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MedKoo Cat#: 413991 | Name: Echothiophate chloride

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Echothiophate is a potent, long-acting cholinesterase inhibitor used as a miotic in the treatment of glaucoma. Echothiophate 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. 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. It is used as an ocular antihypertensive in the treatment of chronic glaucoma and, in some cases, accommodative esotropia.

Chemical Structure

Echothiophate chloride
Echothiophate chloride
CAS#120087-68-5 (chloride)

Theoretical Analysis

MedKoo Cat#: 413991

Name: Echothiophate chloride

CAS#: 120087-68-5 (chloride)

Chemical Formula: C9H23ClNO3PS

Exact Mass: 256.1131

Molecular Weight: 291.77

Elemental Analysis: C, 37.05; H, 7.95; Cl, 12.15; N, 4.80; O, 16.45; P, 10.62; S, 10.99

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
6736-03-4 (cation) 513-10-0 (iodide) 120087-88-9 (hydroxide) 120087-63-0 (bromide) 120087-68-5 (chloride)
Synonym
Echothiophate Free Base; BRN1794025; BRN-1794025; BRN 1794025
IUPAC/Chemical Name
Ammonium, (2-mercaptoethyl)trimethyl-, S-ester with O,O-diethylphosphorothioate, chloride
InChi Key
TWPQIWGWYLZCPK-UHFFFAOYSA-M
InChi Code
InChI=1S/C9H23NO3PS.ClH/c1-6-12-14(11,13-7-2)15-9-8-10(3,4)5;/h6-9H2,1-5H3;1H/q+1;/p-1
SMILES Code
CCOP(OCC)(SCC[N+](C)(C)C)=O.[Cl-]
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 291.77 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006–. Echothiophate. 2021 Apr 19. PMID: 30000715. 2: Pakala RS, Brown KN, Preuss CV. Cholinergic Medications. 2021 Feb 17. In: StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2021 Jan–. PMID: 30844190. 3: Zueva IV, Lushchekina SV, Daudé D, Chabrière E, Masson P. Steady-State Kinetics of Enzyme-Catalyzed Hydrolysis of Echothiophate, a P-S Bonded Organophosphorus as Monitored by Spectrofluorimetry. Molecules. 2020 Mar 17;25(6):1371. doi: 10.3390/molecules25061371. PMID: 32192230; PMCID: PMC7144395. 4: Mindel JS, Yablonski ME, Tavitian HO, Podos SM, Orellana J. Dipivefrin and echothiophate. Efficacy of combined use in human beings. Arch Ophthalmol. 1981 Sep;99(9):1583-6. doi: 10.1001/archopht.1981.03930020457010. PMID: 7283808. 5: Zlobin AS, Zalevsky AO, Mokrushina YA, Kartseva OV, Golovin AV, Smirnov IV. The Preferable Binding Pose of Canonical Butyrylcholinesterase Substrates Is Unproductive for Echothiophate. Acta Naturae. 2018 Oct-Dec;10(4):121-124. PMID: 30713771; PMCID: PMC6351040. 6: Kaufman PL, Axelsson U, Bárány EH. Atropine inhibition of echothiophate cataractogenesis in monkeys. Arch Ophthalmol. 1977 Jul;95(7):1262-8. doi: 10.1001/archopht.1977.04450070160017. PMID: 406884. 7: Abramovsky I, Mindel JS. Dipivefrin and echothiophate: contraindications to combined use. Arch Ophthalmol. 1979 Oct;97(10):1937-40. doi: 10.1001/archopht.1979.01020020385024. PMID: 485920. 8: Kaufman PL, Axelsson U, Bárány EH. Induction of subcapsular cataracts in cynomolgus monkeys by echothiophate. Arch Ophthalmol. 1977 Mar;95(3):499-504. doi: 10.1001/archopht.1977.04450030141021. PMID: 402905. 9: Ballintine EJ. Glaucoma. Arch Ophthalmol. 1968 May;79(5):617-46. doi: 10.1001/archopht.1968.03850040619023. PMID: 4868992. 10: Kaufman PL, Erickson KA, Neider MW. Echothiophate iodide cataracts in monkeys. Occurrence despite loss of accommodation induced by retrodisplacement of ciliary muscle. Arch Ophthalmol. 1983 Jan;101(1):125-8. doi: 10.1001/archopht.1983.01040010127024. PMID: 6849646.