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Details

Stereochemistry ACHIRAL
Molecular Formula C14H30N2O4
Molecular Weight 290.399
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 2

SHOW SMILES / InChI
Structure of SUCCINYLCHOLINE

SMILES

C[N+](C)(C)CCOC(=O)CCC(=O)OCC[N+](C)(C)C

InChI

InChIKey=AXOIZCJOOAYSMI-UHFFFAOYSA-N
InChI=1S/C14H30N2O4/c1-15(2,3)9-11-19-13(17)7-8-14(18)20-12-10-16(4,5)6/h7-12H2,1-6H3/q+2

HIDE SMILES / InChI
Succinylcholine also known as suxamethonium is a quaternary skeletal muscle relaxant usually used in the form of its halogen salt. It is is indicated under brand name anectine as an adjunct to general anesthesia, to facilitate tracheal intubation, and to provide skeletal muscle relaxation during surgery or mechanical ventilation. Succinylcholine activates the muscle-type nicotinic acetylcholine receptor followed by desensitization. Succinylcholine does not inhibit the presynaptic alpha3beta2 autoreceptor at clinically relevant concentrations, that provides a possible mechanistic explanation for the typical lack of tetanic fade in succinylcholine-induced neuromuscular blockade. Finally, was explored, that cardiovascular side effects (e.g., tachyarrhythmias) of succinylcholine were not mediated via direct activation of the autonomic ganglionic alpha3beta4 subtype because succinylcholine didn’t not activate the neuronal nicotinic acetylcholine receptor (nAChR) subtypes.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
ANECTINE

Approved Use

Succinylcholine chloride is indicated as an adjunct to general anesthesia, to facilitate tracheal intubation, and to provide skeletal muscle relaxation during surgery or mechanical ventilation.

Launch Date

1952
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
18.5 μg × min/mL
1 mg/kg bw single, intravenous
dose: 1 mg/kg bw
route of administration: Intravenous
experiment type: SINGLE
co-administered:
SUCCINYLCHOLINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
58.6 μg × min/mL
2 mg/kg bw single, intravenous
dose: 2 mg/kg bw
route of administration: Intravenous
experiment type: SINGLE
co-administered:
SUCCINYLCHOLINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
25.4 s
1 mg/kg bw single, intravenous
dose: 1 mg/kg bw
route of administration: Intravenous
experiment type: SINGLE
co-administered:
SUCCINYLCHOLINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
26.3 s
2 mg/kg bw single, intravenous
dose: 2 mg/kg bw
route of administration: Intravenous
experiment type: SINGLE
co-administered:
SUCCINYLCHOLINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1.5 mg/kg single, intravenous
Higher than recommended
Dose: 1.5 mg/kg
Route: intravenous
Route: single
Dose: 1.5 mg/kg
Sources: Page: p.866
healthy, 31
n = 22
Health Status: healthy
Condition: General anesthesia
Age Group: 31
Sex: F
Population Size: 22
Sources: Page: p.866
1.1 mg/kg single, intravenous (max)
Recommended
Dose: 1.1 mg/kg
Route: intravenous
Route: single
Dose: 1.1 mg/kg
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: General anesthesia|Skeletal muscle relaxation
Sources: Page: p.1
Disc. AE: Rhabdomyolysis, Ventricular arrhythmia...
AEs leading to
discontinuation/dose reduction:
Rhabdomyolysis (acute, rare)
Ventricular arrhythmia (rare)
Cardiac arrest (grade 5, rare)
Sources: Page: p.1
AEs

AEs

AESignificanceDosePopulation
Rhabdomyolysis acute, rare
Disc. AE
1.1 mg/kg single, intravenous (max)
Recommended
Dose: 1.1 mg/kg
Route: intravenous
Route: single
Dose: 1.1 mg/kg
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: General anesthesia|Skeletal muscle relaxation
Sources: Page: p.1
Cardiac arrest grade 5, rare
Disc. AE
1.1 mg/kg single, intravenous (max)
Recommended
Dose: 1.1 mg/kg
Route: intravenous
Route: single
Dose: 1.1 mg/kg
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: General anesthesia|Skeletal muscle relaxation
Sources: Page: p.1
Ventricular arrhythmia rare
Disc. AE
1.1 mg/kg single, intravenous (max)
Recommended
Dose: 1.1 mg/kg
Route: intravenous
Route: single
Dose: 1.1 mg/kg
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: General anesthesia|Skeletal muscle relaxation
Sources: Page: p.1
PubMed

