Identification
- Summary
Cidofovir is an antiviral agent used to treat Cytomegalovirus (CMV) retinitis in patients with AIDS.
- Brand Names
- Vistide
- Generic Name
- Cidofovir
- DrugBank Accession Number
- DB00369
- Background
Cidofovir 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.Label It was manufactured by Gilead and initially approved by the FDA in 1996, but has since been discontinued.1
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Cidofovir (DB00369)
- Weight
- Average: 279.187
Monoisotopic: 279.062021707 - Chemical Formula
- C8H14N3O6P
- Synonyms
- ({[(S)-1-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxypropan-2-yl]oxy}methyl)phosphonic acid
- (S)-(3-(4-amino-2-Oxopyrimidin-1(2H)-yl)-1-hydroxypropan-2-yloxy)methylphosphonic acid
- (S)-1-(3-Hydroxy-2-phosphonomethoxypropyl)cytosine
- (S)-1-[3-Hydroxy-2-(phosphonomethoxy)propyl]cytosine
- (S)-1-[3-Hydroxy-2-(phosphonylmethoxy)propyl]cytosine
- (S)-HPMPC
- [(S)-2-(4-Amino-2-oxo-2H-pyrimidin-1-yl)-1-hydroxymethyl-ethoxymethyl]-phosphonic acid
- [[(S)-2-(4-amino-2-oxo-1(2H)-pyrimidinyl)-1-(hydroxymethyl)ethoxy]methyl]phosphonic acid
- 1-(S)-[3-Hydroxy-2-(phosphonomethoxy)propyl]cytosine
- 1-[(S)-3-Hydroxy-2-(phosphonomethoxy)propyl]cytosine
- CDV
- Cidofovir
- Cidofovir anhydrous
- Cidofovirum
- External IDs
- GS 0504
- GS 504
- HPMPC
Pharmacology
- Indication
For the treatment of CMV retinitis in patients with acquired immunodeficiency syndrome (AIDS)
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- Contraindications & Blackbox Warnings
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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.
- Mechanism of action
Cidofovir acts through the selective inhibition of viral DNA polymerase.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.
Target Actions Organism ADNA polymerase catalytic subunit inhibitorHHV-5 - Absorption
100%
- Volume of distribution
- 537 ± 126 mL/kg [VISTIDE ADMINISTERED WITHOUT PROBENECID]
- 410 ± 102 mL/kg [VISTIDE ADMINISTERED WITH PROBENECID]
- Protein binding
6%
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
2.4 to 3.2 hours
- Clearance
- 179 +/- 23.1 mL/min/1.73 m2 [WITHOUT PROBENECID]
- 148 +/- 38.8 mL/min/1.73 m2 [WITH PROBENECID]
- Adverse Effects
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Kidney damage, fall in the number of white blood cells, decreased platelets
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Cidofovir may decrease the excretion rate of Abacavir which could result in a higher serum level. Aceclofenac The risk or severity of nephrotoxicity can be increased when Cidofovir is combined with Aceclofenac. Acemetacin The risk or severity of nephrotoxicity can be increased when Cidofovir is combined with Acemetacin. Acetaminophen Cidofovir may decrease the excretion rate of Acetaminophen which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Cidofovir which could result in a lower serum level and potentially a reduction in efficacy. Acetylsalicylic acid The risk or severity of nephrotoxicity can be increased when Cidofovir is combined with Acetylsalicylic acid. Aclidinium Cidofovir may decrease the excretion rate of Aclidinium which could result in a higher serum level. Acrivastine Cidofovir may decrease the excretion rate of Acrivastine which could result in a higher serum level. Acyclovir The risk or severity of nephrotoxicity can be increased when Cidofovir is combined with Acyclovir. Adefovir dipivoxil The risk or severity of nephrotoxicity can be increased when Cidofovir is combined with Adefovir dipivoxil. 
