This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Dichlorvos
- DrugBank Accession Number
- DB11397
- Background
Dichlorvos or 2,2-dichlorovinyl dimethyl phosphate is a drug of the organophosphate class, frequently used as an insecticide for the control of indoor pests and for the protection of stored products from insect infestations. The compound has been available on the market since 1961 and its use is a controversial topic due to environmental and health concerns. Dichlorvos is found in urban waterways and its toxicity may impact humans, leading to poisoning, neurotoxicity, and cancer.
- Type
- Small Molecule
- Groups
- Vet approved
- Structure
Structure for Dichlorvos (DB11397)
- Weight
- Average: 220.976
Monoisotopic: 219.945900638 - Chemical Formula
- C4H7Cl2O4P
- Synonyms
- 2,2-Dichloroethenyl dimethyl phosphate
- DDVP
- Dichlorvos
- Dimethyl 2,2-dichlorovinyl phosphate
- Dimethyl-2,2-dichlorovinyl phosphate
- Phosphoric acid, 2,2-dichloroethenyl dimethyl ester
- Phosphoric acid, 2,2-dichlorovinyl dimethyl ester
- External IDs
- NSC-6738
- SD 1750
- SD-1750
Pharmacology
- Indication
Not Available
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism USerotransferrin Not Available Humans UCholinesterase Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- 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 softwareAcebutolol Dichlorvos may increase the bradycardic activities of Acebutolol. Acetylcholine The risk or severity of adverse effects can be increased when Dichlorvos is combined with Acetylcholine. Aclidinium Dichlorvos may increase the neuromuscular blocking activities of Aclidinium. Acrivastine The risk or severity of QTc prolongation can be increased when Acrivastine is combined with Dichlorvos. Adenosine The risk or severity of QTc prolongation can be increased when Dichlorvos is combined with Adenosine. - Food Interactions
- Not Available
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.- International/Other Brands
- Atgard
Categories
- Drug Categories
- Agrochemicals
- Anthelmintics
- Anti-Infective Agents
- Antiparasitic Agents
- Cholinergic Agents
- Cholinesterase Inhibitors
- Compounds used in a research, industrial, or household setting
- Enzyme Inhibitors
- Insecticides
- Neurotransmitter Agents
- Organophosphates
- Organophosphorus Compounds
- Pesticides
- Potential QTc-Prolonging Agents
- QTc Prolonging Agents
- Toxic Actions
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as dialkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly two alkyl chain.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Organic phosphoric acids and derivatives
- Sub Class
- Phosphate esters
- Direct Parent
- Dialkyl phosphates
- Alternative Parents
- Vinyl chlorides / Chloroalkenes / Organooxygen compounds / Organochlorides / Organic oxides / Hydrocarbon derivatives
- Substituents
- Aliphatic acyclic compound / Chloroalkene / Dialkyl phosphate / Haloalkene / Hydrocarbon derivative / Organic oxide / Organic oxygen compound / Organochloride / Organohalogen compound / Organooxygen compound
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- organochlorine acaricide, dialkyl phosphate, organophosphate insecticide, alkenyl phosphate (CHEBI:34690) / Organophosphorus insecticides (C14430) / a small molecule (CPD-10185)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 7U370BPS14
- CAS number
- 62-73-7
- InChI Key
- OEBRKCOSUFCWJD-UHFFFAOYSA-N
- InChI
- InChI=1S/C4H7Cl2O4P/c1-8-11(7,9-2)10-3-4(5)6/h3H,1-2H3
- IUPAC Name
- 2,2-dichloroethenyl dimethyl phosphate
- SMILES
- COP(=O)(OC)OC=C(Cl)Cl
References
- General References
- Authors unspecified: Dichlorvos. IARC Monogr Eval Carcinog Risks Hum. 1991;53:267-307. [Article]
- Authors unspecified: Dichlorvos. IARC Monogr Eval Carcinog Risk Chem Hum. 1979 Oct;20:97-127. [Article]
- Slomka MB, Hine CH: Clinical pharmacology of dichlorvos. Acta Pharmacol Toxicol (Copenh). 1981;49 Suppl 5:105-8. [Article]
- Ellinger C: [Is dichlorvos hepatotoxic?]. Z Gesamte Hyg. 1984 Mar;30(3):156-8. [Article]
- Fowler NG, Evans DA, Wickham RA: Dichlorvos horse anthelmintic. Vet Rec. 1970 Jan 24;86(4):106. [Article]
- Reuber MD: Carcinogenicity of dichlorvos. Clin Toxicol. 1981 Jan;18(1):47-84. [Article]
- Aschmann SM, Tuazon EC, Long WD, Atkinson R: Atmospheric chemistry of dichlorvos. J Phys Chem A. 2011 Apr 7;115(13):2756-64. doi: 10.1021/jp112019s. Epub 2011 Mar 15. [Article]
- Ashwood-Smith MJ, Trevino J, Ring R: Mutagenicity of dichlorvos. Nature. 1972 Dec 15;240(5381):418-20. [Article]
- TSIKARISHVILI TN, KIBARDIN SA: DICHLORVOS--A PROMISING INSECTICIDE. WHO Chron. 1964 Jan;18:26-8. [Article]
