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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-02-19 16:04:42
Primary Accession Number DB00369
Secondary Accession Number
  • APRD00148
Name Cidofovir
Drug Type
  • Approved
  • Small Molecule
Description Cidofovir is an injectable antiviral medication for the treatment of cytomegalovirus (CMV) retinitis in patients with AIDS. It suppresses CMV replication by selective inhibition of viral DNA synthesis. [Wikipedia]
Synonyms
  1. CDV
  2. Cidofovir Anhydrous
Brand Names
  1. HPMPC
  2. Vistide
Brand Mixtures Not Available
Chemical IUPAC Name [(2S)-1-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxypropan-2-yl]oxymethylphosphonic acid
Chemical Formula C8H14N3O6P
Chemical Structure Structure
CAS Registry Number 113852-37-2
InChI Identifier InChI=1/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/f/h14-15H,9H2
InChI Key VWFCHDSQECPREK-JECIRTJFDT
KEGG Drug Not Available
KEGG Compound C06909 Link Image
PubChem Compound 60613 Link Image
PubChem Substance 196891 Link Image
ChEBI ID Not Available
PharmGKB ID Not Available
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] Not Available
RxList Link http://www.rxlist.com/cgi/generic2/cidofovir.htm Link Image
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Cidofovir Link Image
FDA Label
Material Safety Data Sheet (MSDS) Not Available
Synthesis Reference Not Available
Average Molecular Weight 279.1870
Monoisotopic Molecular Weight 279.0620
State Solid
Melting Point 480 oC
Experimental Water Solubility =170 mg/mL at pH 6-8 Source: PhysProp
Predicted Water Solubility 1.15e+01 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity -3.9 Source: PhysProp
Predicted LogP -2.11 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -1.38 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES NC1=NC(=O)N(C[C@@H](CO)OCP(O)(O)=O)C=C1
Canonical SMILES NC1=NC(=O)N(CC(CO)OCP(O)(O)=O)C=C1
Drug Category
  • Anti-HIV Agents
  • Antineoplastic Agents
  • Antiviral Agents
  • Radiation-Sensitizing Agents
ATC Codes
AHFS Codes Not Available
Indication For the treatment of CMV retinitis in patients with acquired immunodeficiency syndrome (AIDS)
Pharmacology Cidofovir is a new anti-viral drug. It is classified as a nucleotide analogue and is active against herpes cytomegalovirus (CMV) retinitis infection. Most adults are infected with CMV. Cidofovir suppresses cytomegalovirus (CMV) replication by selective inhibition of viral DNA synthesis. Biochemical data support selective inhibition of CMV DNA polymerase by cidofovir diphosphate, the active intracellular metabolite of cidofovir. Cidofovir diphosphate inhibits herpesvirus polymerases at concentrations that are 8- to 600-fold lower than those needed to inhibit human cellular DNA polymerase alpha, beta, and gamma(1,2,3). Incorporation of cidofovir into the growing viral DNA chain results in reductions in the rate of viral DNA synthesis.
Mechanism of Action Cidofovir acts through the selective inhibition of viral DNA polymerase.
Absorption 100%
