Daunorubicin

Title: Daunorubicin
CAS Registry Number: 20830-81-3
CAS Name: (8S-cis)-8-Acetyl-10-[(3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione
Additional Names: daunomycin; leukaemomycin C; rubidomycin
Manufacturers' Codes: RP-13057
Trademarks: Cerubidin (M & B)
Molecular Formula: C27H29NO10
Molecular Weight: 527.52
Percent Composition: C 61.47%, H 5.54%, N 2.66%, O 30.33%
Literature References: Anthracycline antibiotic related to the rhodomycins, q.v. Isolated from fermentation broths of Streptomyces peucetius: G. Cassinelli, P. Orezzi, G. Microbiol. 11, 167 (1963), C.A. 62, 9482b (1965); A. Di Marco et al., Nature 201, 706 (1964); eidem, BE 639897; eidem, US 4012284 (1964, 1977 both to Soc. Farmaceut. Italia); S. Pinnert et al., US 3997662 (1976 to Rhone-Poulenc). Daunorubicin is a glycoside formed by a tetracyclic aglycone, daunomycinone, (C21H18O8) and an amino sugar, daunosamine, (C6H13NO3), 3-amino-2,3,6-trideoxy-L-lyxo-hexose: F. Arcamone et al., J. Am. Chem. Soc. 86, 5334, 5335 (1964); R. H. Iwamoto et al., Tetrahedron Lett. 1968, 3891. Absolute stereochemistry: F. Arcamone et al., Gazz. Chim. Ital. 100, 949-989 (1970). Identity with rubidomycin: G. L. Tong et al., J. Pharm. Sci. 56, 1691 (1967). Synthesis of daunosamine: J. P. Marsh et al., Chem. Commun. 1967, 973; T. Yamaguchi, M. Kojimo, Carbohydr. Res. 59, 343 (1977); P. M. Wovkulich, M. R. Uskokovic, J. Am. Chem. Soc. 103, 3956 (1981); of daunomycinone: C. M. Wong et al., Can. J. Chem. 51, 466 (1973); J. S. Swenton, P. W. Reynolds, J. Am. Chem. Soc. 100, 6188 (1978); K. Krohn, K. Tolkiehn, Ber. 112, 3453 (1979); F. M. Hauser, S. Prasanna, J. Am. Chem. Soc. 103, 6378 (1981). Total synthesis of daunorubicin: E. M. Acton et al., J. Med. Chem. 17, 659 (1974). Purification: E. Oppici et al., BE 898506; eidem, GB 2133005 (both 1984 to Farmitalia). Toxicity data: A. Di Marco et al., Cancer Chemother. Rep. Part 1 53, 33 (1969). Review of properties, biosynthesis, fermentation: R. J. White, R. M. Stroshane, Drugs Pharm. Sci. 22, 569-594 (1984); of carcinogenic action in laboratory animals: IARC Monographs 10, 145-152 (1976); of toxicology: R. J. Maral et al., Cancer Treat. Rep. 65, Suppl. 4, 9-18 (1981); of use in treatment of solid tumors: R. B. Weiss et al., ibid. 25-28; of interactions with nucleic acids: S. Neidle, M. R. Sanderson, in Molecular Aspects of Anti-cancer Drug Action, S. Neidle, M. J. Waring, Eds. (Verlag-Chemie, Florida, 1983) pp 35-55; of mechanism of cytotoxicity: H. S. Schwartz, ibid. pp 93-125; of metabolism and clinical pharmacokinetics: C. E. Riggs, Jr., Semin. Oncol. 11, Suppl. 3, 2-11 (1984). Review: A. DiMarco et al., Antibiotics vol. 3, J. W. Corcoran, F. E. Hahn, Eds. (Springer Verlag, New York, 1975) pp 101-128.
Properties: mp 208-209°. LD50 in mice, rats (mg/kg): 20, 13 i.v.; 5, 8 i.p. (DiMarco, 1977).
Melting point: mp 208-209°
Toxicity data: LD50 in mice, rats (mg/kg): 20, 13 i.v.; 5, 8 i.p. (DiMarco, 1977)
Derivative Type: Hydrochloride
CAS Registry Number: 23541-50-6
Trademarks: Cérubidine (Rh>e-Poulenc); Daunoblastina (Farmitalia); Ondena (Bayer)
Molecular Formula: C27H29NO10.HCl
Molecular Weight: 563.98
Percent Composition: C 57.50%, H 5.36%, N 2.48%, O 28.37%, Cl 6.29%
Properties: Thin red needles, dec 188-190°. [a]D20 +248 ±5° (c = 0.05-0.1 in methanol). Sol in water, methanol, aq alcohols. Practically insol in chloroform, ether, benzene. Color of aq soln changes from pink at acid pH to blue at alkaline pH. Absorption max (methanol): 234, 252, 290, 480, 495, and 532 nm (E1%1cm 665, 462, 153, 214, 218, and 112). LD50 in mice (mg/kg): 26 i.v. (DiMarco, 1969).
Optical Rotation: [a]D20 +248 ±5° (c = 0.05-0.1 in methanol)
Absorption maximum: Absorption max (methanol): 234, 252, 290, 480, 495, and 532 nm (E1%1cm 665, 462, 153, 214, 218, and 112)
Toxicity data: LD50 in mice (mg/kg): 26 i.v. (DiMarco, 1969)
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Antibiotics and Analogs; Anthracyclines; Topoisomerase II Inhibitor.
Dauricine DBHBT DBMC d-Bornyl alpha-Bromoisovalerate d-Bornyl Isovalerate

Daunorubicin
Daunorubicin.svg
Daunorubicin ball-and-stick.png
Systematic (IUPAC) name
(8S,10S)-8-acetyl-10-[(2S,4S,5S,6S)-
4-amino-5-hydroxy-6-methyl-oxan-
2-yl]oxy-6,8,11-trihydroxy-1-methoxy-
9,10-dihydro-7H-tetracene-5,12-dione
Clinical data
Trade names Cerubidine
AHFS/Drugs.com monograph
MedlinePlus a682289
Pregnancy cat. D (U.S.)
Legal status -only (US)
Routes Exclusively intravenous. Causes severe necrosis if administered intramuscularly or subcutaneously
Pharmacokinetic data
Metabolism Hepatic
Half-life 26.7 hours (metabolite)
Excretion Biliary and urinary
Identifiers
CAS number 20830-81-3 YesY
ATC code L01DB02
PubChem CID 30323
DrugBank DB00694
ChemSpider 28163 YesY
UNII ZS7284E0ZP YesY
KEGG C01907 YesY
ChEBI CHEBI:41977 YesY
ChEMBL CHEMBL178 YesY
Chemical data
Formula C27H29NO10 
Mol. mass 527.52 g/mol
563.99 g/mol (HCl salt)
 YesY (what is this?)  (verify)

Daunorubicin or daunomycin (daunomycin cerubidine) is chemotherapeutic of the anthracycline family that is given as a treatment for some types of cancer. It is most commonly used to treat specific types of leukemia (acute myeloid leukemia and acute lymphocytic leukemia). It was initially isolated from Streptomyces peucetius.

A liposomal formulation of daunorubicin is marketed in the United States as DaunoXome.