Page last updated: 2024-12-05

echothiophate iodide

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

Description

Echothiophate Iodide: A potent, long-acting cholinesterase inhibitor used as a miotic in the treatment of glaucoma. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ecothiopate iodide : The iodide salt of ecothiopate. An irreversible acetylcholinesterase inhibitor, it is used an ocular antihypertensive in the treatment of open-angle glaucoma, particularly when other drugs have proved inadequate. [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]

Cross-References

ID SourceID
PubMed CID10547
CHEMBL ID1200367
CHEBI ID59849
SCHEMBL ID24839
MeSH IDM0006980

Synonyms (84)

Synonym
ba9qh3p00t ,
2-diaethoxyphosphinyl-thioaethyl-trimethyl-ammonium-jodid
ecothiopate iodide [inn]
echothiophate iodide [usp]
unii-ba9qh3p00t
ethanaminium, 2-((diethoxyphosphinyl)thio)-n,n,n-trimethyl-, iodide
ammonium, (2-(o,o-diethylphosphorothio)ethyl)trimethyl-, iodide
phospholine (the pharmaceutical)
iodure d'ecothiopate [inn-french]
ammonium, (2-mercaptoethyl)trimethyl-, iodide, s-ester with o,o-diethylphosphorothioate
echothiophate iodide
217 mi
ecothiopati iodidum [inn-latin]
(2-mercaptoethyl)trimethylammonium iodide s-ester with o,o-diethyl phosphorothioate
o,o-diethyl s-2-trimethylammonium ethylphosphonothiolate iodide
diethoxyphosphoryl-thiocholine iodide
s-(2-(n,n,n-trimethylammonio)ethyl) o,o-diethylphosphorothiolate iodide
ecothiopate iodide
n-(2-(diethoxyphosphinylthio)ethyl)trimethylammonium iodide
s-(2-dimethylaminoethyl)-o.o-diethylphosphorothioate methiodide
2-diethoxy-phosphinylthioethyl-trimethylammonium iodide
phospholine iodide
ecostigmini jodidum
echodide
s-ester of (2-mercaptoethyl)trimethylammonium iodide with o,o-diethyl phosphorothioate
ioduro de ecotiopato [inn-spanish]
2-((diethoxyphosphinyl)thio)-n,n,n,-trimethylethanaminium iodide
ecothiophate iodide
einecs 208-152-1
2-diaethoxyphosphinyl-thioaethyl-trimethyl-ammonium-jodid [german]
ethanaminium, 2-[(diethoxyphosphinyl)thio]-n,n,n-trimethyl-, iodide
2-{[bis(ethyloxy)phosphoryl]thio}-n,n,n-trimethylethanaminium iodide
phospholine iodide (tn)
ecothiopate iodide (jp17/inn)
echothiophate iodide (usp)
513-10-0
D02193
iodide, echothiophate
iodide, ecothiopate
iodide, ecothiophate
(2-mercaptoethyl)trimethylammonium iodidie o,o-diethyl phosphorothioate
CHEBI:59849 ,
ecothiopati iodidum
diethoxyphosphinylthiocholine iodide
2-[(diethoxyphosphinyl)thio]-n,n,n-trimethylethanaminium iodide
2-[(diethoxyphosphoryl)sulfanyl]-n,n,n-trimethylethanaminium iodide
iodure d'ecothiopate
s-beta-dimethylaminoethyl-o,o-diethylthionophosphate methiodide
s-(2-dimethylaminoethyl)-o,o-diethylphosphorothioate methiodide
ioduro de ecotiopato
CHEMBL1200367
217-mi
bdbm50016940
ecostigmine iodide
AKOS015967621
ecothiopate iodide [who-dd]
ecothiopate iodide [jan]
echothiophate iodide [orange book]
echothiophate iodide [mi]
echothiophate iodide [usp impurity]
ecothiopate iodide [mart.]
echothiophate iodide [usp monograph]
SCHEMBL24839
DTXSID1022976 ,
217mi; diethoxyphosphinylthiocholine iodide; diethylphosphorylthiocholine iodide; echothiopate iodide; ecostigmini jodidum;
2-diethoxyphosphorylsulfanylethyl(trimethyl)azanium;iodide
ecothiopateiodide
echothiopate iodide
HY-16183
diethyl {[2-(trimethylazaniumyl)ethyl]sulfanyl}phosphonate iodide
EN300-10850805
ecothiopati iodidum (inn-latin)
ecothiopate iodide (mart.)
dtxcid502976
s01eb03
2-(diethoxyphosphorylsulfanyl)-n,n,n-trimethylethylaminium iodide
echothiophate iodide (usp impurity)
2-((diethoxyphosphoryl)sulfanyl)-n,n,n-trimethylethanaminium iodide
acothiopate (cation)
iodure d'ecothiopate (inn-french)
echothiophate iodide (usp monograph)
ioduro de ecotiopato (inn-spanish)
(2-mercaptoethyl)trimethylammonium iodide s-ester with o,o-diethyl phosphorothioate, diethoxyphosphoryl-thiocholine iodide
2-((diethoxyphosphinyl)thio)-n,n,n-trimethylethanaminium iodide

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" The ocular drugs causing serious adverse ocular or systemic side effects in children include glaucoma medications, corticosteroids, phenylephrine, and the anticholinergic cycloplegics."( How safe are ocular drugs in pediatrics?
Palmer, EA, 1986
)
0.27
" Pretreatment with clonidine protected against several toxic manifestations of soman, but had little effect on echothiophate toxicity."( Clonidine protection from soman and echothiophate toxicity in mice.
Aronstam, RS; Buccafusco, JJ; Smith, MD, 1986
)
0.27

