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Inhibitor Report for: 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
Stucture | 3 structures: 2XMD, 1XLV, 1XLW
Protein | human-BCHE

References:
Search PubMed for references concerning: Echothiophate

14 more
    Title: Steady-State Kinetics of Enzyme-Catalyzed Hydrolysis of Echothiophate, a P-S Bonded Organophosphorus as Monitored by Spectrofluorimetry
    Zueva IV, Lushchekina SV, Daude D, Chabriere E, Masson P
    Ref: Molecules, 25:, 2020 : PubMed

            

    Title: Site-directed mutagenesis of active site residues reveals plasticity of human butyrylcholinesterase in substrate and inhibitor interactions
    Gnatt A, Loewenstein Y, Yaron A, Schwarz M, Soreq H
    Ref: Journal of Neurochemistry, 62:749, 1994 : PubMed

            

    Title: Organophosphate increases the sensitivity of human exocrine pancreas to acetylcholine
    Kandalaft K, Liu S, Manivel C, Borner JW, Dressel TD, Sutherland DE, Goodale RL
    Ref: Pancreas, 6:398, 1991 : PubMed

            


human-BCHE
MutationKiKsiIc50SubstrateConditionPaper
> Mutations for human-BCHE (9)

WT Kinetics
Kinetic parametersKiKsiIc50SubstrateConditionsPapers
human-BCHE--0.27 uM Butyrylthiocholine100mM Na phosphate pH7.4 T22C Gnatt_1994_J.Neurochem_62_749