Succinylcholine

Identification

Summary

Succinylcholine is a depolarizing skeletal muscle relaxant used adjunctly to anesthesia and for skeletal muscle relaxation during intubation, mechanical ventilation, and surgical procedures.

Brand Names
Anectine, Quelicin
Generic Name
Succinylcholine
DrugBank Accession Number
DB00202
Background

Succinylcholine is a depolarizing skeletal muscle relaxant consisting of two molecules of the endogenous neurotransmitter acetylcholine (ACh) linked by their acetyl groups.2 It has been widely used for over 50 years,1 most commonly in its chloride salt form, as a means of neuromuscular blockade during intubation and surgical procedures. Its rapid onset and offset, with effects beginning within 60 seconds of intravenous administration and lasting between four to six minutes, make succinylcholine particularly useful in the setting of short medical procedures requiring brief periods of muscle relaxation.9

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 290.399
Monoisotopic: 290.220557458
Chemical Formula
C14H30N2O4
Synonyms
  • 2,2'-[(1,4-dioxobutane-1,4-diyl)bis(oxy)]bis(N,N,N-trimethylethanaminium)
  • Dicholine succinate
  • Succinocholine
  • Succinoylcholine
  • Succinylbischoline
  • Succinyldicholine
  • Suxamethonium

Pharmacology

Indication

Succinylcholine is indicated as an adjunct to general anesthesia, to facilitate tracheal intubation, and to provide skeletal muscle relaxation during surgery or mechanical ventilation.9

Pharmacology
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Associated Therapies
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Succinylcholine's neuromuscular blockade takes effect within 60 seconds of intravenous administration and lasts between four to six minutes.2 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.8 Succinylcholine has no direct action on smooth or cardiac muscle, nor does it appear to act on pre-synaptic or ganglionic acetylcholine receptors.5 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.8

Succinylcholine has no effect on consciousness or pain threshold, and must therefore be used in conjunction with adequate anesthesia.9 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).9 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.9

Mechanism of action

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.7

TargetActionsOrganism
ANeuronal Acetylcholine (nACh) Receptor Subunits
agonist
Humans
UMuscarinic acetylcholine receptor M2
agonist
Humans
UMuscarinic acetylcholine receptor M3
agonist
Humans
Absorption

Not Available

Volume of distribution

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.6

Protein binding

Not Available

Metabolism

Succinylcholine is rapidly metabolized by plasma cholinesterase in the bloodstream to succinylmonocholine, which is then further hydrolyzed (albeit more slowly) to succinic acid and choline.8

Hover over products below to view reaction partners

Route of elimination

Approximately 10% of an administered dose is excreted unchanged in the urine.8

Half-life

The mean half-life of elimination following intravenous administration is 47 seconds.4

Clearance

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.3

Adverse Effects
Adverseeffects
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Toxicity

Overdosage of succinylcholine is likely to extend the neuromuscular blockade beyond the time needed for surgery. Symptoms are likely to be consistent with its therapeutic effects, although more pronounced, and may therefore include skeletal muscle weakness, decreased respiratory reserve, low tidal volume, or apnea. Treatment of succinylcholine overdose involves airway and respiratory support until recovery of normal respiration is assured.9

Depending on the extent of the overdose, the characteristic depolarizing (i.e. Phase I) neuromuscular blockade may switch to resemble more closely a non-depolarizing (i.e. Phase II) neuromuscular blockade.9 This occurs primarily when succinylcholine is given over a prolonged period of time or with particularly large doses, and may result in significant respiratory muscle paralysis or weakness.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Voltage-dependent L-type calcium channel subunit alpha-1S---Not Availablec.3257G>A / c.520C>TADR InferredMalignant hyperthermia.Details
Ryanodine receptor 1---Not Availablec.103T>C / c.487C>T  … show all ADR InferredMalignant hyperthermia.Details

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Succinylcholine is combined with 1,2-Benzodiazepine.
AcebutololThe risk or severity of hyperkalemia can be increased when Succinylcholine is combined with Acebutolol.
AceclofenacThe risk or severity of hyperkalemia can be increased when Succinylcholine is combined with Aceclofenac.
AcemetacinThe risk or severity of hyperkalemia can be increased when Succinylcholine is combined with Acemetacin.
AcetazolamideThe risk or severity of adverse effects can be increased when Succinylcholine is combined with Acetazolamide.
AcetophenazineThe risk or severity of adverse effects can be increased when Succinylcholine is combined with Acetophenazine.
AcetyldigitoxinThe risk or severity of Cardiac Arrhythmia can be increased when Succinylcholine is combined with Acetyldigitoxin.
Acetylsalicylic acidThe risk or severity of hyperkalemia can be increased when Succinylcholine is combined with Acetylsalicylic acid.
AclidiniumSuccinylcholine may increase the central nervous system depressant (CNS depressant) activities of Aclidinium.
AgomelatineThe risk or severity of adverse effects can be increased when Succinylcholine is combined with Agomelatine.
Interactions
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Food Interactions
No interactions found.

