Amrubicin hydrochloride Inhibitors Amrubicin hydrochloride (SM-5887 hydrochloride) is a topoisomerase II inhibitor used in the treatment of lung cancer.Target: Topoisomerase IISM-5887 is a novel anthracycline derivative. The distribution of SM-5887 in the bladder mucosa and muscular layer was almost equal, but the concentration of its active metabolite, 13-OH derivative, was 5 to 10 times higher in the bladder mucosa than in the bladder muscular layer. The distributions of SM-5887 in the organs other than the bladder, that is, the cortex and medulla of kidney, heart, lung, liver, and spleen, were very low, and those of a 13-OH active metabolite were even lower. In addition, SM-5887 barely affected the normal bladder mucosa. In dogs instilled with 80 mg of SM-5887, no histological change was observed in the bladder mucosa and submucosal layer even after 6-hour retention at the highest concentration of 8,000 micrograms/ml [1]. SM-5887 is possibly most potent for the treatment of NSCLC, and that these drugs have less cardiotoxicity compared to the mother compound, doxorubicin [2]. 519.9 g/mol
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Formulation: 519.9 g/mol
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Amrubicin hydrochloride - 110311-30-3

Amrubicin hydrochloride

The product is for non-human research only. Not for therapeutic or veterinary use.

Catalog Number: BT-253167

CAS Number: 110311-30-3

Molecular Formula: C25H26ClNO9

Molecular Weight: 519.9 g/mol

CAS Number 110311-30-3
Product Name Amrubicin hydrochloride
Molecular Formula C25H26ClNO9
Molecular Weight 519.9 g/mol
InChI InChI=1S/C25H25NO9.ClH/c1-10(27)25(26)7-13-18(16(8-25)35-17-6-14(28)15(29)9-34-17)24(33)20-19(23(13)32)21(30)11-4-2-3-5-12(11)22(20)31;/h2-5,14-17,28-29,32-33H,6-9,26H2,1H3;1H/t14-,15+,16-,17-,25-;/m0./s1
InChI Key BHMLHEQFWVQAJS-IITOGVPQSA-N
Isomeric SMILES CC(=O)[C@]1(C[C@@H](C2=C(C1)C(=C3C(=C2O)C(=O)C4=CC=CC=C4C3=O)O)O[C@H]5C[C@@H]([C@@H](CO5)O)O)N.Cl
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;hydrochloride
Canonical SMILES CC(=O)C1(CC(C2=C(C1)C(=C3C(=C2O)C(=O)C4=CC=CC=C4C3=O)O)OC5CC(C(CO5)O)O)N.Cl
Description Amrubicin hydrochloride (SM-5887 hydrochloride) is a topoisomerase II inhibitor used in the treatment of lung cancer.Target: Topoisomerase IISM-5887 is a novel anthracycline derivative. The distribution of SM-5887 in the bladder mucosa and muscular layer was almost equal, but the concentration of its active metabolite, 13-OH derivative, was 5 to 10 times higher in the bladder mucosa than in the bladder muscular layer. The distributions of SM-5887 in the organs other than the bladder, that is, the cortex and medulla of kidney, heart, lung, liver, and spleen, were very low, and those of a 13-OH active metabolite were even lower. In addition, SM-5887 barely affected the normal bladder mucosa. In dogs instilled with 80 mg of SM-5887, no histological change was observed in the bladder mucosa and submucosal layer even after 6-hour retention at the highest concentration of 8,000 micrograms/ml [1]. SM-5887 is possibly most potent for the treatment of NSCLC, and that these drugs have less cardiotoxicity compared to the mother compound, doxorubicin [2].
SMILES CC(=O)C1(CC(C2=C(C1)C(=C3C(=C2O)C(=O)C4=CC=CC=C4C3=O)O)OC5CC(C(CO5)O)O)N.Cl
Synonyms (+)-(7S,9S)-9-acetyl-9-amino-7-((2-deoxy-beta-d-erythro-pentopyranosyl)oxy)-6,11-dihydroxy-7,8,9,10-tetrahydrotetracene-5,12-dione hydrochloride
(7S,9S)-9-acetyl-9-amino-7-((2-deoxy-beta-D-erythro-pentopyranosyl)oxy)-7,8,9,10-tetrahydro-6,11-dihydroxy-5,12-naphthacenedione hydrochloride
amrubicin
amrubicin hydrochloride
SM 5887
SM-5887
Reference [1]. Ohmori, H., T. Tsushima, and K. Kobashi, [Experimental studies on intravesical instillation of SM-5887, a novel anthracycline derivative for treatment of bladder carcinoma]. Gan To Kagaku Ryoho, 1996. 23(5): p. 601-6. [2]. Ueoka, H., T. Ohnoshi, and I. Kimura, [New anthracycline analogues in the treatment of lung cancer]. Gan To Kagaku Ryoho, 1992. 19(13): p. 2146-9.
PubChem Compound Amrubicin hydrochloride
Last Modified Nov 11 2021