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Succinylcholine

HCID 5314
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
306-40-1
Standard SMILES
C[N+](C)(C)CCOC(=O)CCC(=O)OCC[N+](C)(C)C
InChIKey
AXOIZCJOOAYSMI-UHFFFAOYSA-N
Molecular formula
C14H30N2O4+2
Average molar mass
290.4 g/mol
Monoisotopic mass
290.22055744

Overview

Succinylcholine is a quaternary ammonium ion that is the bis-choline ester of succinic acid. It has a role as a muscle relaxant, a neuromuscular agent and a drug allergen. It is a quaternary ammonium ion and a succinate ester.

Names & identifiers

Preferred name
Succinylcholine
IUPAC
trimethyl-[2-[4-oxo-4-[2-(trimethylazaniumyl)ethoxy]butanoyl]oxyethyl]azanium
English name
Succinylcholine
Molecular formula
C14H30N2O4
Molecular weight
0

Names & synonyms

succinylcholineSuxamethoniumSuccinyldicholineSuccinocholineSuccinylbischolineSuccinoylcholineDicholine succinate306-40-1DiacetylcholineDitilineCholine, succinyl-Suxamethonium ion
Show more names
2,2'-(succinylbis(oxy))bis(N,N,N-triMethylethanaMiniuM)2,2'-[(1,4-Dioxo-1,4-butanediyl)bis(oxy)]bis[N,N,N-trimethylethanaminium]2,2'-[(1,4-Dioxobutane-1,4-diyl)bis(oxy)]bis[N,N,N-trimethyl-1-ethanaminium]
Succinylcholine ionSuxamethonium cationSuccinic acid, diester with cholineSuccinylcholine cationCholine, succinate (2:1) (ester)2,2'-[(1,4-DIOXOBUTANE-1,4-DIYL)BIS(OXY)]BIS(N,N,N-TRIMETHYLETHANAMINIUM)J2R869A8YFCHEBI:45652

Database identifiers

CAS
306-40-1
PubChem CID
5314
DTXSID
DTXSID7048455
ChEMBL
CHEMBL703
ChEBI
CHEBI:45652
UNII
J2R869A8YF

Properties

Computed structural properties

XLogP
0.6
Topological polar surface area
52.6 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
4
Rotatable bonds
11
Heavy atoms
20
Formal charge
2
Complexity
284

Experimental & physicochemical properties

Drugs · 2 items

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals

Solubility · 5 items

Very soluble

ODORLESS; DIHYDRATE IS HYGROSCOPIC; WHITE CRYSTALLINE POWDER; 1 G SOL IN ABOUT 1 ML H2O & ABOUT 350 ML ALC /CHLORIDE/

Slightly hygroscopic crystals, mp 225 °C. Freely sol in water or normal saline, giving solns which are very slightly acidic. /Bromide/

Exists as a dihydrate at room temperature, crystals, mp 156-163 °C. Anhydrous form mp approximately 190 °C. Slightly bitter taste. Freely soluble in water (about 1 g/1 ml water). Solubility in 95% ethanol: 0.42 g/ 100 ml. Sparingly soluble in benzene, chloroform. Practically insoluble in ether. The pH of a 2-5% aqueous solution may vary from 4.5 to 3.0. /Chloride/

7.57e-04 g/L

Human Drugs · 2 items

Breast Feeding; Lactation; Milk, Human; Muscle Relaxants; Neuromuscular Depolarizing Agents

Muscle relaxants (peripherally-acting) and cholinesterase inhibitors

Decomposition · 2 items

When heated to decomposition it emits toxic fumes of nitroxides.

Succinylcholine chloride ... decomposes in solutions with a pH greater than 4.5. /Succinylcholine chloride/

Physical Description

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Hazard information

FDA Requirements · 1 item

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).

Safety & protection

Disposal Methods · 1 item

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.

Toxicology

Interactions · 5 items

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.

