Cidofovir (CED0003626)

Record Information

Version

1.0

Creation Date

2016-05-22 04:41:25 UTC

Update Date

2026-08-24 15:07:10 UTC

SynCED ID

CED0003626

Secondary Accession Numbers

CHEM017847

Identification

Common Name

Cidofovir

Class

Small Molecule

Description

Cidofovir is an organic compound with the formula C8H14N3O6P and an average molecular weight of 279.19 g/mol. Cidofovir belongs to the pyrimidines and pyrimidine derivatives, a subclass of diazines within the organic compounds. It is classified as an organoheterocyclic compound. The substance is found in or released from healthcare, pharmaceuticals, and veterinary products as an antiviral. The recorded exposure route for this compound is intravenous. Regarding its biological activity, Cidofovir has two recorded protein targets: the DNA polymerase catalytic subunit and the DNA polymerase catalytic subunit (UL54), for which it acts as an inhibitor or modulator.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(S)-(3-(4-Amino-2-oxopyrimidin-1(2H)-yl)-1-hydroxypropan-2-yloxy)methylphosphonic acid	ChEBI
(S)-1-(3-Hydroxy-2-phosphonomethoxypropyl)cytosine	ChEBI
(S)-1-[3-Hydroxy-2-(phosphonomethoxy)propyl]cytosine	ChEBI
(S)-1-[3-Hydroxy-2-(phosphonylmethoxy)propyl]cytosine	ChEBI
(S)-HPMPC	ChEBI
1-(S)-[3-Hydroxy-2-(phosphonomethoxy)propyl]cytosine	ChEBI
1-[(S)-3-Hydroxy-2-(phosphonomethoxy)propyl]cytosine	ChEBI
[(S)-2-(4-Amino-2-oxo-2H-pyrimidin-1-yl)-1-hydroxymethyl-ethoxymethyl]-phosphonic acid	ChEBI
CDV	ChEBI
(S)-(3-(4-Amino-2-oxopyrimidin-1(2H)-yl)-1-hydroxypropan-2-yloxy)methylphosphonate	Generator
[(S)-2-(4-Amino-2-oxo-2H-pyrimidin-1-yl)-1-hydroxymethyl-ethoxymethyl]-phosphonate	Generator
Cidofovir anhydrous	HMDB
HPMPC	HMDB
Cidofovir, (R)-isomer	HMDB
Cidofovir, sodium salt	HMDB
1-((3-Hydroxy-2-phosphonylmethoxy)propyl)cytosine	HMDB
Cidofovir sodium	HMDB
Vistide	HMDB
1-(3-Hydroxy-2-phosphonylmethoxypropyl)cytosine	HMDB
Cidofovir, (+-)-isomer	HMDB
Cidofovir	ChEBI

Chemical Formula

C₈H₁₄N₃O₆P

Average Molecular Mass

279.187 g/mol

Monoisotopic Mass

279.062 g/mol

CAS Registry Number

113852-37-2

IUPAC Name

({[(2S)-1-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxypropan-2-yl]oxy}methyl)phosphonic acid

Traditional Name

cidofovir

SMILES

NC1=NC(=O)N(C[C@@H](CO)OCP(O)(O)=O)C=C1

InChI Identifier

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

InChI Key

VWFCHDSQECPREK-LURJTMIESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidones. Pyrimidones 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

Substituents

Aminopyrimidine
Pyrimidone
Hydropyrimidine
Imidolactam
Organophosphonic acid
Organophosphonic acid derivative
Heteroaromatic compound
Azacycle
Organic oxide
Organopnictogen compound
Primary amine
Primary alcohol
Organophosphorus compound
Organooxygen compound
Organonitrogen compound
Amine
Alcohol
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrimidone (CHEBI:3696 )
phosphonic acids (CHEBI:3696 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	11.5 g/L	ALOGPS
logP	-2.1	ALOGPS
logP	-3.4	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	1.19	ChemAxon
pKa (Strongest Basic)	2.15	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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-003r-9820000000-aa7cf1e5b61efad3d0f9	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-008c-7944000000-f609f0eec561142266d6	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0290000000-038de61e1070c6bf959e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-9530000000-e84e35d965622e5b208a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0j4i-9700000000-0a34ce1648d60bc6bc11	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-2290000000-7c97d41d12fa58e21a13	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-02ci-9480000000-c2815452e80e1a83b618	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01ox-9200000000-6321e41040f16d71637a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0290000000-7d98ba2e3a98c2228dae	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0159-0910000000-6524ca93000937bb1113	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-02u0-9300000000-843eaedb395204ad0128	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0090000000-da9719fb0cbd12dc3e52	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03fr-5950000000-b7fb54b7fe21f1e0e346	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9100000000-cca88b97e143183784da	Not Available	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
3327.0 Log mg/kg [1900:5900]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Health Effects

