Echothiophate
Basic information
- CAS
6736-03-4- Standard SMILES
CCOP(=O)(OCC)SCC[N+](C)(C)C- InChIKey
BJOLKYGKSZKIGU-UHFFFAOYSA-N- Molecular formula
- C9H23NO3PS+
- Average molar mass
- 256.33 g/mol
- Monoisotopic mass
- 256.11362677
Overview
Ecothiopate is the phosphorothioate obtained by formal condensation of diethyl phosphate with N,N,N-trimethyl-2-sulfanylethanaminium. An irreversible acetylcholinesterase inhibitor, its iodide salt is used an ocular antihypertensive in the treatment of open-angle glaucoma, particularly when other drugs have proved inadequate. It has a role as an EC 3.1.1.8 (cholinesterase) inhibitor and a miotic. It is a quaternary ammonium ion, a member of phosphocholines and an organic thiophosphate.
Names & identifiers
- Preferred name
- Echothiophate
- IUPAC
- 2-diethoxyphosphorylsulfanylethyl(trimethyl)azanium
- English name
- PHOSPHOLINE
- Molecular formula
- C9H23NO3PS+
- Molecular weight
- 256.32
Names & synonyms
EchothiophateEcothiopateEcothiopatum6736-03-4Echothiophate ionEcothiopate cationEchothiophate cation0F350BVT6SBRN 1794025UNII-0F350BVT6SCHEBI:4753AMMONIUM, (2-MERCAPTOETHYL)TRIMETHYL-, S-ESTER with O,O-DIETHYLPHOSPHOROTHIOATE
Show more names
2-(Diethoxyphosphinylthio)ethyltrimethylaminium2-[(Diethoxyphosphinyl)thio]-N,N,N-trimethylethanaminium
(2-diethoxyphosphinylthioethyl)trimethylammonium(2-Mercaptoethyl)trimethylammonium S-ester with O,O'-diethylphosphorothioateEthanaminium, 2-[(diethoxyphosphinyl)thio]-N,N,N-trimethyl-ETHANAMINIUM, 2-((DIETHOXYPHOSPHINYL)THIO)-N,N,N-TRIMETHYL-2-((diethoxyphosphoryl)sulfanyl)-N,N,N-trimethylethanaminium2-[(diethoxyphosphoryl)sulfanyl]-N,N,N-trimethylethanaminiumRefChem:569672-diethoxyphosphorylsulfanylethyl(trimethyl)azanium
Database identifiers
- CAS
6736-03-4- PubChem CID
- 10548
- ChEMBL
CHEMBL1201341- ChEBI
Properties
Computed structural properties
- XLogP
- 1
- Topological polar surface area
- 60.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 8
- Heavy atoms
- 15
- Formal charge
- 1
- Complexity
- 208
Experimental & physicochemical properties
LogP-2.25
Solubility
Soluble
2.97e-01 g/L
Human DrugsBreast Feeding; Lactation; Cholinesterase Inhibitors; Miotics; Parasympathomimetics
Melting Point
124-124.5
138 °C
Physical DescriptionSolid
Physicochemical properties
- FDA UNII
- 0 F350BVT6S · 0F350BVT6S
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Chemistry & industry
Pharmacology
ATC Code
S - Sensory organs
QS - Sensory organs
Pharmacodynamics
Echothiophate 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 Action
Echothiophate 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.
FDA Pharmacological Classification
0F350BVT6S
ECHOTHIOPHATE
Established Pharmacologic Class [EPC] - Cholinesterase Inhibitor
Mechanisms of Action [MoA] - Cholinesterase Inhibitors
Chemical Structure [CS] - Iodine
Echothiophate is a Cholinesterase Inhibitor. The mechanism of action of echothiophate is as a Cholinesterase Inhibitor.
Absorption, Distribution and ExcretionThis ophthalmic medication may be systemically absorbed.
Cellular LocationsCytoplasm
Applications
UsesCholinergic (ophthalmic).
Additional notes
DefinitionChEBI: The phosphorothioate obtained by formal condensation of diethyl phosphate with N,N,N-trimethyl-2-sulfanylethanaminium. An irreversible acetylcholinesterase inhibitor, its iodide salt is used an ocula antihypertensive in the treatment of open-angle glaucoma, particularly when other drugs have proved inadequate.
Related reactions
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Compound notes
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