Doxorubicinol hydrochloride

Doxorubicinol hydrochloride (13-Dihydroadriamycin hydrochloride) is a secondary alcohol metabolite of Doxorubicin.

Product information

CAS Number: 63950-05-0

Molecular Weight: 582.00

Formula: C27H32ClNO11

Chemical Name: (8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-8-[(1S)-1,2-dihydroxyethyl]-6,8,11-trihydroxy-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione hydrochloride

Smiles: Cl.C[C@@H]1O[C@H](C[C@H](N)[C@@H]1O)O[C@H]1C[C@@](O)(CC2=C1C(O)=C1C(=O)C3=C(C=CC=C3C(=O)C1=C2O)OC)[C@@H](O)CO

InChiKey: ORLHIGGRLIJIIM-PNOIAXSSSA-N

InChi: InChI=1S/C27H31NO11.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-,16-,17-,22+,27-;/m0./s1

Technical Data

Appearance: Solid Power

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

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Doxorubicinol hydrochloride is produced by a two-electron, NADPH-dependent reduction of the Doxorubicin side-chain carbonyl group (C13) to a secondary alcohol. Doxorubicinol hydrochloride has been shown to have significantly lower DNA binding activity as compared to DOX. Moreover, while Doxorubicinol hydrochloride is retained in the cytoplasm or lysosomes, Doxorubicin is mainly accumulated in the nucleus.

In Vivo:

In vivo, in tumor-bearing mice, Nilotinib, acting as ABCB1 inhibitor, is found to increase the accumulation of Doxorubicin and Doxorubicinol hydrochloride in cancer tissues. This implies that weaker anticancer activity of Doxorubicinol hydrochloride may be related to its increased affinity to ABC transporters, thus leading to a lower intracellular concentration of the agent. In comparison with wild-type mice, the terminal half-life and the area under the plasma concentration-time curve of Doxorubicin in mdr1a(-/-) mice are 1.6- and 1.2-fold higher respectively. The retention of both Doxorubicin and its metabolite Doxorubicinol hydrochloride in the hearts of mdr1a(-/-) mice is substantially prolonged.

Products are for research use only. Not for human use.