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Succinylcholine

PubChem CID
5314
Structure
Succinylcholine_small.png
Succinylcholine_3D_Structure.png
Molecular Formula
Synonyms
  • succinylcholine
  • Suxamethonium
  • Succinyldicholine
  • Succinocholine
  • Succinoylcholine
Molecular Weight
290.40 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-25
  • Modify:
    2025-01-18
Description
Succinylcholine is a quaternary ammonium ion that is the bis-choline ester of succinic acid. It has a role as a neuromuscular agent, a muscle relaxant and a drug allergen. It is a quaternary ammonium ion and a succinate ester.
Succinylcholine is a depolarizing skeletal muscle relaxant consisting of two molecules of the endogenous neurotransmitter [acetylcholine] (ACh) linked by their acetyl groups. It has been widely used for over 50 years, 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.
Succinylcholine is a Depolarizing Neuromuscular Blocker. The physiologic effect of succinylcholine is by means of Neuromuscular Depolarizing Blockade.
See also: Succinylcholine Chloride (has salt form); Succinylcholine chloride dihydrate (active moiety of); Succinylcholine Iodide (is active moiety of).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Succinylcholine.png

1.2 3D Conformer

1.3 Crystal Structures

COD records with this CID as component

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

trimethyl-[2-[4-oxo-4-[2-(trimethylazaniumyl)ethoxy]butanoyl]oxyethyl]azanium
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 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
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

AXOIZCJOOAYSMI-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C[N+](C)(C)CCOC(=O)CCC(=O)OCC[N+](C)(C)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C14H30N2O4+2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

71-27-2

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DrugBank ID

2.3.8 DSSTox Substance ID

2.3.9 HMDB ID

2.3.10 KEGG ID

2.3.11 Metabolomics Workbench ID

2.3.12 NCI Thesaurus Code

2.3.13 Nikkaji Number

2.3.14 PharmGKB ID

2.3.15 Pharos Ligand ID

2.3.16 RXCUI

2.3.17 Wikidata

2.3.18 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Anectine
  • Bromide, Suxamethonium
  • Celocurine
  • Dibromide, Succinylcholine
  • Dichloride, Succinylcholine
  • dicholine succinate
  • Diiodide, Succinylcholine
  • Diperchlorate, Succinylcholine
  • Ditilin
  • Listenon
  • Lysthenon
  • Myorelaxin
  • Quelicin
  • Succicuran
  • Succinate, Dicholine
  • Succinylcholine
  • Succinylcholine Chloride
  • Succinylcholine Dibromide
  • Succinylcholine Dichloride
  • Succinylcholine Dichloride, Di H2O
  • Succinylcholine Dichloride, Di-H2O
  • Succinylcholine Diiodide
  • Succinylcholine Diperchlorate
  • Succinylcholine Iodide
  • Succinyldicholine
  • Suxamethonium
  • Suxamethonium Bromide
  • Suxamethonium Chloride

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
290.40 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
0.6
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
11
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
290.22055744 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
290.22055744 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
52.6 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
20
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
2
Reference
Computed by PubChem
Property Name
Complexity
Property Value
284
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Solid

3.2.2 Solubility

Very soluble
ODORLESS; DIHYDRATE IS HYGROSCOPIC; WHITE CRYSTALLINE POWDER; 1 G SOL IN ABOUT 1 ML H2O & ABOUT 350 ML ALC /CHLORIDE/
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 853
Slightly hygroscopic crystals, mp 225 °C. Freely sol in water or normal saline, giving solns which are very slightly acidic. /Bromide/
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1516
Exists as a dihydrate at room temperature, crystals, mp 156-163 °C. Anhydrous form mp approximately 190 °C. Slightly bitter taste. Freely soluble in water (about 1 g/1 ml water). Solubility in 95% ethanol: 0.42 g/ 100 ml. Sparingly soluble in benzene, chloroform. Practically insoluble in ether. The pH of a 2-5% aqueous solution may vary from 4.5 to 3.0. /Chloride/
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1516
7.57e-04 g/L

