Calanolide A

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 529311

CAS#: 142632-32-4

Description: Calanolide A is a non-nucleoside reverse transcriptase inhibitor potentially for the treatment of HIV infection.


Price and Availability

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Calanolide A is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 529311
Name: Calanolide A
CAS#: 142632-32-4
Chemical Formula: C22H26O5
Exact Mass: 370.178
Molecular Weight: 370.44
Elemental Analysis: C, 71.33; H, 7.07; O, 21.59


Synonym: NSC-675451; NSC675451; NSC 675451

IUPAC/Chemical Name: (10R,11S,12S)-12-hydroxy-6,6,10,11-tetramethyl-4-propyl-11,12-dihydro-2H,6H,10H-dipyrano[2,3-f:2',3'-h]chromen-2-one

InChi Key: NIDRYBLTWYFCFV-FMTVUPSXSA-N

InChi Code: InChI=1S/C22H26O5/c1-6-7-13-10-15(23)26-21-16(13)20-14(8-9-22(4,5)27-20)19-17(21)18(24)11(2)12(3)25-19/h8-12,18,24H,6-7H2,1-5H3/t11-,12-,18+/m1/s1

SMILES Code: O=C1C=C(CCC)C2=C3C(C=CC(C)(C)O3)=C4C([C@@H](O)[C@H](C)[C@@H](C)O4)=C2O1


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Peng ZG, Chen HS, Wang L, Liu G. [Anti-HIV activities of HIV-1 reverse transcriptase inhibitor racemic 11-demethyl-calanolide A]. Yao Xue Xue Bao. 2008 May;43(5):456-60. Chinese. PubMed PMID: 18717330.

2: Ma T, Liu L, Xue H, Li L, Han C, Wang L, Chen Z, Liu G. Chemical library and structure-activity relationships of 11-demethyl-12-oxo calanolide A analogues as anti-HIV-1 agents. J Med Chem. 2008 Mar 13;51(5):1432-46. doi: 10.1021/jm701405p. PubMed PMID: 18284187.

3: Sheng L, Zhang Q, Liu Z, Liu X, Wang B, Chen H, Li Y. Determination of 10-chloromethyl-11-demethyl-12-oxo-calanolide A in rat plasma using liquid chromatography-tandem mass spectrometry and its application to pharmacokinetics. Biomed Chromatogr. 2014 Dec;28(12):1589-91. doi: 10.1002/bmc.3196. PubMed PMID: 24760543.

4: Liu X, Sheng L, Zhao M, Mi J, Liu Z, Li Y. In vitro glucuronidation of the primary metabolite of 10-chloromethyl-11-demethyl-12-oxo-calanolide A by human liver microsomes and its interactions with UDP-glucuronosyltransferase substrates. Drug Metab Pharmacokinet. 2015 Feb;30(1):89-96. doi: 10.1016/j.dmpk.2014.09.007. PubMed PMID: 25760535.

5: Auwerx J, Rodríguez-Barrios F, Ceccherini-Silberstein F, San-Félix A, Velázquez S, De Clercq E, Camarasa MJ, Perno CF, Gago F, Balzarini J. The role of Thr139 in the human immunodeficiency virus type 1 reverse transcriptase sensitivity to (+)-calanolide A. Mol Pharmacol. 2005 Sep;68(3):652-9. PubMed PMID: 15961674.

6: Xu ZQ, Barrow WW, Suling WJ, Westbrook L, Barrow E, Lin YM, Flavin MT. Anti-HIV natural product (+)-calanolide A is active against both drug-susceptible and drug-resistant strains of Mycobacterium tuberculosis. Bioorg Med Chem. 2004 Mar 1;12(5):1199-207. PubMed PMID: 14980631.

7: Eiznhamer DA, Creagh T, Ruckle JL, Tolbert DT, Giltner J, Dutta B, Flavin MT, Jenta T, Xu ZQ. Safety and pharmacokinetic profile of multiple escalating doses of (+)-calanolide A, a naturally occurring nonnucleoside reverse transcriptase inhibitor, in healthy HIV-negative volunteers. HIV Clin Trials. 2002 Nov-Dec;3(6):435-50. PubMed PMID: 12501127.

8: Ma T, Gao Q, Chen Z, Wang L, Liu G. Chemical resolution of +/- -calanolide A, +/- -cordatolide A and their 11-demethyl analogues. Bioorg Med Chem Lett. 2008 Feb 1;18(3):1079-83. PubMed PMID: 18155519.

