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Amrubicin

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Amrubicin
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration
IV
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • (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
PubChemCID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC25H25NO9
Molar mass483.473 g·mol−1
3D model (JSmol)
  • 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=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 checkY
  • Key:VJZITPJGSQKZMX-XDPRQOKASA-N checkY
 ☒NcheckY (what is this?)  (verify)

Amrubicin (INN; previously known asSM-5887) is ananthracycline used in the treatment oflung cancer.[1] It is marketed in Japan since 2002 bySumitomo under the brand nameCalsed.[2]

Amrubicin acts by inhibitingtopoisomerase II, and has been compared in clinical trials withtopotecan, 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

[edit]
  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). Retrieved2008-08-17.[dead link]
  3. ^Celgene Corporation (2008)."Amrubicin(R) Receives FDA Orphan Drug Designation for the Treatment of Small Cell Lung Cancer". Archived fromthe original on 2013-01-19. Retrieved2009-07-10.
  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". Retrieved2009-07-10.
  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, 2012ISBN 9780470601815P 106
SPs/MIs
(M phase)
Blockmicrotubule assembly
Block microtubule disassembly
DNA replication
inhibitor
DNA precursors/
antimetabolites
(S phase)
Folic acid
Purine
Pyrimidine
Deoxyribonucleotide
Topoisomerase inhibitors
(S phase)
I
II
II+Intercalation
Crosslinking of DNA
(CCNS)
Alkylating
Platinum-based
Nonclassical
Intercalation
Photosensitizers/PDT
Other
Enzyme inhibitors
Receptor antagonists
Other/ungrouped


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