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Identification
NameEchothiophate
Accession NumberDB01057  (APRD00942)
TypeSmall Molecule
GroupsApproved
DescriptionA potent, long-acting irreversible cholinesterase inhibitor used as an ocular hypertensive in the treatment of glaucoma. Occasionally used for accomodative esotropia.
Structure
Thumb
Synonyms
2-(Diethoxyphosphorylsulfanyl)ethyl-N,N,N-trimethylazanium iodide
Echothiophate
Ecothiopatum
Phospholine
External Identifiers
  • MI 217
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Phospholine Iodide - Liq Pws 3mg/5mlliquid; powder for solution3 mgophthalmicStorz, Division Of Wyeth Ayerst Canada Inc.1997-04-291999-08-12Canada
Phospholine Iodide - Pws 12.5mg/5mlpowder for solution12.5 mgophthalmicStorz, Division Of Wyeth Ayerst Canada Inc.1997-08-291999-08-12Canada
Phospholine Iodide - Pws 6.25mg/5mlpowder for solution6.25 mgophthalmicStorz, Division Of Wyeth Ayerst Canada Inc.1997-04-292000-08-02Canada
Phospholine Iodide 12.5mg/5mlpowder for solution12.5 mgophthalmicWyeth Ayerst Canada Inc.1994-12-312001-08-30Canada
Phospholine Iodide 3mg/5mlpowder for solution3 mgophthalmicWyeth Ayerst Canada Inc.1998-12-022001-05-07Canada
Phospholine Iodide 6.25mg/5mlpowder for solution6.25 mgophthalmicWyeth Ayerst Canada Inc.1999-10-062001-08-03Canada
Phospholine Iodide OphthalmickitWyeth Pharmaceuticals Inc., a subsidiary of Pfizer Inc.1959-12-04Not applicableUs
Phospholine Iodide Pws 6.25mg/5mlpowder for solution6.25 mgophthalmicWyeth Ayerst Canada Inc.1994-12-311997-08-14Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
EchodideAlcon
Phospholine IodideWyeth-Ayerst
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Echothiophate iodide
ThumbNot applicableDBSALT001098
Categories
UNII0F350BVT6S
CAS number6736-03-4
WeightAverage: 256.323
Monoisotopic: 256.113625809
Chemical FormulaC9H23NO3PS
InChI KeyInChIKey=BJOLKYGKSZKIGU-UHFFFAOYSA-N
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
IUPAC Name
diethyl {[2-(trimethylazaniumyl)ethyl]sulfanyl}phosphonate
SMILES
CCOP(=O)(OCC)SCC[N+](C)(C)C
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as quaternary ammonium salts. These are compounds containing positively charged polyatomic ion of the structure NR4+, R being an alkyl group or an aryl group.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassQuaternary ammonium salts
Sub ClassNot Available
Direct ParentQuaternary ammonium salts
Alternative Parents
Substituents
  • Quaternary ammonium salt
  • Sulfenyl compound
  • Organothiophosphorus compound
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Amine
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Pharmacology
IndicationFor use in the treatment of subacute or chronic angle-closure glaucoma after iridectomy or where surgery is refused or contraindicated.
PharmacodynamicsEchothiophate Iodide is a potent, long-acting cholinesterase inhibitor used as a miotic in the treatment of glaucoma. Echothiophate iodide will depress both plasma and erythrocyte cholinesterase levels in most patients after a few weeks of eyedrop therapy.
Mechanism of actionEchothiophate Iodide is a long-acting cholinesterase inhibitor for topical use which enhances the effect of endogenously liberated acetylcholine in iris, ciliary muscle, and other parasympathetically innervated structures of the eye. Echothiophate iodide binds irreversibly to cholinesterase, and is long acting due to the slow rate of hydrolysis by cholinesterase. It causes miosis, increase in facility of outflow of aqueous humor, fall in intraocular pressure, and potentiation of accommodation.
Related Articles
AbsorptionThis ophthalmic medication may be systemically absorbed.
