CAS 6736-03-4|echothiophate|Phospholine Iodide|Echothiophate|Phospholine|Echothiophate Iodide|diethyl {[2-(trimethylazaniumyl)ethyl]sulfanyl}phosphonate|Phospholine Iodide|Echodide|ecothiopatum|ecot...

General Information

Structure

Molecular Formula

C₉H₂₃NO₃PS+

Molecular Mass

256.322581

Exact Mass

256.11362623

Charge

InChI

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

InChIKey

BJOLKYGKSZKIGU-UHFFFAOYSA-N

Canonic Smiles

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

Isomeric Smiles

S(P(=O)(OCC)OCC)CC[N+](C)(C)C

Calculated Properties

JChem

LogD (pH = 7.4)

-3.05

LogD (pH = 5.5)

-3.05

Log P

-3.05

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

-8.20

Polar Surface Area

35.53

Polarizability

27.38

Molar Refractivity

78.14

Data Source

Academic Data

Data Source

Names and Identifiers

IUPAC Traditional name

echothiophate

Synonyms

Phospholine IodideEchothiophatePhospholineEchothiophate IodideecothiopateEchothiophate(2-diethoxyphosphinylthioethyl)trimethylammonium

IUPAC name

diethyl {[2-(trimethylazaniumyl)ethyl]sulfanyl}phosphonate

Brand Name

Phospholine IodideEchodide

International Nonproprietary Name (INN)

ecothiopatumecothiopate

Names and Identifiers

Registration numbers

PubChem SID

1609643914650594499319104

PubChem CID

1054810547

CAS Number

6736-03-4

BRENDA Ligand Database

47591

BRENDA Database

3.5.1.483.1.1.73.1.1.8

KEGG ID

C06975

Reactom Database

R-HSA-9634834R-HSA-372519

CHEMBL

CHEMBL1201341

SureChEMBL Database

SCHEMBL1048167

Drug Central Database

CHEBI ID

ACToR Database

Wikipedia Title

DrugBank ID

Beilstein Number

BKMS React Database

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

-2.25

Solubility

Soluble

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB01057

Drug Groups

approved

Description

A potent, long-acting irreversible cholinesterase inhibitor used as an ocular hypertensive in the treatment of glaucoma. Occasionally used for accomodative esotropia.

Indication

For use in the treatment of subacute or chronic angle-closure glaucoma after iridectomy or where surgery is refused or contraindicated.

Pharmacology

Echothiophate Iodide is a potent, long-acting cholinesterase inhibitor used as a miotic in the treatment of glaucoma. Echothiophate iodide will depress both plasma and erythrocyte cholinesterase levels in most patients after a few weeks of eyedrop therapy.

Toxicity

Side effects include blurred vision or change in near or distant vision and eye pain.

Affected Organisms

Humans and other mammals

References

• Schmidt KG, Horowitz Y, Buckman G, Segev E, Levinger E, Geyer O: Lowering of IOP by echothiophate iodide in pseudophakic eyes with glaucoma. Curr Eye Res. 2010 Aug;35(8):698-702. [Pubmed]

• Reddy RH: Echothiophate iodide: its use in accommodative esotropia (high Ac/A ratio). Indian J Ophthalmol. 1982 Jul;30(4):225. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

ChEBI

CHEBI:4753

The phosphorothioate obtained by formal condensation of diethyl phosphate with N,N,N-trimethyl-2-sulfanylethanaminium. An irreversible acetylcholinesterase inhibitor, its iodide salt is used an ocular antihypertensive in the treatment of open-angle glaucoma, particularly when other drugs have proved inadequate.

Molecule Details

References

PubChem Literature

From Data Sources

• Schmidt KG, Horowitz Y, Buckman G, Segev E, Levinger E, Geyer O: Lowering of IOP by echothiophate iodide in pseudophakic eyes with glaucoma. Curr Eye Res. 2010 Aug;35(8):698-702. Pubmed

• Reddy RH: Echothiophate iodide: its use in accommodative esotropia (high Ac/A ratio). Indian J Ophthalmol. 1982 Jul;30(4):225. Pubmed

References

Bioactivity

PubChem BioAssay

Bioactivity

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General Information

Calculated Properties

• RDKit

• JChem

Data Source

• Academic Data