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Amrubicin

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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
IUPAC name
  • (7S,9S)-9-Acetyl-9-amino-7-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
3D model (JSmol)
SMILES
  • O=C2c1c(O)c5c(c(O)c1C(=O)c3ccccc23)C(C(=O)C)(N)C5O4OC(O)(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
  • Key:VJZITPJGSQKZMX-XDPRQOKASA-N
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Amrubicin (INN; previously known as SM-5887) is an anthracycline used in the treatment of lung cancer. It is marketed in Japan since 2002 by Sumitomo under the brand name Calsed.

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

It has also been studied for the treatment of bladder carcinoma and gastric cancer.

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

References

  1. Ueoka H, Ohnoshi T, Kimura I (November 1992). "". 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). "". Gan to Kagaku Ryoho (in Japanese). 23 (5): 601–6. PMID 8678519.
  6. Tsushima K, Sakata Y, Munakata A, et al. (June 1991). "". 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
Intracellular chemotherapeutic agents / antineoplastic agents (L01)
SPs/MIs
(M phase)
Block microtubule 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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