Compounds > propetamphos
Page last updated: 2024-11-11

propetamphos

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Cross-References

ID SourceID
PubMed CID5372405
CHEMBL ID1875667
CHEBI ID38864
SCHEMBL ID117991
MeSH IDM0109853

Synonyms (57)

Synonym
2-butenoic acid, 3-(((ethylamino)methoxyphosphinothioyl)oxy)-, 1-methylethyl ester, (e)-
safrotin, analytical standard
31218-83-4
propan-2-yl (2e)-3-{[(ethylamino)(methoxy)phosphorothioyl]oxy}but-2-enoate
CHEBI:38864 ,
o-methyl o-{1-[(propan-2-yl)oxycarbonyl]prop-1-en-2-yl} ethylamidothiophosphate
propetamphos
1-methylethyl (e)-3-(((ethylamino)methoxyphosphinothioyl)oxy)-2-butenoate
(e)-1-methylethyl 3-(((ethylamino)methoxyphosphinothioyl)oxy)-2-butenoate
NCGC00163952-01
isopropyl (2e)-3-{[(ethylamino)(methoxy)phosphorothioyl]oxy}but-2-enoate
NCGC00163952-02
propan-2-yl 3-[ethylamino(methoxy)phosphinothioyl]oxybut-2-enoate
propetamphos (ban)
D08437
seraphos
propan-2-yl (e)-3-[ethylamino(methoxy)phosphinothioyl]oxybut-2-enoate
NCGC00163952-03
C18669
cas-31218-83-4
tox21_300863
NCGC00254767-01
dtxsid7032470 ,
dtxcid5012470
2-butenoic acid, 3-(((ethylamino)methoxyphosphinothioyl)oxy)-, 1-methylethyl ester
58995-37-2
2-butenoic acid, 3-(((ethylamino)methoxyphospinothioyl)oxy)-, 1-methylethyl ester
ai3-27989
AKOS015960933
2-butenoic acid, 3-[[(ethylamino)methoxyphosphinothioyl]oxy]-, 1-methylethyl ester
CHEMBL1875667
(+/-)-propetamphos
propetamphos [mi]
propetamphos [jan]
propetamphos [hsdb]
propetamphos [mart.]
SCHEMBL117991
san 52139
sandoz 52139
2-butenoic acid, 3-(((ethylamino)methoxyphosphinothioyl)oxy)-, isopropyl ester, (e)-
BZNDWPRGXNILMS-VQHVLOKHSA-N
vel 4283
isopropyl (2e)-3-([(ethylamino)(methoxy)phosphorothioyl]oxy)-2-butenoate
(e)-3-[[(ethylamino)methoxyphosphinothioyl]oxy]-2-butenoic acid 1-methyl-ethyl ester
e-propetamphos
2-butenoic acid, 3-[[(ethylamino)methoxyphosphinothioyl]oxy]-, 1-methylethyl ester, (e)-
W-110796
trans-isopropyl-3-[[(ethylamino)methoxyfosfinothioyl]oxy]crotonate
propetamphos, pestanal(r), analytical standard
propetamphos 10 microg/ml in cyclohexane
propetamphos 100 microg/ml in cyclohexane
(e)-isopropyl 3-((ethylamino)(methoxy)phosphorothioyloxy)but-2-enoate
isopropyl (e)-3-(((ethylamino)(methoxy)phosphorothioyl)oxy)but-2-enoate
Q18629963
AKOS040744709
HY-119525
CS-0068655

Research Excerpts

Overview

Propetamphos is a new organophosphorous compound with broad spectrum acaricidal and insecticidal activity. It is mainly used for sheep dipping.

ExcerptReferenceRelevance
"Propetamphos is a new organophosphorous compound with broad spectrum acaricidal and insecticidal activity. "( Control of sheep scab and other sheep ectoparasites with propetamphos.
Bramley, PS; Henderson, D, 1984)		1.96
"Propetamphos is a member of the vinyl phosphate group of insecticides and is mainly used for sheep dipping. "( Development of a urinary biomarker for exposure to the organophosphate propetamphos: data from an oral and dermal human volunteer study.
Cocker, J; Garfitt, SJ; Jones, K; Mason, HJ, )		1.81