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicitySide effects include blurred vision or change in near or distant vision and eye pain. LD50: 174 mcg/kg in rats. (MSDS)
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.7708
Blood Brain Barrier+0.91
Caco-2 permeable+0.5098
P-glycoprotein substrateNon-substrate0.6063
P-glycoprotein inhibitor INon-inhibitor0.8482
P-glycoprotein inhibitor IINon-inhibitor0.962
Renal organic cation transporterNon-inhibitor0.7835
CYP450 2C9 substrateNon-substrate0.8237
CYP450 2D6 substrateNon-substrate0.7603
CYP450 3A4 substrateNon-substrate0.5252
CYP450 1A2 substrateNon-inhibitor0.8317
CYP450 2C9 inhibitorNon-inhibitor0.7972
CYP450 2D6 inhibitorNon-inhibitor0.8991
CYP450 2C19 inhibitorNon-inhibitor0.8013
CYP450 3A4 inhibitorNon-inhibitor0.9093
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9377
Ames testNon AMES toxic0.8524
CarcinogenicityCarcinogens 0.7021
BiodegradationReady biodegradable0.9528
Rat acute toxicity4.3595 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5816
hERG inhibition (predictor II)Non-inhibitor0.7263
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Liquid; powder for solutionophthalmic3 mg
Powder for solutionophthalmic12.5 mg
Powder for solutionophthalmic3 mg
Kit
Powder for solutionophthalmic6.25 mg
Prices
Unit descriptionCostUnit
Phospholine iodide 0.125%16.09USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US2911430 No1958-01-151978-01-15Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point124-124.5Fitch, H.M.; U.S. Patent 2,911,430; November 3, 1959; assigned to Campbell Pharmaceuticals, Inc.
water solubilitySolubleNot Available
logP-2.25Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.297 mg/mLALOGPS
logP-2.1ALOGPS
logP-3.1ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)-8.2ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.53 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity78.14 m3·mol-1ChemAxon
Polarizability27.65 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Fitch, H.M.; U.S. Patent 2,911,430; November 3, 1959; assigned to Campbell Pharmaceuticals, Inc.

General References
  1. Reddy RH: Echothiophate iodide: its use in accommodative esotropia (high Ac/A ratio). Indian J Ophthalmol. 1982 Jul;30(4):225. [PubMed:7166393 ]
  2. Schmidt KG, Horowitz Y, Buckman G, Segev E, Levinger E, Geyer O: Lowering of IOP by echothiophate iodide in pseudophakic eyes with glaucoma. Curr Eye Res. 2010 Aug;35(8):698-702. doi: 10.3109/02713681003794076. [PubMed:20673046 ]
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (45 KB)
MSDSDownload (87.9 KB)
Interactions
Drug Interactions
Drug
4-AndrostenedioneThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Echothiophate.
AcebutololEchothiophate may increase the bradycardic activities of Acebutolol.
AcetylcholineThe risk or severity of adverse effects can be increased when Echothiophate is combined with Acetylcholine.
AclidiniumThe therapeutic efficacy of Aclidinium can be decreased when used in combination with Echothiophate.
AlclometasoneThe risk or severity of adverse effects can be increased when Alclometasone is combined with Echothiophate.
AldosteroneThe risk or severity of adverse effects can be increased when Aldosterone is combined with Echothiophate.
AlprenololEchothiophate may increase the bradycardic activities of Alprenolol.
AmcinonideThe risk or severity of adverse effects can be increased when Amcinonide is combined with Echothiophate.
Anisotropine MethylbromideThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Echothiophate.
ArecolineThe risk or severity of adverse effects can be increased when Echothiophate is combined with Arecoline.
ArotinololEchothiophate may increase the bradycardic activities of Arotinolol.
AtenololEchothiophate may increase the bradycardic activities of Atenolol.
Atracurium besylateThe therapeutic efficacy of Atracurium besylate can be decreased when used in combination with Echothiophate.
AtropineThe therapeutic efficacy of Atropine can be decreased when used in combination with Echothiophate.
Beclomethasone dipropionateThe risk or severity of adverse effects can be increased when Beclomethasone dipropionate is combined with Echothiophate.
BefunololEchothiophate may increase the bradycardic activities of Befunolol.
BenactyzineThe therapeutic efficacy of Benactyzine can be decreased when used in combination with Echothiophate.
BenzatropineThe therapeutic efficacy of Benzatropine can be decreased when used in combination with Echothiophate.
