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

Identification

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Name
Dichlorvos
Accession Number
DB11397
Type
Small Molecule
Groups
Vet approved
Description

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.

Structure
Thumb
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
International/Other Brands
Atgard
Categories
UNII
7U370BPS14
CAS number
62-73-7
Weight
Average: 220.976
Monoisotopic: 219.945900638
Chemical Formula
C4H7Cl2O4P
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

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AbexinostatThe risk or severity of QTc prolongation can be increased when Dichlorvos is combined with Abexinostat.
AcebutololThe risk or severity of QTc prolongation can be increased when Dichlorvos is combined with Acebutolol.
AceprometazineThe risk or severity of QTc prolongation can be increased when Dichlorvos is combined with Aceprometazine.
AcetyldigoxinThe risk or severity of QTc prolongation can be increased when Dichlorvos is combined with Acetyldigoxin.
AclidiniumThe therapeutic efficacy of Aclidinium can be decreased when used in combination with Dichlorvos.
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.
AgmatineThe therapeutic efficacy of Agmatine can be decreased when used in combination with Dichlorvos.
AjmalineThe risk or severity of QTc prolongation can be increased when Ajmaline is combined with Dichlorvos.
AlcuroniumThe therapeutic efficacy of Alcuronium can be decreased when used in combination with Dichlorvos.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

References

General References
  1. Authors unspecified: Dichlorvos. IARC Monogr Eval Carcinog Risks Hum. 1991;53:267-307. [PubMed:1842580]
  2. Authors unspecified: Dichlorvos. IARC Monogr Eval Carcinog Risk Chem Hum. 1979 Oct;20:97-127. [PubMed:397180]
  3. Slomka MB, Hine CH: Clinical pharmacology of dichlorvos. Acta Pharmacol Toxicol (Copenh). 1981;49 Suppl 5:105-8. [PubMed:7344402]
  4. Ellinger C: [Is dichlorvos hepatotoxic?]. Z Gesamte Hyg. 1984 Mar;30(3):156-8. [PubMed:6730571]
  5. Fowler NG, Evans DA, Wickham RA: Dichlorvos horse anthelmintic. Vet Rec. 1970 Jan 24;86(4):106. [PubMed:5412228]
  6. Reuber MD: Carcinogenicity of dichlorvos. Clin Toxicol. 1981 Jan;18(1):47-84. [PubMed:7009035]
  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. [PubMed:21405039]
  8. Ashwood-Smith MJ, Trevino J, Ring R: Mutagenicity of dichlorvos. Nature. 1972 Dec 15;240(5381):418-20. [PubMed:4564322]
  9. TSIKARISHVILI TN, KIBARDIN SA: DICHLORVOS--A PROMISING INSECTICIDE. WHO Chron. 1964 Jan;18:26-8. [PubMed:14075867]
  10. Mennear JH: Dichlorvos: a regulatory conundrum. Regul Toxicol Pharmacol. 1998 Jun;27(3):265-72. [PubMed:9693077]
  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. [PubMed:12186780]
  12. Ebeigbe AB, Campbell PI: Inhibitory effect of dichlorvos on arterial smooth muscle contraction. Pharmacol Res Commun. 1986 Mar;18(3):283-91. [PubMed:3725847]
  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. [PubMed:24021659]
  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. [PubMed:24231740]
  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. [PubMed:24374570]
  16. 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
Wikipedia
Dichlorvos

Clinical Trials

Clinical Trials
Not Available

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

Taxonomy

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
Dialkyl phosphate / Chloroalkene / Haloalkene / Vinyl halide / Vinyl chloride / Organic oxygen compound / Organic oxide / Hydrocarbon derivative / Organooxygen compound / Organochloride
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)

Targets

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. [PubMed:18930948]
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. [PubMed:20229498]

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. [PubMed:15525694]
  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. [PubMed:17188226]

Drug created on February 25, 2016 11:24 / Updated on June 04, 2019 07:20