Echothiophate

Echothiophate

Systematic (IUPAC) name
2-(Diethoxyphosphorylsulfanyl)ethyl-N,N,N-trimethylazanium iodide
Clinical data
Trade names	Phospholine
Pregnancy cat.	?
Legal status	?
Routes	Topical (eye drops)
Identifiers
CAS number	6736-03-4 Y
ATC code	S01EB03
PubChem	CID 10547
DrugBank	APRD00942
ChemSpider	10107 Y
UNII	0F350BVT6S Y
KEGG	D02193 Y
ChEBI	CHEBI:59849 Y
ChEMBL	CHEMBL1201341 N
Chemical data
Formula	C9H23INO3PS
Mol. mass	383.228 g/mol
SMILES	eMolecules & PubChem
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 Y Key:OVXQHPWHMXOFRD-UHFFFAOYSA-M Y
N (what is this?)  (verify)

Echothiophate (Phospholine) is a parasympathomimetic and a phosphorothioate. It is an acetylcholinesterase inhibitor.

Uses

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.

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 After contacting the American Academy of Ophthalmology (AAO), Wyeth rescinded their decision and, according to AAO public relations representative Michelle Stephens, the AAO and Wyeth were in talks for about a year about manufacturing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, S-(2-trimethylaminoethyl)-O,O-diethylthiophosphate, is made by reacting diethylchlorophosphoric acid with 2-dimethylaminoethylmercaptane, giving S-(2-dimethylaminoethyl)-O,O-diethylthiophosphate, which is alkylated by methyl iodide, forming echothiophate. H.M. Fitch, U.S. Patent 2,911,430 (1959).