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.comInternational Drug Names
Routes of
administration		IV
ATC code
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
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC25H25NO9
Molar mass483.473 g·mol−1
3D model (JSmol)
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]

References
  1. Ueoka H, Ohnoshi T, Kimura I (November 1992). "[New anthracycline analogues in the treatment of lung cancer]". Gan to Kagaku Ryoho (in Japanese). 19 (13): 2146–9. PMID 1332624.
  2. Sumitomo Pharmaceuticals Co., Ltd. (2003). "CALSED for Injection (English)" (PDF). Retrieved 2008-08-17.
  3. Celgene Corporation (2008). "Amrubicin(R) Receives FDA Orphan Drug Designation for the Treatment of Small Cell Lung Cancer". Archived from the original on 2013-01-19. Retrieved 2009-07-10.
  4. Medical News Today (2007). "Pharmion's Amrubicin Shows Encouraging Results Compared To Standard Of Care In Second Line Treatment Of Small Cell Lung Cancer". Retrieved 2009-07-10.
  5. Ohmori H, Tsushima T, Kobashi K (April 1996). "[Experimental studies on intravesical instillation of SM-5887, a novel anthracycline derivative for treatment of bladder carcinoma]". Gan to Kagaku Ryoho (in Japanese). 23 (5): 601–6. PMID 8678519.
  6. Tsushima K, Sakata Y, Munakata A, et al. (June 1991). "[A phase II study of SM-5887 for advanced gastric cancer]". Gan to Kagaku Ryoho (in Japanese). 18 (7): 1151–4. PMID 1647150.
  7. Hanada M. Amrubicin, Chapter 6 in Case Studies in Modern Drug Discovery and Development. Eds. Huang X and Aslanian RG. John Wiley & Sons, 2012 ISBN 9780470601815 P 106


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