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

Details

Stereochemistry ACHIRAL
Molecular Formula C14H30N2O4.2Cl
Molecular Weight 361.3054
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SUCCINYLCHOLINE CHLORIDE

SMILES

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

InChI

InChIKey=YOEWQQVKRJEPAE-UHFFFAOYSA-L
InChI=1S/C14H30N2O4.2ClH/c1-15(2,3)9-11-19-13(17)7-8-14(18)20-12-10-16(4,5)6;;/h7-12H2,1-6H3;2*1H/q+2;;/p-2

HIDE SMILES / InChI

Molecular Formula C14H30N2O4
Molecular Weight 290.3996
Charge 2
Count
Stereochemistry MIXED
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

-5.48035199E11
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
Comparison of gallamine with d-tubocurarine effects on fasciculations after succinylcholine.
1975 Jan-Feb
"Precurarization" using pancuronium.
1975 Jan-Feb
Response of the newborn to succinlycholine injection in homozygotic atypical mothers.
1975 Jul
Cardiac arrest related to anesthesia. Contributing factors in infants and children.
1975 Jul 21
Interactions of neuromuscular blocking drugs.
2001
[Clinical administration of muscle relaxants for intubation].
2001
Difficult airway management of a child impaled through the neck.
2001
Newer neuromuscular blocking agents: how do they compare with established agents?
2001
Malignant hyperthermia in a patient with Graves' disease during subtotal thyroidectomy.
2001 Apr
Electroconvulsive therapy impairs systolic performance of the left ventricle.
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
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
The influence of fentanyl vs. s-ketamine on intubating conditions during induction of anaesthesia with etomidate and rocuronium.
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
Intralingual succinylcholine injection provides a rapid onset of muscle relaxation in an emergency.
2001 Dec
A randomized multicenter study of remifentanil compared with halothane in neonates and infants undergoing pyloromyotomy. I. Emergence and recovery profiles.
2001 Dec
Military and civilian penetrating eye trauma: anesthetic implications.
2001 Feb
Effectiveness of continuous positive airway pressure to enhance pre-oxygenation in morbidly obese women.
2001 Jul
Intramuscular ketamine in a parturient in whom pre-operative intravenous access was not possible.
2001 Jun
Facilitation of fiberoptic nasotracheal intubation by simultaneous direct laryngoscopy in anesthetized patients.
2001 Jun
Succinylcholine pretreatment using gallamine or mivacurium during rapid sequence induction in children: a randomized, controlled study.
2001 Jun
Succinylcholine-induced hyperkalemia in a patient with mucositis secondary to chemotherapy.
2001 Jun
Disagree with use of muscle relaxant before euthanasia.
2001 Jun 15
EEG-bispectral index changes with ketamine versus thiamylal induction of anesthesia.
2001 Mar
Cardiac arrest after succinylcholine: mortality greater with rhabdomyolysis than receptor upregulation.
2001 Mar
[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
Anesthesia and critical care of thymectomy for myasthenia gravis.
2001 May
Hemoglobin desaturation after succinylcholine-induced apnea: a study of the recovery of spontaneous ventilation in healthy volunteers.
2001 May
Maternal anaphylactic reaction to a general anaesthetic at emergency caesarean section for fetal bradycardia.
2001 May
The intubating laryngeal mask airway after induction of general anesthesia versus awake fiberoptic intubation in patients with difficult airways.
2001 May
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
Intramuscular succinylcholine and laryngospasm.
2001 Oct
Basotest and suxamethonium allergy.
2001 Oct
[Anesthesia for electroconvulsive therapy during pregnancy--a case report].