Products

Products2
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Product Ingredients
IngredientUNIICASInChI Key
Succinylcholine chlorideI9L0DDD30I71-27-2YOEWQQVKRJEPAE-UHFFFAOYSA-L
Succinylcholine chloride dihydrate8L0S1G435E6101-15-1FFSBEIRFVXGRPR-UHFFFAOYSA-L
International/Other Brands
Scoline / Sucostrin
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AnectineInjection, solution20 mg/1mLIntramuscular; Intravenous; ParenteralSandoz Inc1952-08-202019-05-31US flag
AnectineInjection, solution20 mg/1mLIntramuscular; Intravenous; ParenteralSandoz2015-10-122015-10-12US flag
AnectineInjection, solution20 mg/1mLIntramuscular; Intravenous; ParenteralSandoz Inc2017-06-22Not applicableUS flag
AnectineInjection, solution20 mg/1mLIntramuscular; Intravenous; ParenteralSandoz Inc2019-06-12Not applicableUS flag
AnectineInjection, solution20 mg/1mLIntramuscular; Intravenous; ParenteralCivica, Inc.2020-12-11Not applicableUS flag
Anectine Flopack 500mgPowder, for solution500 mg / pckIntravenousGlaxo Wellcome1959-12-311998-11-03Canada flag
Anectine Inj 20mg/mlLiquid20 mg / mLIntravenousGlaxo Wellcome1952-12-312000-01-19Canada flag
QuelicinInjection, solution100 mg/1mLIntramuscular; IntravenousHospira, Inc.2005-06-232013-08-01US flag
QuelicinInjection, solution20 mg/1mLIntramuscular; IntravenousRemedy Repack2017-12-292018-03-26US flag
QuelicinSolution100 mg / mLIntravenousPfizer Canada Ulc1976-12-312019-04-05Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
SuccinylcholineInjection, solution20 mg/1mLIntramuscular; IntravenousDr.Reddy's Laboratories Inc.,2020-12-31Not applicableUS flag
SuccinylcholineInjection, solution20 mg/1mLIntramuscular; IntravenousMedical Purchasing Solutions, Llc2020-10-07Not applicableUS flag
Succinylcholine ChlorideInjection, solution20 mg/1mLIntramuscular; IntravenousMedical Purchasing Solutions, Llc2019-04-10Not applicableUS flag
Succinylcholine ChlorideInjection, solution20 mg/1mLIntramuscular; IntravenousHF Acquisition Co LLC, DBA HealthFirst2021-05-03Not applicableUS flag
Succinylcholine ChlorideInjection, solution20 mg/1mLIntramuscular; IntravenousBreckenridge Pharmaceutical, Inc.2020-03-01Not applicableUS flag
Succinylcholine ChlorideInjection, solution20 mg/1mLIntramuscular; IntravenousCadila Healthcare Limited2018-05-10Not applicableUS flag
Succinylcholine ChlorideInjection, solution20 mg/1mLIntramuscular; IntravenousGeneral Injectables and Vaccines, Inc.2020-10-21Not applicableUS flag
Succinylcholine ChlorideInjection, solution20 mg/1mLIntramuscular; IntravenousPiramal Critical Care Inc2021-01-20Not applicableUS flag
Succinylcholine ChlorideInjection, solution20 mg/1mLIntramuscular; IntravenousDevatis, Inc.2021-03-12Not applicableUS flag
Succinylcholine ChlorideInjection, solution20 mg/1mLIntramuscular; IntravenousGeneral Injectables & Vaccines, Inc.2019-11-212021-06-30US flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Succinylcholine ChlorideSuccinylcholine chloride (20 mg/1mL)Injection, solutionIntravenousCantrell Drug Company2015-03-122017-12-06US flag

Categories

ATC Codes
M03AB01 — Suxamethonium
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as acyl cholines. These are acylated derivatives of choline. Choline or 2-Hydroxy-N,N,N-trimethylethanaminium is a quaternary ammonium salt with the chemical formula (CH3)3N+(CH2)2OH.
Kingdom
Organic compounds
Super Class
Organic nitrogen compounds
Class
Organonitrogen compounds
Sub Class
Quaternary ammonium salts
Direct Parent
Acyl cholines
Alternative Parents
Fatty acid esters / Dicarboxylic acids and derivatives / Tetraalkylammonium salts / Carboxylic acid esters / Organopnictogen compounds / Organic salts / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds / Amines
show 1 more
Substituents
Acyl choline / Aliphatic acyclic compound / Amine / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Dicarboxylic acid or derivatives / Fatty acid ester / Fatty acyl / Hydrocarbon derivative
show 7 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
quaternary ammonium ion (CHEBI:45652)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
J2R869A8YF
CAS number
306-40-1
InChI Key
AXOIZCJOOAYSMI-UHFFFAOYSA-N
InChI
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
IUPAC Name
trimethyl[2-({4-oxo-4-[2-(trimethylazaniumyl)ethoxy]butanoyl}oxy)ethyl]azanium
SMILES
C[N+](C)(C)CCOC(=O)CCC(=O)OCC[N+](C)(C)C

References

Synthesis Reference

Walter Raml, Gunther Eichberger, "Process for the preparation of succinylcholine halides." U.S. Patent US5206420, issued April 27, 1993.

