Thymectacin: Difference between revisions – Wikipedia

Thymectacin
Other names	NB-1011; NB-101; N-[[5-[(E)-2-Bromovinyl]-2′-deoxyuridin-5′-O-yl]](phenoxy)phosphoryl]-L-alanine methyl ester
	(2S)-methyl 2-((((2R,3S,5R)-5-(5-((E)-2-bromovinyl)-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-hydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphorylamino)propanoate ;
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Formula	C21H25BrN3O9P
Molar mass	574.321 g·mol−1
3D model (JSmol)
	C[C@@H](C(=O)OC)NP(=O)(OC[C@@H]1[C@H](C[C@@H](O1)n2cc(c(=O)[nH]c2=O)/C=C/Br)O)Oc3ccccc3 ;
	InChI=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 ; Key:CFBLUORPOFELCE-BACVZHSASA-N ;
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Latest revision as of 17:07, 10 January 2026

Chemical compound

Pharmaceutical compound

Thymectacin (NB-1011, NB-101) is an experimental anticancer prodrug of brivudine monophosphate. It is being developed by New Biotics and it entered in phase I clinical trials for colon cancer in 2006.^[1]

Thymectacin is a small molecule phosphoramidate derivative of (E)-5-(2-bromovinyl)-2′-deoxyuridine (BVdU) with potential antineoplastic activity.^[2] It is selectively active against tumor cells expressing high levels of thymidylate synthase (TS). Thymectacin is converted intracellularly by TS to bromovinyldeoxyuridine monophosphate (BVdUMP) which competes with the natural substrate, deoxyuridine monophosphate, 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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[2]

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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
 | image = Thymectacin.svg
+| image_class = skin-invert-image
 | alt = Skeletal formula of thymectacin
 | width = 260
 | image2 = Thymectacin-3D-spacefill.png
+| image_class2 = bg-transparent
 | alt2 = Space-filling model of the thymectacin molecule
 | width2 = 240

Latest revision as of 17:07, 10 January 2026

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