Echothiophate

 Echothiophate (Phospholine) is an irreversible acetylcholinesterase inhibitor.[1]

Echothiophate
Echothiophate iodide.svg
Echothiophate-Molecule-3D-balls.png
Clinical data
Trade namesPhospholine
Routes of
administration		Topical (eye drops)
ATC code
  • S01EB03 (WHO)
Identifiers
IUPAC name
  • 2-(Diethoxyphosphorylsulfanyl)ethyl-N,N,N-trimethylazanium iodide
CAS Number
  • 6736-03-4 check
PubChem CID
  • 10547
DrugBank
  • DB01057 check
ChemSpider
  • 10107 check
UNII
  • 0F350BVT6S
KEGG
  • D02193 check
ChEBI
  • CHEBI:59849 check
ChEMBL
  • ChEMBL1201341 ☒
Chemical and physical data
FormulaC9H23INO3PS
Molar mass383.23 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • [I-].O=P(OCC)(OCC)SCC[N+](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 check
  • Key:OVXQHPWHMXOFRD-UHFFFAOYSA-M check
 ☒check (what is this?)  (verify)

UsesEdit

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 (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 After contacting the American Academy of Ophthalmology (AAO), Wyeth rescinded their decision and, according to AAO public relations representative Michelle Stephens, the AAO and Wyeth were in talks for about a year about manufacturing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.

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]

Echothiophate synthesis.png

This article uses material from the Wikipedia article
 Metasyntactic variable, which is released under the 
Creative Commons
Attribution-ShareAlike 3.0 Unported License.