U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C9H23NO3PS.I
Molecular Weight 383.227
Optical Activity NONE
Defined Stereocenters 0 / 0
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
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
Echothiophate iodide: its use in accommodative esotropia (high Ac/A ratio).
1982 Jul
Carboxylesterase: specificity and spontaneous reactivation of an endogenous scavenger for organophosphorus compounds.
2001 Dec
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
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
Serine hydrolase targets of organophosphorus toxicants.
2005 Dec 15
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
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
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
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
Catalytic bioscavengers against toxic esters, an alternative approach for prophylaxis and treatments of poisonings.
2009 Apr
A phase II clinical trial to assess the safety of clonidine in acute organophosphorus pesticide poisoning.
2009 Aug 20
Role of central muscarinic cholinergic receptors in the formalin-induced pain in rats.
2009 Jun
Selective reversal of muscle relaxation in general anesthesia: focus on sugammadex.
2009 Sep 21
Lowering of IOP by echothiophate iodide in pseudophakic eyes with glaucoma.
2010 Aug
Autonomic drugs and the accommodative system in rhesus monkeys.
2010 Jan
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 Jun 16
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 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
INN   MART.   WHO-DD  
INN  
Official 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 Sat Dec 16 15:54:33 GMT 2023 , Edited by admin on Sat Dec 16 15:54:33 GMT 2023
FDA ORPHAN DRUG 871422
Created by admin on Sat Dec 16 15:54:33 GMT 2023 , Edited by admin on Sat Dec 16 15:54:33 GMT 2023
EU-Orphan Drug EU/3/15/1474
Created by admin on Sat Dec 16 15:54:33 GMT 2023 , Edited by admin on Sat Dec 16 15:54:33 GMT 2023
FDA ORPHAN DRUG 430914
Created by admin on Sat Dec 16 15:54:33 GMT 2023 , Edited by admin on Sat Dec 16 15:54:33 GMT 2023
Code System Code Type Description
DRUG BANK
DBSALT001098
Created by admin on Sat Dec 16 15:54:33 GMT 2023 , Edited by admin on Sat Dec 16 15:54:33 GMT 2023
PRIMARY
ECHA (EC/EINECS)
208-152-1
Created by admin on Sat Dec 16 15:54:33 GMT 2023 , Edited by admin on Sat Dec 16 15:54:33 GMT 2023
PRIMARY
SMS_ID
100000080508
Created by admin on Sat Dec 16 15:54:33 GMT 2023 , Edited by admin on Sat Dec 16 15:54:33 GMT 2023
PRIMARY
NCI_THESAURUS
C47505
Created by admin on Sat Dec 16 15:54:33 GMT 2023 , Edited by admin on Sat Dec 16 15:54:33 GMT 2023
PRIMARY
DAILYMED
BA9QH3P00T
Created by admin on Sat Dec 16 15:54:33 GMT 2023 , Edited by admin on Sat Dec 16 15:54:33 GMT 2023
PRIMARY
ChEMBL
CHEMBL1201341
Created by admin on Sat Dec 16 15:54:33 GMT 2023 , Edited by admin on Sat Dec 16 15:54:33 GMT 2023
PRIMARY
CAS
513-10-0
Created by admin on Sat Dec 16 15:54:33 GMT 2023 , Edited by admin on Sat Dec 16 15:54:33 GMT 2023
PRIMARY
FDA UNII
BA9QH3P00T
Created by admin on Sat Dec 16 15:54:33 GMT 2023 , Edited by admin on Sat Dec 16 15:54:33 GMT 2023
PRIMARY
PUBCHEM
10547
Created by admin on Sat Dec 16 15:54:33 GMT 2023 , Edited by admin on Sat Dec 16 15:54:33 GMT 2023
PRIMARY
MESH
D004456
Created by admin on Sat Dec 16 15:54:33 GMT 2023 , Edited by admin on Sat Dec 16 15:54:33 GMT 2023
PRIMARY
MERCK INDEX
m4818
Created by admin on Sat Dec 16 15:54:33 GMT 2023 , Edited by admin on Sat Dec 16 15:54:33 GMT 2023
PRIMARY Merck Index
RXCUI
3740
Created by admin on Sat Dec 16 15:54:33 GMT 2023 , Edited by admin on Sat Dec 16 15:54:33 GMT 2023
PRIMARY RxNorm
CHEBI
59849
Created by admin on Sat Dec 16 15:54:33 GMT 2023 , Edited by admin on Sat Dec 16 15:54:33 GMT 2023
PRIMARY
EVMPD
SUB06451MIG
Created by admin on Sat Dec 16 15:54:33 GMT 2023 , Edited by admin on Sat Dec 16 15:54:33 GMT 2023
PRIMARY
EPA CompTox
DTXSID1022976
Created by admin on Sat Dec 16 15:54:33 GMT 2023 , Edited by admin on Sat Dec 16 15:54:33 GMT 2023
PRIMARY
INN
662
Created by admin on Sat Dec 16 15:54:33 GMT 2023 , Edited by admin on Sat Dec 16 15:54:33 GMT 2023
PRIMARY