Amrubicin

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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 ;
PubChem CID	178149;
ChemSpider	2299344 ;
UNII	93N13LB4Z2;
KEGG	D08854 ;
ChEMBL	ChEMBL1186894 ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C25H25NO9
Molar mass	483.46 g/mol
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 ; Key:VJZITPJGSQKZMX-XDPRQOKASA-N ;
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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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]". Gan To Kagaku Ryoho (in Japanese). 19 (13): 2146–9. PMID 1332624.
↑ Sumitomo Pharmaceuticals Co., Ltd. (2003). "CALSED for Injection (English)" (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". 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". 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]". Gan To Kagaku Ryoho (in Japanese). 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]". Gan To Kagaku Ryoho (in Japanese). 18 (7): 1151–4. PMID 1647150.

[pmid1332624-1] 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.

[/SUMITO17-2] Sumitomo Pharmaceuticals Co., Ltd. (2003). "CALSED for Injection (English)" (PDF). Retrieved 2008-08-17. ^{[dead link]}

[Celgene_Biopharmaceutical-3] Celgene Corporation (2008). "Amrubicin(R) Receives FDA Orphan Drug Designation for the Treatment of Small Cell Lung Cancer". Retrieved 2009-07-10.

[Medical_News_Today-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.

[pmid8678519-5] 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.

[pmid1647150-6] 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.

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v t e Chemotherapeutic agents/Antineoplastic agents (L01)
Alkylating and alkylating-like agents	Nitrogen mustards: (Chlorambucil, Chlormethine, Cyclophosphamide, Ifosfamide, Melphalan, Bendamustine, Uramustine) Nitrosoureas:(Carmustine, Fotemustine, Lomustine, Streptozocin) Platinum (alkylating-like): (Carboplatin, Cisplatin, Oxaliplatin, Triplatin tetranitrate, Satraplatin) Alkyl sulfonates:(Busulfan, Treosulfan) Hydrazines:(Procarbazine, Dacarbazine, Temozolomide) Aziridines:(ThioTEPA)
Antimetabolites	Folic acid: (Aminopterin, Methotrexate, Pemetrexed, Raltitrexed). Purine:(Cladribine, Clofarabine, Fludarabine, Mercaptopurine, Pentostatin, Thioguanine) Pyrimidine:(Capecitabine, Cytarabine, Decitabine, Fluorouracil, Floxuridine, Gemcitabine)
Spindle poison/mitotic inhibitor	Taxane: (Docetaxel, Larotaxel, Paclitaxel). Vinca: (Vinblastine, Vincristine, Vindesine, Vinorelbine).
Cytotoxic/antitumor antibiotics	Anthracycline family: (Daunorubicin, Doxorubicin, Epirubicin, Idarubicin, Mitoxantrone, Pixantrone, Valrubicin) streptomyces (Actinomycin, Bleomycin, Mitomycin, Plicamycin) - Hydroxyurea
Topoisomerase inhibitors	Camptotheca: (Camptothecin, Topotecan, Irinotecan, Rubitecan), Podophyllum:(Etoposide, Teniposide)
CI monoclonal antibodies	Receptor tyrosine kinase (Cetuximab, Panitumumab, Trastuzumab) - CD20 (Rituximab, Tositumomab) - other (Alemtuzumab, Bevacizumab, Gemtuzumab)
Photosensitizers	Aminolevulinic acid, Methyl aminolevulinate, Porfimer sodium, Verteporfin
Tyrosine kinase inhibitors	Axitinib, Bosutinib, Cediranib, Dasatinib, Erlotinib, Gefitinib, Imatinib, Lapatinib, Lestaurtinib, Nilotinib, Semaxanib, Sorafenib, Sunitinib, Vandetanib
Cyclin-dependent kinase inhibitor	Seliciclib
Other	retinoids (Alitretinoin, Tretinoin), Fusion protein (Aflibercept) - Altretamine, Amsacrine, Anagrelide, Arsenic trioxide, Asparaginase (Pegaspargase), Bexarotene, Bortezomib, Celecoxib, Denileukin diftitox, Elesclomol, Estramustine, Irofulven, Ixabepilone, Masoprocol, Mitotane, Oblimersen, Testolactone, Tipifarnib, Trabectedin

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
ChEMBL	ChEMBL1186894^N
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C₂₅H₂₅NO₉
Molar mass	483.46 g/mol
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
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Amrubicin

Overview

References

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