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Daunorubicin

Catalog No. DB00694 Name DrugBank
CAS Number 20830-81-3 Website http://www.ualberta.ca/
M. F. C27H29NO10 Telephone (780) 492-3111
M. W. 527.51986 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 576

SYNONYMS

IUPAC name
(8S,10S)-8-acetyl-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
IUPAC Traditional name
daunorubicin
Brand Name
Daunorubicinum [INN-Latin]
Daunorubicine
Antibiotics From Streptomyces Coeruleorubidus
Daunarubicinum
Daunorubicin, Hydrochloride
Acetyladriamycin
Anthracyline
Cerubidin
Daunamycin
Daunomycin
Daunorrubicina
Daunorubicin Hcl
Daunorubicin Hydrochloride
Daunoxome
Rp 13057 Hydrochloride
Rubidomycin
Rubomycin C
Cerubidine
DM1
Daunoblastin
Daunomycin Hydrochloride
Daunomycin, Hydrochloride
Leukaemomycin C
Ondena
Rcra Waste No. U059
Rubidomycin Hydrochloride

DATABASE IDS

PubChem CID 30323
CAS Number 20830-81-3
PubChem SID 46508433

PROPERTIES

Hydrophobicity(logP) 0.1
Solubility 39.2 mg/L

DETAILS

Description (English)
Item Information
Drug Groups approved
Description A very toxic anthracycline aminoglycoside antineoplastic isolated from Streptomyces peucetius and others, used in treatment of leukemia and other neoplasms. [PubChem]
Indication For remission induction in acute nonlymphocytic leukemia (myelogenous, monocytic, erythroid) of adults and for remission induction in acute lymphocytic leukemia of children and adults.
Pharmacology Daunorubicin 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. Daunorubicin may also inhibit polymerase activity, affect regulation of gene expression, and produce free radical damage to DNA. Daunorubicin possesses an antitumor effect against a wide spectrum of tumors, either grafted or spontaneous. The anthracyclines are cell cycle-nonspecific.
Toxicity LD50=20 mg/kg (mice, IV); LD50=13 mg/kg (rat, IV)
Affected Organisms
Humans and other mammals
Biotransformation Hepatic
Half Life 18.5 hours
Protein Binding 97% binding-albumin
Elimination Twenty-five percent of an administered dose of daunorubicin hydrochloride is eliminated in an active form by urinary excretion and an estimated 40% by biliary excretion.
External Links
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REFERENCES