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Substance Name: Brincidofovir sodium
RN: 496765-79-8
UNII: 8UN8SA9Z5C
InChIKey: CRDDLOITBKEPRN-UQIIZPHYSA-M

Note

  • 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.Na

Molecular Weight

  • 583.6779
 

Classification Codes

  • Anti-Infective Agents
  • Antiviral Agents
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Names and Synonyms

Results Name

  • Brincidofovir sodium

Name of Substance

  • Hexadecyloxypropyl-cidofovir sodium

Synonyms

  • Brincidofovir sodium
  • Phosphonic acid, p-(((1S)-2-(4-amino-2-oxo-1(2H)-pyrimidinyl)-1-(hydroxymethyl)ethoxy]methyl]-, mono(3-(hexadecyloxy)propyl)ester, sodium salt (1:1)
  • Sodium 3-(hexadecyloxy)propyl (((1S)-2-(4-amino-2-oxopyrimidin-1(2H)-yl)-1-(hydroxymethyl)ethoxy)methyl)phosphonate
  • UNII-8UN8SA9Z5C

Registry Numbers

CAS Registry Number

  • 496765-79-8

FDA UNII

  • 8UN8SA9Z5C

System Generated Number

  • 0496765798

Structure Descriptors

InChI

1S/C27H52N3O7P.Na/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);/q;+1/p-1/t25-;/m0./s1

InChIKey

CRDDLOITBKEPRN-UQIIZPHYSA-M

Smiles

CCCCCCCCCCCCCCCCOCCCOP(=O)(CO[C@@H](Cn1ccc(nc1=O)N)CO)[O-].[Na+]