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Details

Stereochemistry ACHIRAL
Molecular Formula C9H23NO3PS.I
Molecular Weight 383.227
Optical Activity NONE
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ECHOTHIOPHATE IODIDE

SMILES

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

InChI

InChIKey=OVXQHPWHMXOFRD-UHFFFAOYSA-M
InChI=1S/C9H23NO3PS.HI/c1-6-12-14(11,13-7-2)15-9-8-10(3,4)5;/h6-9H2,1-5H3;1H/q+1;/p-1

HIDE SMILES / InChI

Molecular Formula HI
Molecular Weight 127.91241
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C9H23NO3PS
Molecular Weight 256.323
Charge 1
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity NONE

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
Acute ocular complications from self-administered topical kermes.
2010-10
Lowering of IOP by echothiophate iodide in pseudophakic eyes with glaucoma.
2010-08
In silico modeling of the specific inhibitory potential of thiophene-2,3-dihydro-1,5-benzothiazepine against BChE in the formation of beta-amyloid plaques associated with Alzheimer's disease.
2010-06-16
Autonomic drugs and the accommodative system in rhesus monkeys.
2010-01
Selective reversal of muscle relaxation in general anesthesia: focus on sugammadex.
2009-09-21
A phase II clinical trial to assess the safety of clonidine in acute organophosphorus pesticide poisoning.
2009-08-20
Role of central muscarinic cholinergic receptors in the formalin-induced pain in rats.
2009-06
Catalytic bioscavengers against toxic esters, an alternative approach for prophylaxis and treatments of poisonings.
2009-04
Five tyrosines and two serines in human albumin are labeled by the organophosphorus agent FP-biotin.
2008-09
Aging pathways for organophosphate-inhibited human butyrylcholinesterase, including novel pathways for isomalathion, resolved by mass spectrometry.
2007-11
Kinetic analysis of butyrylcholinesterase-catalyzed hydrolysis of acetanilides.
2007-09
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.
2007-04-20
Mutant of Bungarus fasciatus acetylcholinesterase with low affinity and low hydrolase activity toward organophosphorus esters.
2006-09
Function-specific blockage of M(1) and M(3) muscarinic acetylcholine receptors by VX and echothiophate.
2006-04-26
Serine hydrolase targets of organophosphorus toxicants.
2005-12-15
Butyrylcholinesterase, paraoxonase, and albumin esterase, but not carboxylesterase, are present in human plasma.
2005-11-25
Role of water in aging of human butyrylcholinesterase inhibited by echothiophate: the crystal structure suggests two alternative mechanisms of aging.
2005-02-01
Albumin, a new biomarker of organophosphorus toxicant exposure, identified by mass spectrometry.
2005-02
Stereoselectivity toward VX is determined by interactions with residues of the acyl pocket as well as of the peripheral anionic site of AChE.
2004-09-07
H-7 effect on outflow facility after trabecular obstruction following long-term echothiophate treatment in monkeys.
2004-08
Long-term outcome of patients with large overcorrection following surgery for exotropia.
2004-07-01
Screening assays for cholinesterases resistant to inhibition by organophosphorus toxicants.
2004-06-01
Resistance to organophosphorus agent toxicity in transgenic mice expressing the G117H mutant of human butyrylcholinesterase.
2004-05-01
The effect of fluoride on the scavenging of organophosphates by human butyrylcholinesterase in buffer solutions and human plasma.
2004-01-01
PI monovision for presbyopia.
2004
Rapid activation of presynaptic nicotinic acetylcholine receptors by nerve-released transmitter.
2003-12
Cholinesterase reactivation in vivo with a novel bis-oxime optimized by computer-aided design.
2003-10
Ocular hypotensive effects of cholinergic and adrenergic drugs may be influenced by prostaglandins E2 in the human and rabbit eye.
2003-03-15
Studies on in vitro degradation of anhydroecgonine methyl ester (methylecgonidine) in human plasma.
2002-12-28
DNA sequence of butyrylcholinesterase from the rat: expression of the protein and characterization of the properties of rat butyrylcholinesterase.
2002-06-15
A non-cholinergic, trophic action of acetylcholinesterase on hippocampal neurones in vitro: molecular mechanisms.
