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Details

Stereochemistry ACHIRAL
Molecular Formula C9H23NO3PS
Molecular Weight 256.323
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

1960
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

1960
PubMed

PubMed

TitleDatePubMed
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
Studies on in vitro degradation of anhydroecgonine methyl ester (methylecgonidine) in human plasma.
2002 Nov-Dec
Rapid activation of presynaptic nicotinic acetylcholine receptors by nerve-released transmitter.
2003 Dec
Ocular hypotensive effects of cholinergic and adrenergic drugs may be influenced by prostaglandins E2 in the human and rabbit eye.
2003 Jan-Feb
Cholinesterase reactivation in vivo with a novel bis-oxime optimized by computer-aided design.
2003 Oct
PI monovision for presbyopia.
2004
H-7 effect on outflow facility after trabecular obstruction following long-term echothiophate treatment in monkeys.
2004 Aug
The effect of fluoride on the scavenging of organophosphates by human butyrylcholinesterase in buffer solutions and human plasma.
2004 Jan 1
Screening assays for cholinesterases resistant to inhibition by organophosphorus toxicants.
2004 Jun 1
Resistance to organophosphorus agent toxicity in transgenic mice expressing the G117H mutant of human butyrylcholinesterase.
2004 May 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
Long-term outcome of patients with large overcorrection following surgery for exotropia.
2005 Jul-Aug
Butyrylcholinesterase, paraoxonase, and albumin esterase, but not carboxylesterase, are present in human plasma.
2005 Nov 25
Sensitivity of butyrylcholinesterase knockout mice to (--)-huperzine A and donepezil suggests humans with butyrylcholinesterase deficiency may not tolerate these Alzheimer's disease drugs and indicates butyrylcholinesterase function in neurotransmission.
2007 Apr 20
Kinetic analysis of butyrylcholinesterase-catalyzed hydrolysis of acetanilides.
2007 Sep
Catalytic bioscavengers against toxic esters, an alternative approach for prophylaxis and treatments of poisonings.
2009 Apr
Lowering of IOP by echothiophate iodide in pseudophakic eyes with glaucoma.
2010 Aug
Acute ocular complications from self-administered topical kermes.
2010 Oct
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
Ecothiopate [WHO-DD]
Common Name English
AMMONIUM, (2-MERCAPTOETHYL)TRIMETHYL-, S-ESTER WITH O,O-DIETHYLPHOSPHOROTHIOATE
Common Name English
ECOTHIOPATE CATION
Common Name English
ECOTHIOPATE
WHO-DD  
Common Name English
Classification Tree Code System Code
WHO-ATC S01EB03
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NCI_THESAURUS C47796
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NDF-RT N0000000177
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NDF-RT N0000007196
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NDF-RT N0000175723
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WHO-VATC QS01EB03
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Code System Code Type Description
CHEBI
4753
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PRIMARY
FDA UNII
0F350BVT6S
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EVMPD
SUB01856MIG
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PUBCHEM
10548
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LACTMED
Echothiophate
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DAILYMED
0F350BVT6S
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PRIMARY
RXCUI
89778
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PRIMARY RxNorm
NCI_THESAURUS
C76040
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SMS_ID
100000087721
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CAS
6736-03-4
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WIKIPEDIA
Echothiophate
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DRUG CENTRAL
982
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DRUG BANK
DB01057
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PRIMARY