Echothiophate Iodide

• CAT Number: I006584
• CAS Number: 513-10-0
• Molecular Formula: C9H23INO3PS
• Molecular Weight: 383.225
• Purity: ≥95%
• Synonyms: Echothiophate Iodide; Phospholine iodide; Ecothiophate iodide; Echodide; Ecostigmini Sodidum; Iodide, Echothiophate; Iodide, Ecothiopate; Iodide, Ecothiophate; Iodide, Phospholine; Phospholine Iodide;;2-diethoxyphosphorylsulfanylethyl(trimethyl)azani
• Target: Cholinesterase (ChE)
• Solubility: Soluble in DMSO, not in water
• Storage: 0 - 4°C for short term or -20 °C for long term
• IUPAC Name: 2-diethoxyphosphorylsulfanylethyl(trimethyl)azanium;iodide
• InChI: 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
• InChIKey: OVXQHPWHMXOFRD-UHFFFAOYSA-M
• SMILES: CCOP(=O)(OCC)SCC[N+](C)(C)C.[I-]

Echothiophate iodide(CAS 513-10-0) is a potent, long-acting cholinesterase inhibitor used as a miotic in the treatment of glaucoma. Echothiophate iodide covalently binds by its phosphate group to serine group at the active site of the cholinesterase. Once bound, the enzyme is permanently inactive and the cell has to make new enzymes. Echothiophate binds irreversibly to cholinesterase. Because of the very slow rate at which echothiophate is hydrolyzed by cholinesterase, its effects can last a week or more. It is used as an ocular antihypertensive in the treatment of chronic glaucoma and, in some cases, accommodative esotropia. It is available under several trade names such as Phospholine Iodide.

Overview of Clinical Research

The phase III trial to investigate the efficacy and safety Echothiophate Iodide in patients with Stargardt's disease was completed in 2015. 

Reference

1: Gorin G. Echothiophate iodide for glaucoma or flat anterior chamber following cataract extraction. Am J Ophthalmol. 1969 Mar;67(3):392-5. PubMed PMID: 5774254.
2: Hussain A, Schurman P, Peter V, Milosovich G. Kinetics and mechanism of degradation of echothiophate iodide in aqueous solution. J Pharm Sci. 1968 Mar;57(3):411-8. PubMed PMID: 5655578.
3: Hiscox PE, McCulloch C. Cardiac arrest occurring in a patient on echothiophate iodide therapy. Am J Ophthalmol. 1965 Sep;60(3):425-7. PubMed PMID: 5825146.
4: HUMPHREYS JA, HOLMES JH. Systemic effects produced by echothiophate iodide in treatment of glaucoma. Arch Ophthalmol. 1963 Jun;69:737-43. PubMed PMID: 13955705.
5: HILL K, STROMBERG AE. Echothiophate iodide in the management of esotropia. Am J Ophthalmol. 1962 Mar;53:488-94. PubMed PMID: 13907355.
6: BECKER B, GAGE T. Demecarium bromide and echothiophate iodide in chronic glaucoma. Arch Ophthalmol. 1960 Jan;63:102-7. PubMed PMID: 13798061.