Human Toxicity ExcerptsSUCCINYLCHOLINE CHLORIDE DOES NOT CAUSE LIBERATION OF HISTAMINE &.../IT/ IS WELL TOLERATED. /CHLORIDE/
Drug Induced Liver Injury

Chemistry & industry

Pharmacology

ATC Code · 4 items

M03AB01

M - Musculo-skeletal system

QM - Musculo-skeletal system

M03AB01

Pharmacodynamics · 1 item

Succinylcholine's neuromuscular blockade takes effect within 60 seconds of intravenous administration and lasts between four to six minutes. Similar to acetylcholine, it binds to cholinergic receptors of the motor endplate to induce membrane depolarization and, eventually, muscle paralysis, which may be maintained for as long as an adequate concentration of succinylcholine remains at the receptor site. Succinylcholine has no direct action on smooth or cardiac muscle, nor does it appear to act on pre-synaptic or ganglionic acetylcholine receptors. The paralysis induced by succinylcholine has been described as "progressive", first involving the muscles of the face and glottis, then the intercostals and diaphragm, then followed by other skeletal muscles. Succinylcholine has no effect on consciousness or pain threshold, and must therefore be used in conjunction with adequate anesthesia. There have been rare reports of the development of acute rhabdomyolysis with hyperkalemia - resulting in ventricular dysrhythmias, cardiac arrest, and death - after the intravenous administration of succinylcholine to apparently healthy pediatric patients who were subsequently found to have undiagnosed skeletal myopathy (most frequently Duchenne's muscular dystrophy). Infants or children experiencing seemingly idiopathic cardiac arrest soon after the administration of succinylcholine should therefore be treated immediately for hyperkalemia. Given that patients may not present with any apparent risk factors, the use of succinylcholine in pediatric patients should be restricted to emergency intubation or other situations in which a suitable alternative is unavailable.

Mechanism of Action · 3 items

Succinylcholine is a depolarizing neuromuscular blocker, meaning it causes a prolonged period of membrane depolarization in order to exert its therapeutic effects. It binds to the post-synaptic cholinergic receptors found on motor endplates, thereby inducing first transient fasciculations followed by skeletal muscle paralysis.

... 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.

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Nikkaji
J11.690D
Solid
Stability/Shelf Life · 5 items

SLIGHTLY HYGROSCOPIC ... AQ SOLN UNDERGO PROGRESSIVE HYDROLYSIS WITH CORRESPONDING LOSS OF ACTIVITY & INCR IN ACIDITY. /BROMIDE/

THE RATE OF THis DECOMP INCR WITH TEMP & AUTOCLAVING OR PROLONGED EXPOSURE TO WARMTH SHOULD BE AVOIDED. /BROMIDE/

MOST STABLE @ PH 4-5; AQ SOLN UNDERGO PROGRESSIVE HYDROLYSIS WITH CORRESPONDING LOSS OF ACTIVITY & INCR IN ACIDITY. /IODIDE/

COMMERCIALLY AVAIL INJECTIONS WHEN REFRIGERATED HAVE EXPIRATION DATE OF 12-24 MO

For more Stability/Shelf Life (Complete) data for SUCCINYLCHOLINE (6 total), please visit the HSDB record page.

Other Experimental Properties · 2 items

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/

Physicochemical properties

Boiling point
432.48 °C · 432.48°C (rough estimate)
Density
1.0386 · 1.0386 (rough estimate)
refractive index
1.506 · 1.5060 (estimate)
FDA UNII
2 R869A8YF · J2R869A8YF
Hazardous Substances Data
306 · 306-40-1(Hazardous Substances Data)
Toxicity
A synthetic muscle relaxant with a curare-like action. Although the selectivity and superficial nature of the paralysis produced by succinylcholine mirrors that of tubocurarine, the specific action is quite different. Succinylcholine is classified as a depolarizing blocking agent, and it blocks acetylcholine receptors by persistent depolarization rather than by the competitive antagonism seen with true curarimimetics. In addition, succinylcholine is inactivated by cholinesterases, limiting the duration of its action.
· 6 items

Benchmark Dataset for the Liver Toxicity Knowledge Base (LTKB)

succinylcholine

Anectine®

Muscle relaxants

Not Applicable

no-DILI-concern

Non-Human Toxicity Excerpts · 2 items

DEATHS FROM SUCCINYLCHOLINE CHLORIDE HAVE BEEN RECORDED IN THE HORSE. THESE WERE ASSUMED ... TO BE DUE TO ... DEPRESSION OF RESPIRATION BUT ARE MORE PROBABLY ASSOCIATED WITH CARDIAC ARREST. /CHLORIDE/

MUSCLE RELAXANTS CAN ACT AS TRIGGERING AGENTS IN GENETICALLY SUSCEPTIBLE PIGS WHICH DEVELOP HYPERMETABOLIC STATE, CHARACTERIZED BY RAPID RISE IN BODY TEMP, MUSCLE RIGIDITY, TACHYCARDIA & TACHYPNEA, CYANOSIS & SEVERE RESP & METABOLIC ACIDOSIS.