Toxicity

ExcerptReferenceRelevance
"This study was aimed at determining the acute and chronic toxic effects of cypermethrin, propetamphos, and combined cypermethrin and propetamphos."( The acute and chronic toxic effect of cypermethrin, propetamphos, and their combinations in rats.
Eraslan, G; Kanbur, M; Karabacak, M; Şahin, S; Siliğ, Y; Soyer Sarica, Z, 2016)		0.91

Pharmacokinetics

ExcerptReferenceRelevance
" Although metabolism of propetamphos has been previously investigated (2,3), there is no pharmacokinetic data available in the literature."( Pharmacokinetics of propetamphos following intravenous administration in the F344 rat.
Burka, LT; Dauterman, WC; Dix, K, 1992)		0.91

Dosage Studied

Cyromazine and Propetamphos are used to control blowfly strike in sheep. The length of protection might be dosage related.

ExcerptRelevanceReference
" Rats were dosed via an indwelling jugular cannula at a dose of 12 mg/kg (one-tenth the oral LD-50)."( Pharmacokinetics of propetamphos following intravenous administration in the F344 rat.
Burka, LT; Dauterman, WC; Dix, K, 1992)		0.61
" It was concluded that if organophosphate resistant blowfly were present, the length of protection might be dosage related and that blowfly strike in sheep was almost equally controlled by Cyromazine and Propetamphos."( Propetamphos: a comparison of three formulations in preventing blowfly strike in sheep.
Gruss, B; Janse van Rensburg, BJ, 1988)		1.91
" No individual showed a significant depression compared with their pre-exposure levels of erythrocyte acetyl cholinesterase or plasma cholinesterase activity for either dosing route."( Development of a urinary biomarker for exposure to the organophosphate propetamphos: data from an oral and dermal human volunteer study.
Cocker, J; Garfitt, SJ; Jones, K; Mason, HJ, )		0.36
" Log dosage probit analysis of propetamphos dose-response regression lines produced a resistance ratio based on LC(50) in the most resistant strain of approximately 103-fold."( Propetamphos resistance in Rhipicephalus bursa (Acari, Ixodidae).
Amouei, A; Asgarian, F; Boudaghi, B; Boujhmehrani, H; Enayati, AA; Hemingway, J; Piazak, N; Sharif, M; Vahedi, N, 2009)		2.08
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
EC 3.1.1.7 (acetylcholinesterase) inhibitorAn EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.
agrochemicalAn agrochemical is a substance that is used in agriculture or horticulture.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (3)

ClassDescription
phosphoramidate esterA phosphoric ester (phosphate) that has an NR2 instead of an OH group.
organophosphate insecticide
isopropyl esterAny carboxylic ester resulting from the formal condensation of a carboxylic acid with the hydroxy group of propan-2-ol.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (17)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
acetylcholinesteraseHomo sapiens (human)Potency63.26090.002541.796015,848.9004AID1347395
pregnane X receptorRattus norvegicus (Norway rat)Potency63.09570.025127.9203501.1870AID651751
SMAD family member 2Homo sapiens (human)Potency17.37390.173734.304761.8120AID1346924
SMAD family member 3Homo sapiens (human)Potency17.37390.173734.304761.8120AID1346924
GLI family zinc finger 3Homo sapiens (human)Potency25.77850.000714.592883.7951AID1259392
AR proteinHomo sapiens (human)Potency36.71950.000221.22318,912.5098AID743063
nuclear receptor subfamily 1, group I, member 3Homo sapiens (human)Potency13.71150.001022.650876.6163AID1224838; AID1224839; AID1224893
progesterone receptorHomo sapiens (human)Potency30.63790.000417.946075.1148AID1346795
retinoic acid nuclear receptor alpha variant 1Homo sapiens (human)Potency61.13060.003041.611522,387.1992AID1159552
estrogen-related nuclear receptor alphaHomo sapiens (human)Potency54.48270.001530.607315,848.9004AID1224849
farnesoid X nuclear receptorHomo sapiens (human)Potency0.00280.375827.485161.6524AID588527
pregnane X nuclear receptorHomo sapiens (human)Potency20.65570.005428.02631,258.9301AID1346982; AID720659
estrogen nuclear receptor alphaHomo sapiens (human)Potency2.18720.000229.305416,493.5996AID743075
aryl hydrocarbon receptorHomo sapiens (human)Potency20.89010.000723.06741,258.9301AID651777; AID743085; AID743122
thyroid hormone receptor beta isoform aHomo sapiens (human)Potency3.98110.010039.53711,122.0200AID588547
histone deacetylase 9 isoform 3Homo sapiens (human)Potency61.13060.037617.082361.1927AID1259364
nuclear factor erythroid 2-related factor 2 isoform 1Homo sapiens (human)Potency61.13060.000627.21521,122.0200AID651741
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (33)

