Amrubicin

Title: Amrubicin
CAS Registry Number: 110267-81-7
CAS Name: (7S,9S)-9-Acetyl-9-amino-7-[(2-deoxy-b-D-erythro-pentopyranosyl)oxy]-7,8,9,10-tetrahydro-6,11-dihydroxy-5,12-naphthacenedione
Additional Names: (+)-9-amino-4-demethoxy-9-deoxy-7-O-(2-deoxy-b-D-erythro-pentopyranosyl)daunomycinone
Molecular Formula: C25H25NO9
Molecular Weight: 483.47
Percent Composition: C 62.11%, H 5.21%, N 2.90%, O 29.78%
Literature References: Synthetic anthracycline antibiotic; inhibits DNA topoisomerase II. Prepn: K. Ishizumi et al., EP 107486; eidem, US 4673668 (1984, 1987 both to Sumitomo); eidem, J. Org. Chem. 52, 4477 (1987). NMR study of complex with DNA: J. Igarashi, M. Sunagawa, Bioorg. Med. Chem. Lett. 5, 2923 (1995). Mechanism of action: M. Hanada et al., Jpn. J. Cancer Res. 89, 1229 (1998). Toxicology: S. Morisada et al., ibid. 80, 77 (1989). Clinical pharmacokinetics: K. Inoue et al., Invest. New Drugs 7, 213 (1989); Y. Matsunaga et al., Ther. Drug Monit. 28, 76 (2006). Clinical evaluation in lung cancer: T. Sugiura et al., Invest. New Drugs 23, 331 (2005); in combination with cisplatin: Y. Ohe et al., Ann. Oncol. 16, 430 (2005).
Properties: mp 172-174°. [a]D20 +119° (c = 0.02 in CHCl3).
Melting point: mp 172-174°
Optical Rotation: [a]D20 +119° (c = 0.02 in CHCl3)
Derivative Type: Hydrochloride
CAS Registry Number: 110311-30-3
Manufacturers' Codes: SM-5887
Trademarks: Calsed (Sumitomo)
Molecular Formula: C25H25NO9.HCl
Molecular Weight: 519.93
Percent Composition: C 57.75%, H 5.04%, N 2.69%, O 27.69%, Cl 6.82%
Properties: mp 145-151°. LD50 i.v. in mice: 32-50 mg/kg (Morisada).
Melting point: mp 145-151°
Toxicity data: LD50 i.v. in mice: 32-50 mg/kg (Morisada)
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Antibiotics and Analogs; Anthracyclines; Topoisomerase II Inhibitor.
Amsacrine Amsonic Acid Amtolmetin Guacil Amygdalin Amyl Chloride

Amrubicin
Amrubicin.png
Systematic (IUPAC) name
(7S,9S)-9-Acetyl-9-amino-7-[(2S,4S,5R)-4,5-dihydroxyoxan-2-yl]oxy-6,11-dihydroxy-8,10-dihydro-7H-tetracene-5,12-dione
Clinical data
AHFS/Drugs.com International Drug Names
Legal status Prescription only
Routes IV
Identifiers
CAS number 110267-81-7 N
ATC code L01DB10
PubChem CID 178149
ChemSpider 2299344 YesY
UNII 93N13LB4Z2 YesY
KEGG D08854 YesY
ChEMBL CHEMBL1186894 N
Chemical data
Formula C25H25NO9 
Mol. mass 483.46 g/mol
 N (what is this?)  (verify)

Amrubicin (INN; previously known as SM-5887) is an anthracycline used in the treatment of lung cancer.[1] It is marketed in Japan since 2002 by Sumitomo Pharmaceuticals under the brand name Calsed.[2]

Amrubicin acts by inhibiting topoisomerase II, and has been compared in clinical trials with topotecan, a Topoisomerase I inhibitor.[3] [4]

It has also been studied for the treatment of bladder carcinoma[5] and gastric cancer.[6]