Epirubicin Hydrochloride

• CAT Number: I004105
• CAS Number: 56390-09-1
• Molecular Formula: C₂₇H₂₉NO₁₁ · HCl
• Molecular Weight: 579.98
• Purity: ≥95%
• Synonyms: (7S,9S)-7-[(2R,4S,5R,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
• Target: Topoisomerase
• Solubility: DMSO 116 mg/mL Water 115 mg/mL Ethanol 3 mg/mL
• Storage: 3 years -20C powder
• 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-FGBSZODSSA-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

Epirubicin Hcl, a semisynthetic L-arabino derivative of doxorubicin, is an antineoplastic agent by inhibiting Topoisomerase.Target: TopoisomeraseApproved: 1999Epirubicin display antineoplastic activity against most cancer cells. Epirubicin is cytotoxic to Hepatoma G2 cells with IC50 of 1.6 μg/mL at 24hr. 1.6 μg/mL Epirubicin induces apoptosis of Hep G2 cells, and higher activity of catalase by 50%, Se-dependent glutathione peroxidase by 110%, Cu, Zn-superoxide dismutase by 172% and Mn-superoxide dismutase by 135%. Epirbicin increases the cellular expression of NADPH-CYP 450 reductase, and reduces GST-π expression [1].Epirubicin are clinically active against a broad range of tumor types, including breast cancer, malignant lymphomas, soft tissue sarcomas, lung cancer, pleural mesothelioma, gastrointestinal cancer, head and neck cancer, ovarian cancer, prostatic carcinoma, transitional bladder carcinoma and so on [2]. Epirubicin at a dose of 3.5 mg/kg suppresses tumor mass of human breast tumor xenograft R-27 by 74.4 % [3].Toxicity: Bone marrow aplasia, grade 4 mucositis, and gastrointestinal bleeding

Reference

1:Synthesis and application of thiol-functionalized magnetic nanoparticles for studying interactions of epirubicin hydrochloride with bovine serum albumin by fluorescence spectrometry. Xiong H, Diao Q, Jin R, Song D, Wang X, Sun Y.Luminescence. 2017 Mar;32(2):142-148. doi: 10.1002/bio.3158. Epub 2016 May 18. PMID: 27193868 2:Retraction Note: RGD peptide-pegylated PLLA nanoparticles containing epirubicin hydrochloride exhibit receptor-dependent tumor trafficking in vitro and in vivo. [No authors listed]Pharm Res. 2016 Apr;33(4):1050. doi: 10.1007/s11095-016-1866-8. No abstract available. PMID: 26839122 3:RGD Peptide-Pegylated PLLA Nanoparticles Containing Epirubicin Hydrochloride Exhibit Receptor-Dependent Tumor Trafficking In Vitro and In Vivo. Huang P, Wu J, Li X, Liu X, Li Y, Cui G.Pharm Res. 2015 Jul;32(7):2328-43. doi: 10.1007/s11095-015-1625-2. Epub 2015 Jan 16. Retraction in: Huang P, Wu J, Li X, Liu X, Li Y, Cui G. Pharm Res. 2016 Apr;33(4):1050. PMID: 25592551 4:[Effect of dexamethasone on vascular pain caused by the administration of fosaprepitant dimeglumine and epirubicin hydrochloride in patients with primary breast cancer]. Kameda K, Kiba T, Ogawa Y, Kimoto S, Kajiume S, Okada Y, Morii N, Takahashi H, Ichiba Y, Yamashiro H.Gan To Kagaku Ryoho. 2014 Oct;41(10):1255-7. Japanese. PMID: 25335710 5:[Adsorption and release behavior of epirubicin hydrochloride on carboxylated single-walled carbon nanotubes]. Lin R, Li LL, He J, Qiu LL, He H.Yao Xue Xue Bao. 2013 Nov;48(11):1710-5. Chinese. PMID: 24475710 6:Comparison of epirubicin hydrochloride and miriplatin hydrate as anticancer agents for transcatheter arterial chemoembolization of hepatocellular carcinoma. Aramaki T, Moriguchi M, Bekku E, Asakura K, Sawada A, Endo M.Hepatol Res. 2013 May;43(5):475-80. doi: 10.1111/j.1872-034X.2012.01100.x. Epub 2012 Oct 10. PMID: 23046493 7:[Preparation and in vivo-in vitro evaluation of compound nanoparticles loaded with epirubicin hydrochloride and gadopentetate meglumine]. Ji JS, Teng GJ, Yang HY, Song JJ, Lu CY, Fu HX.Zhonghua Yi Xue Za Zhi. 2012 Jun 19;92(23):1626-9. Chinese. PMID: 22944133 8:[Promising new injection method to prevent angialgia/phlebitis from epirubicin hydrochloride therapy for breast cancer]. Ono C, Yamagami M, Kamatani R, Yamamoto M, Mukouyama T, Sugimoto M, Suzuki T, Kamo N, Seki N, Eguchi K, Ikeda T.Gan To Kagaku Ryoho. 2012 May;39(5):777-81. Japanese. PMID: 22584330 9:[Preparation and quality control of compound epirubicin hydrochloride-loaded polymeric nanoparticles of L-lactic-co-glycolic acid]. Ji JS, Fu HX, Song JJ, Li H, Zhu YL.Zhonghua Yi Xue Za Zhi. 2011 Dec 20;91(47):3371-3. Chinese. PMID: 22333208 10:[Pharmacokinetics of epirubicin hydrochloride long-circulating thermosensitive liposomes in rat plasma]. Wu Y, Zhang FC, Wu C, Mei XG, Lü WL.Yao Xue Xue Bao. 2010 Mar;45(3):365-70. Chinese. PMID: 21351514