116-38-1 Usage
Description
Edrophonium chloride, also known as ethyl(m-hydroxyphenyl)dimethylammonium chloride (Tensilon), is a reversible anticholinesterase agent. It is a white or almost white, crystalline powder that is bitter and very soluble in water and alcohol. Edrophonium chloride injection has a pH of 5.2 to 5.5. It acts as a specific anticurare agent and has a rapid onset and shorter duration of action compared to other anticholinesterase agents.
Uses
1. Used in Pharmaceutical Industry:
Edrophonium chloride is used as a reversible Acetylcholinesterase inhibitor for its ability to prevent the breakdown of the neurotransmitter acetylcholine by binding specifically to its catalytic site.
2. Used in Myasthenia Gravis Test:
Edrophonium chloride is used as a diagnostic tool for the autoimmune neuromuscular junction disorder, myasthenia gravis. It helps to confirm a diagnosis and distinguish between underor over-treatment with other anticholinesterases.
3. Used in Cholinergic Applications:
Edrophonium chloride is used in cholinergic applications due to its role as an acetylcholinesterase inhibitor, which can be beneficial in various conditions related to the cholinergic system.
4. Used in Neuromuscular Blockade Reversal:
Edrophonium chloride is used for the reversal of neuromuscular blockade in anesthesia, acting within 1 minute to alleviate overdose of d-tubocurarine, dimethyl d-tubocurarine, or gallamine triethiodide.
5. Used in Poisoning Management:
Edrophonium chloride is used for the management of poisoning due to tetrodotoxin, a neuromuscular blocking toxin found in puffer fish and other marine animals.
Brand Names:
Enlon (Baxter Healthcare)
Reversol (Organon)
Tensilon (Valeant)
Originator
Tensilon,Roche,US,1951
Manufacturing Process
A solution made up of 10 grams of m-dimethylaminophenol, 50 cc of acetone
and 13 grams of ethyl iodide was heated at 50°C for five hours. On addition
of ether to the cooled solution, (3-hydroxyphenyl)ethyl dimethylammonium
iodide precipitated as an oil which soon crystallized. Upon recrystallization
from isopropanol the compound had a MP of 113° to 115°C.A slight excess of a 10% sodium hydroxide solution was added to a solution of
23 grams of silver nitrate in 300 cc of water. The precipitated silver oxide was
washed free of silver ion with distilled water. To a suspension of the silver
oxide in 200 cc of water, a solution of 25 grams of (3-hydroxyphenyl)ethyl
dimethylammonium iodide in 300 cc of water was added. The precipitate of
silver iodide was removed by filtration and the filtrate concentrated to a
volume of about 100 cc in vacuo. The remainder of the water was removed by
lyophilization. (3-hydroxyphenyl)ethyl dimethylammonium hydroxide was
obtained as a hygroscopic, amorphous solid.A solution of 5 grams of (3-hydroxyphenyl)ethyl dimethylammonium
hydroxide in about 200 cc of water was neutralized with dilute hydrochloric
acid. On concentration to dry ness in vacuo, (3-hydroxyphenyl)ethyl
dimethylammonium chloride crystallized. The compound was recrystallizedfrom isopropanol; MP 162° to 163°C (with decomposition).
Therapeutic Function
Cholinergic (ophthalmic)
Biological Activity
edrophonium is a competitive inhibitor of acetylcholinesterase (ache) [1]. ache is an extrinsic membrane-hound enzyme that functions in the central and peripheral nervous systems. ache rapidly terminates the ach receptor-mediated signal transmission by hydrolyzing ach. inhibition of ache results in accumulation of ach in the synaptic cleft and leads to impeded neurotransmission [2].
Clinical Use
Edrophonium Chloride is also used to terminate the action of any one ofthese drugs when the physician so desires. It is of no value,however, in terminating the action of the depolarizing (i.e.,noncompetitive) blocking agents, such as decamethoniumand succinylcholine. In addition to inhibiting AChE, edrophoniumchloride has a direct cholinomimetic effect onskeletal muscle, which is greater than that of most otheranticholinesterase drugs.
Veterinary Drugs and Treatments
The primary use for edrophonium is in the diagnosis of myasthenia
gravis. It can also be used for the reversal of nondepolarizing
agents (e.g., vecuronium, pancuronium, metocurine, atracurium,
gallamine or tubocurarine). Because of its short duration of action,
its clinical usefulness for this indication is questionable as
longer acting drugs such as neostigmine or pyridostigmine may be
more useful. Edrophonium, in a controlled intensive
care-type setting,
may also be useful in the diagnosis and treatment of some
supraventricular arrhythmias, particularly when other more traditional
treatments are ineffective.
in vitro
edrophonium inhibited ache activity in human red blood cells, purified calf forebrain, and octopus brain with ki values of 0.2, 0.2, and 0.4 μm, respectively. the ic50s were 0.2, 0.05, and 0.5 μm, respectively [1].
in vivo
in symptomatic patients without coronary artery disease, edrophonium (80 μg/kg, intravenous bolus) induced chest pain [3]. edrophonium increased esophageal amplitude and repetitive contractions. edrophonium was useful for provoking esophageal chest pain [3]. in infants and children during n2o-halothane anesthesia, the ed50 for edrophonium is 128 μg/kg for adults [4]. in patients anaesthetized with nitrous oxide and halothane undergoing kidney transplant nephrectomy or transplantation of a live related donor kidney, patients undergoing transplant nephrectomy showed a significant increase in elimination half-life and a significant decrease (67%) in serum clearance when compared with kidney transplant recipients or patients with normal renal function [5].
references
[1] boyle n a j, talesa v, giovannini e, et al. synthesis and study of thiocarbonate derivatives of choline as potential inhibitors of acetylcholinesterase[j]. journal of medicinal chemistry, 1997, 40(19): 3009-3013.[2] quinn d m. acetylcholinesterase: enzyme structure, reaction dynamics, and virtual transition states[j]. chemical reviews, 1987, 87(5): 955-979.[3] cronnelly r, morris r b, miller r d. edrophonium: duration of action and atropine requirement in humans during halothane anesthesia[j]. anesthesiology, 1982, 57(4): 261-266.[4] fisher d m, cronnelly r, sharma m, et al. clinical pharmacology of edrophonium in infants and children[j]. anesthesiology, 1984, 61(4): 428-433.[5] morris r b, cronnelly r, miller r d, et al. pharmacokinetics of edrophonium in anephric and renal transplant patients[j]. british journal of anaesthesia, 1981, 53(12): 1311-1314.
Check Digit Verification of cas no
The CAS Registry Mumber 116-38-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 6 respectively; the second part has 2 digits, 3 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 116-38:
(5*1)+(4*1)+(3*6)+(2*3)+(1*8)=41
41 % 10 = 1
So 116-38-1 is a valid CAS Registry Number.
InChI:InChI=1/C10H16NO.ClH/c1-4-11(2,3)9-6-5-7-10(12)8-9;/h5-8,12H,4H2,1-3H3;1H