3.2.3 Stability / Shelf Life

SLIGHTLY HYGROSCOPIC ... AQ SOLN UNDERGO PROGRESSIVE HYDROLYSIS WITH CORRESPONDING LOSS OF ACTIVITY & INCR IN ACIDITY. /BROMIDE/
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1516
THE RATE OF THis DECOMP INCR WITH TEMP & AUTOCLAVING OR PROLONGED EXPOSURE TO WARMTH SHOULD BE AVOIDED. /BROMIDE/
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1516
MOST STABLE @ PH 4-5; AQ SOLN UNDERGO PROGRESSIVE HYDROLYSIS WITH CORRESPONDING LOSS OF ACTIVITY & INCR IN ACIDITY. /IODIDE/
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1516
COMMERCIALLY AVAIL INJECTIONS WHEN REFRIGERATED HAVE EXPIRATION DATE OF 12-24 MO
American Society of Hospital Pharmacists. Data supplied on contract from American Hospital Formulary Service and other current ASHP sources., p. 1974
For more Stability/Shelf Life (Complete) data for SUCCINYLCHOLINE (6 total), please visit the HSDB record page.

3.2.4 Decomposition

When heated to decomposition it emits toxic fumes of nitroxides.
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 851
Succinylcholine chloride ... decomposes in solutions with a pH greater than 4.5. /Succinylcholine chloride/
Trissel, L.A. Handbook on Injectable Drugs. 9th ed. Bethesda, MD. American Society of Health-System Pharmacists' Product Development. 1996., p. 1009

3.2.5 Other Experimental Properties

White, odorless, slightly bitter powder and very soluble in water. ...unstable in alkaline solutions but relatively stable in acid solutions. /Chloride/
Arky R; Physicians' Desk Reference. 52nd ed. Oradell, NJ: Medical Economics Co. p. 1003 (1998)
Slightyl hygroscopic crystals, mp 243-245 °C. Freely soluble in water or normal saline, giving solutions which are very slightly acidic. Most stable at pH 4-5. /Iodide/
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1516

3.3 Chemical Classes

3.3.1 Drugs

Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749
Pharmaceuticals
S10 | SWISSPHARMA | Pharmaceutical List with Consumption Data | DOI:10.5281/zenodo.2623484
3.3.1.1 Human Drugs
Breast Feeding; Lactation; Milk, Human; Muscle Relaxants; Neuromuscular Depolarizing Agents
Human drug -> Prescription
Human drug -> Prescription; Discontinued
Muscle relaxants (peripherally-acting) and cholinesterase inhibitors

4 Spectral Information

4.1 1D NMR Spectra

1D NMR Spectra

4.2 Mass Spectrometry

4.2.1 LC-MS

1 of 8
View All
Authors
Kakazu Y, Horai H, Institute for Advanced Biosciences, Keio Univ.
Instrument
API3000, Applied Biosystems
Instrument Type
LC-ESI-QQ
MS Level
MS2
Ionization Mode
POSITIVE
Collision Energy
10 V
Precursor m/z
145
Precursor Adduct
[M]++
Top 5 Peaks

145.1 999

113.1 126

115.8 112

81 97

128.1 62

Thumbnail
Thumbnail
License
CC BY-NC-SA
2 of 8
View All
Authors
Kakazu Y, Horai H, Institute for Advanced Biosciences, Keio Univ.
Instrument
API3000, Applied Biosystems
Instrument Type
LC-ESI-QQ
MS Level
MS2
Ionization Mode
POSITIVE
Collision Energy
20 V
Precursor m/z
145
Precursor Adduct
[M]++
Top 5 Peaks

93.5 999

115.8 705

79.8 525

65.5 324

86.2 122

Thumbnail
Thumbnail
License
CC BY-NC-SA

6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug 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.

7.2 Drug Classes

Breast Feeding; Lactation; Milk, Human; Muscle Relaxants; Neuromuscular Depolarizing Agents

7.3 WHO Essential Medicines

Drug
Drug Classes
Muscle relaxants (peripherally-acting) and cholinesterase inhibitors
Formulation
Parenteral - General injections - IV: 50 mg per mL in 2 mL ampoule (suxamethonium chloride); powder for injection (suxamethonium chloride) in vial
Indication
Muscle relaxants

