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Revision as of 01:36, 24 January 2023

Chemical compound Pharmaceutical compound
Thymectacin
Skeletal formula of thymectacin
Space-filling model of the thymectacin molecule
Clinical data
Other namesNB-1011; NB-101; N--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
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H25BrN3O9P
Molar mass574.321 g·mol
3D model (JSmol)
SMILES
  • C(C(=O)OC)NP(=O)(OC1(C(O1)n2cc(c(=O)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.

Thymectacin is a small molecule phosphoramidate derivative of (E)-5-(2-bromovinyl)-2'-deoxyuridine (BVdU) with potential antineoplastic activity. 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

  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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