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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

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

Molecular Formula HI
Molecular Weight 127.9124
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
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

-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
Studies on in vitro degradation of anhydroecgonine methyl ester (methylecgonidine) in human plasma.
2002 Nov-Dec
PI monovision for presbyopia.
2004
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
Role of water in aging of human butyrylcholinesterase inhibited by echothiophate: the crystal structure suggests two alternative mechanisms of aging.
2005 Feb 1
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
Selective reversal of muscle relaxation in general anesthesia: focus on sugammadex.
2009 Sep 21
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 Sat Dec 16 15:54:33 UTC 2023
Edited
by admin
on Sat Dec 16 15:54:33 UTC 2023
Record UNII
BA9QH3P00T
Record Status Validated (UNII)
Record Version
  • Download
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 UTC 2023 , Edited by admin on Sat Dec 16 15:54:33 UTC 2023
FDA ORPHAN DRUG 871422
Created by admin on Sat Dec 16 15:54:33 UTC 2023 , Edited by admin on Sat Dec 16 15:54:33 UTC 2023
EU-Orphan Drug EU/3/15/1474
Created by admin on Sat Dec 16 15:54:33 UTC 2023 , Edited by admin on Sat Dec 16 15:54:33 UTC 2023
FDA ORPHAN DRUG 430914
Created by admin on Sat Dec 16 15:54:33 UTC 2023 , Edited by admin on Sat Dec 16 15:54:33 UTC 2023
Code System Code Type Description
DRUG BANK
DBSALT001098
Created by admin on Sat Dec 16 15:54:33 UTC 2023 , Edited by admin on Sat Dec 16 15:54:33 UTC 2023
PRIMARY
ECHA (EC/EINECS)
208-152-1
Created by admin on Sat Dec 16 15:54:33 UTC 2023 , Edited by admin on Sat Dec 16 15:54:33 UTC 2023
PRIMARY
SMS_ID
100000080508
Created by admin on Sat Dec 16 15:54:33 UTC 2023 , Edited by admin on Sat Dec 16 15:54:33 UTC 2023
PRIMARY
NCI_THESAURUS
C47505
Created by admin on Sat Dec 16 15:54:33 UTC 2023 , Edited by admin on Sat Dec 16 15:54:33 UTC 2023
PRIMARY
DAILYMED
BA9QH3P00T
Created by admin on Sat Dec 16 15:54:33 UTC 2023 , Edited by admin on Sat Dec 16 15:54:33 UTC 2023
PRIMARY
ChEMBL
CHEMBL1201341
Created by admin on Sat Dec 16 15:54:33 UTC 2023 , Edited by admin on Sat Dec 16 15:54:33 UTC 2023
PRIMARY
CAS
513-10-0
Created by admin on Sat Dec 16 15:54:33 UTC 2023 , Edited by admin on Sat Dec 16 15:54:33 UTC 2023
PRIMARY
FDA UNII
BA9QH3P00T
Created by admin on Sat Dec 16 15:54:33 UTC 2023 , Edited by admin on Sat Dec 16 15:54:33 UTC 2023
PRIMARY
PUBCHEM
10547
Created by admin on Sat Dec 16 15:54:33 UTC 2023 , Edited by admin on Sat Dec 16 15:54:33 UTC 2023
PRIMARY
MESH
D004456
Created by admin on Sat Dec 16 15:54:33 UTC 2023 , Edited by admin on Sat Dec 16 15:54:33 UTC 2023
PRIMARY
MERCK INDEX
m4818
Created by admin on Sat Dec 16 15:54:33 UTC 2023 , Edited by admin on Sat Dec 16 15:54:33 UTC 2023
PRIMARY Merck Index
RXCUI
3740
Created by admin on Sat Dec 16 15:54:33 UTC 2023 , Edited by admin on Sat Dec 16 15:54:33 UTC 2023
PRIMARY RxNorm
CHEBI
59849
Created by admin on Sat Dec 16 15:54:33 UTC 2023 , Edited by admin on Sat Dec 16 15:54:33 UTC 2023
PRIMARY
EVMPD
SUB06451MIG
Created by admin on Sat Dec 16 15:54:33 UTC 2023 , Edited by admin on Sat Dec 16 15:54:33 UTC 2023
PRIMARY
EPA CompTox
DTXSID1022976
Created by admin on Sat Dec 16 15:54:33 UTC 2023 , Edited by admin on Sat Dec 16 15:54:33 UTC 2023
PRIMARY
INN
662
Created by admin on Sat Dec 16 15:54:33 UTC 2023 , Edited by admin on Sat Dec 16 15:54:33 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
TARGET -> INHIBITOR
IRREVERSIBLE INHIBITOR
Related Record Type Details
ACTIVE MOIETY