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- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Cidofovir dihydrate JIL713Q00N 149394-66-1 FPKARFMSZDBYQF-ILKKLZGPSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Vistide Injection, solution, concentrate 75 mg/ml Intravenous Gilead Sciences 2016-09-08 2015-01-19 EU 
Vistide Injection 75 mg/1mL Intravenous Gilead Sciences 1996-06-26 Not applicable US 
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Cidofovir Injection, solution 75 mg/1mL Intravenous Mylan Institutional LLC 2013-06-03 Not applicable US Cidofovir Dihydrate Injection, solution 375 mg/5mL Intravenous Heritage Pharmaceuticals Inc. d/b/a Avet Pharmaceuticals Inc. 2012-08-06 Not applicable US Mar-cidofovir Solution 375 mg / 5 mL Intravenous Marcan Pharmaceuticals Inc 2018-07-11 Not applicable Canada 
Categories
- ATC Codes
- J05AB12 — Cidofovir
- Drug Categories
- Anti-Infective Agents
- Antiinfectives for Systemic Use
- Antiviral Agents
- Antivirals for Systemic Use
- Cytomegalovirus Nucleoside Analog DNA Polymerase Inhibitor
- Cytosine
- Direct Acting Antivirals
- Drugs that are Mainly Renally Excreted
- Enzyme Inhibitors
- Nephrotoxic agents
- Nucleic Acid Synthesis Inhibitors
- Nucleosides and Nucleotides
- Nucleosides and Nucleotides Excl. Reverse Transcriptase Inhibitors
- OAT1/SLC22A6 inhibitors
- OAT1/SLC22A6 Substrates
- Organophosphonates
- Organophosphorus Compounds
- Pyrimidines
- Pyrimidinones
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as pyrimidones. These are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Diazines
- Sub Class
- Pyrimidines and pyrimidine derivatives
- Direct Parent
- Pyrimidones
- Alternative Parents
- Aminopyrimidines and derivatives / Imidolactams / Hydropyrimidines / Organic phosphonic acids / Heteroaromatic compounds / Azacyclic compounds / Primary amines / Primary alcohols / Organopnictogen compounds / Organophosphorus compounds show 2 more
- Substituents
- Alcohol / Amine / Aminopyrimidine / Aromatic heteromonocyclic compound / Azacycle / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine / Imidolactam / Organic nitrogen compound show 11 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- pyrimidone, phosphonic acids (CHEBI:3696)
- Affected organisms
- Human Immunodeficiency Virus
Chemical Identifiers
- UNII
- 768M1V522C
- CAS number
- 113852-37-2
- InChI Key
- VWFCHDSQECPREK-LURJTMIESA-N
- InChI
- InChI=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
- IUPAC Name
- ({[(2S)-1-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxypropan-2-yl]oxy}methyl)phosphonic acid
- SMILES
- NC1=NC(=O)N(C[C@@H](CO)OCP(O)(O)=O)C=C1
References
- Synthesis Reference
- US5142051
- General References
- Cidofovir FDA approval [Link]
- External Links
- Human Metabolome Database
- HMDB0014513
- KEGG Compound
- C06909
- PubChem Compound
- 60613
- PubChem Substance
- 46506054
- ChemSpider
- 54636
- BindingDB
- 31915
- 1546007
- ChEBI
- 3696
- ChEMBL
- CHEMBL152
- ZINC
- ZINC000001530600
- Therapeutic Targets Database
- DAP001083
- PharmGKB
- PA448997
- PDBe Ligand
- L8P
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Cidofovir
- PDB Entries
- 2l8p / 5km8
- FDA label
- Download (828 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Cytomegalovirus Retinitis / Human Immunodeficiency Virus (HIV) Infections 1 4 Completed Treatment Recurrent Respiratory Papillomatosis 1 3 Completed Treatment CMV 1 3 Completed Treatment Cytomegalovirus (CMV) 1 3 Completed Treatment Cytomegalovirus Retinitis / Human Immunodeficiency Virus (HIV) Infections 1 3 Unknown Status Treatment High-grade Anal Intraepithelial Neoplasia 1 2 Active Not Recruiting Treatment Transplantation Infection 1 2 Completed Prevention Prevention of Hair Growth 1 2 Completed Treatment Acquired Immune Deficiency Syndrome (AIDS) / Cytomegalovirus Retinitis 1 2 Completed Treatment Anal Cancer / Precancerous Conditions 1
Pharmacoeconomics
- Manufacturers
- Gilead sciences inc
- Packagers
- Gilead Sciences Inc.
- Pfizer Inc.
- Physicians Total Care Inc.