TimeframeStudies, This Drug (%)All Drugs %
pre-19909 (27.27)18.7374
1990's10 (30.30)18.2507
2000's8 (24.24)29.6817
2010's4 (12.12)24.3611
2020's2 (6.06)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 26.48

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index26.48 (24.57)
Research Supply Index3.56 (2.92)
Research Growth Index4.56 (4.65)
Search Engine Demand Index30.30 (26.88)
Search Engine Supply Index2.20 (0.95)

This Compound (26.48)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (2.94%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other33 (97.06%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
carbamates
[no description available]		2.3820amino-acid anion
bendiocarb
bendiocarb: FICAM 80W contains 80% of the above chemical cpd as the active ingredient		1.9710benzodioxoles;
carbamate ester		agrochemical;
carbamate insecticide;
EC 3.1.1.7 (acetylcholinesterase) inhibitor
chlorpyrifos
Chlorpyrifos: An organothiophosphate cholinesterase inhibitor that is used as an insecticide and as an acaricide.. chlorpyrifos : An organic thiophosphate that is O,O-diethyl hydrogen phosphorothioate in which the hydrogen of the hydroxy group has been replaced by a 3,5,6-trichloropyridin-2-yl group.		7.420chloropyridine;
organic thiophosphate		acaricide;
agrochemical;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
environmental contaminant;
insecticide;
xenobiotic
cypermethrin
cypermethrin : A carboxylic ester resulting from the formal condensation between 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid and the alcoholic hydroxy group of hydroxy(3-phenoxyphenyl)acetonitrile.. zeta-cypermethrin : A diastereoisomeric mixture comprising the isomeric pair (1R)-cis-(alphaS)- and (1S)-trans-(alphaR)-cypermethrin together with the isomeric pair (1S)-cis-(alphaS)- and (1S)-trans-(alphaS)-cypermethrin where the ratio between the isomeric pairs lies in the range 45:55 to 55:45.		2.7330aromatic ether;
cyclopropanecarboxylate ester;
nitrile;
organochlorine compound		agrochemical;
molluscicide;
pyrethroid ester acaricide;
pyrethroid ester insecticide
diazinon
Diazinon: A cholinesterase inhibitor that is used as an organothiophosphorus insecticide.. diazinon : A member of the class of pyrimidines that is pyrimidine carrying an isopropyl group at position 2, a methyl group at position 6 and a (diethoxyphosphorothioyl)oxy group at position 4.		3.4980organic thiophosphate;
pyrimidines		acaricide;
agrochemical;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
environmental contaminant;
nematicide;
xenobiotic
chlorfenvinphos
Chlorfenvinphos: An organophosphorus cholinesterase inhibitor that is used as an insecticide and an acaricide.		1.9710dichlorobenzene;
organic phosphate;
organochlorine acaricide;
organochlorine insecticide;
organophosphate insecticide		agrochemical;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor
malondialdehyde
Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.		2.4520dialdehydebiomarker
fenitrooxone
fenitrooxone: oxone metabolite of fenitrothion		3.1110
dioxacarb
dioxacarb: structure		1.9710benzenes
silver
Silver: An element with the atomic symbol Ag, atomic number 47, and atomic weight 107.87. It is a soft metal that is used medically in surgical instruments, dental prostheses, and alloys. Long-continued use of silver salts can lead to a form of poisoning known as ARGYRIA.		7.610copper group element atom;
elemental silver		Escherichia coli metabolite
iodofenphos
[no description available]		1.9710organic thiophosphate
fenitrothion
Fenitrothion: An organothiophosphate cholinesterase inhibitor that is used as an insecticide.. fenitrothion : An organic thiophosphate that is O,O-dimethyl O-phenyl phosphorothioate substituted by a methyl group at position 3 and a nitro group at position 4.		3.1110C-nitro compound;
organic thiophosphate		acaricide;
agrochemical;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
insecticide
prothiophos
prothiophos: caused hypoglycemia & reduced blood urea levels in rats; structure in first source; inhibits acetylcholinesterase. prothiofos : An organic thiophosphate that is the 2,4-dichlorophenyl ester of O-ethyl S-propyl dithiophosphoric acid.		3.1110dichlorobenzene;
