You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameSuccinylcholine
Accession NumberDB00202  (APRD00159)
TypeSmall Molecule
GroupsApproved
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. [PubChem]

Structure
Thumb
Synonyms
2,2'-[(1,4-DIOXOBUTANE-1,4-diyl)bis(oxy)]bis(N,N,N-trimethylethanaminium)
Dicholine succinate
Succinic acid, diester with choline
Succinocholine
Succinoylcholine
Succinylbischoline
Succinylcholine
Succinyldicholine
Suxamethonium
External Identifiers Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Anectineinjection, solution20 mg/mLintramuscular; intravenous; parenteralSandoz Inc1952-08-20Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Anectine Flopack 500mgpowder for solution500 mgintravenousGlaxo Wellcome Inc.1959-12-311998-11-03Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Anectine Inj 20mg/mlliquid20 mgintravenousGlaxo Wellcome Inc.1952-12-312000-01-19Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Quelicininjection, solution20 mg/mLintramuscular; intravenousHospira, Inc.1953-05-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Quelicin Chloride 100mg/mlsolution100 mgintravenousHospira Healthcare Corporation1976-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Quelicin Chloride Inj 20mg/mlsolution20 mgintravenousHospira Healthcare Corporation1952-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Quelicin Inj 20mg/ml USPsolution20 mgintramuscular; intravenousAbbott Laboratories, Limited1985-12-312009-12-14Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Succinylcholine Chlorideinjection, solution20 mg/mLintravenousCantrell Drug Company2015-03-12Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Succinylcholine Chloride Injectionsolution20 mgintravenousAlveda Pharmaceuticals Inc2014-09-30Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Succinylcholine Chloride Injection USPsolution20 mgintravenousMylan Pharmaceuticals Ulc1996-11-12Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Succinylcholine Chloride Injection, USP 20mg/mlliquid20 mgintravenousAlveda Pharmaceuticals Inc2012-09-13Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
ScolineNot Available
SucostrinNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Succinylcholine Chloride
71-27-2
Thumb
  • InChI Key: YOEWQQVKRJEPAE-UHFFFAOYSA-L
  • Monoisotopic Mass: 360.158262872
  • Average Mass: 361.305
DBSALT000206
Categories
UNIIJ2R869A8YF
CAS number306-40-1
WeightAverage: 290.399
Monoisotopic: 290.220557458
Chemical FormulaC14H30N2O4
InChI KeyInChIKey=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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassQuaternary ammonium salts
Sub ClassCholines
Direct ParentAcyl cholines
Alternative Parents
Substituents
  • Acyl choline
  • Fatty acid ester
  • Fatty acyl
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Amine
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Pharmacology
IndicationUsed in surgical procedures where a rapid onset and brief duration of muscle relaxation is needed (includes intubation, endoscopies, and ECT)
PharmacodynamicsSuccinylcholine 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 actionThe 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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

By pseudocholinesterase, to succinylmonocholine and choline.

