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Revision as of 11:11, 24 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CAS_number').← Previous edit Latest revision as of 23:11, 1 April 2023 edit undoEntranced98 (talk | contribs)Extended confirmed users, Pending changes reviewers, Rollbackers172,960 edits Importing Wikidata short description: "Chemical compound"Tag: Shortdesc helper 
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{{Short description|Chemical compound}}
{{Drugbox {{Drugbox
| Verifiedfields = changed | Verifiedfields = changed
⚫ | verifiedrevid = 457129460
| Watchedfields = changed
⚫ | verifiedrevid = 401206596
| IUPAC_name = (7''S'',9''S'')-9-Acetyl-9-amino-7-oxy-6,11-dihydroxy-8,10-dihydro-7''H''-tetracene-5,12-dione | IUPAC_name = (7''S'',9''S'')-9-Acetyl-9-amino-7-oxy-6,11-dihydroxy-8,10-dihydro-7''H''-tetracene-5,12-dione
| image = amrubicin.png | image = amrubicin.png
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| metabolism = | metabolism =
| elimination_half-life = | elimination_half-life =
| excretion = | excretion =


<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = <!-- blanked - oldvalue: 110267-81-7 --> | CAS_number = 110267-81-7
| ATC_prefix = L01 | ATC_prefix = L01
| ATC_suffix = DB10 | ATC_suffix = DB10
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2299344 | ChemSpiderID = 2299344
| UNII_Ref = {{fdacite|changed|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 93N13LB4Z2 | UNII = 93N13LB4Z2
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D08854 | KEGG = D08854
| ChEBI = 135779
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = <!-- blanked - oldvalue: 1186894 --> | ChEMBL = 1186894

<!--Chemical data-->
| chemical_formula = | chemical_formula =
| C=25 | H=25 | N=1 | O=9 | C=25 | H=25 | N=1 | O=9
| molecular_weight = 483.46 g/mol
| smiles = O=C2c1c(O)c5c(c(O)c1C(=O)c3ccccc23)C(C(=O)C)(N)C5O4OC(O)(O)C4 | smiles = O=C2c1c(O)c5c(c(O)c1C(=O)c3ccccc23)C(C(=O)C)(N)C5O4OC(O)(O)C4
| InChI = 1/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
| InChIKey = VJZITPJGSQKZMX-XDPRQOKABQ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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 | StdInChI = 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
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}} }}


'''Amrubicin''' (]; previously known as '''SM-5887''') is an ] used in the treatment of ].<ref name="pmid1332624">{{cite journal |author=Ueoka H, Ohnoshi T, Kimura I |title= |language=Japanese |journal=Gan To Kagaku Ryoho |volume=19 |issue=13 |pages=2146–9 |year=1992 |month=November |pmid=1332624 |doi= |url=}}</ref> It is marketed in Japan since 2002 by Sumitomo Pharmaceuticals under the brand name '''Calsed'''.<ref name=/SUMITO17>{{cite web | author = Sumitomo Pharmaceuticals Co., Ltd. | year = 2003 | url = http://www.e-search.ne.jp/~jpr/PDF/SUMITO17.PDF | title = CALSED for Injection (English) | accessdate = 2008-08-17}} {{Dead link|date=October 2010|bot=H3llBot}}</ref> '''Amrubicin''' (]; previously known as '''SM-5887''') is an ] used in the treatment of ].<ref name="pmid1332624">{{cite journal |vauthors =Ueoka H, Ohnoshi T, Kimura I |title= |language=ja |journal=Gan to Kagaku Ryoho |volume=19 |issue=13 |pages=2146–9 |date=November 1992 |pmid=1332624 }}</ref> It is marketed in Japan since 2002 by ] under the brand name '''Calsed'''.<ref name="/SUMITO17">{{cite web | author = Sumitomo Pharmaceuticals Co., Ltd. | year = 2003 | url = http://www.e-search.ne.jp/~jpr/PDF/SUMITO17.PDF | title = CALSED for Injection (English) | access-date = 2008-08-17}} {{Dead link|date=October 2010|bot=H3llBot}}</ref>


Amrubicin acts by inhibiting ], and has been compared in clinical trials with ], a Topoisomerase I inhibitor.<ref name=Celgene_Biopharmaceutical>{{cite web | author = Celgene Corporation | year = 2008 | url = http://ir.celgene.com/phoenix.zhtml?c=111960&p=irol-newsArticle&ID=1121403&highlight | title = Amrubicin(R) Receives FDA Orphan Drug Designation for the Treatment of Small Cell Lung Cancer | accessdate = 2009-07-10}}</ref> <ref name=Medical_News_Today>{{cite web | author = Medical News Today | year = 2007 | url = http://www.medicalnewstoday.com/articles/73140.php | title = Pharmion's Amrubicin Shows Encouraging Results Compared To Standard Of Care In Second Line Treatment Of Small Cell Lung Cancer | accessdate = 2009-07-10}}</ref> Amrubicin acts by inhibiting ], and has been compared in clinical trials with ], a Topoisomerase I inhibitor.<ref name=Celgene_Biopharmaceutical>{{cite web|author=Celgene Corporation |year=2008 |url=http://ir.celgene.com/phoenix.zhtml?c=111960&p=irol-newsArticle&ID=1121403&highlight |archive-url=https://archive.today/20130119043057/http://ir.celgene.com/phoenix.zhtml?c=111960&p=irol-newsArticle&ID=1121403&highlight |url-status=dead |archive-date=2013-01-19 |title=Amrubicin(R) Receives FDA Orphan Drug Designation for the Treatment of Small Cell Lung Cancer |access-date=2009-07-10 }}</ref><ref name=Medical_News_Today>{{cite web | author = Medical News Today | year = 2007 | url = http://www.medicalnewstoday.com/articles/73140.php | title = Pharmion's Amrubicin Shows Encouraging Results Compared To Standard Of Care In Second Line Treatment Of Small Cell Lung Cancer | access-date = 2009-07-10}}</ref>


It has also been studied for the treatment of bladder carcinoma<ref name="pmid8678519">{{cite journal |author=Ohmori H, Tsushima T, Kobashi K |title= |language=Japanese |journal=Gan To Kagaku Ryoho |volume=23 |issue=5 |pages=601–6 |year=1996 |month=April |pmid=8678519 |doi= |url=}}</ref> and gastric cancer.<ref name="pmid1647150">{{cite journal |author=Tsushima K, Sakata Y, Munakata A, ''et al.'' |title= |language=Japanese |journal=Gan To Kagaku Ryoho |volume=18 |issue=7 |pages=1151–4 |year=1991 |month=June |pmid=1647150 |doi= |url=}}</ref> It has also been studied for the treatment of bladder carcinoma<ref name="pmid8678519">{{cite journal |vauthors =Ohmori H, Tsushima T, Kobashi K |title= |language=ja |journal=Gan to Kagaku Ryoho |volume=23 |issue=5 |pages=601–6 |date=April 1996 |pmid=8678519 }}</ref> and gastric cancer.<ref name="pmid1647150">{{cite journal |vauthors =Tsushima K, Sakata Y, Munakata A |title= |language=ja |journal=Gan to Kagaku Ryoho |volume=18 |issue=7 |pages=1151–4 |date=June 1991 |pmid=1647150 |display-authors=etal}}</ref>

Amrubicin was the first anthracycline derivative created by de novo synthesis and was first published in 1989 by scientists from Sumitomo.<ref>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}} </ref>


==References== ==References==
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