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Identification
NameEchothiophate
Accession NumberDB01057  (APRD00942)
TypeSmall Molecule
GroupsApproved
Description

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

Structure
Thumb
Synonyms
SynonymLanguageCode
2-(Diethoxyphosphorylsulfanyl)ethyl-N,N,N-trimethylazanium iodideNot AvailableIUPAC
EchothiophateNot AvailableNot Available
EcothiopatumNot AvailableNot Available
PhospholineNot AvailableNot Available
Salts
Name/CAS Structure Properties
Ecothiopate Iodide
Thumb Not applicable DBSALT001098
Brand names
NameCompany
EchodideAlcon
Phospholine IodideWyeth-Ayerst
Brand mixtures
Brand NameIngredients
Phospholine Iodide PWS 3mg/5mlDiluent + Echothiophate Iodide
Categories
CAS number6736-03-4
WeightAverage: 256.323
Monoisotopic: 256.113625809
Chemical FormulaC9H23NO3PS
InChI KeyBJOLKYGKSZKIGU-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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganonitrogen Compounds
ClassAmines
SubclassPolyamines
Direct parentPolyamines
Alternative parentsOrganothiophosphorus Compounds
SubstituentsNot Available
Classification descriptionThis compound belongs to the polyamines. These are compounds containing more than one amine group.
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.
AbsorptionThis ophthalmic medication may be systemically absorbed.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
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
Property Value Probability
Human Intestinal Absorption - 0.7708
Blood Brain Barrier + 0.91
Caco-2 permeable + 0.5098
P-glycoprotein substrate Non-substrate 0.6063
P-glycoprotein inhibitor I Non-inhibitor 0.8482
P-glycoprotein inhibitor II Non-inhibitor 0.962
Renal organic cation transporter Non-inhibitor 0.7835
CYP450 2C9 substrate Non-substrate 0.8237
CYP450 2D6 substrate Non-substrate 0.7603
CYP450 3A4 substrate Non-substrate 0.5252
CYP450 1A2 substrate Non-inhibitor 0.8317
CYP450 2C9 substrate Non-inhibitor 0.7972
CYP450 2D6 substrate Non-inhibitor 0.8991
CYP450 2C19 substrate Non-inhibitor 0.8013
CYP450 3A4 substrate Non-inhibitor 0.9093
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9377
Ames test Non AMES toxic 0.8524
Carcinogenicity Carcinogens 0.7021
Biodegradation Ready biodegradable 0.9528
Rat acute toxicity 4.3595 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.5816
hERG inhibition (predictor II) Non-inhibitor 0.7263
Pharmacoeconomics
Manufacturers
  • Wyeth pharmaceuticals inc
Packagers
Dosage forms
FormRouteStrength
Solution / dropsOphthalmic
Prices
Unit descriptionCostUnit
Phospholine iodide 0.125%16.09USDml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
United States29114301958-01-151978-01-15
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 Solubility0.297ALOGPS
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 FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

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

General Reference
  1. 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. Pubmed 20673046
  2. Reddy RH: Echothiophate iodide: its use in accommodative esotropia (high Ac/A ratio). Indian J Ophthalmol. 1982 Jul;30(4):225. Pubmed
External Links
ResourceLink
KEGG DrugD02193
PubChem Compound10547
PubChem Substance46505944
ChEBI4753
ChEMBLCHEMBL1201341
Therapeutic Targets DatabaseDAP000962
PharmGKBPA164743139
Drug Product Database2238076
RxListhttp://www.rxlist.com/cgi/generic2/phospholine.htm
Drugs.comhttp://www.drugs.com/cdi/echothiophate-eye-drops.html
WikipediaEchothiophate
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelshow(45 KB)
MSDSshow(87.9 KB)
Interactions
Drug Interactions
Drug
SuccinylcholineEchothiophate iodide may increase the effect of succinylcholine.
Food InteractionsNot Available

Targets

1. Cholinesterase

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Cholinesterase P06276 Details

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
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on December 16, 2014 16:25