SPL Set ID: e0349f98-42fa-4003-b6d8-a1db1401b0ef

Doxorubicin is a cytotoxic anthracycline antibiotic isolated from cultures of Streptomyces peucetius var . caesius . Doxorubicin consists of a naphthacenequinone nucleus linked through a glycosidic bond at ring atom 7 to an amino sugar, daunosamine. Chemically, doxorubicin hydrochloride is: 5,12-Naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-α-L- lyxo -hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxylacetyl)-1-methoxy-, hydrochloride (8 S - cis )-. (8 S , 10 S )-10-[(3-Amino-2,3,6-trideoxy-α-L- lyxo -hexopyranosyl)-oxy]-8-glycoloyl-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione hydrochloride [ 25316-40-9 ]. The structural formula is as follows: C 27 H 29 NO 11 • HCl M.W. 579.99 Doxorubicin binds to nucleic acids, presumably by specific intercalation of the planar anthracycline nucleus with the DNA double helix. The anthracycline ring is lipophilic, but the saturated end of the ring system contains abundant hydroxyl groups adjacent to the amino sugar, producing a hydrophilic center. The molecule is amphoteric, containing acidic functions in the ring phenolic groups and a basic function in the sugar amino group. It binds to cell membranes as well as plasma proteins. Doxorubicin Hydrochloride Injection, USP is a sterile, isotonic, preservative-free solution for intravenous use. It is available in 5 mL (10 mg), 10 mL (20 mg) and 25 mL (50 mg) single dose vials and 100 mL (200 mg) multiple dose vials. Each mL contains: Doxorubicin hydrochloride 2 mg; sodium chloride 9 mg for Isotonicity: Water for Injection q.s. Hydrochloric acid and/or sodium hydroxide may have been added for pH adjustment (2.5 to 4.5). structure