Thymectacin

Thymectacin
Clinical data
Other names	NB-1011; NB-101; N-[[5-[(E)-2-Bromovinyl]-2'-deoxyuridin-5'-O-yl]](phenoxy)phosphoryl]-L-alanine methyl ester
Identifiers
	IUPAC name (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	232925-18-7 ;
PubChem CID	6440764;
ChemSpider	4945015 ;
UNII	2ZRZ4TSW3F;
CompTox Dashboard (EPA)	DTXSID00177862 ;
Chemical and physical data
Formula	C21H25BrN3O9P
Molar mass	574.321 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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 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 ;
	(what is this?) (verify)

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.

References

^ Wilson RH (October 2006). "Novel therapeutic developments other than EGFR and VEGF inhibition in colorectal cancer". The Oncologist. 11 (9): 1018–24. doi:10.1634/theoncologist.11-9-1018. PMID 17030644.
^ "Brivudine phosphoramidate". NCI Drug Dictionary. National Institutes of Health.

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[1] Wilson RH (October 2006). "Novel therapeutic developments other than EGFR and VEGF inhibition in colorectal cancer". The Oncologist. 11 (9): 1018–24. doi:10.1634/theoncologist.11-9-1018. PMID 17030644.

[2] "Brivudine phosphoramidate". NCI Drug Dictionary. National Institutes of Health.

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