Toxicity Kidney damage, fall in the number of white blood cells, decreased platelets
Protein Binding 6%
Biotransformation Not Available
Half Life 2.4 to 3.2 hours
Dosage Forms
Form Route
Solution Intravenous
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References
  1. Drugs.com Link Image
  2. Wikipedia Link Image
  3. RxList Link Image
Organisms Affected
  • Human Immunodeficiency Virus
Targets
  1. DNA polymerase
Drug Target 1 [top]
Target 1 ID 379
Target 1 Name DNA polymerase
Target 1 Synonyms
  1. EC 2.7.7.7
Target 1 Gene Name UL54
Target 1 Protein Sequence >DNA polymerase 
MFFNPYLSGGVTGGAVAGGRRQRSQPGSAQGSGKRPPQKQFLQIVPRGVMFDGQTGLIKH
KTGRLPLMFYREIKHLLSHDMVWPCPWRETLVGRVVGPIRFHTYDQTDAVLFFDSPENVS
PRYRQHLVPSGNVLRFFGATEHGYSICVNVFGQRSYFYCEYSDTDRLREVIASVGELVPE
PRTPYAVSVTPATKTSIYGYGTRPVPDLQCVSISNWTMARKIGEYLLEQGFPVYEVRVDP
LTRLVIDRRITTFGWCSVNRYDWRQQGRASTCDIEVDCDVSDLVAVPDDSSWPRYRCLSF
DIECMSGEGGFPCAEKSDDIVIQISCVCYETGGNTAVDQGIPNGNDGRGCTSEGVIFGHS
GLHLFTIGTCGQVGPDVDVYEFPSEYELLLGFMLFFQRYAPAFVTGYNINSFDLKYILTR
LEYLYKVDSQRFCKLPTAQGGRFFLHSPAVGFKRQYAAAFPSASHNNPASTAATKVYIAG
SVVIDMYPVCMAKTNSPNYKLNTMAELYLRQRKDDLSYKDIPRCFVANAEGRAQVGRYCL
QDAVLVRDLFNTINFHYEAGAIARLAKIPLRRVIFDGQQIRIYTSLLDECACRDFILPNH
YSKGTTVPETNSVAVSPNAAIISTAAVPGDAGSVAAMFQMSPPLQSAPSSQDGVSPGSGS
NSSSSVGVFSVGSGSSGGVGVSNDNHGAGGTAAVSYQGATVFEPEVGYYNDPVAVFDFAS
LYPSIIMAHNLCYSTLLVPGGEYPVDPADVYSVTLENGVTHRFVRASVRVSVLSELLNKW
VSQRRAVRECMRECQDPVRRMLLDKEQMALKVTCNAFYGFTGVVNGMMPCLPIAASITRI
GRDMLERTARFIKDNFSEPCFLHNFFNQEDYVVGTREGDSEESSALPEGLETSSGGSNER
RVEARVIYGDTDSVFVRFRGLTPQALVARGPSLAHYVTACLFVEPVKLEFEKVFVSLMMI
CKKRYIGKVEGASGLSMKGVDLVRKTACEFVKGVTRDVLSLLFEDREVSEAAVRLSRLSL
DEVKKYGVPRGFWRILRRLVQARDDLYLHRVRVEDLVLSSVLSKDISLYRQSNLPHIAVI
KRLAARSEELPSVGDRVFYVLTAPGVRTAPQGSSDNGDSVTAGVVSRSDAIDGTDDDADG
GGVEESNRRGGEPAKKRARKPPSAVCNYEVAEDPSYVREHGVPIHADKYFEQVLKAVTNV
LSPVFPGGETARKDKFLHMVLPRRLHLEPAFLPYSVKAHECC
Target 1 Number of Residues 1262
Target 1 Molecular Weight 137103
Target 1 Theoretical pI 7.33
Target 1 GO Classification
Function
hydrolase activity
hydrolase activity, acting on ester bonds
nuclease activity
exonuclease activity
3'-5' exonuclease activity
catalytic activity
transferase activity
transferase activity, transferring phosphorus-containing groups
nucleotidyltransferase activity
DNA-directed DNA polymerase activity
nucleic acid binding
DNA binding
binding
nucleotide binding
Process
physiological process
metabolism
cellular metabolism
nucleobase, nucleoside, nucleotide and nucleic acid metabolism
DNA metabolism
DNA replication
Component
Not Available
Target 1 General Function Replication, recombination and repair
Target 1 Specific Function Not Available
Target 1 Pathways
Name SMPDB Link KEGG Link
DNA polymerase map03030 Link Image
Purine metabolism SMP00050 Link Image map00230 Link Image
Pyrimidine metabolism SMP00046 Link Image map00240 Link Image
Target 1 Reactions
  • deoxynucleoside triphosphate + DNAn = diphosphate + DNAn+1
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • None
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 1780831 Link Image