7.4 FDA National Drug Code Directory

7.5 Drug Labels

Drug and label

7.6 Clinical Trials

7.6.1 ClinicalTrials.gov

7.6.2 EU Clinical Trials Register

7.6.3 NIPH Clinical Trials Search of Japan

7.7 Therapeutic Uses

Neuromuscular Depolarizing Agents
National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)
The neuromuscular blocking agents are indicated as adjuncts to anesthesia to induce skeletal muscle relaxation and to facilitate the management of patients undergoing mechanical ventilation. Generally, a relatively short-acting nondepolarizing neuromuscular blocking agent or a single dose of the depolarizing neuromuscular blocking agent succinylcholine is used to facilitate endotracheal intubation. Continuous infusion of succinylcholine may be used for short surgical procedures requiring muscle relaxation. Nondepolarizing neuromuscular blocking agents, or, less commonly, succinylcholine administered by continuous infusion, are used for surgical procedures requiring an intermediate or prolonged duration of muscle relaxant action and to facilitate controlled ventilation. /Neuromuscular blocking agents; Included in US product labeling/
USP. Convention. USPDI - Drug Information for the Health Care Professional. 19th ed. Volume I.Micromedex, Inc. Englewood, CO., 1999. Content Prepared by the U.S. Pharmacopieal Convention, Inc., p. 2099
Neuromuscular blocking agents are also used to decrease the muscular manifestations of persistent convulsions associated with toxic reactions to other medications. /Neuromuscular blocking agents; NOT included in US product labeling/
USP. Convention. USPDI - Drug Information for the Health Care Professional. 19th ed. Volume I.Micromedex, Inc. Englewood, CO., 1999. Content Prepared by the U.S. Pharmacopieal Convention, Inc., p. 2099
Succinylcholine /is/ indicated to reduce the intensity of muscle contractions of pharmacologically or electrically induced convulsions. Succinylcholine is generally preferred because of its short duration of action. /Included in US product labeling/
USP. Convention. USPDI - Drug Information for the Health Care Professional. 19th ed. Volume I.Micromedex, Inc. Englewood, CO., 1999. Content Prepared by the U.S. Pharmacopieal Convention, Inc., p. 2099
For more Therapeutic Uses (Complete) data for SUCCINYLCHOLINE (13 total), please visit the HSDB record page.

7.8 Drug Warnings

... Succinylcholine at doses causing neuromuscular relaxation rarely causes effects attributable to ganglionic blockade. However, cardiovascular effects are sometimes observed that are poblably due to the successive stimulation of vagal ganglia (manifested by bradycardia) and of sympathetic ganglia (resulting in hypertension and tachycardia).
Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 187
GREAT CARE SHOULD BE TAKEN WHEN ADMINISTERING MUSCLE RELAXANTS TO DEHYDRATED OR SEVERELY ILL PATIENTS. /NEUROMUSCULAR BLOCKING AGENTS/
Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 188
CONTINUOUS INFUSION OF SUCCINYLCHOLINE IN BOTH NEONATES & CHILDREN IS CONSIDERED UNSAFE. /CHLORIDE/
American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 316
THE RESPONSE TO SUCCINYLCHOLINE MAY BE PROLONGED IN THE PRESENCE OF HYPOKALEMIA. PATIENTS WITH MYASTHENIA GRAVIS MAY BE RESISTANT TO DEPOLARIZING AGENTS AND HAVE A PREDISPOSITION TO PHASE II BLOCK. /CHLORIDE/
American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 207
For more Drug Warnings (Complete) data for SUCCINYLCHOLINE (28 total), please visit the HSDB record page.

7.9 Drug Idiosyncrasies

A VERY RARE BUT UNUSUAL TYPE OF SERUM CHOLINESTERASE IS CALLED THE CYNTHIANA VARIANT. AFFECTED INDIVIDUALS HAVE NEARLY 3 TIMES AS MUCH SERUM CHOLINESTERASE ACTIVITY AS NORMAL & THEY HYDROLYZE SUCCINYLCHOLINE VERY RAPIDLY. DRUG IS DESTROYED SO QUICKLY THAT THESE INDIVIDUALS ARE RESISTANT, RATHER THAN SENSITIVE, TO DRUG.
LaDu, B.N., H.G. Mandel, and E.L. Way. Fundamentals of Drug Metabolism and Disposition. Baltimore: Williams and Wilkins, 1971., p. 313

8 Pharmacology and Biochemistry

8.1 Pharmacodynamics

Succinylcholine's neuromuscular blockade takes effect within 60 seconds of intravenous administration and lasts between four to six minutes. 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. Succinylcholine has no direct action on smooth or cardiac muscle, nor does it appear to act on pre-synaptic or ganglionic acetylcholine receptors. 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. Succinylcholine has no effect on consciousness or pain threshold, and must therefore be used in conjunction with adequate anesthesia. 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). 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.

