513-10-0 Usage
Description
ECOTHIOPATE IODIDE is an iodide salt of ecothiopate, which functions as an irreversible acetylcholinesterase inhibitor. It is a pharmaceutical compound with significant applications in the treatment of specific medical conditions.
Used in Ophthalmic Industry:
ECOTHIOPATE IODIDE is used as an ocular antihypertensive for the treatment of open-angle glaucoma, particularly when other drugs have proved inadequate. It helps in managing the intraocular pressure, which is crucial in preventing further damage to the optic nerve and vision loss.
Brand Name:
Phospholine Iodide (Wyeth) is the brand name under which ECOTHIOPATE IODIDE is marketed, making it more recognizable to healthcare professionals and patients.
Originator
Phospholine Iodide,Ayerst,US,1959
Manufacturing Process
The reaction is carried out in an atmosphere of nitrogen. To a solution of 4.60
grams sodium (0.20 mol) in 60 cc of methanol is added 14.17 grams β-
dimethylaminoethyl mercaptan hydro chloride (0.10 mol), rinsed in with 10 cc
methanol. Solvent is removed at a water-pump vacuum while blowing with a
slow stream of nitrogen to 100°C/20 mm. To the residue suspended in 150 cc
benzene and cooled in an ice bath is added 17.25 grams
diethylchlorophosphate (0.10 mol) in 3 portions at 10-minute intervals. After
each addition, the temperature increases from about 4° to about 14°C and
then falls. The mixture is stirred in an ice bath for one-half hour and while
warming to room temperature during 2 hours is washed with 35 and 5 cc
portions of water with two 10 cc portions of saturated brine and is dried over
calcium sulfate and filtered.After removal of solvent by distillation under reduced pressure to 55°C/20
mm, the residue is 23.0 grams crude base (95% theory) as a pale yellow
liquid. A sample of the crude base distills with some decomposition at 105° to
112°C/0.8 mm.A sample of distilled base in cold isopropanol is treated with excess methyl
iodide, left at room temperature overnight, diluted with 5 volumes of ethyl
acetate and filtered from the methiodide salt. This is purified by crystallization
from mixtures of isopropanol and ethyl acetate, filtering hot to remove an
impurity of low solubility. The pure methiodide is obtained as a white solid, MP
124° to 124.5°C, containing 99 mol percent thiol isomer.
Clinical Use
Echothiophate iodide has found therapeutic application for the treatment of glaucoma and strabismus. Echothiophate is applied topically as a
solution and is the only irreversible AChEI for the treatment of glaucoma. The decrease in intraocular pressure observed can last up to 4 weeks.
Phosphoester AChEIs exhibit cataractogenic properties; thus, their use should be reserved for patients who are refractory to other forms of
treatment (i.e., short-acting miotics, β-blockers, epinephrine, and possibly, carbonic anhydrase inhibitors). Because of its toxicity, echothiophate
is not used for its systemic action. Selectivity of echothiophate for the AChE catalytic site was enhanced by incorporation in the molecule of a
quaternary ammonium salt functional group two carbons removed from the phosphoryl group.
Check Digit Verification of cas no
The CAS Registry Mumber 513-10-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,1 and 3 respectively; the second part has 2 digits, 1 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 513-10:
(5*5)+(4*1)+(3*3)+(2*1)+(1*0)=40
40 % 10 = 0
So 513-10-0 is a valid CAS Registry Number.
InChI:InChI=1/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
513-10-0Relevant articles and documents
Echothiophate Iodide Process
-
Paragraph 0060; 0065-0069, (2017/01/23)
The present invention relates to a process for preparation of Echothiophate Iodide (I). Echothiophate Iodide (I) obtained by the process of the present invention is obtained as new crystalline form designated as Form-SET. The process for preparation of Echothiophate Iodide (I) according to present invention is an ecofriendly process that avoids the use of hazardous solvent systems and provides Echothiophate Iodide (I) of high purity. Pharmaceutical composition of the said crystalline Form-SET of Echothiophate Iodide (I) of high purity is useful in the treatment of ocular disorders like Glaucoma.