Populations at Special Risk · 1 item

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/

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Non-Human Toxicity Values · 5 items

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

Regulatory information

FDA Requirements · 1 item

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).

Safety data

Toxicity
A synthetic muscle relaxant with a curare-like action. Although the selectivity and superficial nature of the paralysis produced by succinylcholine mirrors that of tubocurarine, the specific action is quite different. Succinylcholine is classified as a depolarizing blocking agent, and it blocks acetylcholine receptors by persistent depolarization rather than by the competitive antagonism seen with true curarimimetics. In addition, succinylcholine is inactivated by cholinesterases, limiting the duration of its action.
Hazardous Substances Data
306-40-1(Hazardous Substances Data)

... /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.

Biological Half-LifeThe mean half-life of elimination following intravenous administration is 47 seconds.
Metabolism/MetabolitesSuccinylcholine is rapidly metabolized by plasma cholinesterase in the bloodstream to succinylmonocholine, which is then further hydrolyzed (albeit more slowly) to succinic acid and choline.
FDA Pharmacological Classification · 6 items

J2R869A8YF

SUCCINYLCHOLINE

Established Pharmacologic Class [EPC] - Depolarizing Neuromuscular Blocker

Physiologic Effects [PE] - Neuromuscular Depolarizing Blockade

Succinylcholine is a Depolarizing Neuromuscular Blocker. The physiologic effect of succinylcholine is by means of Neuromuscular Depolarizing Blockade.

SUCCINYLCHOLINE

MeSH Pharmacological ClassificationDrugs 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.
Absorption, Distribution and Excretion · 6 items

Approximately 10% of an administered dose is excreted unchanged in the urine.

At intravenous doses of 1 mg/kg and 2 mg/kg in 14 patients, the mean apparent volumes of distribution were 16.4 ± 14.7 and 5.6 ± 6.8 mL/kg, respectively.

The mean _in vivo_ plasma clearance of succinylcholine following an intravenous dose of 1 mg/kg in 18 patients was approximately 4.17 ± 2.37 L/min.

... 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. ...

Cellular LocationsCytoplasm

Uses & manufacturing

Uses · 3 items

MEDICATION

MEDICATION (VET)

Use (kg; approx.) in Germany (2009): >100

Methods of Manufacturing · 5 items

... 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/

Formulations/Preparations · 2 items

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/

General Manufacturing Information · 3 items

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/

Applications · 2 items

DescriptionSuccinylcholine is the only therapeutically used depolarizing neuromuscular blocker. Unlike nondepolarizing substances, succinylchloride is not a competitive antagonist; conversely, it is a more stable agonist than acetylcholine. In this manner, succinylcholine differs from acetylcholine only in duration—it lasts longer, causing a more stable depolarization. Thus the process of repolarization is blocked and the muscles relax. During this period, muscles that cause fine movement (ocular, facial, neck) are the most sensitive and are blocked first, after which muscles of the extremities are blocked, and finally the most stable respiratory muscles. Restoration occurs upon completion of drug action.

UsesTherapeutic use of succinylcholine consists of preventing involuntary patient movement. It is used for brief operations, intubation of the trachea, and other endoscopic procedures. Synonyms of this drug are listenon, midarine, sucostrin, ditilin, and others.

Upstream & downstream products

Upstream raw materials

Sodium hydroxideChloromethane

Suppliers5 total

北京华美互利生物化工010-56205725 · [email protected]
Sinoway Industrial co., ltd.+86-0592-5800732 +86-13806035118 · [email protected]
Syntechem Co.,Ltd[email protected]
梯希爱(上海)化工贸易有限公司021-61109150 · [email protected]
陕西缔都医药化工有限公司029-81024372 17792795018 · [email protected]

Additional notes

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