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{{Short description|Chemical compound}} |
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| verifiedrevid = 413604140 |
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| verifiedrevid = 451224667 |
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| IUPAC_name = (2''S'')-methyl 2-((((2''R'',3''S'',5''R'')-5-(5-((''E'')-2-bromovinyl)-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-hydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphorylamino)propanoate |
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| IUPAC_name = (2''S'')-methyl 2-((((2''R'',3''S'',5''R'')-5-(5-((''E'')-2-bromovinyl)-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-hydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphorylamino)propanoate |
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| image = Thymectacin.svg |
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| image = Thymectacin.svg |
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| alt = Skeletal formula of thymectacin |
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| width = 260 |
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| image2 = Thymectacin-3D-spacefill.png |
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| alt2 = Space-filling model of the thymectacin molecule |
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| width2 = 240 |
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<!--Clinical data--> |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 232925-18-7 |
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| CAS_number = 232925-18-7 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem = 6440764 |
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| UNII = 2ZRZ4TSW3F |
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| PubChem = 6440764| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 4945015 |
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| synonyms = NB-1011; NB-101; ''N''--2'-deoxyuridin-5'-O-yl]](phenoxy)phosphoryl]-<small>L</small>-alanine methyl ester |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=21 | H=25 | Br=1 | N=3 | O=9 | P=1 |
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| C=21 | H=25 | Br=1 | N=3 | O=9 | P=1 |
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| smiles = C(C(=O)OC)NP(=O)(OC1(C(O1)n2cc(c(=O)c2=O)/C=C/Br)O)Oc3ccccc3 |
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| molecular_weight = 574.3185 g/mol |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C21H25BrN3O9P/c1-13(20(28)31-2)24-35(30,34-15-6-4-3-5-7-15)32-12-17-16(26)10-18(33-17)25-11-14(8-9-22)19(27)23-21(25)29/h3-9,11,13,16-18,26H,10,12H2,1-2H3,(H,24,30)(H,23,27,29)/b9-8+/t13-,16-,17+,18+,35?/m0/s1 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = CFBLUORPOFELCE-BACVZHSASA-N |
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'''Thymectacin''' (NB-1011, NB-101, N--2'-deoxyuridin-5'-O-yl](phenoxy)phosphoryl]-L-alanine methyl ester) is an anticancer ] of ] monophosphate. It developed by ] and it has entered in phase I clinical trials for colon cancer.<ref>{{cite journal | author= Wilson, R. H. | title = Novel Therapeutic Developments Other Than EGFR and VEGF Inhibition in Colorectal Cancer | journal = The Oncologist | volume = 11 | issue = 9 | pages = 1018–1024 | url = http://theoncologist.alphamedpress.org/cgi/content/full/11/9/1018 | doi= 10.1634/theoncologist.11-9-1018 | pmid= 17030644 | year= 2006 | last1= Wilson | first1= RH}}</ref> |
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'''Thymectacin''' ('''NB-1011''', '''NB-101''') is an experimental anticancer ] of ] monophosphate. It is being ] by ] and it entered in phase I clinical trials for colon cancer in 2006.<ref>{{cite journal | vauthors = Wilson RH | title = Novel therapeutic developments other than EGFR and VEGF inhibition in colorectal cancer | journal = The Oncologist | volume = 11 | issue = 9 | pages = 1018–24 | date = October 2006 | pmid = 17030644 | doi = 10.1634/theoncologist.11-9-1018 | url = http://theoncologist.alphamedpress.org/cgi/content/full/11/9/1018 | doi-access = free }}</ref> |
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Thymectacin is a small molecule phosphoramidate derivative of (''E'')-5-(2-bromovinyl)-2'-deoxyuridine (BVdU) with potential antineoplastic activity.<ref>{{cite web | url = https://www.cancer.gov/publications/dictionaries/cancer-drug/def/brivudine-phosphoramidate | title = Brivudine phosphoramidate | work = NCI Drug Dictionary | publisher = ] }}</ref> It is selectively active against tumor cells expressing high levels of ] (TS). Thymectacin is converted intracellularly by TS to bromovinyldeoxyuridine monophosphate (BVdUMP) which competes with the natural substrate, ], for binding to TS. Unlike TS inhibitors, this agent is a reversible substrate for TS catalysis. Thus, TS retains activity and converts BVdUMP into cytotoxic metabolites. |
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==References== |
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== References == |
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