Health Effect	Relationship	Direction	Description	Reference

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000070	Stormwater runoff?Stormwater runoff refers to the flow of rainwater or melted snow that does not soak into the ground and instead collects pollutants as it travels over impervious surfaces such as roads and parking lots.	Automotive & urban infrastructure	PubChem
CEDs000233	Brushes?Brushes used in personal care and cosmetics can be a source of synthetic chemical contamination due to the materials and coatings used in their manufacturing.	Personal care & cosmetics	PubChem
CEDs000351	Antivirals?Antivirals are synthetic chemicals designed to inhibit the replication of viruses and are widely used in the treatment of viral infections in humans and animals.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000524	Hybrid Capacitors?Hybrid capacitors are energy storage devices that combine the properties of electrolytic and supercapacitors, utilizing a combination of electrochemical principles to achieve higher energy density and power density.	Electrical & Electronic Equipment	PubChem
CEDs000545	Food Preservation?Food preservation often involves the use of synthetic chemicals, such as preservatives, flavor enhancers, and color additives, to extend shelf life and enhance the sensory qualities of food products.	Food, food processing & cookware	PubChem
CEDs000569	Tobacco Smoke Filters?Tobacco smoke filters are designed to reduce the inhalation of harmful substances in cigarette smoke, including tar and other particulate matter.	Household cleaning & consumer products	PubChem
CEDs000580	Manufacture Preparation Of Tobacco Products?The manufacture and preparation of tobacco products involve various processes that can result in the introduction of synthetic chemicals into the environment.	Industrial manufacturing & chemical processing	PubChem
CEDs000605	Pest Repellants?Pest repellents, often formulated from synthetic chemicals, are widely used to protect crops from insect infestations and other pests.	Agriculture & land management	PubChem
CEDs000606	Plant Growth Regulators?Plant Growth Regulators (PGRs) are synthetic chemicals designed to influence the growth and development of plants.	Agriculture & land management	PubChem
CEDs000610	Aftersun Products?Aftersun products are designed to soothe and hydrate the skin after sun exposure, often containing various synthetic chemicals such as emollients, preservatives, and fragrances.	Personal care & cosmetics	PubChem
CEDs000611	Anti Perspirants Or Body Deoderants?Antiperspirants and body deodorants commonly contain synthetic chemicals such as aluminum compounds, parabens, and synthetic fragrances.	Personal care & cosmetics	PubChem
CEDs000615	Eye Makeup Products?Eye makeup products, including mascaras, eyeliners, and eyeshadows, often contain a variety of synthetic chemicals such as pigments, preservatives, and film-forming agents.	Personal care & cosmetics	PubChem
CEDs000618	Lip Makeup Products?Lip makeup products, such as lipsticks, lip glosses, and lip liners, often contain a variety of synthetic chemicals, including pigments, preservatives, and emollients.	Personal care & cosmetics	PubChem
CEDs000632	Apparel?Apparel production often involves the use of various synthetic chemicals, including dyes, finishing agents, and preservatives.	Textiles, leather & furnishings	PubChem
CEDs000671	Airplanes And Helicopters?Airplanes and helicopters are significant sources of synthetic chemical contamination primarily through the use of aviation fuels, lubricants, and de-icing agents.	Aviation & Aerospace	PubChem
CEDs000673	Unmanned Aerial Vehicles?Unmanned Aerial Vehicles (UAVs), commonly known as drones, utilize various synthetic chemicals in their manufacturing, operation, and maintenance processes.	Aviation & Aerospace	PubChem
CEDs000685	Ceramics?Ceramics can be a source of synthetic chemical contamination through various additives and processing agents used in their production.	Building & Construction	PubChem
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	PubChem
CEDs000744	Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.	Wastewater, sanitation & biosolids	PubChem

