U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C14H30N2O4
Molecular Weight 290.3996
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

-548035200000
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:
healthy, 31
Health Status: healthy
Age Group: 31
Sex: F
Sources:
1.1 mg/kg single, intravenous
Recommended
Dose: 1.1 mg/kg
Route: intravenous
Route: single
Dose: 1.1 mg/kg
Sources:
unhealthy
Disc. AE: Rhabdomyolysis, Ventricular arrhythmia...
AEs leading to
discontinuation/dose reduction:
Rhabdomyolysis (acute, rare)
Ventricular arrhythmia (rare)
Cardiac arrest (grade 5, rare)
Sources:
AEs

AEs

AESignificanceDosePopulation
Rhabdomyolysis acute, rare
Disc. AE
1.1 mg/kg single, intravenous
Recommended
Dose: 1.1 mg/kg
Route: intravenous
Route: single
Dose: 1.1 mg/kg
Sources:
unhealthy
Cardiac arrest grade 5, rare
Disc. AE
1.1 mg/kg single, intravenous
Recommended
Dose: 1.1 mg/kg
Route: intravenous
Route: single
Dose: 1.1 mg/kg
Sources:
unhealthy
Ventricular arrhythmia rare
Disc. AE
1.1 mg/kg single, intravenous
Recommended
Dose: 1.1 mg/kg
Route: intravenous
Route: single
Dose: 1.1 mg/kg
Sources:
unhealthy
PubMed

