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Details

Stereochemistry ACHIRAL
Molecular Formula C9H23NO3PS
Molecular Weight 256.324
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 1

SHOW SMILES / InChI
Structure of ECHOTHIOPHATE

SMILES

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

InChI

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

HIDE SMILES / InChI
Echothiophate is a potent, long-acting irreversible cholinesterase inhibitor used as an ocular hypertensive in the treatment of glaucoma. Occasionally used for accomodative esotropia. Echothiophate iodide for ophthalmic solution will depress both plasma and erythrocyte cholinesterase levels in most patients after a few weeks of eye drop therapy by binding irreversibly to cholinesterase, and thus 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.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
PHOSPHOLINE IODIDE

Approved Use

Glaucoma Chronic open-angle glaucoma. Subacute or chronic angle-closure glaucoma after iridectomy or where surgery is refused or contraindicated. Certain non-uveitic secondary types of glaucoma, especially glaucoma following cataract surgery. Accommodative Esotropia Concomitant esotropias with a significant accommodative component.

Launch Date

-3.00240011E11
Palliative
PHOSPHOLINE IODIDE

Approved Use

Glaucoma Chronic open-angle glaucoma. Subacute or chronic angle-closure glaucoma after iridectomy or where surgery is refused or contraindicated. Certain non-uveitic secondary types of glaucoma, especially glaucoma following cataract surgery. Accommodative Esotropia Concomitant esotropias with a significant accommodative component.

Launch Date

-3.00240011E11
PubMed

PubMed

TitleDatePubMed
Echothiophate iodide: its use in accommodative esotropia (high Ac/A ratio).
1982 Jul
Is succinylcholine appropriate or obsolete in the intensive care unit?
2001 Oct
A non-cholinergic, trophic action of acetylcholinesterase on hippocampal neurones in vitro: molecular mechanisms.
2002
DNA sequence of butyrylcholinesterase from the rat: expression of the protein and characterization of the properties of rat butyrylcholinesterase.
2002 Jun 15
Screening assays for cholinesterases resistant to inhibition by organophosphorus toxicants.
2004 Jun 1
Stereoselectivity toward VX is determined by interactions with residues of the acyl pocket as well as of the peripheral anionic site of AChE.
2004 Sep 7
Albumin, a new biomarker of organophosphorus toxicant exposure, identified by mass spectrometry.
2005 Feb
Role of water in aging of human butyrylcholinesterase inhibited by echothiophate: the crystal structure suggests two alternative mechanisms of aging.
2005 Feb 1
Butyrylcholinesterase, paraoxonase, and albumin esterase, but not carboxylesterase, are present in human plasma.
2005 Nov 25
Function-specific blockage of M(1) and M(3) muscarinic acetylcholine receptors by VX and echothiophate.
2006 Apr 26
Mutant of Bungarus fasciatus acetylcholinesterase with low affinity and low hydrolase activity toward organophosphorus esters.
2006 Sep
Aging pathways for organophosphate-inhibited human butyrylcholinesterase, including novel pathways for isomalathion, resolved by mass spectrometry.
2007 Nov
Kinetic analysis of butyrylcholinesterase-catalyzed hydrolysis of acetanilides.
2007 Sep
Five tyrosines and two serines in human albumin are labeled by the organophosphorus agent FP-biotin.
2008 Sep
A phase II clinical trial to assess the safety of clonidine in acute organophosphorus pesticide poisoning.
2009 Aug 20
Patents

