Dichlorvos

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

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
Thumb
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

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
USerotransferrinNot AvailableHumans
UCholinesteraseNot AvailableHumans
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
Medicalerrors
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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.
DrugInteraction
AcetylcholineThe risk or severity of adverse effects can be increased when Dichlorvos is combined with Acetylcholine.
AclidiniumDichlorvos may increase the neuromuscular blocking activities of Aclidinium.
AcrivastineThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Dichlorvos.
AdenosineThe risk or severity of QTc prolongation can be increased when Dichlorvos is combined with Adenosine.
AjmalineThe risk or severity of QTc prolongation can be increased when Ajmaline is combined with Dichlorvos.
AlfuzosinThe risk or severity of QTc prolongation can be increased when Alfuzosin is combined with Dichlorvos.
AlimemazineThe risk or severity of QTc prolongation can be increased when Alimemazine is combined with Dichlorvos.
AmantadineThe risk or severity of QTc prolongation can be increased when Dichlorvos is combined with Amantadine.
AmifampridineThe risk or severity of adverse effects can be increased when Dichlorvos is combined with Amifampridine.
AmiodaroneThe risk or severity of QTc prolongation can be increased when Dichlorvos is combined with Amiodarone.
Interactions
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Food Interactions
Not Available

Products

Products
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International/Other Brands
Atgard

Categories

Drug Categories
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
  1. Authors unspecified: Dichlorvos. IARC Monogr Eval Carcinog Risks Hum. 1991;53:267-307. [Article]
  2. Authors unspecified: Dichlorvos. IARC Monogr Eval Carcinog Risk Chem Hum. 1979 Oct;20:97-127. [Article]
  3. Slomka MB, Hine CH: Clinical pharmacology of dichlorvos. Acta Pharmacol Toxicol (Copenh). 1981;49 Suppl 5:105-8. [Article]
  4. Ellinger C: [Is dichlorvos hepatotoxic?]. Z Gesamte Hyg. 1984 Mar;30(3):156-8. [Article]
  5. Fowler NG, Evans DA, Wickham RA: Dichlorvos horse anthelmintic. Vet Rec. 1970 Jan 24;86(4):106. [Article]
  6. Reuber MD: Carcinogenicity of dichlorvos. Clin Toxicol. 1981 Jan;18(1):47-84. [Article]
  7. 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]
  8. Ashwood-Smith MJ, Trevino J, Ring R: Mutagenicity of dichlorvos. Nature. 1972 Dec 15;240(5381):418-20. [Article]
  9. TSIKARISHVILI TN, KIBARDIN SA: DICHLORVOS--A PROMISING INSECTICIDE. WHO Chron. 1964 Jan;18:26-8. [Article]
  10. Mennear JH: Dichlorvos: a regulatory conundrum. Regul Toxicol Pharmacol. 1998 Jun;27(3):265-72. [Article]
  11. 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]
  12. Ebeigbe AB, Campbell PI: Inhibitory effect of dichlorvos on arterial smooth muscle contraction. Pharmacol Res Commun. 1986 Mar;18(3):283-91. [Article]
  13. 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]
  14. 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]
  15. 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]
  16. Yannai, Shmuel (2003). Dictionary of Food Compounds with : Additives, Flavors, and Ingredients. CRC Press LLC. [ISBN:1584884169]
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
PhaseStatusPurposeConditionsCount

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
PropertyValueSource
Water Solubility9.77 mg/mLALOGPS
logP1.27ALOGPS
logP1.37ChemAxon
logS-1.4ALOGPS
pKa (Strongest Basic)-9.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area44.76 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity52.19 m3·mol-1ChemAxon
Polarizability16.82 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0a4i-1900000000-09877a8cb478a3cc6839
Mass Spectrum (Electron Ionization)MSsplash10-0a4i-7900000000-0efae19e253ed849b729
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-001i-0900000000-f98de9faf1be0bb7aa83
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-001i-0900000000-93c62701332435cee993
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-001i-0900000000-f922e6ba3c6c6b90775a
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-001i-1900000000-40a51b0033ce31d71432
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-001i-1900000000-9ef61f0d99a23257c13d
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-001i-3900000000-c65f2474371722a3bcc8
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00fr-0690000000-26446ccc45ba04ecd6a2
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-004i-0930000000-5337a3d357153a9b46f2
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-004i-0900000000-65501644b18b2b26ba71
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-004i-2900000000-051c8cc88647cdf4959e
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-004i-4900000000-dccb667225335d52f6d1
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-004i-6900000000-8c14f2901d28ffb6e55a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0900000000-cc2455ee44a59b12a9f4
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-2900000000-c792ae223d6916b397d8
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4l-0900000000-ca0ee2a0d7d29061a4c4
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-052f-0900000000-347f95538a81149f9317
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-004i-0930000000-62f725b3cb5b2d33fd64
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Targets

Drugtargets
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transferrin receptor binding
Specific 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 si...
Gene Name
TF
Uniprot ID
P02787
Uniprot Name
Serotransferrin
Molecular Weight
77063.195 Da
References
  1. 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
Identical protein binding
Specific Function
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name
BCHE
Uniprot ID
P06276
Uniprot Name
Cholinesterase
Molecular Weight
68417.575 Da
References
  1. 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
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. 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]
  2. 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 on February 25, 2016 18:24 / Updated on February 21, 2021 18:53