PubMed

TitleDatePubMed
Succinylcholine-induced ventricular fibrillation in the paralyzed urology patient.
1975 Jan
Influence of tetrahydro-aminacrine on muscle pains after suxamethonium.
1975 Jan 18
Hypersensitivity to suxamethonium in a Suffolk family.
1976 Jul
Cardiac arrest due to succinylcholine-induced hyperkalemia in a patient with wound botulism.
2000 Feb
Out-of-hospital succinylcholine-assisted endotracheal intubation by paramedics.
2000 Jun
[Anesthetic complications. The incidence of severe anesthetic complications in patients and families with progressive muscular dystrophy of the Duchenne and Becker types].
2000 Mar
Choice of the muscle relaxant for rapid-sequence induction.
2001
Choice of the hypnotic and the opioid for rapid-sequence induction.
2001
Increased sensitivity to depolarization and nondepolarizing neuromuscular blocking agents in young rat hemidiaphragms.
2001 Aug
Safety and efficacy of rocuronium for controlled intubation with paralytics in the pediatric emergency department.
2001 Aug
Second dose thiopentone attenuates the haemodynamic response to laryngoscopy and intubation.
2001 Feb
Sore throat following tracheal intubation.
2001 Feb
Effectiveness of continuous positive airway pressure to enhance pre-oxygenation in morbidly obese women.
2001 Jul
Asystole during electroconvulsive therapy: a case report.
2001 Jun
Disagree with use of muscle relaxant before euthanasia.
2001 Jun 15
Measurement of succinylcholine concentration in human plasma by electrospray tandem mass spectrometry.
2001 Mar
Maternal anaphylactic reaction to a general anaesthetic at emergency caesarean section for fetal bradycardia.
2001 May
Rapid sequence induction: a national survey of practice.
2001 Nov
Basotest and suxamethonium allergy.
2001 Oct
[Anesthesia for electroconvulsive therapy during pregnancy--a case report].
2001 Sep
Autosomal dominant canine malignant hyperthermia is caused by a mutation in the gene encoding the skeletal muscle calcium release channel (RYR1).
2001 Sep
Succinylcholine in the intensive care unit.
2002 Jan
Patents

