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Doxorubicin

Catalog No. DB00997 Name DrugBank
CAS Number 23214-92-8 Website http://www.ualberta.ca/
M. F. C27H29NO11 Telephone (780) 492-3111
M. W. 543.51926 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 870

SYNONYMS

IUPAC name
(8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
IUPAC Traditional name
doxorubicin
Brand Name
Resmycin
Myocet
Doxo
Adriblastina
Rubex
Adriamycin
Adriamycin PFS
DM2
RDF Rubex
ADM
Adriablastin
Adriamycin RDF
Adriamycin Semiquinone
Adriblastin
Caelyx
Doxil
Synonyms
Doxorubicin HCl
Doxorubicin Hydrochloride
Doxorubicina [INN-Spanish]
Doxorubicine [INN-French]
Doxorubicinum [INN-Latin]
doxorubicin

DATABASE IDS

CAS Number 23214-92-8
PubChem SID 46507641
PubChem CID 31703

PROPERTIES

Hydrophobicity(logP) -0.5
Solubility Soluble

DETAILS

Description (English)
Item Information
Drug Groups approved; investigational
Description Antineoplastic antibiotic obtained from Streptomyces peucetius. It is a hydroxy derivative of daunorubicin. [PubChem]
Indication For the treatment of Koposi's sarcome connected to AIDS.
Pharmacology Doxorubicin is an antineoplastic in the anthracycline class. General properties of drugs in this class include: interaction with DNA in a variety of different ways including intercalation (squeezing between the base pairs), DNA strand breakage and inhibition with the enzyme topoisomerase II. Most of these compounds have been isolated from natural sources and antibiotics. However, they lack the specificity of the antimicrobial antibiotics and thus produce significant toxicity. The anthracyclines are among the most important antitumor drugs available. Doxorubicin is widely used for the treatment of several solid tumors while daunorubicin and idarubicin are used exclusively for the treatment of leukemia. Doxorubicin may also inhibit polymerase activity, affect regulation of gene expression, and produce free radical damage to DNA. Doxorubicin possesses an antitumor effect against a wide spectrum of tumors, either grafted or spontaneous. The anthracyclines are cell cycle-nonspecific.
Toxicity LD50=21800 ug/kg (rat, subcutaneous)
Affected Organisms
Humans and other mammals
Half Life 55 hours
Protein Binding 70%
Elimination Plasma clearance is in the range 324 to 809 mL/min/m2 and is predominately by metabolism and biliary excretion.
Clearance * 324-809 mL/min/m2
* 1088 mL/min/m2 [Men]
* 433 mL/min/m2 [Women]
* 1540 mL/min/m2 [children greater than 2 years of age receiving administration of 10 to 75 mg/m2 doses]
* 813 mL/min/m2 [infants younger than 2 years of age receiving administration of 10 to 75 mg/m2 doses]
References
Weiss RB: The anthracyclines: will we ever find a better doxorubicin? Semin Oncol. 1992 Dec;19(6):670-86. [Pubmed]
Tan C, Tasaka H, Yu KP, Murphy ML, Karnofsky DA: Daunomycin, an antitumor antibiotic, in the treatment of neoplastic disease. Clinical evaluation with special reference to childhood leukemia. Cancer. 1967 Mar;20(3):333-53. [Pubmed]
Arcamone F, Cassinelli G, Fantini G, Grein A, Orezzi P, Pol C, Spalla C: Adriamycin, 14-hydroxydaunomycin, a new antitumor antibiotic from S. peucetius var. caesius. Biotechnol Bioeng. 1969 Nov;11(6):1101-10. [Pubmed]
Di Marco A, Gaetani M, Scarpinato B: Adriamycin (NSC-123,127): a new antibiotic with antitumor activity. Cancer Chemother Rep. 1969 Feb;53(1):33-7. [Pubmed]
Lomovskaya N, Otten SL, Doi-Katayama Y, Fonstein L, Liu XC, Takatsu T, Inventi-Solari A, Filippini S, Torti F, Colombo AL, Hutchinson CR: Doxorubicin overproduction in Streptomyces peucetius: cloning and characterization of the dnrU ketoreductase and dnrV genes and the doxA cytochrome P-450 hydroxylase gene. J Bacteriol. 1999 Jan;181(1):305-18. [Pubmed]
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REFERENCES

  • Tan C, Tasaka H, Yu KP, Murphy ML, Karnofsky DA: Daunomycin, an antitumor antibiotic, in the treatment of neoplastic disease. Clinical evaluation with special reference to childhood leukemia. Cancer. 1967 Mar;20(3):333-53. Pubmed
  • Arcamone F, Cassinelli G, Fantini G, Grein A, Orezzi P, Pol C, Spalla C: Adriamycin, 14-hydroxydaunomycin, a new antitumor antibiotic from S. peucetius var. caesius. Biotechnol Bioeng. 1969 Nov;11(6):1101-10. Pubmed
  • Di Marco A, Gaetani M, Scarpinato B: Adriamycin (NSC-123,127): a new antibiotic with antitumor activity. Cancer Chemother Rep. 1969 Feb;53(1):33-7. Pubmed
  • Lomovskaya N, Otten SL, Doi-Katayama Y, Fonstein L, Liu XC, Takatsu T, Inventi-Solari A, Filippini S, Torti F, Colombo AL, Hutchinson CR: Doxorubicin overproduction in Streptomyces peucetius: cloning and characterization of the dnrU ketoreductase and dnrV genes and the doxA cytochrome P-450 hydroxylase gene. J Bacteriol. 1999 Jan;181(1):305-18. Pubmed
  • Weiss RB: The anthracyclines: will we ever find a better doxorubicin? Semin Oncol. 1992 Dec;19(6):670-86. Pubmed