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Details

Stereochemistry ACHIRAL
Molecular Formula C4H7Cl2O4P
Molecular Weight 220.976
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DICHLORVOS

SMILES

COP(=O)(OC)OC=C(Cl)Cl

InChI

InChIKey=OEBRKCOSUFCWJD-UHFFFAOYSA-N
InChI=1S/C4H7Cl2O4P/c1-8-11(7,9-2)10-3-4(5)6/h3H,1-2H3

HIDE SMILES / InChI

Description

Dichlorvos is a synthetic organic chemical used as an insecticide. Dichlorvos does not occur naturally in the environment, but is manufactured by industry. Dichlorvos is sold under many trade names including Vapona®, Atgard®, Nuvan®, and Task®. It is also used as an insecticide for slow release on pest-strips for pest control in homes.  Dichlorvos is used as an anthelmintic (worming agent) for dogs, swine, and horses, as a botacide (agent that kills fly larvae) for horses, and in flea collars for dogs. In 1995, EPA proposed cancellation of dichlorvos for all home uses, and for many commercial and industrial uses.

CNS Activity

CNS Active
3913
Curator's Comment: Dichlorvos crosses blood brain barrier and causes neurotoxicity in animals including humans.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 269.0 nM [IC50]
Inhibitor
8297
 230.0 nM [IC50]
Inhibitor
8297
 44.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8429
Atgard

Approved Use

For the removal and control of the sexually mature (adult), sexually immature, and/or 4th stage larvae of the whipworm (Trichuris suis), nodular worms (Oesophagostomum sp.), large roundworm (Ascaris suum) and the mature thick stomach worm (Ascarops stongylina) occurring in the lumen of the gastro-intestinal tract of pigs, boars, and open or bred gilts and sows.
PubMed

PubMed

TitleDatePubMed
Biochemical characterization of dichlorvos-induced delayed neurotoxicity in rat.
2000 Feb
Identification and characterization of mutations in housefly (Musca domestica) acetylcholinesterase involved in insecticide resistance.
2001 Oct 1
Short- and long-term effect of acetylcholinesterase inhibition on the expression and metabolism of the amyloid precursor protein.
2001 Sep
Transient and reversible parkinsonism after acute organophosphate poisoning.
2003
Dizocilpine improves beneficial effects of cholinergic antagonists in anticholinesterase-treated mice.
2003 Apr
Extrapyramidal syndrome as a delayed and reversible complication of acute dichlorvos organophosphate poisoning.
2004 Aug
Dimethyl 2,2-dichlorovinyl phosphate (DDVP) markedly inhibits activities of natural killer cells, cytotoxic T lymphocytes and lymphokine-activated killer cells via the Fas-ligand/Fas pathway in perforin-knockout (PKO) mice.
2004 Nov 1
Hazardous effect of organophosphate compound, dichlorvos in transgenic Drosophila melanogaster (hsp70-lacZ): induction of hsp70, anti-oxidant enzymes and inhibition of acetylcholinesterase.
2005 Aug 30
Poor efficacy of the most commonly used anthelmintics in sport horse nematodes in Morocco in relation to resistance.
2005 Dec
Albumin, a new biomarker of organophosphorus toxicant exposure, identified by mass spectrometry.
2005 Feb
Weak inhibitors protect cholinesterases from stronger inhibitors (dichlorvos): in vitro effect of tiapride.
2005 Mar-Apr
Measuring sorption of hydrophilic organic compounds in soils by an unsaturated transient flow method.
2005 May-Jun
Acute pancreatitis subsequent to voluntary methomyl and dichlorvos intoxication.
2005 Nov
Weak inhibitors protect cholinesterases from strong inhibitors (paraoxon): in vitro effect of tiapride.
2005 Nov-Dec
Pesticides associated with wheeze among commercial pesticide applicators in the Agricultural Health Study.
2006 Jun 15
The L-type calcium channel blocker nimodipine mitigates cytoskeletal proteins phosphorylation in dichlorvos-induced delayed neurotoxicity in rats.
2006 May
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Adverse effect of organophosphate compounds, dichlorvos and chlorpyrifos in the reproductive tissues of transgenic Drosophila melanogaster: 70kDa heat shock protein as a marker of cellular damage.
2007 Aug 16
Pesticide use and chronic bronchitis among farmers in the Agricultural Health Study.
2007 Dec
Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry assay for organophosphorus toxicants bound to human albumin at Tyr411.
2007 Feb 15
Brain regional acetylcholinesterase activity and muscarinic acetylcholine receptors in rats after repeated administration of cholinesterase inhibitors and its withdrawal.
2007 Mar
Impaired mitochondrial energy metabolism and neuronal apoptotic cell death after chronic dichlorvos (OP) exposure in rat brain.
2007 Nov
DDVP markedly decreases the expression of granzyme B and granzyme 3/K in human NK cells.
2008 Jan 20
Patents