BetamethasoneThe risk or severity of adverse effects can be increased when Betamethasone is combined with Echothiophate.
BetaxololEchothiophate may increase the bradycardic activities of Betaxolol.
BethanecholThe risk or severity of adverse effects can be increased when Echothiophate is combined with Bethanechol.
BevantololEchothiophate may increase the bradycardic activities of Bevantolol.
BiperidenThe therapeutic efficacy of Biperiden can be decreased when used in combination with Echothiophate.
BisoprololEchothiophate may increase the bradycardic activities of Bisoprolol.
BopindololEchothiophate may increase the bradycardic activities of Bopindolol.
BudesonideThe risk or severity of adverse effects can be increased when Budesonide is combined with Echothiophate.
BufuralolEchothiophate may increase the bradycardic activities of Bufuralol.
BupranololEchothiophate may increase the bradycardic activities of Bupranolol.
CarbacholThe risk or severity of adverse effects can be increased when Echothiophate is combined with Carbachol.
CarteololEchothiophate may increase the bradycardic activities of Carteolol.
CarvedilolEchothiophate may increase the bradycardic activities of Carvedilol.
CeliprololEchothiophate may increase the bradycardic activities of Celiprolol.
CevimelineThe risk or severity of adverse effects can be increased when Echothiophate is combined with Cevimeline.
ChlorphenoxamineThe therapeutic efficacy of Chlorphenoxamine can be decreased when used in combination with Echothiophate.
CiclesonideThe risk or severity of adverse effects can be increased when Ciclesonide is combined with Echothiophate.
Clobetasol propionateThe risk or severity of adverse effects can be increased when Clobetasol propionate is combined with Echothiophate.
ClocortoloneThe risk or severity of adverse effects can be increased when Clocortolone is combined with Echothiophate.
Cortisone acetateThe risk or severity of adverse effects can be increased when Cortisone acetate is combined with Echothiophate.
CyclopentolateThe therapeutic efficacy of Cyclopentolate can be decreased when used in combination with Echothiophate.
DarifenacinThe therapeutic efficacy of Darifenacin can be decreased when used in combination with Echothiophate.
DehydroepiandrosteroneThe risk or severity of adverse effects can be increased when Dehydroepiandrosterone is combined with Echothiophate.
dehydroepiandrosterone sulfateThe risk or severity of adverse effects can be increased when dehydroepiandrosterone sulfate is combined with Echothiophate.
DesloratadineThe therapeutic efficacy of Desloratadine can be decreased when used in combination with Echothiophate.
DesoximetasoneThe risk or severity of adverse effects can be increased when Desoximetasone is combined with Echothiophate.
Desoxycorticosterone acetateThe risk or severity of adverse effects can be increased when Desoxycorticosterone acetate is combined with Echothiophate.
DexamethasoneThe risk or severity of adverse effects can be increased when Dexamethasone is combined with Echothiophate.
Dexamethasone isonicotinateThe risk or severity of adverse effects can be increased when Dexamethasone isonicotinate is combined with Echothiophate.
DexetimideThe therapeutic efficacy of Dexetimide can be decreased when used in combination with Echothiophate.
DicyclomineThe therapeutic efficacy of Dicyclomine can be decreased when used in combination with Echothiophate.
DiflorasoneThe risk or severity of adverse effects can be increased when Diflorasone is combined with Echothiophate.
DifluocortoloneThe risk or severity of adverse effects can be increased when Difluocortolone is combined with Echothiophate.
DifluprednateThe risk or severity of adverse effects can be increased when Difluprednate is combined with Echothiophate.
DipyridamoleThe therapeutic efficacy of Echothiophate can be decreased when used in combination with Dipyridamole.
EPIBATIDINEThe risk or severity of adverse effects can be increased when Echothiophate is combined with EPIBATIDINE.
EquileninThe risk or severity of adverse effects can be increased when Equilenin is combined with Echothiophate.
EquilinThe risk or severity of adverse effects can be increased when Equilin is combined with Echothiophate.
EsmololEchothiophate may increase the bradycardic activities of Esmolol.
EstroneThe risk or severity of adverse effects can be increased when Estrone is combined with Echothiophate.
EthopropazineThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Echothiophate.