8.2 MeSH Pharmacological Classification

Neuromuscular Depolarizing Agents
Drugs that interrupt transmission at the skeletal neuromuscular junction by causing sustained depolarization of the motor end plate. These agents are primarily used as adjuvants in surgical anesthesia to cause skeletal muscle relaxation. (See all compounds classified as Neuromuscular Depolarizing Agents.)

8.3 FDA Pharmacological Classification

1 of 2
FDA UNII
J2R869A8YF
Active Moiety
SUCCINYLCHOLINE
Pharmacological Classes
Established Pharmacologic Class [EPC] - Depolarizing Neuromuscular Blocker
Pharmacological Classes
Physiologic Effects [PE] - Neuromuscular Depolarizing Blockade
FDA Pharmacology Summary
Succinylcholine is a Depolarizing Neuromuscular Blocker. The physiologic effect of succinylcholine is by means of Neuromuscular Depolarizing Blockade.
2 of 2
Non-Proprietary Name
SUCCINYLCHOLINE
Pharmacological Classes
Neuromuscular Depolarizing Blockade [PE]; Depolarizing Neuromuscular Blocker [EPC]

8.4 ATC Code

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

M - Musculo-skeletal system

M03 - Muscle relaxants

M03A - Muscle relaxants, peripherally acting agents

M03AB - Choline derivatives

M03AB01 - Suxamethonium

8.5 Absorption, Distribution and Excretion

Route of Elimination
Approximately 10% of an administered dose is excreted unchanged in the urine.
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.
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.
... APPROX 10% OF ... /SUCCINYLCHOLINE/ IS EXCRETED UNCHANGED.
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 585
ONLY VERY LIMITED PLACENTAL TRANSFER OF...SUCCINYLCHOLINE WAS OBSERVED IN HUMANS, & DID NOT PRODUCE CLINICALLY OBSERVABLE EFFECTS IN NEW-BORN.
The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 635
... The impression prevails that suxamethonium chloride (succinylcholine chloride) and doxorubicin donot cross the placenta. ... Analysis of the literature suggests that this impression is wrong and that all drugs cross the placenta, although the extent transfer varies considerably. ...
Pacifici GM, Nottoli R; Clin Pharmacokinet 28 (3): 235-69 (1995)

8.6 Metabolism / Metabolites

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.

8.7 Biological Half-Life

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

8.8 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.
... SUCCINYLCHOLINE PRODUCES A BLOCKADE THAT COMBINES CERTAIN FEATURES OF ... THE DEPOLARIZING & THE COMPETITIVE AGENTS ... & THAT HAS SOME CHARACTERISTICS NOT ASSOC WITH EITHER; ... THIS TYPE OF ACTION /HAS BEEN TERMED/ A "DUAL" MECHANISM.
Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 184
... /ITS/ INITIAL ACTION IS TO DEPOLARIZE THE MEMBRANE BY OPENING CHANNELS IN THE SAME MANNER AS ACETYL CHOLINE. HOWEVER, SINCE /IT/ PERSISTS FOR LONGER DURATIONS AT THE NEUROMUSCULAR JUNCTION, PRIMARILY BECAUSE OF THEIR RESISTANCE TO ACETYLCHOLINESTERASE, THE DEPOLARIZATION IS LONGER LASTING, RESULTING IN A BRIEF PERIOD OF REPETITIVE EXCITATION THAT MAY ELICIT TRANSIENT MUSCULAR FASCICULATIONS. THE INITIAL PHASE IS FOLLOWED BY BLOCK OF NEUROMUSCULAR TRANSMISSION AND FLACCID PARALYSIS.
Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 183

8.9 Human Metabolite Information

8.9.1 Cellular Locations

  • Cytoplasm
  • Membrane

9 Use and Manufacturing

9.1 Uses

MEDICATION
MEDICATION (VET)