Target 1 UniProtKB/Swiss-Prot ID P08546 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name DPOL_HCMVA Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Nucleus
Target 1 Gene Sequence >3729 bp 
TCAACAGCATTCGTGCGCCTTGACACTGTACGGCAGAAAAGCCGGCTCCAAGTGCAAGCG
CCGCGGCAGCACCATGTGCAAAAACTTGTCCTTGCGCGCGGTTTCGCCGCCGGGAAAGAC
GGGCGACAGCACGTTAGTTACAGCCTTGAGAACCTGCTCAAAGTACTTGTCGGCGTGAAT
GGGCACGCCGTGCTCGCGCACGTAGCTCGGATCTTCGGCTACCTCGTAGTTGCACACGGC
CGACGGTGGTTTCCGCGCCCTCTTCTTTGCCGGCTCTCCTCCTCTCCTGTTGCTCTCCTC
TACCCCGCCGCCGTCAGCGTCGTCGTCCGTGCCATCAATCGCGTCCGACCGGGAAACCAC
GCCGGCGGTTACAGAATCACCGTTGTCGGAGGAACCCTGCGGCGCCGTCCGGACACCGGG
CGCCGTCAGAACGTAAAAGACCCGATCCCCGACCGAGGGTAGCTCCTCAGAACGGGCCGC
CAATCGCTTAATGACGGCAATGTGCGGCAGGTTAGATTGACGGTACAGCGAGATGTCCTT
AGAGAGCACCGACGAAAGCACCAGGTCCTCGACACGCACACGGTGCAGGTACAGATCGTC
GCGGGCCTGCACCAAGCGGCGTAAGATACGCCAGAAACCGCGTGGCACGCCGTACTTCTT
GACTTCATCGAGTGAGAGGCGCGACAGGCGCACGGCTGCTTCCGAGACCTCGCGATCCTC
AAAGAGCAGCGAGAGGACGTCACGCGTGACGCCCTTGACGAACTCGCAGGCCGTCTTGCG
CACCAGATCCACGCCCTTCATGCTCAGACCCGAGGCGCCCTCCACTTTGCCGATGTAACG
TTTCTTGCAGATCATCATAAGAGAGACGAAGACCTTTTCAAACTCCAGCTTGACGGGCTC
CACAAAAAGACAGGCCGTCACGTAGTGCGCCAGGCTGGGCCCACGCGCCACCAGAGCCTG
CGGCGTCAGGCCACGAAAGCGGACAAACACGCTGTCCGTGTCCCCGTAGATGACCCGCGC
CTCCACCCGCCGTTCGTTCGAGCCCCCTGACGATGTTTCGAGCCCCTCCGGTAACGCGCT
GCTCTCCTCCGAATCCCCCTCCCGCGTTCCCACTACATAGTCTTCCTGATTAAAAAAATT
GTGCAAAAAACACGGCTCTGAAAAGTTGTCTTTGATGAACCGCGCCGTGCGCTCTAGCAT
GTCGCGACCGATGCGCGTGATGCTGGCGGCGATGGGCAGACACGGCATCATACCGTTGAC
CACGCCGGTAAAACCGTAGAAAGCGTTGCACGTTACTTTGAGCGCCATCTGTTCCTTGTC
GAGCAGCATACGGCGCACAGGGTCTTGACACTCGCGCATGCATTCGCGCACGGCACGCCG
CTGCGAAACCCACTTGTTGAGCAGTTCCGAGAGCACCGAGACGCGCACCGAAGCACGCAC
AAAGCGGTGGGTCACGCCGTTCTCTAGCGTGACGCTGTATACGTCGGCGGGGTCCACAGG
GTACTCGCCACCCGGCACCAGCAGGGTGGAGTAGCAGAGGTTGTGGGCCATGATGATGGA
AGGGTAGAGGCTGGCAAAGTCGAACACGGCCACGGGGTCGTTGTAGTAACCCACCTCGGG
CTCAAACACCGTGGCGCCCTGGTACGAAACCGCCGCAGTACCGCCGGCGCCGTGATTGTC
GTTGGAAACGCCGACGCCGCCACTACTGCCGGAGCCGACGCTGAAAACGCCGACGCTGCT
ACTACTGTTACTGCCGGAGCCGGGTGAAACGCCGTCCTGACTGGACGGCGCAGATTGCAA
GGGCGGCGACATCTGAAACATAGCCGCCACAGAACCCGCGTCGCCGGGCACAGCGGCGGT
AGAGATGATAGCAGCGTTAGGTGACACAGCAACGCTATTCGTTTCGGGCACCGTCGTACC
TTTGCTGTAGTGGTTGGGCAGGATAAAATCGCGGCAGGCGCACTCGTCCAGCAGCGAGGT
GTAGATACGGATCTGCTGTCCGTCAAAGATGACACGCCGCAACGGAATTTTAGCCAGCCG
CGCGATGGCCCCGGCCTCGTAGTGAAAATTAATGGTGTTGAACAGATCGCGCACCAATAC
GGCGTCCTGCAGACAGTAACGGCCTACCTGGGCGCGGCCCTCGGCATTAGCCACGAAACA
ACGCGGGATGTCCTTGTAAGACAGGTCATCCTTGCGTTGCCGCAGGTAAAGCTCGGCCAT
AGTGTTGAGCTTATAGTTGGGCGAGTTAGTCTTGGCCATGCATACAGGGTACATGTCGAT
AACCACCGAACCCGCAATATACACCTTGGTGGCGGCCGTGCTGGCCGGATTGTTGTGAGA
AGCCGAGGGAAAAGCGGCGGCGTACTGCCGCTTAAAACCCACGGCGGGGCTGTGTAAAAA
GAAACGGCCGCCCTGCGCCGTAGGCAACTTGCAGAAGCGCTGCGAGTCCACCTTATACAG
GTACTCGAGACGCGTGAGGATGTACTTCAAGTCAAAAGAGTTGATGTTGTAACCGGTCAC
AAAGGCCGGCGCGTACCGTTGAAAGAAAAGCATAAAGCCCAGCAGCAGCTCGTATTCGGA
AGGGAACTCGTAGACGTCCACGTCTGGGCCCACCTGCCCGCAGGTGCCGATCGTAAAGAG
ATGAAGACCCGAGTGCCCAAAGATCACACCCTCCGAAGTGCAGCCCCGACCATCGTTCCC
GTTTGGGATCCCCTGATCCACGGCGGTGTTTCCCCCCGTCTCGTAGCACACGCACGAGAT
CTGAATGACAATGTCATCGGACTTCTCGGCGCAGGGAAAACCACCCTCGCCGCTCATGCA
