Doxorubicin hydrochloride
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MedKoo CAT#: 100280

CAS#: 25316-40-9 (HCl)

Description: Doxorubicin is an anthracycline antibiotic with antineoplastic activity. Doxorubicin, isolated from the bacterium Streptomyces peucetius var. caesius, is the hydroxylated congener of daunorubicin. Doxorubicin intercalates between base pairs in the DNA helix, thereby preventing DNA replication and ultimately inhibiting protein synthesis. Additionally, doxorubicin inhibits topoisomerase II which results in an increased and stabilized cleavable enzyme-DNA linked complex during DNA replication and subsequently prevents the ligation of the nucleotide strand after double-strand breakage. Doxorubicin also forms oxygen free radicals resulting in cytotoxicity secondary to lipid peroxidation of cell membrane lipids; the formation of oxygen free radicals also contributes to the toxicity of the anthracycline antibiotics, namely the cardiac and cutaneous vascular effects.


Price and Availability

Size
Price

500mg
USD 190
5g
USD 1450
50g
USD 9750
Size
Price

1g
USD 350
10g
USD 2550
Size
Price

2g
USD 650
20g
USD 4350

Doxorubicin HCl, purity > 98%, is in stock. The same day shipping out after order is received. Bulk quantity (>100g) and kilograms with high quality are available in ~ 2 weeks.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 100280
Name: Doxorubicin hydrochloride
CAS#: 25316-40-9 (HCl)
Chemical Formula: C27H30ClNO11
Exact Mass:
Molecular Weight: 579.98
Elemental Analysis: C, 55.91; H, 5.21; Cl, 6.11; N, 2.42; O, 30.34


Related CAS #: 23214-92-8 (free base)   25316-40-9 (HCl)    

Synonym: FI106; FI-106; FI 106; ADR; Doxo; Dox HCl; Adriamycin; Adriacin; Adriblastina; Adriblastine; Adrimedac; DOXOCELL; Doxolem; Doxorubin; Farmiblastina; Rubex.

IUPAC/Chemical Name: (8S,10S)-10-(((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione hydrochloride

InChi Key: MWWSFMDVAYGXBV-RUELKSSGSA-N

InChi Code: 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

SMILES Code: O=C1C2=C(O)C(C[C@](C(CO)=O)(O)C[C@@H]3O[C@H]4C[C@H](N)[C@H](O)[C@H](C)O4)=C3C(O)=C2C(C5=C1C=CC=C5OC)=O.[H]Cl


Technical Data

Appearance:
Red solid powder

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

Safety Data Sheet (MSDS):

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, not in water

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


Additional Information


References

1: Zhong YJ, Shao LH, Li Y. Cathepsin B-cleavable doxorubicin prodrugs for targeted cancer therapy (Review). Int J Oncol. 2013 Feb;42(2):373-83. doi: 10.3892/ijo.2012.1754. Epub 2012 Dec 28. Review. PubMed PMID: 23291656; PubMed Central PMCID: PMC3583876.

2: Xi L, Zhu SG, Das A, Chen Q, Durrant D, Hobbs DC, Lesnefsky EJ, Kukreja RC. Dietary inorganic nitrate alleviates doxorubicin cardiotoxicity: mechanisms and implications. Nitric Oxide. 2012 May 15;26(4):274-84. doi: 10.1016/j.niox.2012.03.006. Epub 2012 Apr 5. Review. PubMed PMID: 22484629; PubMed Central PMCID: PMC3360792.

3: Octavia Y, Tocchetti CG, Gabrielson KL, Janssens S, Crijns HJ, Moens AL. Doxorubicin-induced cardiomyopathy: from molecular mechanisms to therapeutic strategies. J Mol Cell Cardiol. 2012 Jun;52(6):1213-25. doi: 10.1016/j.yjmcc.2012.03.006. Epub 2012 Mar 21. Review. PubMed PMID: 22465037.

4: Prados J, Melguizo C, Ortiz R, Vélez C, Alvarez PJ, Arias JL, Ruíz MA, Gallardo V, Aranega A. Doxorubicin-loaded nanoparticles: new advances in breast cancer therapy. Anticancer Agents Med Chem. 2012 Nov;12(9):1058-70. Review. PubMed PMID: 22339066.

5: Airoldi M, Amadori D, Barni S, Cinieri S, De Placido S, Di Leo A, Gennari A, Iacobelli S, Ionta MT, Lorusso V, Lotrionte M, Marchetti P, Mattioli R, Minotti G, Pronzato P, Rosti G, Tondini CA, Veronesi A. Clinical activity and cardiac tolerability of non-pegylated liposomal doxorubicin in breast cancer: a synthetic review. Tumori. 2011 Nov-Dec;97(6):690-2. doi: 10.1700/1018.11082. Review. PubMed PMID: 22322832.

6: Khasraw M, Bell R, Dang C. Epirubicin: is it like doxorubicin in breast cancer? A clinical review. Breast. 2012 Apr;21(2):142-9. doi: 10.1016/j.breast.2011.12.012. Epub 2012 Jan 17. Review. PubMed PMID: 22260846.

7: Rakowski JA, Ahmad S, Holloway RW. Use of pegylated liposomal doxorubicin in the management of platinum-sensitive recurrent ovarian cancer: current concepts. Expert Rev Anticancer Ther. 2012 Jan;12(1):31-40. doi: 10.1586/era.11.187. Review. PubMed PMID: 22149430.

8: Duggan ST, Keating GM. Pegylated liposomal doxorubicin: a review of its use in metastatic breast cancer, ovarian cancer, multiple myeloma and AIDS-related Kaposi's sarcoma. Drugs. 2011 Dec 24;71(18):2531-58. doi: 10.2165/11207510-000000000-00000. Review. PubMed PMID: 22141391.

9: Meng L, Zhang X, Lu Q, Fei Z, Dyson PJ. Single walled carbon nanotubes as drug delivery vehicles: targeting doxorubicin to tumors. Biomaterials. 2012 Feb;33(6):1689-98. doi: 10.1016/j.biomaterials.2011.11.004. Epub 2011 Dec 2. Review. PubMed PMID: 22137127.

10: Maeda M, Mabuchi S, Matsumoto Y, Hisamatsu T, Ohashi H, Kimura T. Activity of pegylated liposomal doxorubicin for extragenital mullerian adenosarcoma with sarcomatous overgrowth: a case report and a review of the literature. Eur J Gynaecol Oncol. 2011;32(5):542-6. Review. PubMed PMID: 22053671.