L8P

({[(2S)-1-(4-amino-2-oxopyrimidin-1(2H)-yl)-3-hydroxypropan-2-yl]oxy}methyl)phosphonic acid



Chemical Component Summary

Name({[(2S)-1-(4-amino-2-oxopyrimidin-1(2H)-yl)-3-hydroxypropan-2-yl]oxy}methyl)phosphonic acid
SynonymsCidofovir
Identifiers[(2S)-1-(4-azanyl-2-oxo-pyrimidin-1-yl)-3-hydroxy-propan-2-yl]oxymethylphosphonic acid
FormulaC8 H14 N3 O6 P
Molecular Weight279.187
TypeNON-POLYMER
Isomeric SMILESC1=CN(C(=O)N=C1N)C[C@@H](CO)OCP(=O)(O)O
InChIInChI=1S/C8H14N3O6P/c9-7-1-2-11(8(13)10-7)3-6(4-12)17-5-18(14,15)16/h1-2,6,12H,3-5H2,(H2,9,10,13)(H2,14,15,16)/t6-/m0/s1
InChIKeyVWFCHDSQECPREK-LURJTMIESA-N

Chemical Details

Formal Charge0
Atom Count32
Chiral Atom Count1
Bond Count32
Aromatic Bond Count0

Drug Info: DrugBank

DrugBank IDDB00369 
NameCidofovir
Groups approved
DescriptionCidofovir is an injectable antiviral medication employed in the treatment of cytomegalovirus (CMV) retinitis in patients diagnosed with AIDS. It suppresses CMV replication through selective inhibition of viral DNA synthesis.[FDA label] It was manufactured by _Gilead_ and initially approved by the FDA in 1996, but has since been discontinued.[L6223]
Synonyms
  • [(S)-2-(4-Amino-2-oxo-2H-pyrimidin-1-yl)-1-hydroxymethyl-ethoxymethyl]-phosphonic acid
  • ({[(S)-1-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxypropan-2-yl]oxy}methyl)phosphonic acid
  • (S)-1-[3-Hydroxy-2-(phosphonomethoxy)propyl]cytosine
  • 1-(S)-[3-Hydroxy-2-(phosphonomethoxy)propyl]cytosine
  • Cidofovir anhydrous
Brand Names
  • Mar-cidofovir
  • Cidofovir Dihydrate
  • Cidofovir
  • Vistide
IndicationFor the treatment of CMV retinitis in patients with acquired immunodeficiency syndrome (AIDS)
Categories
  • Anti-Infective Agents
  • Antiinfectives for Systemic Use
  • Antiviral Agents
  • Antivirals for Systemic Use
  • Cytomegalovirus Nucleoside Analog DNA Polymerase Inhibitor
ATC-CodeJ05AB12
CAS number113852-37-2

Drug Targets

NameTarget SequencePharmacological ActionActions
DNA polymerase catalytic subunitMFFNPYLSGGVTGGAVAGGRRQRSQPGSAQGSGKRPPQKQFLQIVPRGVM...unknowninhibitor
Thymidine phosphorylaseMAALMTPGTGAPPAPGDFSGEGSQGLPDPSPEPKQLPELIRMKRDGGRLS...unknowninhibitor
Solute carrier family 22 member 6MAFNDLLQQVGGVGRFQQIQVTLVVLPLLLMASHNTLQNFTAAIPTHHCR...unknownsubstrate,inhibitor
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 60613
ChEMBL CHEMBL152
ChEBI CHEBI:3696