- Dosage Forms
Form Route Strength Injection, solution Intravenous 75 mg/1mL Injection, solution Intravenous 375 mg/5mL Injection, solution, concentrate Intravenous 375 mg/5ml Solution Intravenous 375 mg / 5 mL Injection Intravenous 375 mg/5ml Injection Intravenous 75 mg/1mL Injection, solution, concentrate Intravenous 75 mg/ml - Prices
Unit description Cost Unit Vistide 75 mg/ml Solution 5ml Vial 923.52USD vial Vistide 75 mg/ml vial 205.71USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5142051 No 1992-08-25 2010-06-26 US CA1340856 No 1999-12-21 2016-12-21 Canada
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 480 °C Not Available water solubility =170 mg/mL at pH 6-8 Not Available logP -3.9 Not Available - Predicted Properties
Property Value Source Water Solubility 11.5 mg/mL ALOGPS logP -2.1 ALOGPS logP -2.4 Chemaxon logS -1.4 ALOGPS pKa (Strongest Acidic) 1.26 Chemaxon pKa (Strongest Basic) 4.71 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 145.68 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 60.43 m3·mol-1 Chemaxon Polarizability 24.44 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.9299 Blood Brain Barrier + 0.9061 Caco-2 permeable - 0.6933 P-glycoprotein substrate Non-substrate 0.5589 P-glycoprotein inhibitor I Non-inhibitor 0.8796 P-glycoprotein inhibitor II Non-inhibitor 0.9247 Renal organic cation transporter Non-inhibitor 0.9415 CYP450 2C9 substrate Non-substrate 0.791 CYP450 2D6 substrate Non-substrate 0.839 CYP450 3A4 substrate Non-substrate 0.6246 CYP450 1A2 substrate Non-inhibitor 0.8679 CYP450 2C9 inhibitor Non-inhibitor 0.8338 CYP450 2D6 inhibitor Non-inhibitor 0.8796 CYP450 2C19 inhibitor Non-inhibitor 0.8039 CYP450 3A4 inhibitor Non-inhibitor 0.941 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9492 Ames test Non AMES toxic 0.5853 Carcinogenicity Non-carcinogens 0.8317 Biodegradation Not ready biodegradable 0.9148 Rat acute toxicity 2.3450 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9371 hERG inhibition (predictor II) Non-inhibitor 0.6893
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- HHV-5
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Nucleotide binding
- Specific Function
- Replicates viral genomic DNA in the late phase of lytic infection, producing long concatemeric DNA. The replication complex is composed of six viral proteins: the DNA polymerase, processivity facto...
- Gene Name
- UL54
- Uniprot ID
- P08546
- Uniprot Name
- DNA polymerase catalytic subunit
- Molecular Weight
- 137100.705 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
- 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. 2008 Jan;77(1):77-80. Epub 2007 Sep 17. [Article]
- 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. [Article]
- Andrei G, De Clercq E, Snoeck R: Drug targets in cytomegalovirus infection. Infect Disord Drug Targets. 2009 Apr;9(2):201-22. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Transferase activity, transferring pentosyl groups
- Specific Function
- May have a role in maintaining the integrity of the blood vessels. Has growth promoting activity on endothelial cells, angiogenic activity in vivo and chemotactic activity on endothelial cells in v...
- Gene Name
- TYMP
- Uniprot ID
- P19971
- Uniprot Name
- Thymidine phosphorylase
- Molecular Weight
- 49954.965 Da
References
- De Clercq E: The next ten stories on antiviral drug discovery (part E): advents, advances, and adventures. Med Res Rev. 2011 Jan;31(1):118-60. doi: 10.1002/med.20179. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
- Gene Name
- SLC22A6
- Uniprot ID
- Q4U2R8
- Uniprot Name
- Solute carrier family 22 member 6
- Molecular Weight
- 61815.78 Da
References
- Cihlar T, Ho ES: Fluorescence-based assay for the interaction of small molecules with the human renal organic anion transporter 1. Anal Biochem. 2000 Jul 15;283(1):49-55. [Article]
- Cihlar T, Lin DC, Pritchard JB, Fuller MD, Mendel DB, Sweet DH: The antiviral nucleotide analogs cidofovir and adefovir are novel substrates for human and rat renal organic anion transporter 1. Mol Pharmacol. 1999 Sep;56(3):570-80. [Article]
- Ho ES, Lin DC, Mendel DB, Cihlar T: Cytotoxicity of antiviral nucleotides adefovir and cidofovir is induced by the expression of human renal organic anion transporter 1. J Am Soc Nephrol. 2000 Mar;11(3):383-93. [Article]
Drug created at June 13, 2005 13:24 / Updated at October 03, 2023 16:58