echothiophate echothiophate echothiophate (phospholine) is an irreversible acetylcholinesterase inhibitor. echothiophateclinical datatrade namesphospholineroutes ofadministrationtopical (eye drops)atc codes01eb03 (who) identifiers iupac name 2-(diethoxyphosphorylsulfanyl)ethyl-n,n,n-trimethylazanium iodide cas number6736-03-4 ypubchem cid10547drugbankdb01057 ychemspider10107 yunii0f350bvt6skeggd02193 ychebichebi:59849 ychemblchembl1201341 nchemical and physical dataformulac9h23ino3psmolar mass383.23 g·mol−13d model (jsmol)interactive image smiles .o=p(occ)(occ)scc(c)(c)c 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 ykey:ovxqhpwhmxofrd-uhfffaoysa-m y ny (what is this?) (verify) uses it is used as an ocular antihypertensive in the treatment of open angle glaucoma and, in some cases, accommodative esotropia. it is available under several trade names such as phospholine iodide (wyeth-ayerst). 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. adverse effects include muscle spasm and other systemic effects. mechanism of action it 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. shortage wyeth pharmaceuticals stopped manufacturing echothiophate iodide in the us in 2003. after contacting the american academy of ophthalmology (aao), wyeth rescinded their decision and, according to aao public relations representative michelle stephens, the aao and wyeth were in talks for about a year about manufacturing it. in the meantime, a worldwide shortage of the drug has occurred. chemistry echothiophate is made by reacting diethylchlorophosphoric acid with 2-dimethylaminoethylmercaptan, giving s-(2-dimethylaminoethyl)-o,o-diethylthiophosphate, which is alkylated by methyl iodide, forming echothiophate.