Use (kg; approx.) in Germany (2009): >100

Consumption (g per capita; approx.) in Germany (2009): 0.00122

Calculated removal (%): 92.1

9.2 Methods of Manufacturing

... By reacting beta-bromoethyl succinate with trimethylamine. /Bromide/
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1516
Prepd by reacting beta-bromoethyl succinate with trimethylamine. /Iodide/
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1516
Succinic acid chloride may be coupled with choline chloride directly or with dimethylaminoethanol, followed by quarternization with methyl iodide. /Iodide/
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1516
A third method is to start with the diethyl ester of succinic acid, then bring about the exchange reaction with dimethylaminoethanol, and quaternize with methyl iodide. /Iodide/
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1516
Prepared by reaction of ethylene bromohydrin with succinic acid and subsequent reaction with trimethylamine in a sealed tube. It can also be prepared in one step from succinic anhydride and choline cloride. /Chloride/
Gerhartz, W. (exec ed.). Ullmann's Encyclopedia of Industrial Chemistry. 5th ed.Vol A1: Deerfield Beach, FL: VCH Publishers, 1985 to Present., p. VA24 213

9.3 Formulations / Preparations

Suxamethonium bromide; IS-370; compd 48/268; LT-1; M & B 2207; Brevidil M. /Bromide/
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1516
SUCCINYLCHOLINE CHLORIDE, USP (ANECTINE, QUELICIN, SCOLINE, SUCOSTRIN, SUX-CERT), IS MARKETED AS STERILE POWDER (0.5 & 1.0 G) & AS STERILE SOLN CONTAINING 20, 50, OR 100 MG/ML. /CHLORIDE/
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 586

9.4 General Manufacturing Information

Incompatible with soln of alkaline salts. /Iodide/
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1516
Soln without stabilizers ... Are incompatible with alkaline agents such as thiopental sodium. /Chloride/
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1516
Prepare soln just before using. /Bromide/
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1516

10 Identification

10.1 Analytic Laboratory Methods

FOUR THIN-LAYER CHROMATOGRAPHIC SYSTEMS ARE DESCRIBED, FOLLOWED BY DETECTION UNDER UV LIGHT OR WITH POTASSIUM IODOPLATINATE REAGENT FOR SUCCINYLCHOLINE CHLORIDE.
CAVRINI V ET AL; SIMPLE METHOD FOR DETECTION OF D-TUBOCURARINE CHLORIDE & SUCCINYLCHOLINE CHLORIDE IN PLASMA EXPANDER; FARMACO, ED PRAT 34(1) 15 (1979)

10.2 Clinical Laboratory Methods

THIS APPROACH PROVED SUITABLE FOR HUMAN URINE SAMPLES.
FRANKE JP ET AL; ISOLATION & DETERMINATION OF QUATERNARY AMMONIUM COMPD BY MEANS OF AMBERLITE XAD-COLUMNS & THIN LAYER CHROMATOGRAPHY; ARCH TOXICOL 42(2) 115 (1979)

11 Safety and Hazards

11.1 Hazards Identification

11.1.1 GHS Classification

Pictogram(s)
Acute Toxic
Irritant
Signal
Danger
GHS Hazard Statements

H301 (93.1%): Toxic if swallowed [Danger Acute toxicity, oral]

H311 (62.1%): Toxic in contact with skin [Danger Acute toxicity, dermal]

H315 (69%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (69%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H332 (62.1%): Harmful if inhaled [Warning Acute toxicity, inhalation]

H335 (65.5%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes

P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P317, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 29 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

11.1.2 Hazard Classes and Categories

Acute Tox. 3 (93.1%)

Acute Tox. 3 (62.1%)

Skin Irrit. 2 (69%)

Eye Irrit. 2 (69%)

Acute Tox. 4 (62.1%)

STOT SE 3 (65.5%)

11.2 Accidental Release Measures

11.2.1 Disposal Methods

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

11.3 Regulatory Information

11.3.1 FDA Requirements

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
21 CFR 200-299, 300-499, 820, and 860 (4/1/99)

12 Toxicity

12.1 Toxicological Information

12.1.1 Drug Induced Liver Injury

Compound
succinylcholine
DILI Annotation
No-DILI-Concern
Label Section
No match
References

M Chen, V Vijay, Q Shi, Z Liu, H Fang, W Tong. FDA-Approved Drug Labeling for the Study of Drug-Induced Liver Injury, Drug Discovery Today, 16(15-16):697-703, 2011. PMID:21624500 DOI:10.1016/j.drudis.2011.05.007

