Identification

Name
Succinylcholine
Accession Number
DB00202  (APRD00159)
Type
Small Molecule
Groups
Approved
Description

A quaternary skeletal muscle relaxant usually used in the form of its bromide, chloride, or iodide. It is a depolarizing relaxant, acting in about 30 seconds and with a duration of effect averaging three to five minutes. Succinylcholine is used in surgical, anesthetic, and other procedures in which a brief period of muscle relaxation is called for.

Structure
Thumb
Synonyms
  • 2,2'-[(1,4-dioxobutane-1,4-diyl)bis(oxy)]bis(N,N,N-trimethylethanaminium)
  • Dicholine succinate
  • Succinocholine
  • Succinoylcholine
  • Succinylbischoline
  • Succinyldicholine
  • Suxamethonium
Product Ingredients
IngredientUNIICASInChI Key
Succinylcholine chlorideI9L0DDD30I71-27-2YOEWQQVKRJEPAE-UHFFFAOYSA-L
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AnectineInjection, solution20 mg/1mLIntramuscular; Intravenous; ParenteralSandoz1952-08-20Not applicableUs
AnectineInjection, solution20 mg/1mLIntramuscular; Intravenous; ParenteralSandoz2017-06-22Not applicableUs
AnectineInjection, solution20 mg/1mLIntramuscular; Intravenous; ParenteralSandoz2015-10-122015-10-12Us
Anectine Flopack 500mgPowder, for solution500 mgIntravenousGlaxo Wellcome1959-12-311998-11-03Canada
Anectine Inj 20mg/mlLiquid20 mgIntravenousGlaxo Wellcome1952-12-312000-01-19Canada
QuelicinInjection, solution20 mg/1mLIntramuscular; IntravenousMedical Purchasing Solutions, Llc2014-03-31Not applicableUs
QuelicinInjection, solution100 mg/1mLIntramuscular; IntravenousHospira, Inc.2005-06-232013-08-01Us
QuelicinInjection, solution20 mg/1mLIntramuscular; IntravenousRemedy Repack2017-12-292018-03-26Us
QuelicinSolution100 mgIntravenousPfizer1976-12-31Not applicableCanada
QuelicinInjection, solution20 mg/1mLIntramuscular; IntravenousHospira, Inc.2005-04-30Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Succinylcholine ChlorideInjection, solution20 mg/1mLIntramuscular; IntravenousCadila Healthcare Limited2018-05-10Not applicableUs
Succinylcholine ChlorideInjection, solution20 mg/1mLIntramuscular; IntravenousZydus Pharmaceuticals (USA) Inc.2018-05-10Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Succinylcholine ChlorideSuccinylcholine chloride (20 mg/1mL)Injection, solutionIntravenousCantrell Drug Company2015-03-122017-12-06Us
International/Other Brands
Scoline / Sucostrin
Categories
UNII
J2R869A8YF
CAS number
306-40-1
Weight
Average: 290.399
Monoisotopic: 290.220557458
Chemical Formula
C14H30N2O4
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

Pharmacology

Indication

Used in surgical procedures where a rapid onset and brief duration of muscle relaxation is needed (includes intubation, endoscopies, and ECT)

Pharmacodynamics

Succinylcholine is indicated as an adjunct to general anesthesia, to facilitate tracheal intubation, and to provide skeletal muscle relaxation during surgery or mechanical ventilation. Succinylcholine is a depolarizing skeletal muscle relaxant. As does acetylcholine, it combines with the cholinergic receptors of the motor end plate to produce depolarization. This depolarization may be observed as fasciculations. Subsequent neuromuscular transmission is inhibited so long as adequate concentration of succinylcholine remains at the receptor site. Succinylcholine has no direct action on the uterus or other smooth muscle structures.

Mechanism of action

The mechanism of action of Succinylcholine involves what appears to be a "persistent" depolarization of the neuromuscular junction. This depolarization is caused by Succinylcholine mimicking the effect of acetylcholine but without being rapidly hydrolysed by acetylcholinesterase. This depolarization leads to desensitization.

TargetActionsOrganism
ANeuronal acetylcholine receptor subunit alpha-10
agonist
Human
AAlpha-7 nicotinic cholinergic receptor subunit
agonist
Human
AMuscarinic acetylcholine receptor M1
agonist
Human
UMuscarinic acetylcholine receptor M2
agonist
Human
UMuscarinic acetylcholine receptor M3
agonist
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

By pseudocholinesterase, to succinylmonocholine and choline.

Route of elimination

About 10% of the drug is excreted unchanged in the urine.

Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
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
DrugInteraction
1,10-Phenanthroline1,10-Phenanthroline may increase the neuromuscular blocking activities of Succinylcholine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Succinylcholine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when Succinylcholine is combined with 3,4-Methylenedioxyamphetamine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when Succinylcholine is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when Succinylcholine is combined with 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Succinylcholine is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when Succinylcholine is combined with 7-Nitroindazole.
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.
Food Interactions
Not Available

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. [PubMed:16571968]
External Links
Human Metabolome Database
HMDB0014347
KEGG Compound
C07546
PubChem Compound
5314
PubChem Substance
46506023
ChemSpider
5123
BindingDB
50061568
ChEBI
45652
ChEMBL
CHEMBL703
Therapeutic Targets Database
DAP001132
PharmGKB
PA451522
IUPHAR
4004
Guide to Pharmacology
GtP Drug Page
HET
SCK
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Succinylcholine
ATC Codes
M03AB01 — Suxamethonium
AHFS Codes
  • 12:20.20 — Neuromuscular Blocking Agents
PDB Entries
2ha2 / 2ha6
MSDS
Download (75.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentIntubation Conditions1
3CompletedTreatmentNeuromuscular Blockade1
3CompletedTreatmentAdjunct to general anesthesia therapy1
3RecruitingTreatmentStrokes1
4CompletedOtherDepolarizing Muscle Relaxants / Smooth muscle relaxation prior to radiological procedures1
4CompletedPreventionIntubation, Endotracheal1
4CompletedPreventionNeuromuscular Blockade / Postoperative Complications1
4CompletedTreatmentAnaesthesia therapy1
4CompletedTreatmentCaesarean Sections / Pregnancy1
4CompletedTreatmentDepression1
4CompletedTreatmentIntubation, Endotracheal1
4CompletedTreatmentIntubations1
4TerminatedTreatmentAnaesthesia therapy1
4Unknown StatusTreatmentCesarean Section1
4WithdrawnNot AvailableNeuromuscular Blockade1
Not AvailableActive Not RecruitingPreventionLaparoscopic Appendectomy1
Not AvailableCompletedNot AvailableNeuromuscular Blockade1
Not AvailableCompletedBasic ScienceDepression1
Not AvailableCompletedTreatmentElectroconvulsive Therapy / Neuromuscular Blockade1
Not AvailableCompletedTreatmentFasciculations / Intubating Conditions / Patients Satisfaction / Postoperative Myalgia / Throat Pain1
Not AvailableCompletedTreatmentIntubating Conditions / Performance With Respiratory Exercise Device / Postoperative Myalgia1
Not AvailableCompletedTreatmentPain NOS1
Not AvailableRecruitingOtherAtelectasis / Complication of Ventilation Therapy / Tumor of Lung Parenchyma1
Not AvailableRecruitingTreatmentAnaesthesia therapy / General Surgery / Pain NOS1
Not AvailableSuspendedTreatmentIntubating Conditions / Patients Satisfaction / Postoperative Myalgia1

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
LiquidIntravenous20 mg
Injection, solutionIntramuscular; Intravenous100 mg/1mL
Injection, solutionIntramuscular; Intravenous20 mg/1mL
SolutionIntravenous100 mg
SolutionIntramuscular; Intravenous20 mg
Injection, solutionIntravenous20 mg/1mL
SolutionIntravenous20 mg
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
Not Available
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

Taxonomy

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 / Fatty acid ester / Dicarboxylic acid or derivatives / Fatty acyl / Tetraalkylammonium salt / Carboxylic acid ester / Carboxylic acid derivative / Organic oxygen compound / Amine / Organooxygen compound
show 7 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
quaternary ammonium ion (CHEBI:45652)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
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...
Gene Name
CHRNA10
Uniprot ID
Q9GZZ6
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-10
Molecular Weight
49704.295 Da
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. [PubMed:16571968]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Not Available
Specific Function
Not Available
Gene Name
CHRNA7
Uniprot ID
Q693P7
Uniprot Name
Alpha-7 nicotinic cholinergic receptor subunit
Molecular Weight
2987.635 Da
References
  1. Rogers KR, Fernando JC, Thompson RG, Valdes JJ, Eldefrawi ME: Detection of nicotinic receptor ligands with a light addressable potentiometric sensor. Anal Biochem. 1992 Apr;202(1):111-6. [PubMed:1621972]
  2. Fiacchino F, Ariano C, Gemma M, Cerrato D: Abnormal responses to succinylcholine and pancuronium in a patient with hemiparesis. Ital J Neurol Sci. 1990 Oct;11(5):497-9. [PubMed:2272786]
  3. Marshall CG, Ogden DC, Colquhoun D: The actions of suxamethonium (succinyldicholine) as an agonist and channel blocker at the nicotinic receptor of frog muscle. J Physiol. 1990 Sep;428:155-74. [PubMed:2133043]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Phosphatidylinositol phospholipase c 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
CHRM1
Uniprot ID
P11229
Uniprot Name
Muscarinic acetylcholine receptor M1
Molecular Weight
51420.375 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Fisher DM: Clinical pharmacology of neuromuscular blocking agents. Am J Health Syst Pharm. 1999 Jun 1;56(11 Suppl 1):S4-9. [PubMed:10437710]
Kind
Protein
Organism
Human
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. [PubMed:9523819]
Kind
Protein
Organism
Human
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. [PubMed:9523819]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
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. Ostergaard D, Engbaek J, Viby-Mogensen J: Adverse reactions and interactions of the neuromuscular blocking drugs. Med Toxicol Adverse Drug Exp. 1989 Sep-Oct;4(5):351-68. [PubMed:2682131]

Drug created on June 13, 2005 07:24 / Updated on November 17, 2018 07:06