Doxorubicin.HCl

  • CAT Number: I002864
  • CAS Number: 25316-40-9
  • Molecular Formula: C27H29NO11 .HCl
  • Molecular Weight: 579.98
  • Purity: ≥95%
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Doxorubicin Hydrochloride (CAT: I002864) is an anthracycline chemotherapy drug commonly used in the treatment of various cancers, including breast cancer, lung cancer, and leukemia. It exerts its cytotoxic effects by intercalating into DNA, inhibiting DNA replication and transcription, and inducing DNA damage. Doxorubicin also generates free radicals that further contribute to its antitumor activity. It is typically administered intravenously and has a broad spectrum of antitumor activity. However, doxorubicin can cause side effects such as cardiotoxicity, myelosuppression, and gastrointestinal toxicity. The hydrochloride salt form of doxorubicin is commonly used for clinical applications due to its improved stability and solubility compared to the free base form.

Catalog Number I002864
CAS Number 25316-40-9
Molecular Formula

C27H29NO11 .HCl

Purity 95%
Target Topoisomerase
Solubility DMSO: ≥ 30 mg/mL
Storage 3 years -20C powder
Overview of Clinical Research

<span style=”font-family:arial,helvetica,sans-serif;”><span style=”color:#000000;”><span style=”font-size:12px;”>Doxorubicin is a&nbsp;<span style=”font-variant-ligatures: normal; orphans: 2; widows: 2;”>DNA intercalator and a Type II DNA topoisomerase inhibitor. There is no new molecular entity and orphan drug status.&nbsp;</span></span></span></span>

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
InChI InChI=1S/C27H29NO11.ClH/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34;/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3;1H/t10-,13-,15-,17-,22+,27-;/m0./s1
InChIKey MWWSFMDVAYGXBV-RUELKSSGSA-N
SMILES CC1C(C(CC(O1)OC2CC(CC3=C(C4=C(C(=C23)O)C(=O)C5=C(C4=O)C=CC=C5OC)O)(C(=O)CO)O)N)O.Cl
Reference

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[1]. Zykova MG, Medvedeva NV, Torkhovskaya TI, et al. Influence of doxorubicin inclusion into phospholipid nanoformulation on its antitumor activity in mice: increased efficiency for resistant tumor model. Exp Oncol. 2012 Dec;34(4):323-6.<br />
[2]. Patel S, Sprung AU, Keller BA, et al. Identification of yeast DNA topoisomerase II mutants resistant to the antitumor drug doxorubicin: implications for the mechanisms of doxorubicin action and cytotoxicity. Mol Pharmacol. 1997 Oct;52(4):658-66.<br />
[3]. Zeman SM, Phillips DR, Crothers DM. Characterization of covalent adriamycin-DNA adducts. Proc Natl Acad Sci U S A. 1998 Sep 29;95(20):11561-5.<br />
[4]. Pourquier P, Montaudon D, Huet S, et al. Doxorubicin-induced alterations of c-myc and c-jun gene expression in rat glioblastoma cells: role of c-jun in drug resistance and cell death. Biochem Pharmacol. 1998 Jun 15;55(12):1963-71.<br />
[5]. Gewirtz DA. A critical evaluation of the mechanisms of action proposed for the antitumor effects of the anthracycline antibiotics adriamycin and daunorubicin. Biochem Pharmacol. 1999 Apr 1;57(7):727-41.</p>

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