- Mennear JH: Dichlorvos: a regulatory conundrum. Regul Toxicol Pharmacol. 1998 Jun;27(3):265-72. [Article]
- Choudhary S, Raheja G, Gupta V, Gill KD: Possible involvement of dopaminergic neurotransmitter system in dichlorvos induced delayed neurotoxicity. J Biochem Mol Biol Biophys. 2002 Feb;6(1):29-36. [Article]
- Ebeigbe AB, Campbell PI: Inhibitory effect of dichlorvos on arterial smooth muscle contraction. Pharmacol Res Commun. 1986 Mar;18(3):283-91. [Article]
- Liu W, Kou J, Xing H, Li B: Paper-based chromatographic chemiluminescence chip for the detection of dichlorvos in vegetables. Biosens Bioelectron. 2014 Feb 15;52:76-81. doi: 10.1016/j.bios.2013.08.024. Epub 2013 Aug 24. [Article]
- Wani WY, Sunkaria A, Sharma DR, Kandimalla RJ, Kaushal A, Gerace E, Chiarugi A, Gill KD: Caspase inhibition augments Dichlorvos-induced dopaminergic neuronal cell death by increasing ROS production and PARP1 activation. Neuroscience. 2014 Jan 31;258:1-15. doi: 10.1016/j.neuroscience.2013.11.004. Epub 2013 Nov 11. [Article]
- Wang H, Li S, Qi L, Xu W, Zeng Y, Hou Y, Zhao X, Sun C: Metabonomic analysis of quercetin against the toxicity of chronic exposure to low-level dichlorvos in rats via ultra-performance liquid chromatography-mass spectrometry. Toxicol Lett. 2014 Mar 3;225(2):230-9. doi: 10.1016/j.toxlet.2013.12.017. Epub 2013 Dec 27. [Article]
- Yannai, Shmuel (2003). Dictionary of Food Compounds with : Additives, Flavors, and Ingredients. CRC Press LLC. [ISBN:1584884169]
- External Links
- Human Metabolome Database
- HMDB0033956
- KEGG Drug
- D03791
- KEGG Compound
- C14430
- ChemSpider
- 2931
- BindingDB
- 50286926
- ChEBI
- 34690
- ChEMBL
- CHEMBL167911
- ZINC
- ZINC000001853865
- Wikipedia
- Dichlorvos
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 9.77 mg/mL ALOGPS logP 1.27 ALOGPS logP 1.37 Chemaxon logS -1.4 ALOGPS pKa (Strongest Basic) -9.1 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 44.76 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 52.19 m3·mol-1 Chemaxon Polarizability 16.82 Å3 Chemaxon Number of Rings 0 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
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 133.4839202 predictedDarkChem Lite v0.1.0 [M-H]- 132.7560202 predictedDarkChem Lite v0.1.0 [M-H]- 135.01385 predictedDeepCCS 1.0 (2019) [M+H]+ 134.4612202 predictedDarkChem Lite v0.1.0 [M+H]+ 133.9241202 predictedDarkChem Lite v0.1.0 [M+H]+ 137.90227 predictedDeepCCS 1.0 (2019) [M+Na]+ 134.1560202 predictedDarkChem Lite v0.1.0 [M+Na]+ 133.8370202 predictedDarkChem Lite v0.1.0 [M+Na]+ 146.97511 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Transferrins are iron binding transport proteins which can bind two Fe(3+) ions in association with the binding of an anion, usually bicarbonate. It is responsible for the transport of iron from sites of absorption and heme degradation to those of storage and utilization. Serum transferrin may also have a further role in stimulating cell proliferation
- Specific Function
- Ferric iron binding
- Gene Name
- TF
- Uniprot ID
- P02787
- Uniprot Name
- Serotransferrin
- Molecular Weight
- 77049.175 Da
References
- Li B, Schopfer LM, Grigoryan H, Thompson CM, Hinrichs SH, Masson P, Lockridge O: Tyrosines of human and mouse transferrin covalently labeled by organophosphorus agents: a new motif for binding to proteins that have no active site serine. Toxicol Sci. 2009 Jan;107(1):144-55. doi: 10.1093/toxsci/kfn211. Epub 2008 Oct 16. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters
- Specific Function
- Acetylcholinesterase activity
- Gene Name
- BCHE
- Uniprot ID
- P06276
- Uniprot Name
- Cholinesterase
- Molecular Weight
- 68417.575 Da
References
- Tacal O, Lockridge O: Methamidophos, dichlorvos, O-methoate and diazinon pesticides used in Turkey make a covalent bond with butyrylcholinesterase detected by mass spectrometry. J Appl Toxicol. 2010 Jul;30(5):469-75. doi: 10.1002/jat.1518. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
- Specific Function
- Antioxidant activity
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Albumin
- Molecular Weight
- 69365.94 Da
References
- Peeples ES, Schopfer LM, Duysen EG, Spaulding R, Voelker T, Thompson CM, Lockridge O: Albumin, a new biomarker of organophosphorus toxicant exposure, identified by mass spectrometry. Toxicol Sci. 2005 Feb;83(2):303-12. Epub 2004 Nov 3. [Article]
- Li B, Schopfer LM, Hinrichs SH, Masson P, Lockridge O: Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry assay for organophosphorus toxicants bound to human albumin at Tyr411. Anal Biochem. 2007 Feb 15;361(2):263-72. Epub 2006 Dec 4. [Article]
Drug created at February 25, 2016 18:24 / Updated at February 21, 2021 18:53