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Home > Encyclopedia > Succinylcholine

Succinylcholine

Succinylcholine structure

Succinylcholine 

structure
  • CAS No:

    306-40-1

  • Formula:

    C14H30N2O4

  • Chemical Name:

    Succinylcholine

  • Synonyms:

    Ethanaminium,2,2′-[(1,4-dioxo-1,4-butanediyl)bis(oxy)]bis[N,N,N-trimethyl-;Choline,succinate (2:1) (ester);2,2′-[(1,4-Dioxo-1,4-butanediyl)bis(oxy)]bis[N,N,N-trimethylethanaminium];Succinoylcholine;Succinylbischoline;Suxamethonium;Choline,succinyl-;Succinylcholine;Succinocholine;Suxemethonium;Dicholine succinate;Succinic acid dicholine diester;2,2′-[(1,4-dioxobutane-1,4-diyl)bis(oxy)]bis(N,N,N-trimethylethanaminium)

  • Categories:

    Organic Chemistry  >  Amides

Description

ChEBI: A quaternary ammonium ion that is the bis-choline ester of succinic acid.


Solid


Succinylcholine is a quaternary ammonium ion that is the bis-choline ester of succinic acid. It has a role as a neuromuscular agent, a muscle relaxant and a drug allergen. It is a quaternary ammonium ion and a succinate ester.|A quaternary skeletal muscle relaxant usually used in the form of its bromide, chloride, or iodide. It is a depolarizing relaxant, acting in about 30 seconds and with a duration of effect averaging three to five minutes. Succinylcholine is used in surgical, anesthetic, and other procedures in which a brief period of muscle relaxation is called for.|Succinylcholine is a Depolarizing Neuromuscular Blocker. The physiologic effect of succinylcholine is by means of Neuromuscular Depolarizing Blockade.|Succinylcholine is a quaternary ammonium compound and depolarizing agent with short-term muscle relaxant properties. Succinylcholine binds to nicotinic receptors at the neuromuscular junction and opening the ligand-gated channels in the same way as acetylcholine, resulting in depolarization and inhibition of neuromuscular transmission. Depolarization may be prolonged due to succinylcholine's resistance to acetylcholinesterases thereby leading to disorganized muscle contraction followed by skeletal muscle relaxation and flaccid paralysis.

Succinylcholine Basic Attributes

290.404

290.221

200-747-4

J2R869A8YF

DTXSID7048455

C61955

M03AB01|M - Musculo-skeletal system

Characteristics

52.6

0.6

Solid

1.0386 (rough estimate)

7.57e-04 g/L

White, odorless, slightly bitter powder and very soluble in water. ...unstable in alkaline solutions but relatively stable in acid solutions. /Chloride/|Slightyl hygroscopic crystals, mp 243-245 °C. Freely soluble in water or normal saline, giving solutions which are very slightly acidic. Most stable at pH 4-5. /Iodide/

Safety Information

Succinylcholine chloride is unstable in alkaline solutions /Succinylcholine chloride/

P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P403+P233, P405, P501

H301

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

|Danger|H301 (92.86%): Toxic if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 28 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Malignant hyperthermia can be triggered by inhalational anesthetics such as halogenated hydrocarbons, and by depolarizing muscle relaxants such as succinylcholine. ... The clinical features of the myopathy include hyperthermia, metabolic acidosis, tachycardia, accelerated muscle metabolism and contractures.|NODAL ARRHYTHMIAS, BRADYCARDIA & SINUS ARREST HAVE OCCURRED ... AFTER FRACTIONAL DOSES WERE GIVEN IV AT 3 TO 10 MIN INTERVALS TO PATIENTS RECEIVING HALOTHANE. /CHLORIDE/|FEW CASES OF SEVERE BRONCHOSPASM HAVE BEEN REPORTED WHEN SUCCINYLCHOLINE WAS ADMIN WITH HEXAFLUORENIUM ... /CHLORIDE/|POLYMYXIN B CAN INCR PARALYZING EFFECTS. /CHLORIDE/|For more Interactions (Complete) data for SUCCINYLCHOLINE (35 total), please visit the HSDB record page.

