(+)-Calanolide A
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(+)-Calanolide A
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CAS No:
142632-32-4
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Formula:
C22H26O5
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Chemical Name:
(+)-Calanolide A
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Synonyms:
2H,6H,10H-Dipyrano[2,3-f:2′,3′-h][1]benzopyran-2-one,11,12-dihydro-12-hydroxy-6,6,10,11-tetramethyl-4-propyl-,(10R,11S,12S)-;2H,6H,10H-Benzo[1,2-b:3,4-b′:5,6-b′′]tripyran-2-one,11,12-dihydro-12-hydroxy-6,6,10,11-tetramethyl-4-propyl-,[10R-(10α,11β,12α)]-;2H,6H,10H-Benzo[1,2-b:3,4-b′:5,6-b′′]tripyran-2-one,11,12-dihydro-12-hydroxy-6,6,10,11-tetramethyl-4-propyl-,(10R,11S,12S)-;(10R,11S,12S)-11,12-Dihydro-12-hydroxy-6,6,10,11-tetramethyl-4-propyl-2H,6H,10H-dipyrano[2,3-f:2′,3′-h][1]benzopyran-2-one;Calanolide A;(+)-Calanolide A;NSC 650886
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CAS No:
Description
(+)-calanolide A is an organic heterotetracyclic compound that is 11,12-dihydro-2H,6H,10H-dipyrano[2,3-f:2',3'-h]chromen-2-one substituted by a hydroxy group at position 12, methyl groups at positions 6, 6, 10 and 11 and a propyl group at position 4 (the 10R,11S,12S stereoisomer). Isolated from Calophyllum lanigerum var austrocoriaceum and Calophyllum brasiliense, it exhibits potent activity against HIV-1 reverse transcriptase. It has a role as a HIV-1 reverse transcriptase inhibitor and a plant metabolite. It is an organic heterotetracyclic compound, a delta-lactone, a cyclic ether and a secondary alcohol.|Calanolide A is a new non-nucleoside reverse transcriptase inhibitor (NNRTI) derived from a plant found in the Malaysian rain forest. A related compound, calanolide B, also has anti-HIV activity. Both drugs are being developed by Sarawak Pharmaceuticals. A preliminary dosing study among HIV-infected individuals showed a significant antiviral effect compared with placebo.
Drug Information
For use in combination treatment of HIV infection (AIDS).
Calanolide A is a new non-nucleoside reverse transcriptase inhibitor (NNRTI) derived from a plant found in the Malaysian rain forest. A related compound, calanolide B, also has anti-HIV activity. Both drugs are being developed by Sarawak Pharmaceuticals. The drug is metabolised by cytochrome P450 CYP3A, and its developers have suggested that drug levels may be enhanced if co-administered with ritonavir (Norvir). The drug is active in the test tube against HIV with the two most common NNRTI-related mutations, K103N and Y181C, and selects for a mutation which does not cause cross-resistance with any other NNRTIs currently under investigation. A substitution at codon Y188H of reverse transcriptase has been associated with 30-fold resistance to calanolide A in vitro (Quan 1999). The compound is essentially inactive against strains of the less common HIV type 2.
Agents used to treat AIDS and/or stop the spread of the HIV infection. These do not include drugs used to treat symptoms or opportunistic infections associated with AIDS. (See all compounds classified as Anti-HIV Agents.)
Hepatic.
20 hours for 800mg
Viral life-cycle studies indicate that calanolide A acts early in the infection process, similar to the known HIV reverse transcriptase (RT) inhibitor 2', 3'-dideoxycytidine. In enzyme inhibition assays, calanolide A potently and selectively inhibits recombinant HIV type 1 RT but not cellular DNA polymerases or HIV type 2 RT within the concentration range tested.
calanolide A
Computed Properties
Molecular Weight:370.4
XLogP3:3.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:2
Exact Mass:370.17802393
Monoisotopic Mass:370.17802393
Topological Polar Surface Area:65
Heavy Atom Count:27
Complexity:666
Defined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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