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

• ChemBase ID: 928
• Molecular Formular: C9H23NO3PS+
• Molecular Mass: 256.322581
• Monoisotopic Mass: 256.11362623
• SMILES: S(P(=O)(OCC)OCC)CC[N+](C)(C)C
• Canonical SMILES: CCOP(=O)(SCC[N+](C)(C)C)OCC
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: diethyl {[2-(trimethylazaniumyl)ethyl]sulfanyl}phosphonate
• IUPAC Traditional name: echothiophate
• Brand Name: Echodide; Phospholine Iodide
• Synonyms: Phospholine; Echothiophate Iodide; Phospholine Iodide; Echothiophate

Database IDs

• CAS Number: 6736-03-4
• PubChem SID: 160964391; 46505944
• PubChem CID: 10548; 10547

CALCULATED PROPERTIES

JChem

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): -3.0500553
• LogD (pH = 7.4): -3.0500553
• Log P: -3.0500553
• Molar Refractivity: 78.138 cm^3
• Polarizability: 26.59859 Å^3
• Polar Surface Area: 35.53 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.15
• LOG S: -2.99
• Solubility (Water): 2.97e-01 g/l

PROPERTIES

Physical Property

• Solubility: Soluble
• Hydrophobicity(logP): -2.25

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

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