Pathways

3 pathwaysPathway Source: PathBank

Cidofovir Action Pathway

Brincidofovir Action Pathway

Cidofovir Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Reverse transcriptase/RNaseH	Q72547	Human immunodeficiency virus 1	Predicted (SEA)	Prediction Confidence Score 0.322 Applicability Domain 0.344 Statistical Significance 0.0031 Supporting Reference Compounds 79 E-value 24.0554
Click to view 3D structure	Tyrosine--tRNA ligase	P0AGJ9	Escherichia coli (strain K12)	Predicted (SEA)	Prediction Confidence Score 0.244 Applicability Domain 0.244 Low confidence Statistical Significance 0.0027 Supporting Reference Compounds 1 E-value 20.7079
Click to view 3D structure	Xanthine-guanine phosphoribosyltransferase	P0A9M5	Escherichia coli (strain K12)	Predicted (SEA)	Prediction Confidence Score 0.231 Applicability Domain 0.274 Low confidence Statistical Significance 8.80e-04 Supporting Reference Compounds 2 E-value 6.85073
Click to view 3D structure	Glutamate receptor 1	P19490	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.229 Applicability Domain 0.291 Low confidence Statistical Significance 0.0196 Supporting Reference Compounds 37 E-value 152.974
Click to view 3D structure	Glutamate receptor 2	P19491	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.226 Applicability Domain 0.291 Low confidence Statistical Significance 0.0026 Supporting Reference Compounds 34 E-value 20.1629
Click to view 3D structure	Hypoxanthine-guanine phosphoribosyltransferase	P9WHQ9	Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)	Predicted (SEA)	Prediction Confidence Score 0.223 Applicability Domain 0.268 Low confidence Statistical Significance 0.0013 Supporting Reference Compounds 3 E-value 10.1204
Click to view 3D structure	DNA polymerase subunit gamma-1	P54098	Humans	Predicted (SEA)	Prediction Confidence Score 0.222 Applicability Domain 0.319 Statistical Significance 0.0013 Supporting Reference Compounds 8 E-value 10.5096
Click to view 3D structure	Purine nucleoside phosphorylase	P00491	Humans	Predicted (SEA)	Prediction Confidence Score 0.222 Applicability Domain 0.232 Low confidence Statistical Significance 0.0024 Supporting Reference Compounds 19 E-value 18.5281
Click to view 3D structure	Hypoxanthine-guanine phosphoribosyltransferase	P00492	Humans	Predicted (SEA)	Prediction Confidence Score 0.22 Applicability Domain 0.235 Low confidence Statistical Significance 0.0011 Supporting Reference Compounds 7 E-value 8.56341
Click to view 3D structure	Ribonuclease pancreatic	P61823	Bos taurus	Predicted (SEA)	Prediction Confidence Score 0.217 Applicability Domain 0.217 Low confidence Statistical Significance 0.0032 Supporting Reference Compounds 1 E-value 24.6782
Click to view 3D structure	Protein deacetylase HDAC6	Q9UBN7	Humans	Predicted (SEA)	Prediction Confidence Score 0.214 Applicability Domain 0.301 Statistical Significance 0.6128 Supporting Reference Compounds 553 E-value 4770.99
Click to view 3D structure	Histone deacetylase 1	Q13547	Humans	Predicted (SEA)	Prediction Confidence Score 0.214 Applicability Domain 0.301 Statistical Significance 0.5802 Supporting Reference Compounds 497 E-value 4517.2
Click to view 3D structure	Glutamate receptor ionotropic, kainate 1	P22756	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.212 Applicability Domain 0.217 Low confidence Statistical Significance 0.0162 Supporting Reference Compounds 45 E-value 126.271
Click to view 3D structure	GIM-1 protein	Q704V1	Pseudomonas aeruginosa	Predicted (SEA)	Prediction Confidence Score 0.211 Applicability Domain 0.232 Low confidence Statistical Significance 0.0129 Supporting Reference Compounds 2 E-value 100.737
Click to view 3D structure	Core antigen	Q03732	Hepatitis B virus	Predicted (SEA)	Prediction Confidence Score 0.21 Applicability Domain 0.344 Statistical Significance 1.90e-04 Supporting Reference Compounds 4 E-value 1.47914
Click to view 3D structure	Glutamate receptor 1	P42261	Humans	Predicted (SEA)	Prediction Confidence Score 0.205 Applicability Domain 0.217 Low confidence Statistical Significance 0.0164 Supporting Reference Compounds 37 E-value 127.439
Click to view 3D structure	4-diphosphocytidyl-2-C-methyl-D-erythritol kinase	P62615	Escherichia coli (strain K12)	Predicted (SEA)	Prediction Confidence Score 0.205 Applicability Domain 0.205 Low confidence Statistical Significance 0.009 Supporting Reference Compounds 1 E-value 70.4535
Click to view 3D structure	Fibroblast growth factor receptor 1	P11362	Humans	Predicted (SEA)	Prediction Confidence Score 0.204 Applicability Domain 0.35 Statistical Significance 0.8209 Supporting Reference Compounds 1010 E-value 6390.72
Click to view 3D structure	Farnesyl pyrophosphate synthase	P14324	Humans	Predicted (SEA)	Prediction Confidence Score 0.202 Applicability Domain 0.22 Low confidence Statistical Significance 0.0242 Supporting Reference Compounds 22 E-value 188.395
Click to view 3D structure	Glutamate receptor 3	P19492	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.202 Applicability Domain 0.217 Low confidence Statistical Significance 0.012 Supporting Reference Compounds 30 E-value 93.6526
Click to view 3D structure	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	P06802	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.2 Applicability Domain 0.2 Low confidence Statistical Significance 0.0137 Supporting Reference Compounds 1 E-value 106.965
Click to view 3D structure	Genome polyprotein	P03300	Poliovirus type 1 (strain Mahoney)	Predicted (SEA)	Prediction Confidence Score 0.2 Applicability Domain 0.2 Low confidence Statistical Significance 0.0052 Supporting Reference Compounds 1 E-value 40.8708
Click to view 3D structure	Mandelate racemase	P11444	Pseudomonas putida	Predicted (SEA)	Prediction Confidence Score 0.2 Applicability Domain 0.2 Low confidence Statistical Significance 0.0093 Supporting Reference Compounds 1 E-value 72.2441
Click to view 3D structure	5'-nucleotidase	P21588	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.2 Applicability Domain 0.215 Low confidence Statistical Significance 0.0183 Supporting Reference Compounds 21 E-value 142.775
Click to view 3D structure	DNA polymerase beta	P06746	Humans	Predicted (SEA)	Prediction Confidence Score 0.199 Applicability Domain 0.314 Statistical Significance 0.0073 Supporting Reference Compounds 13 E-value 57.2192