Amrubicin

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Amrubicin

Systematic (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
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy cat.	?
Legal status	℞ Prescription only
Routes	IV
Identifiers
CAS number	110267-81-7^N
ATC code	L01DB10
PubChem	CID 178149
ChemSpider	2299344^Y
UNII	93N13LB4Z2^Y
KEGG	D08854^Y
ChEMBL	CHEMBL1186894^N
Chemical data
Formula	C₂₅H₂₅N O₉
Mol. mass	483.46 g/mol
SMILES	eMolecules & PubChem
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
N(what is this?) (verify)

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 Pharmaceuticals under the brand name Calsed.^[2]

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]

References

^ Ueoka H, Ohnoshi T, Kimura I (November 1992). "[New anthracycline analogues in the treatment of lung cancer]" (in Japanese). Gan To Kagaku Ryoho 19 (13): 2146–9. PMID 1332624.
^ Sumitomo Pharmaceuticals Co., Ltd. (2003). "CALSED for Injection (English)". http://www.e-search.ne.jp/~jpr/PDF/SUMITO17.PDF. Retrieved 2008-08-17. ^{[dead link]}
^ Celgene Corporation (2008). "Amrubicin(R) Receives FDA Orphan Drug Designation for the Treatment of Small Cell Lung Cancer". http://ir.celgene.com/phoenix.zhtml?c=111960&p=irol-newsArticle&ID=1121403&highlight. Retrieved 2009-07-10.
^ Medical News Today (2007). "Pharmion's Amrubicin Shows Encouraging Results Compared To Standard Of Care In Second Line Treatment Of Small Cell Lung Cancer". http://www.medicalnewstoday.com/articles/73140.php. Retrieved 2009-07-10.
^ 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]" (in Japanese). Gan To Kagaku Ryoho 23 (5): 601–6. PMID 8678519.
^ Tsushima K, Sakata Y, Munakata A, et al. (June 1991). "[A phase II study of SM-5887 for advanced gastric cancer]" (in Japanese). Gan To Kagaku Ryoho 18 (7): 1151–4. PMID 1647150.

Intracellular chemotherapeutic agents/antineoplastic agents (L01)

SPs/MIs
(M phase)

Block microtubule assembly	Vinca alkaloids (Vinblastine, Vincristine, Vinflunine, Vindesine, Vinorelbine)

Block microtubule disassembly	Taxanes (Cabazitaxel, Docetaxel, Larotaxel, Ortataxel, Paclitaxel, Tesetaxel) • Epothilones (Ixabepilone)

DNA replication
inhibitor

DNA precursors/
antimetabolites
(S phase)

Topoisomerase inhibitors
(S phase)

I	Camptotheca (Camptothecin, Topotecan, Irinotecan, Rubitecan, Belotecan)

II	Podophyllum (Etoposide, Teniposide)

II+Intercalation	Anthracyclines (Aclarubicin, Daunorubicin, Doxorubicin, Epirubicin, Idarubicin, Amrubicin, Pirarubicin, Valrubicin, Zorubicin) • Anthracenediones (Mitoxantrone, Pixantrone)

Crosslinking of DNA
(CCNS)

Alkylating	Nitrogen mustards: Mechlorethamine • Cyclophosphamide (Ifosfamide, Trofosfamide) • Chlorambucil (Melphalan, Prednimustine) • Bendamustine • Uramustine • Estramustine Nitrosoureas: Carmustine • Lomustine (Semustine) • Fotemustine • Nimustine • Ranimustine • Streptozocin Alkyl sulfonates: Busulfan (Mannosulfan, Treosulfan) Aziridines: Carboquone • ThioTEPA • Triaziquone • Triethylenemelamine

Alkylating-like	Platinum (Carboplatin, Cisplatin, Nedaplatin, Oxaliplatin, Triplatin tetranitrate, Satraplatin)

Nonclassical	Hydrazines (Procarbazine) • Triazenes (Dacarbazine, Temozolomide) • Altretamine • Mitobronitol

Intercalation	Streptomyces (Actinomycin, Bleomycin, Mitomycin, Plicamycin)

Photosensitizers/PDT

Aminolevulinic acid/Methyl aminolevulinate • Efaproxiral • Porphyrin derivatives (Porfimer sodium, Talaporfin, Temoporfin, Verteporfin)

Other

Enzyme inhibitors	FI (Tipifarnib) • CDK inhibitors (Alvocidib, Seliciclib) • PrI (Bortezomib) • PhI (Anagrelide) • IMPDI (Tiazofurine) • LI (Masoprocol) • PARP inhibitor (Olaparib) • HDAC (Vorinostat, Romidepsin)

Receptor antagonists	ERA (Atrasentan) • retinoid X receptor (Bexarotene) • sex steroid (Testolactone)

Other/ungrouped	Amsacrine • Trabectedin • retinoids (Alitretinoin, Tretinoin) • Arsenic trioxide • asparagine depleters (Asparaginase/Pegaspargase) • Celecoxib • Demecolcine • Elesclomol • Elsamitrucin • Etoglucid • Lonidamine • HAMLET (human alpha-lactalbumin made lethal to tumor cells) • Lucanthone • Mitoguazone • Mitotane • Oblimersen • Omacetaxine mepesuccinate • mTOR inhibitors (Everolimus, Temsirolimus)

M: NEO

tsoc, mrkr

tumr, epon, para

drug (L1i/1e/V03)

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Wikipedia on Answers.com This article is licensed under the Creative Commons Attribution/Share-Alike License. It uses material from the Wikipedia article Amrubicin. Read