2002
Carboxylesterase: specificity and spontaneous reactivation of an endogenous scavenger for organophosphorus compounds.
2001-12
Is succinylcholine appropriate or obsolete in the intensive care unit?
2001-10
Echothiophate iodide: its use in accommodative esotropia (high Ac/A ratio).
1982-07
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
Substance Class Chemical
Created
by admin
on Wed Apr 02 06:54:10 GMT 2025
Edited
by admin
on Wed Apr 02 06:54:10 GMT 2025
Record UNII
BA9QH3P00T
Record Status Validated (UNII)
Record Version
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Name Type Language
ECOTHIOPATE IODIDE
INN   MART.   WHO-DD  
INN  
Preferred Name English
ECHOTHIOPHATE IODIDE
MI   ORANGE BOOK   USP   VANDF  
Common Name English
ECOTHIOPATE IODIDE [JAN]
Common Name English
(2-Mercaptoethyl)trimethylammonium iodide S-ester with O,O-diethyl phosphorothioate
Common Name English
ETHANAMINIUM, 2-((DIETHOXYPHOSPHINYL)THIO)-N,N,N-TRIMETHYL-, IODIDE
Systematic Name English
PHOSPHOLINE IODIDE
Systematic Name English
ECOSTIGMINE IODIDE
Common Name English
ECHOTHIOPHATE IODIDE [USP IMPURITY]
Common Name English
ECHOTHIOPHATE IODIDE [USP MONOGRAPH]
Common Name English
ecothiopate iodide [INN]
Common Name English
ECHOTHIOPHATE IODIDE [ORANGE BOOK]
Common Name English
Ecothiopate iodide [WHO-DD]
Common Name English
217-MI
Code English
ECHODIDE
Common Name English
ECOTHIOPATE IODIDE [MART.]
Common Name English
ECHOTHIOPHATE IODIDE [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C47792
Created by admin on Wed Apr 02 06:54:10 GMT 2025 , Edited by admin on Wed Apr 02 06:54:10 GMT 2025
FDA ORPHAN DRUG 871422
Created by admin on Wed Apr 02 06:54:10 GMT 2025 , Edited by admin on Wed Apr 02 06:54:10 GMT 2025
EU-Orphan Drug EU/3/15/1474
Created by admin on Wed Apr 02 06:54:10 GMT 2025 , Edited by admin on Wed Apr 02 06:54:10 GMT 2025
FDA ORPHAN DRUG 430914
Created by admin on Wed Apr 02 06:54:10 GMT 2025 , Edited by admin on Wed Apr 02 06:54:10 GMT 2025
Code System Code Type Description
DRUG BANK
DBSALT001098
Created by admin on Wed Apr 02 06:54:10 GMT 2025 , Edited by admin on Wed Apr 02 06:54:10 GMT 2025
PRIMARY
ECHA (EC/EINECS)
208-152-1
Created by admin on Wed Apr 02 06:54:10 GMT 2025 , Edited by admin on Wed Apr 02 06:54:10 GMT 2025
PRIMARY
SMS_ID
100000080508
Created by admin on Wed Apr 02 06:54:10 GMT 2025 , Edited by admin on Wed Apr 02 06:54:10 GMT 2025
PRIMARY
NCI_THESAURUS
C47505
Created by admin on Wed Apr 02 06:54:10 GMT 2025 , Edited by admin on Wed Apr 02 06:54:10 GMT 2025
PRIMARY
DAILYMED
BA9QH3P00T
Created by admin on Wed Apr 02 06:54:10 GMT 2025 , Edited by admin on Wed Apr 02 06:54:10 GMT 2025
PRIMARY
ChEMBL
CHEMBL1201341
Created by admin on Wed Apr 02 06:54:10 GMT 2025 , Edited by admin on Wed Apr 02 06:54:10 GMT 2025
PRIMARY
CAS
513-10-0
Created by admin on Wed Apr 02 06:54:10 GMT 2025 , Edited by admin on Wed Apr 02 06:54:10 GMT 2025
PRIMARY
FDA UNII
BA9QH3P00T
Created by admin on Wed Apr 02 06:54:10 GMT 2025 , Edited by admin on Wed Apr 02 06:54:10 GMT 2025
PRIMARY
PUBCHEM
10547
Created by admin on Wed Apr 02 06:54:10 GMT 2025 , Edited by admin on Wed Apr 02 06:54:10 GMT 2025
PRIMARY
MESH
D004456
Created by admin on Wed Apr 02 06:54:10 GMT 2025 , Edited by admin on Wed Apr 02 06:54:10 GMT 2025
PRIMARY
MERCK INDEX
m4818
Created by admin on Wed Apr 02 06:54:10 GMT 2025 , Edited by admin on Wed Apr 02 06:54:10 GMT 2025
PRIMARY Merck Index
RXCUI
3740
Created by admin on Wed Apr 02 06:54:10 GMT 2025 , Edited by admin on Wed Apr 02 06:54:10 GMT 2025
PRIMARY RxNorm
CHEBI
59849
Created by admin on Wed Apr 02 06:54:10 GMT 2025 , Edited by admin on Wed Apr 02 06:54:10 GMT 2025
PRIMARY
EVMPD
SUB06451MIG
Created by admin on Wed Apr 02 06:54:10 GMT 2025 , Edited by admin on Wed Apr 02 06:54:10 GMT 2025
PRIMARY
EPA CompTox
DTXSID1022976
Created by admin on Wed Apr 02 06:54:10 GMT 2025 , Edited by admin on Wed Apr 02 06:54:10 GMT 2025
PRIMARY
INN
662
Created by admin on Wed Apr 02 06:54:10 GMT 2025 , Edited by admin on Wed Apr 02 06:54:10 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
TARGET -> INHIBITOR
IRREVERSIBLE INHIBITOR
Related Record Type Details
ACTIVE MOIETY