Route of eliminationAbout 10% of the drug is excreted unchanged in the urine.
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
Manufacturers
  • Sandoz canada inc
  • Hospira inc
  • International medication systems ltd
  • Organon usa inc
  • Apothecon inc div bristol myers squibb
Packagers
Dosage forms
FormRouteStrength
Injection, solutionintramuscular; intravenous; parenteral20 mg/mL
Powder for solutionintravenous500 mg
Injection, solutionintramuscular; intravenous20 mg/mL
Solutionintravenous100 mg
Solutionintravenous20 mg
Solutionintramuscular; intravenous20 mg
Injection, solutionintravenous20 mg/mL
Liquidintravenous20 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.
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot 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
External Links
ATC CodesM03AB01
AHFS Codes
  • 12:20.00
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (75.1 KB)
Interactions
Drug Interactions
Drug
AlfentanilSuccinylcholine may increase the bradycardic activities of Alfentanil.
AmikacinAmikacin may increase the activities of Succinylcholine.
ArbekacinArbekacin may increase the activities of Succinylcholine.
BambuterolThe therapeutic efficacy of Succinylcholine can be increased when used in combination with Bambuterol.
Botulinum Toxin Type ABotulinum Toxin Type A may increase the neuromuscular blocking activities of Succinylcholine.
Botulinum Toxin Type BSuccinylcholine may increase the neuromuscular blocking activities of Botulinum Toxin Type B.
BuprenorphineSuccinylcholine may increase the bradycardic activities of Buprenorphine.
ButorphanolSuccinylcholine may increase the bradycardic activities of Butorphanol.
CapreomycinCapreomycin may increase the neuromuscular blocking activities of Succinylcholine.
ClindamycinClindamycin may increase the neuromuscular blocking activities of Succinylcholine.
ColistimethateColistimethate may increase the neuromuscular blocking activities of Succinylcholine.
CyclophosphamideThe serum concentration of Succinylcholine can be increased when it is combined with Cyclophosphamide.
CyclosporineCyclosporine may increase the neuromuscular blocking activities of Succinylcholine.
DigoxinSuccinylcholine may increase the arrhythmogenic activities of Digoxin.
DonepezilThe serum concentration of Succinylcholine can be increased when it is combined with Donepezil.
EchothiophateThe serum concentration of Succinylcholine can be increased when it is combined with Echothiophate.
EdrophoniumThe serum concentration of Succinylcholine can be increased when it is combined with Edrophonium.
FentanylSuccinylcholine may increase the bradycardic activities of Fentanyl.
FramycetinFramycetin may increase the activities of Succinylcholine.
GalantamineThe serum concentration of Succinylcholine can be increased when it is combined with Galantamine.
GentamicinGentamicin may increase the activities of Succinylcholine.
HydrocodoneSuccinylcholine may increase the bradycardic activities of Hydrocodone.
HydromorphoneSuccinylcholine may increase the bradycardic activities of Hydromorphone.
KanamycinKanamycin may increase the activities of Succinylcholine.
LevorphanolSuccinylcholine may increase the bradycardic activities of Levorphanol.
LincomycinLincomycin may increase the neuromuscular blocking activities of Succinylcholine.
LithiumLithium may increase the neuromuscular blocking activities of Succinylcholine.
Magnesium SulfateMagnesium Sulfate may increase the neuromuscular blocking activities of Succinylcholine.
MethadoneSuccinylcholine may increase the bradycardic activities of Methadone.
MinocyclineMinocycline may increase the neuromuscular blocking activities of Succinylcholine.
MorphineSuccinylcholine may increase the bradycardic activities of Morphine.
NalbuphineSuccinylcholine may increase the bradycardic activities of Nalbuphine.
NeomycinNeomycin may increase the activities of Succinylcholine.
NeostigmineThe serum concentration of Succinylcholine can be increased when it is combined with Neostigmine.
NetilmicinNetilmicin may increase the activities of Succinylcholine.
OxycodoneSuccinylcholine may increase the bradycardic activities of Oxycodone.
OxymorphoneSuccinylcholine may increase the bradycardic activities of Oxymorphone.
OxytetracyclineOxytetracycline may increase the neuromuscular blocking activities of Succinylcholine.
PentazocineSuccinylcholine may increase the bradycardic activities of Pentazocine.
PethidineSuccinylcholine may increase the bradycardic activities of Pethidine.
PhenelzinePhenelzine may increase the neuromuscular blocking activities of Succinylcholine.
PhysostigmineThe serum concentration of Succinylcholine can be increased when it is combined with Physostigmine.
Polymyxin B SulfatePolymyxin B Sulfate may increase the neuromuscular blocking activities of Succinylcholine.
ProcainamideProcainamide may increase the neuromuscular blocking activities of Succinylcholine.
PyridostigmineThe serum concentration of Succinylcholine can be increased when it is combined with Pyridostigmine.
QuinidineQuinidine may increase the neuromuscular blocking activities of Succinylcholine.
QuinineQuinine may increase the neuromuscular blocking activities of Succinylcholine.
RemifentanilSuccinylcholine may increase the bradycardic activities of Remifentanil.
RibostamycinRibostamycin may increase the activities of Succinylcholine.
RivastigmineThe serum concentration of Succinylcholine can be increased when it is combined with Rivastigmine.
SpectinomycinSpectinomycin may increase the activities of Succinylcholine.
StreptomycinStreptomycin may increase the activities of Succinylcholine.
SufentanilSuccinylcholine may increase the bradycardic activities of Sufentanil.
TacrineThe serum concentration of Succinylcholine can be increased when it is combined with Tacrine.
TapentadolSuccinylcholine may increase the bradycardic activities of Tapentadol.
TobramycinTobramycin may increase the activities of Succinylcholine.
TorasemideTorasemide may decrease the neuromuscular blocking activities of Succinylcholine.
TramadolSuccinylcholine may increase the bradycardic activities of Tramadol.
VancomycinVancomycin may increase the neuromuscular blocking activities of Succinylcholine.
Food InteractionsNot Available

Targets

1. Neuronal acetylcholine receptor subunit alpha-10

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Neuronal acetylcholine receptor subunit alpha-10 Q9GZZ6 Details

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

2. Alpha-7 nicotinic cholinergic receptor subunit

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Alpha-7 nicotinic cholinergic receptor subunit Q693P7 Details

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
  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
  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

3. Muscarinic acetylcholine receptor M1

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M1 P11229 Details

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
  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
  3. Fisher DM: Clinical pharmacology of neuromuscular blocking agents. Am J Health Syst Pharm. 1999 Jun 1;56(11 Suppl 1):S4-9. Pubmed

4. Muscarinic acetylcholine receptor M2

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M2 P08172 Details

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

5. Muscarinic acetylcholine receptor M3

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M3 P20309 Details

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
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

Enzymes

1. Cholinesterase

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cholinesterase P06276 Details

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

Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:08