Dosage Studied

ExcerptRelevanceReference
"Iris damage in the area with loop contact can be prevented by lowering the dosage of steroids."( Management of some complications of the medallion circular loop lens.
Dethmers, HW, 1978
)
0.26
" Dose-response studies with acetylcholine were done on viable pancreas fragments from nine human donors, without pancreatic disease (group I)."( Organophosphate increases the sensitivity of human exocrine pancreas to acetylcholine.
Borner, JW; Dressel, TD; Goodale, RL; Kandalaft, K; Liu, S; Manivel, C; Sutherland, DE, 1991
)
0.28
" The treated to control eye ratios for the number of binding sites and accommodative response to pilocarpine were correlated and the plot of log treated to control binding site ratio versus treated to control accommodation ratio resembled a dose-response curve."( Accommodation and ciliary muscle muscarinic receptors after echothiophate.
Croft, MA; Erickson-Lamy, K; Kaufman, PL; Polansky, JR, 1991
)
0.28
" In 2-h dose-response studies, there was a fivefold increase in sensitivity to acetylcholine when fragments were preincubated 1 h with iso-OMPA."( Inhibition of acetyl- and butyrylcholinesterase and amylase release from canine pancreas.
Borner, JW; Dressel, TD; Goodale, RL; Miller, J; Oguchi, Y, 1989
)
0.28
" At intervals up to 77 days after dosing animals were killed and muscle action potentials and endplate potentials were recorded intracellularly in mouse phrenic-nerve/hemidiaphragm preparations."( Electrophysiological and biochemical effects following single doses of organophosphates in the mouse.
Blain, PG; Kelly, SS; Mutch, E; Williams, FM, 1994
)
0.29
" At 7 and 28 days after dosing action potentials and evoked endplate potentials, produced by stimulating the phrenic nerve at 30 Hz, were recorded in diaphragm muscle."( Effects of multiple doses of organophosphates on evoked potentials in mouse diaphragm.
Blain, PG; de Blaquière, GE; Kelly, SS; Williams, FM, 1997
)
0.3
" Mipafox caused an increase in prejunctional (end-plate potential) jitter at 28 days after dosing in both muscles."( A comparison of the electrophysiological effects of two organophosphates, mipafox and ecothiopate, on mouse limb muscles.
Blain, PG; de Blaquière, GE; Kelly, SS; Williams, FM, 1998
)
0.3
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
antiglaucoma drugAny drug which can be used to prevent or alleviate glaucoma, a disease in which the optic nerve is damaged, resulting in progressive, irreversible loss of vision. It is often, though not always, associated with increased pressure of the fluid in the eye.
EC 3.1.1.8 (cholinesterase) inhibitorAn EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of cholinesterase (EC 3.1.1.8).
mioticAn agent causing contraction of the pupil of the eye. Because the size of the pupil is under the antagonistic control of the sympathetic and parasympathetic systems, drugs affecting either system can cause miosis. Drugs that mimic or potentiate the parasympathetic input to the circular constrictor muscle and drugs that inhibit sympathetic input to the radial dilator muscle tend to contract the pupils.
[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 (2)

ClassDescription
iodide salt
quaternary ammonium saltDerivatives of ammonium compounds, (NH4(+))Y(-), in which all four of the hydrogens bonded to nitrogen have been replaced with univalent (usually organyl) groups.
[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]

Bioassays (4)

Assay IDTitleYearJournalArticle
AID1150747Induction of electric eel AChE phosphorylation1976Journal of medicinal chemistry, Jun, Volume: 19, Issue:6
Synthesis and properties of 2-S-(N,N-dialkylamino)ethyl)thio-1,3,2-dioxaphosphorinane 2-oxide and of the corresponding quaternary derivatives as potential nontoxic antiglaucoma agents.
AID1150749Acute toxicity in sc dosed Ness-Ziona mouse assessed as mortality after 24 hrs1976Journal of medicinal chemistry, Jun, Volume: 19, Issue:6
Synthesis and properties of 2-S-(N,N-dialkylamino)ethyl)thio-1,3,2-dioxaphosphorinane 2-oxide and of the corresponding quaternary derivatives as potential nontoxic antiglaucoma agents.
AID1150746Binding affinity to electric eel AChE1976Journal of medicinal chemistry, Jun, Volume: 19, Issue:6
Synthesis and properties of 2-S-(N,N-dialkylamino)ethyl)thio-1,3,2-dioxaphosphorinane 2-oxide and of the corresponding quaternary derivatives as potential nontoxic antiglaucoma agents.
AID1150748Inhibition of electric eel AChE assessed as decrease in thiophenol formation using acetylthiocholine as substrate by Ellman's method1976Journal of medicinal chemistry, Jun, Volume: 19, Issue:6
Synthesis and properties of 2-S-(N,N-dialkylamino)ethyl)thio-1,3,2-dioxaphosphorinane 2-oxide and of the corresponding quaternary derivatives as potential nontoxic antiglaucoma agents.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (363)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990314 (86.50)18.7374
1990's32 (8.82)18.2507
2000's11 (3.03)29.6817
2010's6 (1.65)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 30.05

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 Index30.05 (24.57)
Research Supply Index6.00 (2.92)
Research Growth Index3.95 (4.65)
Search Engine Demand Index45.70 (26.88)
Search Engine Supply Index2.24 (0.95)

This Compound (30.05)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials8 (2.04%)5.53%
Reviews8 (2.04%)6.00%
Case Studies25 (6.36%)4.05%
Observational0 (0.00%)0.25%
Other352 (89.57%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (1)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
Echothiophate Iodide for the Prevention of Progression of Myopia [NCT02544529]Phase 433 participants (Anticipated)Interventional2016-06-30Not yet recruiting
[information is prepared from clinicaltrials.gov, extracted Sep-2024]