Patents

JP2003267809A
1
JP2011526599A
45
JPH0249706A
1
JPH05294801A
1
JPH09202704A
1
JPH107505A
1

Sample Use Guides

In Vivo Use Guide
Rats received orally 2.5, 5 and 10mg/kg body weight of Dichlorvos (DDVP) respectively for 28 days.
Route of Administration: Oral
In Vitro Use Guide
Acylpeptide hydrolase from porcine brain was found to be potently inhibited by dichlorvos (20-min IC(50) value of 118.7 +/- 9.7 nM).
Name Type Language
DICHLORVOS
GREEN BOOK   HSDB   INN   ISO   MART.   MI   USAN   USP-RS   WHO-DD  
INN   USAN  
Official Name English
DICHLORVOS [GREEN BOOK]
Common Name English
DICHLORVOS [USAN]
Common Name English
DDVP
Common Name English
DICHLORVOS [IARC]
Common Name English
DICHLORVOS [HSDB]
Common Name English
SD-1750
Code English
SD 1750
Code English
PHOSPHORIC ACID, 2,2-DICHLOROETHENYL DIMETHYL ESTER
Common Name English
2,2-Dichlorovinyl dimethyl phosphate
Systematic Name English
DICHLORVOS [MI]
Common Name English
Dichlorvos [WHO-DD]
Common Name English
DICHLORVOS [USP-RS]
Common Name English
DICHLORVOS [ISO]
Common Name English
ATGARD
Brand Name English
2,2-DICHLOROETHENYL DIMETHYL PHOSPHATE
Systematic Name English
DICHLORVOS [MART.]
Common Name English
dichlorvos [INN]
Common Name English
NSC-6738
Code English
Classification Tree Code System Code
IARC Dichlorvos
EPA PESTICIDE CODE 600020
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CFR 21 CFR 520.600
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WHO-VATC QP53AF04
Created by admin on Sat Dec 16 17:05:28 GMT 2023 , Edited by admin on Sat Dec 16 17:05:28 GMT 2023
CFR 21 CFR 558.205
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CFR 21 CFR 556.180
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NCI_THESAURUS C737
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WHO-VATC QP53AF54
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WHO-VATC QP52AB03
Created by admin on Sat Dec 16 17:05:28 GMT 2023 , Edited by admin on Sat Dec 16 17:05:28 GMT 2023
Code System Code Type Description
CAS
62-73-7
Created by admin on Sat Dec 16 17:05:28 GMT 2023 , Edited by admin on Sat Dec 16 17:05:28 GMT 2023
PRIMARY
PUBCHEM
3039
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PRIMARY
RS_ITEM_NUM
1188301
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PRIMARY
DAILYMED
7U370BPS14
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PRIMARY
CHEBI
34690
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PRIMARY
FDA UNII
7U370BPS14
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PRIMARY
NSC
6738
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PRIMARY
MESH
D004006
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PRIMARY
SMS_ID
100000082915
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PRIMARY
ECHA (EC/EINECS)
200-547-7
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PRIMARY
MERCK INDEX
m4359
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PRIMARY Merck Index
EPA CompTox
DTXSID5020449
Created by admin on Sat Dec 16 17:05:28 GMT 2023 , Edited by admin on Sat Dec 16 17:05:28 GMT 2023
PRIMARY
ChEMBL
CHEMBL167911
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PRIMARY
DRUG BANK
DB11397
Created by admin on Sat Dec 16 17:05:28 GMT 2023 , Edited by admin on Sat Dec 16 17:05:28 GMT 2023
PRIMARY
ALANWOOD
dichlorvos
Created by admin on Sat Dec 16 17:05:28 GMT 2023 , Edited by admin on Sat Dec 16 17:05:28 GMT 2023
PRIMARY
NCI_THESAURUS
C76871
Created by admin on Sat Dec 16 17:05:28 GMT 2023 , Edited by admin on Sat Dec 16 17:05:28 GMT 2023
PRIMARY
WIKIPEDIA
DICHLORVOS
Created by admin on Sat Dec 16 17:05:28 GMT 2023 , Edited by admin on Sat Dec 16 17:05:28 GMT 2023
PRIMARY
INN
3285
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PRIMARY
HSDB
319
Created by admin on Sat Dec 16 17:05:28 GMT 2023 , Edited by admin on Sat Dec 16 17:05:28 GMT 2023
PRIMARY
EVMPD
SUB07088MIG
Created by admin on Sat Dec 16 17:05:28 GMT 2023 , Edited by admin on Sat Dec 16 17:05:28 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of DICHLORVOS
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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