Synonym
Doxorubicin citrate
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 2-hydroxypropane-1,2,3-tricarboxylate
InChi Key
INEKNBHAPBIAFK-RUELKSSGSA-N
InChi Code
InChI=1S/C27H29NO11.C6H8O7/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;7-3(8)1-6(13,5(11)12)2-4(9)10/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/t10-,13-,15-,17-,22+,27-;/m0./s1
SMILES Code
COc1cccc2C(=O)c3c(O)c4C[C@](O)(C[C@H](O[C@H]5C[C@H](N)[C@H](O)[C@H](C)O5)c4c(O)c3C(=O)c12)C(=O)CO.OC(=O)CC(O)(CC(=O)O)C(=O)O
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
735.65
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
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, RuÃz 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.
