Echothiophate

A potent, long-acting irreversible cholinesterase inhibitor used as an ocular hypertensive in the treatment of glaucoma. Occasionally used for accomodative esotropia.

General

Type : Drug, Organophosphate, Sulfur Compound, Organothiophosphate, Trimethylammonium

Chemical_Nomenclature : 2-diethoxyphosphorylsulfanylethyl(trimethyl)azanium

Canonical SMILES : CCOP(=O)(OCC)SCC[N+](C)(C)C

InChI : InChI=1S\/C9H23NO3PS\/c1-6-12-14(11,13-7-2)15-9-8-10(3,4)5\/h6-9H2,1-5H3\/q+1

InChIKey : BJOLKYGKSZKIGU-UHFFFAOYSA-N

Other name(s) : O,O'-diethyl S-ethyltrimethylamine phosphorothiolate iodide  ||  (2-mercaptoethyl) trimethylammonium iodide O,O'diethylphosphorothioate  ||  6736-03-4  ||  Echodide  ||  Phospholine iodide  ||  217-MI, ecothiopate iodide  ||  Ecothiopate  ||  Ecothiopatum  ||  Phospholine  ||  UNII-0F350BVT6S  ||  CHEBI:4753  ||  SCHEMBL1048167  ||  CHEMBL1201341  ||  DB01057


MW : 383.23

Formula : C9H23INO3PS

CAS_number : 513-10-0

PubChem : 10548

UniChem : BJOLKYGKSZKIGU-UHFFFAOYSA-N

IUPHAR : 9074

Wikipedia : Echothiophate

Target

Families : Echothiophate ligand of proteins in family
BCHE

Structure :
2XMD 1XLV 1XLW

Protein :
human-BCHE

References (19)

Title : Steady-State Kinetics of Enzyme-Catalyzed Hydrolysis of Echothiophate, a P-S Bonded Organophosphorus as Monitored by Spectrofluorimetry - Zueva_2020_Molecules_25_
Author(s) : Zueva IV , Lushchekina SV , Daude D , Chabriere E , Masson P
Ref : Molecules , 25 : , 2020
Abstract :
PubMedSearch : Zueva_2020_Molecules_25_
PubMedID: 32192230

Title : X-ray crystallographic snapshots of reaction intermediates in the G117H mutant of human butyrylcholinesterase, a nerve agent target engineered into a catalytic bioscavenger - Nachon_2011_Biochem.J_434_73
Author(s) : Nachon F , Carletti E , Wandhammer M , Nicolet Y , Schopfer LM , Masson P , Lockridge O
Ref : Biochemical Journal , 434 :73 , 2011
Abstract :
PubMedSearch : Nachon_2011_Biochem.J_434_73
PubMedID: 21091433
Gene_locus related to this paper: human-BCHE

Title : Role of water in aging of human butyrylcholinesterase inhibited by echothiophate: the crystal structure suggests two alternative mechanisms of aging - Nachon_2005_Biochemistry_44_1154
Author(s) : Nachon F , Asojo OA , Borgstahl GE , Masson P , Lockridge O
Ref : Biochemistry , 44 :1154 , 2005
Abstract :
PubMedSearch : Nachon_2005_Biochemistry_44_1154
PubMedID: 15667209
Gene_locus related to this paper: human-BCHE

Title : Effects of organophosphates on cholinesterase activity and neurite regeneration in Aplysia - Srivatsan_1999_Chem.Biol.Interact_119-120_371
Author(s) : Srivatsan M
Ref : Chemico-Biological Interactions , 119-120 :371 , 1999
Abstract :
PubMedSearch : Srivatsan_1999_Chem.Biol.Interact_119-120_371
PubMedID: 10421473

Title : A comparison of the electrophysiological effects of two organophosphates, mipafox and ecothiopate, on mouse limb muscles - de Blaquiere_1998_Toxicol.Appl.Pharmacol_150_350
Author(s) : de Blaquiere GE , Williams FM , Blain PG , Kelly SS
Ref : Toxicol Appl Pharmacol , 150 :350 , 1998
Abstract :
PubMedSearch : de Blaquiere_1998_Toxicol.Appl.Pharmacol_150_350
PubMedID: 9653066

Title : Importance of aspartate-70 in organophosphate inhibition, oxime re-activation and aging of human butyrylcholinesterase - Masson_1997_Biochem.J_325_53
Author(s) : Masson P , Froment MT , Bartels CF , Lockridge O
Ref : Biochemical Journal , 325 :53 , 1997
Abstract :
PubMedSearch : Masson_1997_Biochem.J_325_53
PubMedID: 9224629

Title : Acetylcholinesterase promotes regeneration of neurites in cultured adult neurons of Aplysia - Srivatsan_1997_Neurosci_77_921
Author(s) : Srivatsan M , Peretz B
Ref : Neuroscience , 77 :921 , 1997
Abstract :
PubMedSearch : Srivatsan_1997_Neurosci_77_921
PubMedID: 9070763