9: Creagh T, Ruckle JL, Tolbert DT, Giltner J, Eiznhamer DA, Dutta B, Flavin MT, Xu ZQ. Safety and pharmacokinetics of single doses of (+)-calanolide a, a novel, naturally occurring nonnucleoside reverse transcriptase inhibitor, in healthy, human immunodeficiency virus-negative human subjects. Antimicrob Agents Chemother. 2001 May;45(5):1379-86. PubMed PMID: 11302799; PubMed Central PMCID: PMC90477.

10: Xue H, Lu X, Zheng P, Liu L, Han C, Hu J, Liu Z, Ma T, Li Y, Wang L, Chen Z, Liu G. Highly suppressing wild-type HIV-1 and Y181C mutant HIV-1 strains by 10-chloromethyl-11-demethyl-12-oxo-calanolide A with druggable profile. J Med Chem. 2010 Feb 11;53(3):1397-401. doi: 10.1021/jm901653e. PubMed PMID: 20050672.

11: Buckheit RW Jr, White EL, Fliakas-Boltz V, Russell J, Stup TL, Kinjerski TL, Osterling MC, Weigand A, Bader JP. Unique anti-human immunodeficiency virus activities of the nonnucleoside reverse transcriptase inhibitors calanolide A, costatolide, and dihydrocostatolide. Antimicrob Agents Chemother. 1999 Aug;43(8):1827-34. PubMed PMID: 10428899; PubMed Central PMCID: PMC89377.

12: Sekino E, Kumamoto T, Tanaka T, Ikeda T, Ishikawa T. Concise synthesis of anti-HIV-1 active (+)-inophyllum B and (+)-calanolide A by application of (-)-quinine-catalyzed intramolecular oxo-Michael addition. J Org Chem. 2004 Apr 16;69(8):2760-7. PubMed PMID: 15074925.

13: Xu ZQ, Norris KJ, Weinberg DS, Kardatzke J, Wertz P, Frank P, Flavin MT. Quantification of (+)-calanolide A, a novel and naturally occurring anti-HIV agent, by high-performance liquid chromatography in plasma from rat, dog and human. J Chromatogr B Biomed Sci Appl. 2000 Jun 9;742(2):267-75. PubMed PMID: 10901131.

14: Quan Y, Motakis D, Buckheit R Jr, Xu ZQ, Flavin MT, Parniak MA, Wainberg MA. Sensitivity and resistance to (+)-calanolide A of wild-type and mutated forms of HIV-1 reverse transcriptase. Antivir Ther. 1999;4(4):203-9. PubMed PMID: 10723499.

15: Currens MJ, Gulakowski RJ, Mariner JM, Moran RA, Buckheit RW Jr, Gustafson KR, McMahon JB, Boyd MR. Antiviral activity and mechanism of action of calanolide A against the human immunodeficiency virus type-1. J Pharmacol Exp Ther. 1996 Nov;279(2):645-51. PubMed PMID: 8930167.

16: Currens MJ, Mariner JM, McMahon JB, Boyd MR. Kinetic analysis of inhibition of human immunodeficiency virus type-1 reverse transcriptase by calanolide A. J Pharmacol Exp Ther. 1996 Nov;279(2):652-61. PubMed PMID: 8930168.

17: Hanna L. Calanolide A: a natural non-nucleoside reverse transcriptase inhibitor. BETA. 1999 Apr;12(2):8-9. PubMed PMID: 11366704.

18: Xu ZQ, Hollingshead MG, Borgel S, Elder C, Khilevich A, Flavin MT. In vivo anti-HIV activity of (+)-calanolide A in the hollow fiber mouse model. Bioorg Med Chem Lett. 1999 Jan 18;9(2):133-8. PubMed PMID: 10021914.

19: Galinis DL, Fuller RW, McKee TC, Cardellina JH 2nd, Gulakowski RJ, McMahon JB, Boyd MR. Structure-activity modifications of the HIV-1 inhibitors (+)-calanolide A and (-)-calanolide B. J Med Chem. 1996 Oct 25;39(22):4507-10. PubMed PMID: 8893846.

20: Flavin MT, Rizzo JD, Khilevich A, Kucherenko A, Sheinkman AK, Vilaychack V, Lin L, Chen W, Greenwood EM, Pengsuparp T, Pezzuto JM, Hughes SH, Flavin TM, Cibulski M, Boulanger WA, Shone RL, Xu ZQ. Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (+/-)-calanolide A and its enantiomers. J Med Chem. 1996 Mar 15;39(6):1303-13. PubMed PMID: 8632437.