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Substance Name: Brincidofovir [USAN:INN]
RN: 444805-28-1
UNII: 6794O900AX
InChIKey: WXJFKKQWPMNTIM-VWLOTQADSA-N

Note

  • Has antiviral activity.

    NCI: An alkoxyalkyl ester prodrug containing the synthetic, acyclic nucleoside monophosphate analog cidofovir linked, through its phosphonate group, to a lipid, 3-hexadecyloxy-1-propanol, with antiviral activity against double-stranded DNA viruses. Upon oral administration, hexadecyloxypropyl-cidofovir crosses the intestinal wall and penetrates target viral-infected cells before being cleaved to the free antiviral agent cidofovir. In turn, cidofovir is phosphorylated by pyruvate kinases to its active metabolite cidofovir diphosphate. Cidofovir diphosphate, bearing structural similarity to nucleotides, competes with deoxycytosine-5-triphosphate (dCTP) for viral DNA polymerase and gets incorporated into the growing viral DNA strands. As a result, it prevents further DNA polymerization and disrupts DNA replication of viruses. Compared to cidofovir, which is given intravenously, hexadecyloxypropyl-cidofovir shows better oral bioavailability, less toxicity and enhanced cellular penetration. (NCI Thesaurus)

Molecular Formula

  • C27-H52-N3-O7-P

Molecular Weight

  • 561.6958
 

Classification Codes

  • Anti-Infective Agents
  • Antiviral Agents
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Names and Synonyms

Results Name

  • Brincidofovir [USAN:INN]

Name of Substance

  • Brincidofovir [USAN:INN]
  • Hexadecyloxypropyl cidofovir

Synonyms

  • BCV
  • Brincidofovir
  • Cidofovir-HDP
  • CMX 001
  • CMX-001
  • CMX001
  • HDP-CDV
  • HDP-Cidofovir
  • Hexadecyloxypropyl - cidofovir
  • Hexadecyloxypropyl-cidofovir
  • Phosphonic acid, p-(((1S)-2-(4-amino-2-oxo-1(2H)-pyrimidinyl)-1-(hydroxymethyl)ethoxy)methyl)-, mono(3-(hexadecyloxy)propyl) ester
  • UNII-6794O900AX

Registry Numbers

CAS Registry Number

  • 444805-28-1

FDA UNII

  • 6794O900AX

System Generated Number

  • 0444805281

Structure Descriptors

InChI

1S/C27H52N3O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-35-20-16-21-37-38(33,34)24-36-25(23-31)22-30-18-17-26(28)29-27(30)32/h17-18,25,31H,2-16,19-24H2,1H3,(H,33,34)(H2,28,29,32)/t25-/m0/s1

InChIKey

WXJFKKQWPMNTIM-VWLOTQADSA-N

Smiles

CCCCCCCCCCCCCCCCOCCCOP(=O)(CO[C@@H](Cn1ccc(nc1=O)N)CO)O