PubMed

TitleDatePubMed
Comparison of gallamine with d-tubocurarine effects on fasciculations after succinylcholine.
1975 Jan-Feb
"Precurarization" using pancuronium.
1975 Jan-Feb
Cardiac arrest related to anesthesia. Contributing factors in infants and children.
1975 Jul 21
Interactions of neuromuscular blocking drugs.
2001
Rapacuronium: first experience in clinical practice.
2001
Rapacuronium: clinical pharmacology.
2001
Choice of the muscle relaxant for rapid-sequence induction.
2001
Choice of the hypnotic and the opioid for rapid-sequence induction.
2001
Muscle relaxants in paediatric day case surgery.
2001
Muscle relaxants suitable for day case surgery.
2001
Malignant hyperthermia in a patient with Graves' disease during subtotal thyroidectomy.
2001 Apr
A comparison of the effects of sarin and succinylcholine on respiratory parameters in anesthetized domestic swine.
2001 Apr
Giant multimodal heart motoneurons of Achatina fulica: a new cardioregulatory input in pulmonates.
2001 Aug
[Anesthetic management of a patient with a history of acute intermittent porphyria and an elevation of urinary porphobilinogen].
2001 Aug
Tracheal intubation without muscle relaxant--a technique using sevoflurane vital capacity induction and alfentanil.
2001 Aug
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
Effects of combined methohexitone-remifentanil anaesthesia in electroconvulsive therapy.
2001 Aug
Why do we still use suxamethonium for caesarean section?
2001 Dec
Analysis of mutations in the plasma cholinesterase gene of patients with a history of prolonged neuromuscular block during anesthesia.
2001 Dec
The laryngeal mask airway is effective (and probably safe) in selected healthy parturients for elective Cesarean section: a prospective study of 1067 cases.
2001 Dec
Intubating trauma patients before reaching hospital -- revisited.
2001 Dec
The effect of rocuronium on intraocular pressure: a comparison with succinylcholine.
2001 Dec
A randomized multicenter study of remifentanil compared with halothane in neonates and infants undergoing pyloromyotomy. I. Emergence and recovery profiles.
2001 Dec
Neuromuscular blockers in surgery and intensive care, Part 2.
2001 Dec 15
Military and civilian penetrating eye trauma: anesthetic implications.
2001 Feb
Sore throat following tracheal intubation.
2001 Feb
Use of a multidisciplinary continuous-quality-improvement process to investigate succinylcholine treatment failures.
2001 Feb 1
[Concerning the new presentation of Celocurine].
2001 Jan
[A case of ventricular tachycardia immediately after electroconvulsive therapy in a schinzophrenic patient].
2001 Jan
Muscle relaxant choices for rapid sequence induction.
2001 Jan-Feb
Frequency of haemoglobin desaturation with the use of succinylcholine during rapid sequence induction of anaesthesia.
2001 Jul
Intramuscular ketamine in a parturient in whom pre-operative intravenous access was not possible.
2001 Jun
Asystole during electroconvulsive therapy: a case report.
2001 Jun
[Systemic lupus erythematosus in the pregnant patient. Implications for anesthesia].
2001 Mar
Conquer difficult airways. Strategies to help you identify & control a problem airway.
2001 Mar
Measurement of succinylcholine concentration in human plasma by electrospray tandem mass spectrometry.
2001 Mar
Succinylcholine-assisted endotracheal intubation by paramedics.
2001 Mar
Duration of action of vecuronium after an intubating dose of rapacuronium, vecuronium, or succinylcholine.
2001 May
[Pseudocholinesterase (ChE)].
2001 Nov
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Rapid sequence induction: a national survey of practice.
2001 Nov
Is succinylcholine appropriate or obsolete in the intensive care unit?
2001 Oct
The substitute for the intravenous route.
2001 Oct
Basotest and suxamethonium allergy.
2001 Oct
Hyperkalaemic cardiac arrest in a manifesting carrier of Duchenne muscular dystrophy following general anaesthesia.
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
Different patterns of mast cell activation by muscle relaxants in human skin.
2001 Sep
Are fade and sustained post-tetanic facilitation characteristics of typical succinylcholine-induced block?
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.
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
SUXAMETHONIUM [WHO-DD]
Common 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
Classification Tree Code System Code
NDF-RT N0000175733
Created by admin on Sat Jun 26 16:01:23 UTC 2021 , Edited by admin on Sat Jun 26 16:01:23 UTC 2021
WHO-ATC M03AB01
Created by admin on Sat Jun 26 16:01:23 UTC 2021 , Edited by admin on Sat Jun 26 16:01:23 UTC 2021
NDF-RT N0000175719
Created by admin on Sat Jun 26 16:01:23 UTC 2021 , Edited by admin on Sat Jun 26 16:01:23 UTC 2021
WHO-VATC QM03AB01
Created by admin on Sat Jun 26 16:01:23 UTC 2021 , Edited by admin on Sat Jun 26 16:01:23 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 20
Created by admin on Sat Jun 26 16:01:23 UTC 2021 , Edited by admin on Sat Jun 26 16:01:23 UTC 2021
NCI_THESAURUS C29696
Created by admin on Sat Jun 26 16:01:23 UTC 2021 , Edited by admin on Sat Jun 26 16:01:23 UTC 2021
Code System Code Type Description
LACTMED
Succinylcholine
Created by admin on Sat Jun 26 16:01:23 UTC 2021 , Edited by admin on Sat Jun 26 16:01:23 UTC 2021
PRIMARY
DRUG CENTRAL
2489
Created by admin on Sat Jun 26 16:01:23 UTC 2021 , Edited by admin on Sat Jun 26 16:01:23 UTC 2021
PRIMARY
NCI_THESAURUS
C61955
Created by admin on Sat Jun 26 16:01:23 UTC 2021 , Edited by admin on Sat Jun 26 16:01:23 UTC 2021
PRIMARY
RXCUI
10154
Created by admin on Sat Jun 26 16:01:23 UTC 2021 , Edited by admin on Sat Jun 26 16:01:23 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB00202
Created by admin on Sat Jun 26 16:01:23 UTC 2021 , Edited by admin on Sat Jun 26 16:01:23 UTC 2021
PRIMARY
EVMPD
SUB04653MIG
Created by admin on Sat Jun 26 16:01:23 UTC 2021 , Edited by admin on Sat Jun 26 16:01:23 UTC 2021
PRIMARY
MESH
D013390
Created by admin on Sat Jun 26 16:01:23 UTC 2021 , Edited by admin on Sat Jun 26 16:01:23 UTC 2021
PRIMARY
EPA CompTox
306-40-1
Created by admin on Sat Jun 26 16:01:23 UTC 2021 , Edited by admin on Sat Jun 26 16:01:23 UTC 2021
PRIMARY
CAS
306-40-1
Created by admin on Sat Jun 26 16:01:23 UTC 2021 , Edited by admin on Sat Jun 26 16:01:23 UTC 2021
PRIMARY
WIKIPEDIA
Succinylcholine
Created by admin on Sat Jun 26 16:01:23 UTC 2021 , Edited by admin on Sat Jun 26 16:01:23 UTC 2021
PRIMARY
IUPHAR
4004
Created by admin on Sat Jun 26 16:01:23 UTC 2021 , Edited by admin on Sat Jun 26 16:01:23 UTC 2021
PRIMARY
HSDB
3254
Created by admin on Sat Jun 26 16:01:23 UTC 2021 , Edited by admin on Sat Jun 26 16:01:23 UTC 2021
PRIMARY
FDA UNII
J2R869A8YF
Created by admin on Sat Jun 26 16:01:23 UTC 2021 , Edited by admin on Sat Jun 26 16:01:23 UTC 2021
PRIMARY
PUBCHEM
5314
Created by admin on Sat Jun 26 16:01:23 UTC 2021 , Edited by admin on Sat Jun 26 16:01:23 UTC 2021
PRIMARY