LD50 Mouse oral 125 mg/kg|LD50 Mouse ip 2140 ug/kg|LD50 Mouse sc 7500 ug/kg|LD50 Mouse iv 280 ug/kg|LD50 rabbit iv 800 ug/kg

All neuromuscular blocking agents should be used with caution in patients with renal, hepatic, or pulmonary impairment, or respiratory depression, and in geriatric or debilitated patients. The drugs should be used with extreme caution, if at all, in patients with myasthenia gravis. Other conditions that are associated with increased response to the neuromuscular blocking agents are the myasthenic syndrome associated with lung cancer, dehydration, thyroid disorder, collagen diseases, porphyria, and familial periodic paralysis. Potent inhalation anesthetics and neuromuscular blocking agents should be avoided if possible in patients who have experienced malignant hyperthermia and in members of their families, and the possibility that this reaction could occur in any patient undergoing general anesthesia should be considered. During the first month of life, neonates are particularly sensitive to the action of most nondepolarizing agents and respond with prolonged neuromuscular blockade to usual doses of the drugs. /Neuromuscular blocking agents/

Drug Information

Used in surgical procedures where a rapid onset and brief duration of muscle relaxation is needed (includes intubation, endoscopies, and ECT)

Neuromuscular Depolarizing Agents|The neuromuscular blocking agents are indicated as adjuncts to anesthesia to induce skeletal muscle relaxation and to facilitate the management of patients undergoing mechanical ventilation. Generally, a relatively short-acting nondepolarizing neuromuscular blocking agent or a single dose of the depolarizing neuromuscular blocking agent succinylcholine is used to facilitate endotracheal intubation. Continuous infusion of succinylcholine may be used for short surgical procedures requiring muscle relaxation. Nondepolarizing neuromuscular blocking agents, or, less commonly, succinylcholine administered by continuous infusion, are used for surgical procedures requiring an intermediate or prolonged duration of muscle relaxant action and to facilitate controlled ventilation. /Neuromuscular blocking agents; Included in US product labeling/|Neuromuscular blocking agents are also used to decrease the muscular manifestations of persistent convulsions associated with toxic reactions to other medications. /Neuromuscular blocking agents; NOT included in US product labeling/|Succinylcholine /is/ indicated to reduce the intensity of muscle contractions of pharmacologically or electrically induced convulsions. Succinylcholine is generally preferred because of its short duration of action. /Included in US product labeling/|For more Therapeutic Uses (Complete) data for SUCCINYLCHOLINE (13 total), please visit the HSDB record page.

... Succinylcholine at doses causing neuromuscular relaxation rarely causes effects attributable to ganglionic blockade. However, cardiovascular effects are sometimes observed that are poblably due to the successive stimulation of vagal ganglia (manifested by bradycardia) and of sympathetic ganglia (resulting in hypertension and tachycardia).|GREAT CARE SHOULD BE TAKEN WHEN ADMINISTERING MUSCLE RELAXANTS TO DEHYDRATED OR SEVERELY ILL PATIENTS. /NEUROMUSCULAR BLOCKING AGENTS/|CONTINUOUS INFUSION OF SUCCINYLCHOLINE IN BOTH NEONATES & CHILDREN IS CONSIDERED UNSAFE. /CHLORIDE/|THE RESPONSE TO SUCCINYLCHOLINE MAY BE PROLONGED IN THE PRESENCE OF HYPOKALEMIA. PATIENTS WITH MYASTHENIA GRAVIS MAY BE RESISTANT TO DEPOLARIZING AGENTS AND HAVE A PREDISPOSITION TO PHASE II BLOCK. /CHLORIDE/|For more Drug Warnings (Complete) data for SUCCINYLCHOLINE (28 total), please visit the HSDB record page.

Succinylcholine is indicated as an adjunct to general anesthesia, to facilitate tracheal intubation, and to provide skeletal muscle relaxation during surgery or mechanical ventilation. Succinylcholine is a depolarizing skeletal muscle relaxant. As does acetylcholine, it combines with the cholinergic receptors of the motor end plate to produce depolarization. This depolarization may be observed as fasciculations. Subsequent neuromuscular transmission is inhibited so long as adequate concentration of succinylcholine remains at the receptor site. Succinylcholine has no direct action on the uterus or other smooth muscle structures.

Drugs that interrupt transmission at the skeletal neuromuscular junction by causing sustained depolarization of the motor end plate. These agents are primarily used as adjuvants in surgical anesthesia to cause skeletal muscle relaxation. (See all compounds classified as Neuromuscular Depolarizing Agents.)