Sample Use Guides

Early Chronic Simple Glaucoma: echothiophate iodide for ophthalmic solution 0.03% instilled twice a day, just before retiring and in the morning, may be prescribed advantageously for cases of early chronic simple glaucoma that are not controlled around-the-clock with other less potent agents. Because of prolonged action, control during the night and early morning hours may then sometimes be obtained. A change in therapy is indicated if, at any time, the tension fails to remain at an acceptable level on this regimen. Advanced Chronic Simple Glaucoma and Glaucoma Secondary to Cataract Surgery: these cases may respond satisfactorily to echothiophate iodide for ophthalmic solution 0.03% twice a day as above. When the patient is being transferred to echothiophate iodide for ophthalmic solution because of unsatisfactory control with pilocarpine, carbachol, epinephrine, etc., one of the higher strengths, 0.06%, 0.125%, or 0.25% will usually be needed. In this case, a brief trial with the 0.03% eyedrops will be advantageous in that the higher strengths will then be more easily tolerated. Concomitant Therapy: echothiophate iodide for ophthalmic solution may be used concomitantly with epinephrine, a carbonic anhydrase inhibitor, or both. Technique – Good technique in the administration of echothiophate iodide for ophthalmic solution requires that finger pressure at the inner canthus should be exerted for a minute or two following instillation of the eyedrops, to minimize drainage into the nose and throat. Excess solution around the eye should be removed with tissue and any medication on the hands should be rinsed off. Accommodative Esotropia (Pediatric Use) In Diagnosis: one drop of 0.125% may be instilled once a day in both eyes on retiring, for a period of two or three weeks. If the esotropia is accommodative, a favorable response will usually be noted which may begin within a few hours. In Treatment – Echothiophate iodide for ophthalmic solution is prescribed at the lowest concentration and frequency which gives satisfactory results. After the initial period of treatment for diagnostic purposes, the schedule may be reduced to 0.125% every other day or 0.06% every day. These dosages can often be gradually lowered as treatment progresses. The 0.03% strength has proven to be effective in some cases. The maximum usually recommended dosage is 0.125% once a day, although more intensive therapy has been used for short periods.
Route of Administration: Other
In Vitro Use Guide
Unknown
Name Type Language
ECHOTHIOPHATE
Common Name English
ECHOTHIOPHATE ION
Common Name English
ECHOTHIOPHATE CATION
Common Name English
PHOSPHOLINE
Systematic Name English
ETHANAMINIUM, 2-((DIETHOXYPHOSPHINYL)THIO)-N,N,N-TRIMETHYL-
Systematic Name English
AMMONIUM, (2-MERCAPTOETHYL)TRIMETHYL-, S-ESTER WITH O,O-DIETHYLPHOSPHOROTHIOATE
Common Name English
ECOTHIOPATE [WHO-DD]
Common Name English
ECOTHIOPATE CATION
Common Name English
ECOTHIOPATE
WHO-DD  
Common Name English
Classification Tree Code System Code
WHO-ATC S01EB03
Created by admin on Sat Jun 26 15:40:05 UTC 2021 , Edited by admin on Sat Jun 26 15:40:05 UTC 2021
NCI_THESAURUS C47796
Created by admin on Sat Jun 26 15:40:05 UTC 2021 , Edited by admin on Sat Jun 26 15:40:05 UTC 2021
NDF-RT N0000000177
Created by admin on Sat Jun 26 15:40:05 UTC 2021 , Edited by admin on Sat Jun 26 15:40:05 UTC 2021
NDF-RT N0000007196
Created by admin on Sat Jun 26 15:40:05 UTC 2021 , Edited by admin on Sat Jun 26 15:40:05 UTC 2021
NDF-RT N0000175723
Created by admin on Sat Jun 26 15:40:05 UTC 2021 , Edited by admin on Sat Jun 26 15:40:05 UTC 2021
WHO-VATC QS01EB03
Created by admin on Sat Jun 26 15:40:05 UTC 2021 , Edited by admin on Sat Jun 26 15:40:05 UTC 2021
Code System Code Type Description
FDA UNII
0F350BVT6S
Created by admin on Sat Jun 26 15:40:05 UTC 2021 , Edited by admin on Sat Jun 26 15:40:05 UTC 2021
PRIMARY
EVMPD
SUB01856MIG
Created by admin on Sat Jun 26 15:40:05 UTC 2021 , Edited by admin on Sat Jun 26 15:40:05 UTC 2021
PRIMARY
PUBCHEM
10548
Created by admin on Sat Jun 26 15:40:05 UTC 2021 , Edited by admin on Sat Jun 26 15:40:05 UTC 2021
PRIMARY
LACTMED
Echothiophate
Created by admin on Sat Jun 26 15:40:05 UTC 2021 , Edited by admin on Sat Jun 26 15:40:05 UTC 2021
PRIMARY
RXCUI
89778
Created by admin on Sat Jun 26 15:40:05 UTC 2021 , Edited by admin on Sat Jun 26 15:40:05 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C76040
Created by admin on Sat Jun 26 15:40:05 UTC 2021 , Edited by admin on Sat Jun 26 15:40:05 UTC 2021
PRIMARY
CAS
6736-03-4
Created by admin on Sat Jun 26 15:40:05 UTC 2021 , Edited by admin on Sat Jun 26 15:40:05 UTC 2021
PRIMARY
WIKIPEDIA
Echothiophate
Created by admin on Sat Jun 26 15:40:05 UTC 2021 , Edited by admin on Sat Jun 26 15:40:05 UTC 2021
PRIMARY
DRUG CENTRAL
982
Created by admin on Sat Jun 26 15:40:05 UTC 2021 , Edited by admin on Sat Jun 26 15:40:05 UTC 2021
PRIMARY
DRUG BANK
DB01057
Created by admin on Sat Jun 26 15:40:05 UTC 2021 , Edited by admin on Sat Jun 26 15:40:05 UTC 2021
PRIMARY