Title : Cholinergic toxicity resulting from ocular instillation of echothiophate iodide eye drops - Manoguerra_1995_J.Toxicol.Clin.Toxicol_33_463
Author(s) : Manoguerra A , Whitney C , Clark RF , Anderson B , Turchen S
Ref : Journal of Toxicology Clinical Toxicology , 33 :463 , 1995
Abstract :
PubMedSearch : Manoguerra_1995_J.Toxicol.Clin.Toxicol_33_463
PubMedID: 7650771

Title : Site-directed mutagenesis of active site residues reveals plasticity of human butyrylcholinesterase in substrate and inhibitor interactions - Gnatt_1994_J.Neurochem_62_749
Author(s) : Gnatt A , Loewenstein Y , Yaron A , Schwarz M , Soreq H
Ref : Journal of Neurochemistry , 62 :749 , 1994
Abstract :
PubMedSearch : Gnatt_1994_J.Neurochem_62_749
PubMedID: 8294937

Title : Correlation of the anticholinesterase activity of a series of organophosphates with their ability to compete with agonist binding to muscarinic receptors - Ward_1993_Toxicol.Appl.Pharmacol_122_300
Author(s) : Ward TR , Ferris DJ , Tilson HA , Mundy WR
Ref : Toxicology & Applied Pharmacology , 122 :300 , 1993
Abstract :
PubMedSearch : Ward_1993_Toxicol.Appl.Pharmacol_122_300
PubMedID: 8212012

Title : Electroconvulsive therapy and the chronic use of pseudocholinesterase- inhibitor (echothiophate iodide) eye drops for glaucoma. A case report - Messer_1992_Gen.Hosp.Psychiatry_14_56
Author(s) : Messer GJ , Stoudemire A , Knos G , Johnson GC
Ref : General Hospital Psychiatry , 14 :56 , 1992
Abstract :
PubMedSearch : Messer_1992_Gen.Hosp.Psychiatry_14_56
PubMedID: 1730402

Title : Preferential inhibition of acetylcholinesterase molecular forms in rat brain - Ogane_1992_Neurochem.Res_17_489
Author(s) : Ogane N , Giacobini E , Messamore E
Ref : Neurochemical Research , 17 :489 , 1992
Abstract :
PubMedSearch : Ogane_1992_Neurochem.Res_17_489
PubMedID: 1528356

Title : Organophosphate increases the sensitivity of human exocrine pancreas to acetylcholine - Kandalaft_1991_Pancreas_6_398
Author(s) : Kandalaft K , Liu S , Manivel C , Borner JW , Dressel TD , Sutherland DE , Goodale RL
Ref : Pancreas , 6 :398 , 1991
Abstract :
PubMedSearch : Kandalaft_1991_Pancreas_6_398
PubMedID: 1715083

Title : Putative M2 muscarinic receptors of rat heart have high affinity for organophosphorus anticholinesterases - Silveira_1990_Toxicol.Appl.Pharmacol_103_474
Author(s) : Silveira CL , Eldefrawi AT , Eldefrawi ME
Ref : Toxicol Appl Pharmacol , 103 :474 , 1990
Abstract :
PubMedSearch : Silveira_1990_Toxicol.Appl.Pharmacol_103_474
PubMedID: 2339420

Title : Inhibition of acetyl- and butyrylcholinesterase and amylase release from canine pancreas - Oguchi_1989_Pancreas_4_423
Author(s) : Oguchi Y , Dressel TD , Borner JW , Miller J , Goodale RL
Ref : Pancreas , 4 :423 , 1989
Abstract :
PubMedSearch : Oguchi_1989_Pancreas_4_423
PubMedID: 2474812

Title : Clonidine protection from soman and echothiophate toxicity in mice - Aronstam_1986_Life.Sci_39_2097
Author(s) : Aronstam RS , Smith MD , Buccafusco JJ
Ref : Life Sciences , 39 :2097 , 1986
Abstract :
PubMedSearch : Aronstam_1986_Life.Sci_39_2097
PubMedID: 3784771

Title : Activation and blockade of cardiac muscarinic receptors by endogenous acetylcholine and cholinesterase inhibitors - Brown_1982_J.Pharmacol.Exp.Ther_223_20
Author(s) : Brown JH , Wetzel GT , Dunlap J
Ref : Journal of Pharmacology & Experimental Therapeutics , 223 :20 , 1982
Abstract :
PubMedSearch : Brown_1982_J.Pharmacol.Exp.Ther_223_20
PubMedID: 6288918

Title : Serum cholinesterase, serum lipase, and serum amylase levels during long-term echothiophate iodide therapy - Friberg_1981_Am.J.Ophthalmol_91_530
Author(s) : Friberg TR , Thomas JV , Dressel TD
Ref : American Journal of Ophthalmology , 91 :530 , 1981
Abstract :
PubMedSearch : Friberg_1981_Am.J.Ophthalmol_91_530
PubMedID: 6164295

Title : Echothiophate iodide treatment of glaucoma in pregnancy -
Author(s) : Birks DA , Prior VJ , Silk E , Whittaker M
Ref : Archives of Ophthalmology , 79 :283 , 1968
PubMedID: 5640850