organic thiophosphate;
organosulfur compound		agrochemical;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
insecticide
permethrin
hemoglobin Atlanta-Coventry: Leu replaced by Pro at beta75 and Leu deleted at beta141		7.6830cyclopropanecarboxylate ester;
cyclopropanes		agrochemical;
ectoparasiticide;
pyrethroid ester acaricide;
pyrethroid ester insecticide;
scabicide
cyromazine
cyromazine: RN given refers to parent cpd		1.9710triamino-1,3,5-triazinemouse metabolite;
triazine insecticide
fluvalinate
fluvalinate: RN given refers to 2-cyano isomer (DL)-isomer		1.9710(trifluoromethyl)benzenes;
aromatic ether;
monochlorobenzenes;
nitrile;
organochlorine acaricide;
organochlorine insecticide;
organofluorine acaricide;
organofluorine insecticide		agrochemical;
pyrethroid ester acaricide;
pyrethroid ester insecticide
flucythrinate
[no description available]		1.9710
phosphoramidic acid
phosphoramidic acid: urease inhibitor; RN given refers to parent cpd; structure; do not confuse with phosphoramidites, which are organophosphorus compounds		3.1110phosphoric acid derivative
3-chloroperbenzoic acid
3-chloroperbenzoic acid: oxidizing agent		3.1110monochlorobenzenes;
peroxy acid
azamethiphos
[no description available]		7.610organic thiophosphate;
organochlorine acaricide;
organochlorine insecticide;
organothiophosphate insecticide		agrochemical;
EC 3.1.1.7 (acetylcholinesterase) inhibitor
cyfluthrin
cyfluthrin: effective against mosquitoes. cyfluthrin : A carboxylic ester obtained by formal condensation between 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid and (4-fluoro-3-phenoxyphenyl)(hydroxy)acetonitrile.		710aromatic ether;
cyclopropanecarboxylate ester;
nitrile;
organochlorine compound;
organofluorine compound		agrochemical;
pyrethroid ester insecticide
nadp
[no description available]		3.1110
chrysin
chrysin : A dihydroxyflavone in which the two hydroxy groups are located at positions 5 and 7.		7.41107-hydroxyflavonol;
dihydroxyflavone		anti-inflammatory agent;
antineoplastic agent;
antioxidant;
EC 2.7.11.18 (myosin-light-chain kinase) inhibitor;
hepatoprotective agent;
plant metabolite
lead
Lead: A soft, grayish metal with poisonous salts; atomic number 82, atomic weight 207.2, symbol Pb.		2.0610carbon group element atom;
elemental lead;
metal atom		neurotoxin
flumethrin
flumethrin: synthetic pyrethrin insecticide		210
acid phosphatase
Acid Phosphatase: An enzyme that catalyzes the conversion of an orthophosphoric monoester and water to an alcohol and orthophosphate. EC 3.1.3.2.		2.0610
pyrethrins
[no description available]		3.3870
ConditionIndicatedRelationship StrengthStudiesTrials
Body Weight
The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.		02.420
Pediculosis
[description not available]		02.3720
Ovine Diseases
[description not available]		03.77110
Tick Infestations
Infestations with soft-bodied (Argasidae) or hard-bodied (Ixodidae) ticks.		02.3720
Acariasis
[description not available]		02.8940
Ectoparasitic Infestations
Infestations by PARASITES which live on, or burrow into, the surface of their host's EPIDERMIS. Most ectoparasites are ARTHROPODS.		02.6730
Lice Infestations
Parasitic attack or subsistence on the skin by members of the order Phthiraptera, especially on humans by Pediculus humanus of the family Pediculidae. The hair of the head, eyelashes, and pubis is a frequent site of infestation. (From Dorland, 28th ed; Stedman, 26th ed)		02.3720
Diathesis
[description not available]		01.9810
Mange, Sarcoptic
[description not available]		01.9910
Scabies
A contagious cutaneous inflammation caused by the bite of the mite SARCOPTES SCABIEI. It is characterized by pruritic papular eruptions and burrows and affects primarily the axillae, elbows, wrists, and genitalia, although it can spread to cover the entire body.		01.9910
Agricultural Worker Disease
[description not available]		01.9710
Parasitic Skin Diseases
[description not available]		01.9710
Infections, Nematode
[description not available]		01.9710
Bovine Diseases
[description not available]		01.9710