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Doxorubicin is an anthracycline that exhibits anticancer chemotherapeutic and anti-parasitic, antimalarial activities. Doxorubicin is a DNA intercalator that inhibits topoisomerase II and is clinically used to treat various cancers; it is part of the CHOP and ABVD chemotherapy regimens. Doxorubicin also promotes histone H2AX eviction from chromatin, limiting DNA repair mechanisms. Additionally, this compound inhibits growth of Plasmodium.
| Cas No. | 25316-40-9 |
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| Purity | ≥98% |
| Formula | C27H29NO11 • HCl |
| Formula Wt. | 579.99 |
| Chemical Name | (8S-cis)10-[(3-Amino-2,3,6-trideoxy-α-L-lyxo- hexopyranosyl)oxy-7,8,9,10-tetrahydro-6,8,11- trihydroxy-8-(hydroacetyl)-1-methoxy-5,12- naphthacenedione |
| IUPAC Name | (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9, 11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5, 12-dione;hydrochloride |
| Synonym | Adriacin, Adriblastina, Adriamycin, Caelyx |
| Melting Point | 204-205°C(dec.) |
| Solubility | Soluble in water, methanol or aqueous alcohols. Soluble in DMSO to 10 mg/mL. Insoluble in acetone or chloroform. |
| Appearance | Orange-Red Crystal Powder |
| Store Temp | 4°C |
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| Ship Temp | Ambient |
| MSDS | |
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| Info Sheet |
Pang B, Qiao X, Janssen L, et al. Drug-induced histone eviction from open chromatin contributes to the chemotherapeutic effects of doxorubicin. Nat Commun. 2013;4:1908. PMID: 23715267.
Tacar O, Sriamornsak P, Dass CR. Doxorubicin: an update on anticancer molecular action, toxicity and novel drug delivery systems. J Pharm Pharmacol. 2013 Feb;65(2):157-70. PMID: 23278683.
Gamo FJ, Sanz LM, Vidal J, et al. Thousands of chemical starting points for antimalarial lead identification. Nature. 2010 May 20;465(7296):305-10. PMID: 20485427.
Squillace RM, Miller D, Cookson M, et al. Antitumor activity of ridaforolimus and potential cell-cycle determinants of sensitivity in sarcoma and endometrial cancer models. Mol Cancer Ther. 2011 Oct;10(10):1959-1968. PMID: 21825008.