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 actionedit
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.
Shortageedit
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 After contacting the American Academy of Ophthalmology (AAO), Wyeth rescinded their decision and, according to AAO public relations representative Michelle Stephens, the AAO and Wyeth were in talks for about a year about manufacturing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]
Chemistryedit
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.[3]
Referencesedit
^Gabelt BT, Hennes EA, Seeman JL, Tian B, Kaufman PL (August 2004). "H-7 effect on outflow facility after trabecular obstruction following long-term echothiophate treatment in monkeys". Invest. Ophthalmol. Vis. Sci. 45 (8): 2732–6. doi:10.1167/iovs.04-0083. PMID 15277498.
^. Archived from the original on 2006-06-19. Retrieved 2006-08-13.
echothiophate, phospholine, irreversible, acetylcholinesterase, inhibitor, clinical, datatrade, namesphospholineroutes, ofadministrationtopical, drops, codes01eb03, identifiersiupac, name, diethoxyphosphorylsulfanyl, ethyl, trimethylazanium, iodidecas, number6. Echothiophate Phospholine is an irreversible acetylcholinesterase inhibitor 1 EchothiophateClinical dataTrade namesPhospholineRoutes ofadministrationTopical eye drops ATC codeS01EB03 WHO IdentifiersIUPAC name 2 Diethoxyphosphorylsulfanyl ethyl N N N trimethylazanium iodideCAS Number6736 03 4 YPubChem CID10547DrugBankDB01057 YChemSpider10107 YUNII0F350BVT6SKEGGD02193 YChEBICHEBI 59849 YChEMBLChEMBL1201341 NChemical and physical dataFormulaC 9H 23I N O 3P SMolar mass383 23 g mol 13D model JSmol Interactive imageSMILES I O P OCC OCC SCC N C C CInChI 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 N Y what is this verify Contents 1 Uses 2 Mechanism of action 3 Shortage 4 Chemistry 5 ReferencesUses editIt 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 editIt 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 editWyeth 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 Chemistry editEchothiophate is made by reacting diethylchlorophosphoric acid with 2 dimethylaminoethylmercaptan giving S 2 dimethylaminoethyl O O diethylthiophosphate which is alkylated by methyl iodide forming echothiophate 3 nbsp References edit Gabelt BT Hennes EA Seeman JL Tian B Kaufman PL August 2004 H 7 effect on outflow facility after trabecular obstruction following long term echothiophate treatment in monkeys Invest Ophthalmol Vis Sci 45 8 2732 6 doi 10 1167 iovs 04 0083 PMID 15277498 Eurotimes article Echothiophate iodide shortage leaves US specialists struggling to find alternative for acute cases Archived from the original on 2006 06 19 Retrieved 2006 08 13 H M Fitch U S Patent 2 911 430 1959 Retrieved from https en wikipedia org w index php title Echothiophate amp oldid 1150314872, wikipedia, wiki, book, books, library,