CTCGATATCGAAGGACAGGCATCGATAGCGCGGCCACGAGCTGTCGTCGGGCACAGCCAC
CAGGTCAGAGACATCGCAGTCTACCTCGATATCACAAGTCGACGCGCGACCCTGCTGCCG
CCAGTCGTAACGATTCACGGAGCACCAGCCGAACGTGGTGATCCGCCGATCGATGACCAA
ACGCGTCAGCGGATCCACACGGACCTCGTACACGGGAAAACCCTGCTCCAGCAGATACTC
GCCGATTTTTCTGGCCATGGTCCAGTTGCTGATAGACACACACTGCAAATCGGGCACGGG
TCGCGTCCCGTACCCATAGATGGAGGTCTTGGTGGCCGGCGTGACAGACACGGCGTATGG
CGTCCGCGGTTCGGGCACTAGTTCGCCCACGCTGGCAATGACCTCACGCAGCCTATCGGT
GTCGCTGTACTCACAGTAAAAGTAGCTGCGCTGCCCGAAAACGTTGACGCAGATACTGTA
GCCGTGTTCTGTGGCCCCGAAGAAACGCAACACGTTCCCCGAAGGCACCAGATGCTGACG
ATAGCGCGGCGACACGTTTTCGGGCGAGTCGAAGAAGAGCACGGCGTCCGTCTGATCGTA
GGTGTGAAAACGAATAGGTCCCACCACGCGACCCACCAGGGTCTCGCGCCAAGGACACGG
CCAAACCATGTCATGACTCAACAAATGTTTAATCTCTCGATAGAACATGAGAGGCAGCCG
TCCCGTCTTATGCTTGATCAACCCCGTCTGACCGTCGAACATGACACCTCGCGGCACGAT
CTGCAAAAACTGTTTCTGTGGCGGCCGCTTGCCCGAGCCCTGCGCGGAGCCGGGCTGCGA
ACGCTGACGCCGGCCACCCGCGACCGCACCGCCGGTCACGCCGCCGCTCAGATACGGGTT
GAAAAACAT
Target 1 GenBank Gene ID
Target 1 GeneCard ID Not Available
Target 1 GenAtlas ID Not Available
Target 1 HGNC ID Not Available
Target 1 Chromosome Location Not Available
Target 1 Locus Not Available
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Davison AJ, Dolan A, Akter P, Addison C, Dargan DJ, Alcendor DJ, McGeoch DJ, Hayward GS: The human cytomegalovirus genome revisited: comparison with the chimpanzee cytomegalovirus genome. J Gen Virol. 2003 Jan;84(Pt 1):17-28. [PubMed Link Image]
  2. Chee MS, Bankier AT, Beck S, Bohni R, Brown CM, Cerny R, Horsnell T, Hutchison CA 3rd, Kouzarides T, Martignetti JA, et al.: Analysis of the protein-coding content of the sequence of human cytomegalovirus strain AD169. Curr Top Microbiol Immunol. 1990;154:125-69. [PubMed Link Image]
  3. Kouzarides T, Bankier AT, Satchwell SC, Weston K, Tomlinson P, Barrell BG: Sequence and transcription analysis of the human cytomegalovirus DNA polymerase gene. J Virol. 1987 Jan;61(1):125-33. [PubMed Link Image]
  4. Kouzarides T, Bankier AT, Satchwell SC, Weston K, Tomlinson P, Barrell BG: Large-scale rearrangement of homologous regions in the genomes of HCMV and EBV. Virology. 1987 Apr;157(2):397-413. [PubMed Link Image]
Target 1 Drug References
  1. Magee WC, Hostetler KY, Evans DH: Mechanism of inhibition of vaccinia virus DNA polymerase by cidofovir diphosphate. Antimicrob Agents Chemother. 2005 Aug;49(8):3153-62. [PubMed Link Image]
  2. Gilbert C, Boivin G: New reporter cell line to evaluate the sequential emergence of multiple human cytomegalovirus mutations during in vitro drug exposure. Antimicrob Agents Chemother. 2005 Dec;49(12):4860-6. [PubMed Link Image]
  3. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed Link Image]
  4. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]
  5. Sergerie Y, Boivin G: Hydroxyurea enhances the activity of acyclovir and cidofovir against herpes simplex virus type 1 resistant strains harboring mutations in the thymidine kinase and/or the DNA polymerase genes. Antiviral Res. 2007 Sep 17;. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.