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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
SynonymLanguageCode
2,2'-[(1,4-DIOXOBUTANE-1,4-diyl)bis(oxy)]bis(N,N,N-trimethylethanaminium)Not AvailableNot Available
Dicholine succinateNot AvailableNot Available
Succinic acid, diester with cholineNot AvailableNot Available
SuccinocholineNot AvailableNot Available
SuccinoylcholineNot AvailableNot Available
SuccinylbischolineNot AvailableNot Available
SuccinylcholineNot AvailableNot Available
SuccinyldicholineNot AvailableNot Available
SuxamethoniumNot AvailableNot Available
Salts
Name/CAS Structure Properties
Succinylcholine Chloride
71-27-2
Thumb
  • InChI Key: YOEWQQVKRJEPAE-UHFFFAOYSA-L
  • Monoisotopic Mass: 360.158262872
  • Average Mass: 361.305
DBSALT000206
Brand names
NameCompany
AnectineNot Available
QuelicinNot Available
ScolineNot Available
SucostrinNot Available
Brand mixturesNot Available
Categories
CAS number306-40-1
WeightAverage: 290.399
Monoisotopic: 290.220557458
Chemical FormulaC14H30N2O4
InChI KeyAXOIZCJOOAYSMI-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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganonitrogen Compounds
ClassQuaternary Ammonium Salts
SubclassCholines
Direct parentCholines
Alternative parentsFatty Acid Esters; Dicarboxylic Acids and Derivatives; Carboxylic Acid Esters; Ethers; Enolates; Polyamines
Substituentsdicarboxylic acid derivative; carboxylic acid ester; ether; polyamine; enolate; carboxylic acid derivative; amine
Classification descriptionThis compound belongs to the cholines. These are organic compounds containing a N,N,N-trimethylethanolammonium cation.
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
Property Value Probability
Human Intestinal Absorption - 0.9962
Blood Brain Barrier + 0.7717
Caco-2 permeable + 0.5871
P-glycoprotein substrate Substrate 0.5916
P-glycoprotein inhibitor I Non-inhibitor 0.9036
P-glycoprotein inhibitor II Non-inhibitor 0.8503
Renal organic cation transporter Non-inhibitor 0.7974
CYP450 2C9 substrate Non-substrate 0.8434
CYP450 2D6 substrate Non-substrate 0.8173
CYP450 3A4 substrate Non-substrate 0.5158
CYP450 1A2 substrate Non-inhibitor 0.936
CYP450 2C9 substrate Non-inhibitor 0.9381
CYP450 2D6 substrate Non-inhibitor 0.9278
CYP450 2C19 substrate Non-inhibitor 0.9142
CYP450 3A4 substrate Non-inhibitor 0.9281
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9831
Ames test Non AMES toxic 0.8556
Carcinogenicity Carcinogens 0.5298
Biodegradation Ready biodegradable 0.7156
Rat acute toxicity 2.3010 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9012
hERG inhibition (predictor II) Non-inhibitor 0.8418
Pharmacoeconomics
Manufacturers
  • Sandoz canada inc
  • Hospira inc
  • International medication systems ltd
  • Organon usa inc
  • Apothecon inc div bristol myers squibb
Packagers
Dosage forms
FormRouteStrength
LiquidIntravenous
SolutionIntravenous
SolutionIntravenous
SolutionIntravenous
Prices
Unit descriptionCostUnit
Succinylcholine-ns 140 mg/7 ml2.08USDml
Quelicin 100 mg/ml vial1.2USDml
Quelicin 20 mg/ml vial0.22USDml
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 Solubility0.000757ALOGPS
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
Spectra
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 Reference
  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
ResourceLink
KEGG CompoundC07546
PubChem Compound5314
PubChem Substance46506023
ChemSpider5123
ChEBI45652
ChEMBLCHEMBL703
Therapeutic Targets DatabaseDAP001132
PharmGKBPA451522
IUPHAR4004
Guide to Pharmacology4004
Drug Product Database2062232
RxListhttp://www.rxlist.com/cgi/generic2/succinyl.htm
Drugs.comhttp://www.drugs.com/cdi/succinylcholine.html
WikipediaSuccinylcholine
ATC CodesM03AB01
AHFS Codes
  • 12:20.00
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(75.1 KB)
Interactions
Drug Interactions
Drug
AmikacinThe agent increases the effect of muscle relaxant
ClindamycinThe agent increases the effect of muscle relaxant
CyclophosphamideCyclophosphamide may increase the effect of succinylcholine.
DihydrocodeineMay enhance the bradycardic effect of opioid analgesics. It is recommended to monitor therapy.
EchothiophateEchothiophate iodide may increase the effect of succinylcholine.
GentamicinThe agent increases the effect of muscle relaxant
LincomycinThe agent increases the effect of muscle relaxant
NetilmicinThe agent increases the effect of muscle relaxant
PiperacillinThe agent increases the effect of the muscle relaxant
QuinidineThe quinine derivative increases the effect of the muscle relaxant
QuinineThe quinine derivative increases the effect of the muscle relaxant
TacrineTacrine may increase the effects of Succinylcholine. Monitor Succinylcholine therapy for increased effects.
TobramycinThe agent increases the effect of the muscle relaxant
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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:08