Patents

Sample Use Guides

Adults: For Short Surgical Procedures: the average dose required to produce neuromuscular blockade and to facilitate tracheal intubation is 0.6 mg/kg ANECTINE (Succinylcholine Chloride Injection) given intravenously. The optimum dose will vary among individuals and may be from 0.3 to 1.1 mg/kg for adults. Following administration of doses in this range, neuromuscular blockade develops in about 1 minute; maximum blockade may persist for about 2 minutes, after which recovery takes place within 4 to 6 minutes. However, very large doses may result in more prolonged blockade. A 5- to 10-mg test dose may be used to determine the sensitivity of the patient and the individual recovery time (see PRECAUTIONS). For Long Surgical Procedures The dose of succinylcholine administered by infusion depends upon the duration of the surgical procedure and the need for muscle relaxation. The average rate for an adult ranges between 2.5 and 4.3 mg per minute. Solutions containing from 1 to 2 mg per mL succinylcholine have commonly been used for continuous infusion. The more dilute solution (1 mg per mL) is probably preferable from the standpoint of ease of control of the rate of administration of the drug and, hence, of relaxation. This IV solution containing 1 mg per mL may be administered at a rate of 0.5 mg (0.5 mL) to 10 mg (10 mL) per minute to obtain the required amount of relaxation. Intermittent IV injections of succinylcholine may also be used to provide muscle relaxation for long procedures. An IV injection of 0.3 to 1.1 mg/kg may be given initially, followed, at appropriate intervals, by further injections of 0.04 to 0.07 mg/kg to maintain the degree of relaxation required. Pediatrics: for emergency tracheal intubation or in instances where immediate securing of the airway is necessary, the IV dose of succinylcholine is 2 mg/kg for infants and small children; for older children and adolescents the dose is 1 mg/kg. Rarely, IV bolus administration of succinylcholine in infants and children may result in malignant ventricular arrhythmias and cardiac arrest secondary to acute rhabdomyolysis with hyperkalemia. In such situations, an underlying myopathy should be suspected. Intravenous bolus administration of succinylcholine in infants or children may result in profound bradycardia or, rarely, asystole. As in adults, the incidence of bradycardia in children is higher Intramuscular Use: If necessary, succinylcholine may be given intramuscularly to infants, older children, or adults when a suitable vein is inaccessible. A dose of up to 3 to 4 mg/kg may be given, but not more than 150 mg total dose should be administered by this route. The onset of effect of succinylcholine given intramuscularly is usually observed in about 2 to 3 minutes.
Route of Administration: Other
In Vitro Use Guide
The rat diaphragm was used as an in vitro model for studies of contractures synergistically-induced by halothane and suxamethonium (succinylcholine). The effects of three agents reported to inhibit phospholipase A2 activity (quinacrine, spermine and indomethacin), tubocurarine and dantrolene were examined on these contractures. Contractures induced by 1% halothane (0.26 +/- 0.02 g) (mean +/- SEM) were increased (0.60 +/- 0.04 g) if suxamethonium 50 mmol litre-1 was also in the bathing medium. Suxamethonium-induced contractures (0.22 +/- 0.03 g) were also enhanced when halothane was present (0.51 +/- 0.03 g). Spermine, indomethacin and dantrolene antagonized both halothane- and suxamethonium-induced contractures. Quinacrine potentiated contractures induced by either halothane or suxamethonium. Contractures induced by suxamethonium were antagonized by tubocurarine; however, contractures induced by halothane were not antagonized by tubocurarine. These results suggest that free fatty acids may be involved in contractures induced synergistically by halothane and suxamethonium. Different mechanisms are involved in the induction of contractures by suxamethonium than by halothane.
Name Type Language
SUCCINYLCHOLINE
HSDB   VANDF  
Common Name English
SUXAMETHONIUM
WHO-DD  
Common Name English
ETHANAMINIUM, 2,2'-((1,4-DIOXO-1,4-BUTANEDIYL)BIS(OXY))BIS(N,N,N-TRIMETHYL-
Systematic Name English
SUCCINYLCHOLINE CATION
Common Name English
SUXAMETHONIUM ION
Common Name English
SUCCINYLCHOLINE ION
Common Name English
SUCCINYLCHOLINE [VANDF]
Common Name English
SUXAMETHONIUM CATION
Common Name English
SUCCINYLCHOLINE [HSDB]
Common Name English
Suxamethonium [WHO-DD]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175733
Created by admin on Fri Dec 15 17:20:03 GMT 2023 , Edited by admin on Fri Dec 15 17:20:03 GMT 2023
WHO-ATC M03AB01
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NDF-RT N0000175719
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WHO-VATC QM03AB01
Created by admin on Fri Dec 15 17:20:03 GMT 2023 , Edited by admin on Fri Dec 15 17:20:03 GMT 2023
WHO-ESSENTIAL MEDICINES LIST 20
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NCI_THESAURUS C29696
Created by admin on Fri Dec 15 17:20:03 GMT 2023 , Edited by admin on Fri Dec 15 17:20:03 GMT 2023
Code System Code Type Description
LACTMED
Succinylcholine
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PRIMARY
DRUG CENTRAL
2489
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NCI_THESAURUS
C61955
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RXCUI
10154
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PRIMARY RxNorm
DRUG BANK
DB00202
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EVMPD
SUB04653MIG
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MESH
D013390
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CHEBI
45652
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EPA CompTox
DTXSID7048455
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CAS
306-40-1
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WIKIPEDIA
Succinylcholine
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DAILYMED
J2R869A8YF
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IUPHAR
4004
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SMS_ID
100000086059
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HSDB
3254
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FDA UNII
J2R869A8YF
Created by admin on Fri Dec 15 17:20:03 GMT 2023 , Edited by admin on Fri Dec 15 17:20:03 GMT 2023
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PUBCHEM
5314
Created by admin on Fri Dec 15 17:20:03 GMT 2023 , Edited by admin on Fri Dec 15 17:20:03 GMT 2023
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