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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. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Scoline
Succinylcholine Chloride
Suxamethonium chloride
Salts Not Available
Brand names
Name Company
Anectine
Quelicin
Sucostrin
Brand mixtures Not Available
Categories
  • Skeletal Muscle Relaxants
  • Neuromuscular Depolarizing Agents
CAS number 306-40-1
Weight Average: 290.399
Monoisotopic: 290.220557458
Chemical Formula C14H30N2O4
InChI Key InChIKey=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
Plain Text
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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Carboxylic Acids and Derivatives
  • Quaternary Ammonium Salts
  • Keto-Acids
Substructures
  • Carboxylic Acids and Derivatives
  • Acetates
  • Ethers
  • Quaternary Ammonium Salts
  • Keto-Acids
  • Cations
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.
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
Pharmacoeconomics
Manufacturers
  • Sandoz canada inc
  • Hospira inc
  • International medication systems ltd
  • Organon usa inc
  • Apothecon inc div bristol myers squibb
Packagers
Dosage forms
Form Route Strength
Liquid Intravenous
Solution Intravenous
Solution Intravenous
Solution Intravenous
Prices
Unit description Cost Unit
Succinylcholine-ns 140 mg/7 ml 2.08 USD ml
Quelicin 100 mg/ml vial 1.2 USD ml
Quelicin 20 mg/ml vial 0.22 USD 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
Property Value Source
water solubility 7.57e-04 g/l ALOGPS
logP -2.5 ALOGPS
logP -8.4 ChemAxon
logS -5.7 ALOGPS
pKa (strongest basic) -6.8 ChemAxon
physiological charge 2 ChemAxon
hydrogen acceptor count 2 ChemAxon
hydrogen donor count 0 ChemAxon
polar surface area 52.6 ChemAxon
rotatable bond count 11 ChemAxon
refractivity 100.94 ChemAxon
polarizability 33.15 ChemAxon
References
Synthesis Reference Not Available
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
Resource Link
KEGG Compound C07546 Link_out
PubChem Compound 5314 Link_out
PubChem Substance 46506023 Link_out
ChemSpider 5123 Link_out
ChEBI 45652 Link_out
ChEMBL 45652 Link_out
Therapeutic Targets Database DAP001132 Link_out
PharmGKB PA451522 Link_out
IUPHAR 4004 Link_out
Guide to Pharmacology 4004 Link_out
Drug Product Database 2062232 Link_out
RxList http://www.rxlist.com/cgi/generic2/succinyl.htm Link_out
Drugs.com http://www.drugs.com/cdi/succinylcholine.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Succinylcholine Link_out
ATC Codes
  • M03AB01
AHFS Codes
  • 12:20.00
PDB Entries Not Available
FDA label Not Available
MSDS show (75.1 KB)
Interactions
Drug Interactions
Drug Interaction
Amikacin The agent increases the effect of muscle relaxant
Clindamycin The agent increases the effect of muscle relaxant
Cyclophosphamide Cyclophosphamide may increase the effect of succinylcholine.
Echothiophate Echothiophate iodide may increase the effect of succinylcholine.
Gentamicin The agent increases the effect of muscle relaxant
Lincomycin The agent increases the effect of muscle relaxant
Netilmicin The agent increases the effect of muscle relaxant
Piperacillin The agent increases the effect of the muscle relaxant
Quinidine The quinine derivative increases the effect of the muscle relaxant
Quinine The quinine derivative increases the effect of the muscle relaxant
Tacrine Tacrine may increase the effects of Succinylcholine. Monitor Succinylcholine therapy for increased effects.
Tobramycin The agent increases the effect of the muscle relaxant
Food Interactions Not Available
Targets

1. Neuronal acetylcholine receptor subunit alpha-10

Pharmacological action: yes
Actions: agonist

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 ion-conducting channel across the plasma membrane. The channel is permeable to a range of divalent cations including calcium, the influx of which may activate a potassium current which hyperpolarizes the cell membrane. In the ear, this may lead to a reduction in basilar membrane motion, altering the activity of auditory nerve fibers and reducing the range of dynamic hearing. This may protect against acoustic trauma

Organism class: human
UniProt ID: Q9GZZ6 Link_out
Gene: CHRNA10 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: yes
Actions: agonist
Organism class: human
UniProt ID: Q693P7 Link_out
Gene: CHRFAM7A
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: yes
Actions: agonist

The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover

Organism class: human
UniProt ID: P11229 Link_out
Gene: CHRM1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: unknown
Actions: agonist

The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition

Organism class: human
UniProt ID: P08172 Link_out
Gene: CHRM2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: unknown
Actions: agonist

The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover

Organism class: human
UniProt ID: P20309 Link_out
Gene: CHRM3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: substrate

An acylcholine + H(2)O = choline + a carboxylate

UniProt ID: P06276 Link_out
Gene: BCHE Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19