FesoterodineThe therapeutic efficacy of Fesoterodine can be decreased when used in combination with Echothiophate.
FludrocortisoneThe risk or severity of adverse effects can be increased when Fludrocortisone is combined with Echothiophate.
FlumethasoneThe risk or severity of adverse effects can be increased when Flumethasone is combined with Echothiophate.
FlunisolideThe risk or severity of adverse effects can be increased when Flunisolide is combined with Echothiophate.
Fluocinolone AcetonideThe risk or severity of adverse effects can be increased when Fluocinolone Acetonide is combined with Echothiophate.
FluocinonideThe risk or severity of adverse effects can be increased when Fluocinonide is combined with Echothiophate.
FluocortoloneThe risk or severity of adverse effects can be increased when Fluocortolone is combined with Echothiophate.
FluorometholoneThe risk or severity of adverse effects can be increased when Fluorometholone is combined with Echothiophate.
FluprednideneThe risk or severity of adverse effects can be increased when Fluprednidene is combined with Echothiophate.
FluprednisoloneThe risk or severity of adverse effects can be increased when Fluprednisolone is combined with Echothiophate.
FlurandrenolideThe risk or severity of adverse effects can be increased when Flurandrenolide is combined with Echothiophate.
Fluticasone furoateThe risk or severity of adverse effects can be increased when Fluticasone furoate is combined with Echothiophate.
Fluticasone PropionateThe risk or severity of adverse effects can be increased when Fluticasone Propionate is combined with Echothiophate.
Gallamine TriethiodideThe therapeutic efficacy of Gallamine Triethiodide can be decreased when used in combination with Echothiophate.
GlycopyrroniumThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Echothiophate.
GTS-21The risk or severity of adverse effects can be increased when Echothiophate is combined with GTS-21.
HexamethoniumThe therapeutic efficacy of Hexamethonium can be decreased when used in combination with Echothiophate.
HomatropineThe therapeutic efficacy of Homatropine can be decreased when used in combination with Echothiophate.
HydrocortisoneThe risk or severity of adverse effects can be increased when Hydrocortisone is combined with Echothiophate.
HyoscyamineThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Echothiophate.
IndenololEchothiophate may increase the bradycardic activities of Indenolol.
Ipratropium bromideThe therapeutic efficacy of Ipratropium bromide can be decreased when used in combination with Echothiophate.
LabetalolEchothiophate may increase the bradycardic activities of Labetalol.
LobelineThe risk or severity of adverse effects can be increased when Echothiophate is combined with Lobeline.
MecamylamineThe therapeutic efficacy of Mecamylamine can be decreased when used in combination with Echothiophate.
MedrysoneThe risk or severity of adverse effects can be increased when Medrysone is combined with Echothiophate.
MelengestrolThe risk or severity of adverse effects can be increased when Melengestrol is combined with Echothiophate.
MethacholineThe risk or severity of adverse effects can be increased when Echothiophate is combined with Methacholine.
MethanthelineThe therapeutic efficacy of Methantheline can be decreased when used in combination with Echothiophate.
MethylprednisoloneThe risk or severity of adverse effects can be increased when Methylprednisolone is combined with Echothiophate.
MetixeneThe therapeutic efficacy of Metixene can be decreased when used in combination with Echothiophate.
MetoprololEchothiophate may increase the bradycardic activities of Metoprolol.
MivacuriumEchothiophate may decrease the neuromuscular blocking activities of Mivacurium.
MometasoneThe risk or severity of adverse effects can be increased when Mometasone is combined with Echothiophate.
N-butylscopolammonium bromideThe therapeutic efficacy of N-butylscopolammonium bromide can be decreased when used in combination with Echothiophate.
NadololEchothiophate may increase the bradycardic activities of Nadolol.
NicotineThe risk or severity of adverse effects can be increased when Echothiophate is combined with Nicotine.
Nicotine bitartrateThe risk or severity of adverse effects can be increased when Echothiophate is combined with Nicotine bitartrate.
NVA237The therapeutic efficacy of NVA237 can be decreased when used in combination with Echothiophate.
OrphenadrineThe therapeutic efficacy of Orphenadrine can be decreased when used in combination with Echothiophate.
OxprenololEchothiophate may increase the bradycardic activities of Oxprenolol.