US5206420
General References
  1. Jonsson M, Dabrowski M, Gurley DA, Larsson O, Johnson EC, Fredholm BB, Eriksson LI: Activation and inhibition of human muscular and neuronal nicotinic acetylcholine receptors by succinylcholine. Anesthesiology. 2006 Apr;104(4):724-33. [Article]
  2. Alvarellos ML, McDonagh EM, Patel S, McLeod HL, Altman RB, Klein TE: PharmGKB summary: succinylcholine pathway, pharmacokinetics/pharmacodynamics. Pharmacogenet Genomics. 2015 Dec;25(12):622-30. doi: 10.1097/FPC.0000000000000170. [Article]
  3. Kato M, Shiratori T, Yamamuro M, Haga S, Hoshi K, Matsukawa S, Jalal IM, Hashimoto Y: Comparison between in vivo and in vitro pharmacokinetics of succinylcholine in humans. J Anesth. 1999 Oct 30;13(4):189-92. doi: 10.1007/s005400050055. [Article]
  4. Torda TA, Graham GG, Warwick NR, Donohue P: Pharmacokinetics and pharmacodynamics of suxamethonium. Anaesth Intensive Care. 1997 Jun;25(3):272-8. doi: 10.1177/0310057X9702500312. [Article]
  5. Martyn J, Durieux ME: Succinylcholine: new insights into mechanisms of action of an old drug. Anesthesiology. 2006 Apr;104(4):633-4. [Article]
  6. Hoshi K, Hashimoto Y, Matsukawa S: Pharmacokinetics of succinylcholine in man. Tohoku J Exp Med. 1993 Aug;170(4):245-50. doi: 10.1620/tjem.170.245. [Article]
  7. Hager HH, Burns B: Succinylcholine Chloride . [Article]
  8. Health Canada Product Monograph: Quelicin (succinylcholine chloride) for injection [Link]
  9. FDA Approved Drug Products: Anectine (succinylcholine chloride) for intravenous injection [Link]
  10. Pfizer SDS: Succinylcholine Chloride injection [Link]
Human Metabolome Database
HMDB0014347
KEGG Compound
C07546
PubChem Compound
5314
PubChem Substance
46506023
ChemSpider
5123
BindingDB
50061568
RxNav
10154
ChEBI
45652
ChEMBL
CHEMBL703
ZINC
ZINC000001530820
Therapeutic Targets Database
DAP001132
PharmGKB
PA451522
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
SCK
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Suxamethonium_chloride
PDB Entries
2ha2 / 2ha6
MSDS
Download (75.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedOtherSmooth muscle relaxation prior to radiological procedures1
4CompletedPreventionIntubation, Endotracheal1
4CompletedPreventionNeuromuscular Blockade / Postoperative Complications1
4CompletedTreatmentAnaesthesia therapy1
4CompletedTreatmentCaesarean Sections / Pregnant State1
4CompletedTreatmentCesarean Sections1
4CompletedTreatmentDepression1
4CompletedTreatmentIntubation, Endotracheal1
4CompletedTreatmentIntubations1
4RecruitingTreatmentIntubation Conditions1