About 10% of the drug is excreted unchanged in the urine.|... APPROX 10% OF ... /SUCCINYLCHOLINE/ IS EXCRETED UNCHANGED.|ONLY VERY LIMITED PLACENTAL TRANSFER OF...SUCCINYLCHOLINE WAS OBSERVED IN HUMANS, & DID NOT PRODUCE CLINICALLY OBSERVABLE EFFECTS IN NEW-BORN.|... The impression prevails that suxamethonium chloride (succinylcholine chloride) and doxorubicin donot cross the placenta. ... Analysis of the literature suggests that this impression is wrong and that all drugs cross the placenta, although the extent transfer varies considerably. ...

By pseudocholinesterase, to succinylmonocholine and choline.

The mechanism of action of Succinylcholine involves what appears to be a "persistent" depolarization of the neuromuscular junction. This depolarization is caused by Succinylcholine mimicking the effect of acetylcholine but without being rapidly hydrolysed by acetylcholinesterase. This depolarization leads to desensitization.|... SUCCINYLCHOLINE PRODUCES A BLOCKADE THAT COMBINES CERTAIN FEATURES OF ... THE DEPOLARIZING & THE COMPETITIVE AGENTS ... & THAT HAS SOME CHARACTERISTICS NOT ASSOC WITH EITHER; ... THIS TYPE OF ACTION /HAS BEEN TERMED/ A "DUAL" MECHANISM.|... /ITS/ INITIAL ACTION IS TO DEPOLARIZE THE MEMBRANE BY OPENING CHANNELS IN THE SAME MANNER AS ACETYL CHOLINE. HOWEVER, SINCE /IT/ PERSISTS FOR LONGER DURATIONS AT THE NEUROMUSCULAR JUNCTION, PRIMARILY BECAUSE OF THEIR RESISTANCE TO ACETYLCHOLINESTERASE, THE DEPOLARIZATION IS LONGER LASTING, RESULTING IN A BRIEF PERIOD OF REPETITIVE EXCITATION THAT MAY ELICIT TRANSIENT MUSCULAR FASCICULATIONS. THE INITIAL PHASE IS FOLLOWED BY BLOCK OF NEUROMUSCULAR TRANSMISSION AND FLACCID PARALYSIS.

SUCCINYLCHOLINE CHLORIDE DOES NOT CAUSE LIBERATION OF HISTAMINE &.../IT/ IS WELL TOLERATED. /CHLORIDE/

Anectine

Succinylcholine Use and Manufacturing

Methods of Manufacturing

... By reacting beta-bromoethyl succinate with trimethylamine. /Bromide/|Prepd by reacting beta-bromoethyl succinate with trimethylamine. /Iodide/|Succinic acid chloride may be coupled with choline chloride directly or with dimethylaminoethanol, followed by quarternization with methyl iodide. /Iodide/|A third method is to start with the diethyl ester of succinic acid, then bring about the exchange reaction with dimethylaminoethanol, and quaternize with methyl iodide. /Iodide/|Prepared by reaction of ethylene bromohydrin with succinic acid and subsequent reaction with trimethylamine in a sealed tube. It can also be prepared in one step from succinic anhydride and choline cloride. /Chloride/

Suxamethonium bromide; IS-370; compd 48/268; LT-1; M & B 2207; Brevidil M. /Bromide/|SUCCINYLCHOLINE CHLORIDE, USP (ANECTINE, QUELICIN, SCOLINE, SUCOSTRIN, SUX-CERT), IS MARKETED AS STERILE POWDER (0.5 & 1.0 G) & AS STERILE SOLN CONTAINING 20, 50, OR 100 MG/ML. /CHLORIDE/

Incompatible with soln of alkaline salts. /Iodide/|Soln without stabilizers ... Are incompatible with alkaline agents such as thiopental sodium. /Chloride/|Prepare soln just before using. /Bromide/

FOUR THIN-LAYER CHROMATOGRAPHIC SYSTEMS ARE DESCRIBED, FOLLOWED BY DETECTION UNDER UV LIGHT OR WITH POTASSIUM IODOPLATINATE REAGENT FOR SUCCINYLCHOLINE CHLORIDE.

THIS APPROACH PROVED SUITABLE FOR HUMAN URINE SAMPLES.

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:290.40
XLogP3:0.6
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:11
Exact Mass:290.22055744
Monoisotopic Mass:290.22055744
Topological Polar Surface Area:52.6
Heavy Atom Count:20
Formal Charge:2
Complexity:284
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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