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Substance Name: Thymectacin
RN: 232925-18-7
UNII: 2ZRZ4TSW3F
InChIKey: CFBLUORPOFELCE-BACVZHSASA-N

Note

  • An anti-cancer agent.

    NCI: A small molecule phosphoramidate derivative of (E)-5-(2-bromovinyl)-2'-deoxyuridine with potential antineoplastic activity. Selectively active against tumor cells expressing high levels of thymidylate synthase (TS), brivudine phosphoramidate 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. As key enzyme in the de novo synthesis of dTMP, TS is an enzyme critical to DNA biosynthesis and is overexpressed in many solid tumors. (NCI Thesaurus)

Molecular Formula

  • C21-H25-Br-N3-O9-P

Molecular Weight

  • 574.3185
 

Classification Codes

  • Antineoplastic
  • Pronucleotides
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Names and Synonyms

Name of Substance

  • Thymectacin

Synonyms

  • (E)-5-(2-Bromovinyl)-2'-deoxy-5'-uridyl phenyl L-methoxyalaninylphosphoramidate
  • Brivudine phosphoramidate
  • BVDU prodrug
  • E-5-(2-bromovinyl)-2'-deoxyuridine-5'-(L-methylalaninyl)-phenylphosphoramidate
  • NB 1011
  • NB1011
  • UNII-2ZRZ4TSW3F

Systematic Names

  • 5-(2-Bromovinyl)-2'-deoxy-5'-uridyl-phenyl-alanylphosphoramidate, trans-
  • L-Alanine, N-(5-((1E)-2-bromoethenyl)-2'-deoxy-P-phenyl-5'-uridylyl)-, methyl ester

Registry Numbers

CAS Registry Number

  • 232925-18-7

FDA UNII

  • 2ZRZ4TSW3F

System Generated Number

  • 0232925187

Structure Descriptors

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

InChIKey

CFBLUORPOFELCE-BACVZHSASA-N

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