Pharmacoeconomics

Manufacturers
  • Sandoz canada inc
  • Hospira inc
  • International medication systems ltd
  • Organon usa inc
  • Apothecon inc div bristol myers squibb
Packagers
  • Hospira Inc.
  • Pharmedium
  • Sandoz
  • Strides Arcolab Limited
Dosage Forms
FormRouteStrength
Injection, solutionIntramuscular; Intravenous; Parenteral20 mg/1mL
Powder, for solutionIntravenous500 mg / pck
LiquidIntravenous20 mg / mL
InjectionIntravenous103 mg/2mL
SolutionIntravenous40 mg/ml
Injection, powder, for solutionIntramuscular; Intravenous100 mg
Injection, solutionParenteral
Injection, solution
Injection, solutionIntramuscular; Intravenous50 MG/ML
Injection, solutionIntravenous; Parenteral100 MG/2ML
SolutionIntravenous500 mg/10ml
SolutionIntramuscular; Intravenous100 mg
Injection, solutionIntravenous
Solution
Injection, solutionIntramuscular; Intravenous100 mg/1mL
Injection, solutionIntramuscular; Intravenous20 mg/1mL
SolutionIntravenous100 mg / mL
SolutionIntravenous1 g
SolutionIntramuscular; Intravenous20 mg / mL
InjectionIntramuscular; Intravenous20 mg/1mL
InjectionIntramuscular; Intravenous200 mg/10mL
InjectionParenteral200 mg/10mL
Injection, solutionIntravenous20 mg/1mL
SolutionIntravenous20 mg / mL
Solution50 mg/1ml
Injection
Prices
Unit descriptionCostUnit
Succinylcholine-ns 140 mg/7 ml2.08USD ml
Quelicin 100 mg/ml vial1.2USD ml
Quelicin 20 mg/ml vial0.22USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilityVery solublehttps://pdf.hres.ca/dpd_pm/00058027.PDF
Predicted Properties
PropertyValueSource
Water Solubility0.000757 mg/mLALOGPS
logP-2.5ALOGPS
logP-8.4ChemAxon
logS-5.7ALOGPS
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity100.94 m3·mol-1ChemAxon
Polarizability33.15 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9962
Blood Brain Barrier+0.7717
Caco-2 permeable+0.5871
P-glycoprotein substrateSubstrate0.5916
P-glycoprotein inhibitor INon-inhibitor0.9036
P-glycoprotein inhibitor IINon-inhibitor0.8503
Renal organic cation transporterNon-inhibitor0.7974
CYP450 2C9 substrateNon-substrate0.8434
CYP450 2D6 substrateNon-substrate0.8173
CYP450 3A4 substrateNon-substrate0.5158
CYP450 1A2 substrateNon-inhibitor0.936
CYP450 2C9 inhibitorNon-inhibitor0.9381
CYP450 2D6 inhibitorNon-inhibitor0.9278
CYP450 2C19 inhibitorNon-inhibitor0.9142
CYP450 3A4 inhibitorNon-inhibitor0.9281
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9831
Ames testNon AMES toxic0.8556
CarcinogenicityCarcinogens 0.5298
BiodegradationReady biodegradable0.7156
Rat acute toxicity2.3010 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9012
hERG inhibition (predictor II)Non-inhibitor0.8418
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Targets

Drugtargets2
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Kind
Protein group
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
Curator comments
Note: Nicotinic acetylcholine receptors are composed of several subunits - the specific subunit with which succinylcholine interacts is unclear.
General Function
Receptor binding
Specific Function
Ionotropic receptor with a probable role in the modulation of auditory stimuli. Agonist binding may induce an extensive change in conformation that affects all subunits and leads to opening of an i...

Components:
References
  1. Alvarellos ML, McDonagh EM, Patel S, McLeod HL, Altman RB, Klein TE: PharmGKB summary: succinylcholine pathway, pharmacokinetics/pharmacodynamics. Pharmacogenet Genomics. 2015 Dec;25(12):622-30. doi: 10.1097/FPC.0000000000000170. [Article]
  2. FDA Approved Drug Products: Anectine (succinylcholine chloride) for intravenous injection [Link]
  3. Health Canada Product Monograph: Quelicin (succinylcholine chloride) for injection [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
G-protein coupled acetylcholine receptor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM2
Uniprot ID
P08172
Uniprot Name
Muscarinic acetylcholine receptor M2
Molecular Weight
51714.605 Da
References
  1. Hou VY, Hirshman CA, Emala CW: Neuromuscular relaxants as antagonists for M2 and M3 muscarinic receptors. Anesthesiology. 1998 Mar;88(3):744-50. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Receptor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM3
Uniprot ID
P20309
Uniprot Name
Muscarinic acetylcholine receptor M3
Molecular Weight
66127.445 Da
References
  1. Hou VY, Hirshman CA, Emala CW: Neuromuscular relaxants as antagonists for M2 and M3 muscarinic receptors. Anesthesiology. 1998 Mar;88(3):744-50. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Identical protein binding
Specific Function
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name
BCHE
Uniprot ID
P06276
Uniprot Name
Cholinesterase
Molecular Weight
68417.575 Da
References
  1. Alvarellos ML, McDonagh EM, Patel S, McLeod HL, Altman RB, Klein TE: PharmGKB summary: succinylcholine pathway, pharmacokinetics/pharmacodynamics. Pharmacogenet Genomics. 2015 Dec;25(12):622-30. doi: 10.1097/FPC.0000000000000170. [Article]
  2. FDA Approved Drug Products: Anectine (succinylcholine chloride) for intravenous injection [Link]
  3. Health Canada Product Monograph: Quelicin (succinylcholine chloride) for injection [Link]

Drug created on June 13, 2005 13:24 / Updated on October 19, 2021 07:39