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| Trade names | Phospholine |
| Routes of administration | Topical (eye drops) |
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| Formula | C9H23INO3PS |
| Molar mass | 383.23 g·mol−1 |
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Echothiophate (Phospholine) is an irreversibleacetylcholinesterase inhibitor.[1]
It is used as anocular antihypertensive in the treatment of open angleglaucoma and, in some cases, accommodativeesotropia. It is available under several trade names such as Phospholine Iodide (Wyeth-Ayerst).
Echothiophate binds irreversibly tocholinesterase. Because of the very slow rate at which echothiophate is hydrolyzed by cholinesterase, its effects can last a week or more.Adverse effects includemuscle spasm and othersystemic effects.
It covalently binds by its phosphate group to serine group at the active site of thecholinesterase. Once bound, the enzyme is permanently inactive and the cell has to make new enzymes.
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 After contacting the American Academy of Ophthalmology (AAO), Wyeth rescinded their decision and, according to AAO public relations representative Michelle Stephens, the AAO and Wyeth were in talks for about a year about manufacturing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.[2]
In the meantime, a worldwide shortage of the drug has occurred.[when?][citation needed]
Echothiophate is made by reacting diethylchlorophosphoric acid with 2-dimethylaminoethylmercaptan, givingS-(2-dimethylaminoethyl)-O,O-diethylthiophosphate, which is alkylated bymethyl iodide, forming echothiophate.[3]
