitabine^† · Stampidine^† · Elvucitabine^† · Racivir^† · Amdoxovir^† · Stavudine (d4T)^# · Zalcitabine (ddC)^◊ Nucleotide analogues/NtRTIs: Tenofovir°^#
Non-Nucleoside (NNRTI) (Discovery & development)	(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 & development)

Atazanavir° · Fosamprenavir° · Lopinavir°^# · Darunavir · Nelfinavir^# · Ritonavir^# · Saquinavir^# · Tipranavir · Amprenavir^◊ · Indinavir^◊^#

Combined formulations

Combivir · Atripla · Trizivir · Truvada · Kaletra · Epzicom

Experimental agents

Uncoating inhibitors	TRIM5alpha (gene)
Transcription inhibitors	Tat antagonists
Translation inhibitors	Trichosanthin
Other	Abzyme · Calanolide A · Ceragenin · Cyanovirin-N · Diarylpyrimidines · Epigallocatechin gallate (EGCG) · Foscarnet · Griffithsin · Hydroxyurea · Miltefosine · Portmanteau inhibitors · Seliciclib^† · Synergistic enhancers · Tre recombinase · Zinc finger protein transcription factor · KP-1461^†
Failed agents	Dexelvucitabine · Capravirine · Emivirine · Lodenosine · Atevirdine · Brecanavir · Aplaviroc

^#WHO-EM. ^‡Withdrawn from market. CLINICAL TRIALS: ^†Phase III. ^§Never to phase III
°DHHS preferred first-line agent. ^◊Formerly or rarely used agent.

This pharmacology-related article is a stub. You can help Wikipedia by expanding it.

All translations of Calanolide_A

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Arabic (ar)	Bulgarian (bg)	Chinese (zh)	Czech (cs)
Danish (da)	Dutch (nl)	English (en)	Estonian (et)
Finnish (fi)	French (fr)	German (de)	Greek (el)
Hungarian (hu)	Italian (it)	Japanese (ja)	Korean (ko)
Norwegian (no)	Polish (pl)	Portuguese (pt)	Romanian (ro)
Russian (ru)	Serbian (sr)	Slovenian (sl)	Spanish (es)
Swedish (sv)	Turkish (tr)	Latvian (lv)	Persian (fa)
Lithuanian (lt)	Icelandic (is)	Slovak (sk)	Croatian (hr)
Hindi (hi)	Vietnamese (vi)	Hebrew (he)	Thai (th)
Indonesian (id)

Arabic (ar)	Bulgarian (bg)	Chinese (zh)	Czech (cs)
Danish (da)	Dutch (nl)	English (en)	Estonian (et)
Finnish (fi)	French (fr)	German (de)	Greek (el)
Hungarian (hu)	Italian (it)	Japanese (ja)	Korean (ko)
Norwegian (no)	Polish (pl)	Portuguese (pt)	Romanian (ro)
Russian (ru)	Serbian (sr)	Slovenian (sl)	Spanish (es)
Swedish (sv)	Turkish (tr)	Latvian (lv)	Persian (fa)
Lithuanian (lt)	Icelandic (is)	Slovak (sk)	Croatian (hr)
Hindi (hi)	Vietnamese (vi)	Hebrew (he)	Thai (th)
Indonesian (id)

Wikipedia

Calanolide A

From Wikipedia, the free encyclopedia

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References