2001 Sep
Hyperkalaemic cardiac arrest in a manifesting carrier of Duchenne muscular dystrophy following general anaesthesia.
2001 Sep
Different patterns of mast cell activation by muscle relaxants in human skin.
2001 Sep
In patients with head injuries who undergo rapid sequence intubation using succinylcholine, does pretreatment with a competitive neuromuscular blocking agent improve outcome? A literature review.
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. 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.
Substance Class Chemical
Created
by admin
on Fri Jun 25 20:59:46 UTC 2021
Edited
by admin
on Fri Jun 25 20:59:46 UTC 2021
Record UNII
I9L0DDD30I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SUCCINYLCHOLINE CHLORIDE
MI   ORANGE BOOK   USAN   USP   VANDF  
USAN  
Official Name English
SUXAMETHONIUM CHLORIDE [MART.]
Common Name English
SUXAMETHONIUM CHLORIDE [EP MONOGRAPH]
Common Name English
ETHANAMINIUM, 2,2'-((1,4-DIOXO-1,4-BUTANEDIYL)BIS(OXY))BIS(N,N,N-TRIMETHYL-), DICHLORIDE
Common Name English
ANECTINE
Brand Name English
SUCCINYLCHOLINE CHLORIDE [USP-RS]
Common Name English
SUCCINYLCHOLINE CHLORIDE [USAN]
Common Name English
SUXAMETHONIUM CHLORIDE
EP   INN   JAN   MART.   WHO-DD  
INN  
Official Name English
SUCCINYLCHOLINE CHLORIDE [USP MONOGRAPH]
Common Name English
SUCCINYLCHOLINE CHLORIDE [MI]
Common Name English
SUXAMETHONIUM CHLORIDE [INN]
Common Name English
SUCCINYLCHOLINE CHLORIDE [VANDF]
Common Name English
CHOLINE CHLORIDE SUCCINATE (2:1)
Common Name English
NSC-49132
Code English
SUCCINYLCHOLINE CHLORIDE [ORANGE BOOK]
Common Name English
QUELICIN
Brand Name English
SUXAMETHONIUM CHLORIDE [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29696
Created by admin on Fri Jun 25 20:59:46 UTC 2021 , Edited by admin on Fri Jun 25 20:59:46 UTC 2021
Code System Code Type Description
EPA CompTox
71-27-2
Created by admin on Fri Jun 25 20:59:46 UTC 2021 , Edited by admin on Fri Jun 25 20:59:46 UTC 2021
PRIMARY
DRUG BANK
DBSALT000206
Created by admin on Fri Jun 25 20:59:46 UTC 2021 , Edited by admin on Fri Jun 25 20:59:46 UTC 2021
PRIMARY
RXCUI
3565
Created by admin on Fri Jun 25 20:59:46 UTC 2021 , Edited by admin on Fri Jun 25 20:59:46 UTC 2021
PRIMARY RxNorm
CAS
71-27-2
Created by admin on Fri Jun 25 20:59:46 UTC 2021 , Edited by admin on Fri Jun 25 20:59:46 UTC 2021
PRIMARY
PUBCHEM
22475
Created by admin on Fri Jun 25 20:59:46 UTC 2021 , Edited by admin on Fri Jun 25 20:59:46 UTC 2021
PRIMARY
USP_CATALOG
1623502
Created by admin on Fri Jun 25 20:59:46 UTC 2021 , Edited by admin on Fri Jun 25 20:59:46 UTC 2021
PRIMARY USP-RS
MERCK INDEX
M10276
Created by admin on Fri Jun 25 20:59:46 UTC 2021 , Edited by admin on Fri Jun 25 20:59:46 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C47730
Created by admin on Fri Jun 25 20:59:46 UTC 2021 , Edited by admin on Fri Jun 25 20:59:46 UTC 2021
PRIMARY
INN
26
Created by admin on Fri Jun 25 20:59:46 UTC 2021 , Edited by admin on Fri Jun 25 20:59:46 UTC 2021
PRIMARY
WIKIPEDIA
SUXAMETHONIUM CHLORIDE
Created by admin on Fri Jun 25 20:59:46 UTC 2021 , Edited by admin on Fri Jun 25 20:59:46 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-747-4
Created by admin on Fri Jun 25 20:59:46 UTC 2021 , Edited by admin on Fri Jun 25 20:59:46 UTC 2021
PRIMARY
EVMPD
SUB10786MIG
Created by admin on Fri Jun 25 20:59:46 UTC 2021 , Edited by admin on Fri Jun 25 20:59:46 UTC 2021
PRIMARY
ChEMBL
CHEMBL703
Created by admin on Fri Jun 25 20:59:46 UTC 2021 , Edited by admin on Fri Jun 25 20:59:46 UTC 2021
PRIMARY
FDA UNII
I9L0DDD30I
Created by admin on Fri Jun 25 20:59:46 UTC 2021 , Edited by admin on Fri Jun 25 20:59:46 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY