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D9099-44 Doxorubicin, Hydrochloride (Adriacin, Adriblastina, Adriamycin, Caelyx) CAS: 25316-40-9

Specifications
References
CAS Number
25316-40-9
Grade
Highly Purified
MDL Number
MFCD28988663
Molecular Formula
C27H29NO11•HCl
Molecular Weight
579.98
EU Commodity Code
38220090
Shipping Temp
RT
Storage Temp
-20°C
(8S,10S)-10-[(3-Amino-2,3,6-trideoxy-α-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione Hydrochloride; Adriacin; Adriblastina; Adriamycin; Caelyx; ADM hydrochloride

The hydrochloride salt of doxorubicin, 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.

Synonyms
(8S,10S)-10-[(3-Amino-2,3,6-trideoxy-α-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione Hydrochloride; Adriacin; Adriblastina; Adriamycin; Caelyx; ADM hydrochloride
CAS No
25316-40-9 Free Base: 23214-92-8
Molecular Formula
C27H29NO11•HCl
Molecular Weight
579.98
Appearance
Orange-red solid
Purity
≥99%
Identity (IR)
Conforms to reference
Melting Point
>160°C (dec.) (lit)
pH
4.0-5.5
Acetone
≤0.5%
Total Impurities
≤2%
Water
≤4%
Storage and Stability
May be stored at RT for short-term only. Long-term storage is recommended at -20°C. For maximum recovery of product, centrifuge the original vial prior to removing the cap.
Important Note
This product as supplied is intended for research use only, not for use in human, therapeutic or diagnostic applications without the expressed written authorization of United States Biological.
Toxicity and Hazards
 All products should be handled by qualified personnel only, trained in laboratory procedures.
References
1. Adriamycin (14-hydroxydaunomycin), a novel antitumor antibiotic. Arcamone F. et al., Tet. Letters 1969, 13, 1007. |2. Interference by doxorubicin with DNA unwinding in MCF-7 breast tumor cells. Fornari F.L. et al., Mol. Pharmacology 1994, 45, 649. 3. Effect of Adriamycin on DNA, RNA, and protein synthesis in cell-free systems and intact cells. Momarier |R. et al., Cancer Research 1976, 36, 2891. 4. Di Marco, A., et al.: Cancer Chemother. Rep., (part 1), 53, 33 (1969).5. Mihich, E. and Ehrke, M.J.: Transplant. Proc., 16, 499 (1984)
USBio References
No references available
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