OxybutyninThe therapeutic efficacy of Oxybutynin can be decreased when used in combination with Echothiophate.
OxyphenoniumThe therapeutic efficacy of Oxyphenonium can be decreased when used in combination with Echothiophate.
PancuroniumThe therapeutic efficacy of Pancuronium can be decreased when used in combination with Echothiophate.
ParamethasoneThe risk or severity of adverse effects can be increased when Paramethasone is combined with Echothiophate.
PenbutololEchothiophate may increase the bradycardic activities of Penbutolol.
PentoliniumThe therapeutic efficacy of Pentolinium can be decreased when used in combination with Echothiophate.
PilocarpineThe risk or severity of adverse effects can be increased when Echothiophate is combined with Pilocarpine.
PindololEchothiophate may increase the bradycardic activities of Pindolol.
PipecuroniumThe therapeutic efficacy of Pipecuronium can be decreased when used in combination with Echothiophate.
PirenzepineThe therapeutic efficacy of Pirenzepine can be decreased when used in combination with Echothiophate.
PractololEchothiophate may increase the bradycardic activities of Practolol.
PrednicarbateThe risk or severity of adverse effects can be increased when Prednicarbate is combined with Echothiophate.
PrednisoloneThe risk or severity of adverse effects can be increased when Prednisolone is combined with Echothiophate.
PrednisoneThe risk or severity of adverse effects can be increased when Prednisone is combined with Echothiophate.
PregnenoloneThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Echothiophate.
ProcyclidineThe therapeutic efficacy of Procyclidine can be decreased when used in combination with Echothiophate.
PropanthelineThe therapeutic efficacy of Propantheline can be decreased when used in combination with Echothiophate.
PropranololEchothiophate may increase the bradycardic activities of Propranolol.
QuinidineThe therapeutic efficacy of Quinidine can be decreased when used in combination with Echothiophate.
RapacuroniumEchothiophate may decrease the neuromuscular blocking activities of Rapacuronium.
RimexoloneThe risk or severity of adverse effects can be increased when Rimexolone is combined with Echothiophate.
ScopolamineThe therapeutic efficacy of Scopolamine can be decreased when used in combination with Echothiophate.
Scopolamine butylbromideThe therapeutic efficacy of Scopolamine butylbromide can be decreased when used in combination with Echothiophate.
SolifenacinThe therapeutic efficacy of Solifenacin can be decreased when used in combination with Echothiophate.
SotalolEchothiophate may increase the bradycardic activities of Sotalol.
SuccinylcholineThe serum concentration of Succinylcholine can be increased when it is combined with Echothiophate.
TimololEchothiophate may increase the bradycardic activities of Timolol.
TiotropiumThe therapeutic efficacy of Tiotropium can be decreased when used in combination with Echothiophate.
TixocortolThe risk or severity of adverse effects can be increased when Tixocortol is combined with Echothiophate.
TolterodineThe therapeutic efficacy of Tolterodine can be decreased when used in combination with Echothiophate.
TriamcinoloneThe risk or severity of adverse effects can be increased when Triamcinolone is combined with Echothiophate.
TrihexyphenidylThe therapeutic efficacy of Trihexyphenidyl can be decreased when used in combination with Echothiophate.
TrimethaphanThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Echothiophate.
TropicamideThe therapeutic efficacy of Tropicamide can be decreased when used in combination with Echothiophate.
TrospiumThe therapeutic efficacy of Trospium can be decreased when used in combination with Echothiophate.
TubocurarineThe therapeutic efficacy of Tubocurarine can be decreased when used in combination with Echothiophate.
UmeclidiniumThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with Echothiophate.
VareniclineThe risk or severity of adverse effects can be increased when Echothiophate is combined with Varenicline.
VecuroniumThe therapeutic efficacy of Vecuronium can be decreased when used in combination with Echothiophate.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Identical protein binding
Specific Function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular Weight:
68417.575 Da
References
  1. Henderson EG, Post-Munson DJ, Reynolds LS, Epstein PM: Echothiophate and cogeners decrease the voltage dependence of end-plate current decay in frog skeletal muscle. J Pharmacol Exp Ther. 1989 Dec;251(3):810-6. [PubMed:2481033 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23