Amrubicin

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 under the brand name Calsed.^[2]

Amrubicin

Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	IV
ATC code	L01DB10 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
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
CAS Number	110267-81-7 N
PubChem CID	178149
ChemSpider	2299344 Y
UNII	93N13LB4Z2
KEGG	D08854 Y
ChEBI	CHEBI:135779
ChEMBL	ChEMBL1186894 N
CompTox Dashboard (EPA)	DTXSID30869526
Chemical and physical data
Formula	C25H25NO9
Molar mass	483.473 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C2c1c(O)c5c(c(O)c1C(=O)c3ccccc23)C[C@](C(=O)C)(N)C[C@@H]5O[C@@H]4OC[C@@H](O)[C@@H](O)C4
InChI InChI=1S/C25H25NO9/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/t14-,15+,16-,17-,25-/m0/s1 Y Key:VJZITPJGSQKZMX-XDPRQOKASA-N Y
NY (what is this?)  (verify)

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]

Amrubicin was the first anthracycline derivative created by de novo synthesis and was first published in 1989 by scientists from Sumitomo.^[7]