M Chen, A Suzuki, S Thakkar, K Yu, C Hu, W Tong. DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans. Drug Discov Today 2016, 21(4): 648-653. PMID:26948801 DOI:10.1016/j.drudis.2016.02.015

12.1.2 Effects During Pregnancy and Lactation

◉ Summary of Use during Lactation

No information is available on the use of succinylcholine during breastfeeding. Because it is rapidly eliminated and poorly absorbed orally, it is not likely to reach the bloodstream of the infant or cause any adverse effects in breastfed infants. General anesthetic regimens that include succinylcholine for cesarean section caused a delay in the time to the first breastfeeding, but the part that succinylcholine played in this difference in outcome in unknown.

◉ Effects in Breastfed Infants

Relevant published information was not found as of the revision date.

◉ Effects on Lactation and Breastmilk

A randomized, but nonblinded, study in women undergoing cesarean section compared epidural anesthesia with bupivacaine to general anesthesia with intravenous thiopental 4 mg/kg and succinylcholine 1.5 mg/kg for induction followed by nitrous oxide and isoflurane. The time to the first breastfeed was significantly shorter (107 vs 228 minutes) with the epidural anesthesia than with general anesthesia. This difference was probably caused by the anesthesia's effects on the infant, because the Apgar and neurologic and adaptive scores were significantly lower in the general anesthesia group of infants. It is not known what part succinylcholine played in this difference in outcome.

A nonrandomized, nonblinded study in a Serbian hospital of women near term who underwent cesarean section compared general anesthesia (n = 284) to spinal or epidural anesthesia (n = 249). Spinal anesthesia consisted of hyperbaric bupivacaine 12 mg and fentanyl 0.01 mg; epidural anesthesia consisted of isobaric bupivacaine 0.5% (0.5 mg per 10 cm height) and fentanyl 0.05 mg. General anesthesia consisted of propofol 2.3 mg/kg and succinylcholine 1.5 mg/kg for induction and intubation, followed by an anesthetic gas mixture and oxygen. Reportedly, nitric oxide (possibly nitrous oxide) was 50% of the gas before delivery and 67% after delivery. Sevoflurane was also used in some cases. After delivery and cord clamping, mothers received fentanyl 3 mcg/kg and rocuronium 0.5 mg/kg intravenously for placental delivery. After surgery, neuromuscular block reversal was performed with neostigmine and atropine. All patients received 1 mg/kg of diclofenac every 8 h for 24 hours after delivery and 98% of general anesthesia patients also received 100 mg of tramadol and 78.5% received acetaminophen 1 gram. No regional anesthesia patients received tramadol or acetaminophen. Patients receiving one of the regional anesthetic protocols established lactation sooner (56% and 29% after 18 and 24 hours, respectively), while 86% of women receiving general anesthesia did not establish lactation until 36 to 48 hours after surgery. It is not known what part succinylcholine played in this difference in outcome.

12.1.3 Acute Effects

12.1.4 Interactions

Malignant hyperthermia can be triggered by inhalational anesthetics such as halogenated hydrocarbons, and by depolarizing muscle relaxants such as succinylcholine. ... The clinical features of the myopathy include hyperthermia, metabolic acidosis, tachycardia, accelerated muscle metabolism and contractures.
Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 188
NODAL ARRHYTHMIAS, BRADYCARDIA & SINUS ARREST HAVE OCCURRED ... AFTER FRACTIONAL DOSES WERE GIVEN IV AT 3 TO 10 MIN INTERVALS TO PATIENTS RECEIVING HALOTHANE. /CHLORIDE/
American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 207
FEW CASES OF SEVERE BRONCHOSPASM HAVE BEEN REPORTED WHEN SUCCINYLCHOLINE WAS ADMIN WITH HEXAFLUORENIUM ... /CHLORIDE/
American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 316
POLYMYXIN B CAN INCR PARALYZING EFFECTS. /CHLORIDE/
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 854
For more Interactions (Complete) data for SUCCINYLCHOLINE (35 total), please visit the HSDB record page.

12.1.5 Human Toxicity Excerpts

SUCCINYLCHOLINE CHLORIDE DOES NOT CAUSE LIBERATION OF HISTAMINE &.../IT/ IS WELL TOLERATED. /CHLORIDE/
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 853

12.1.6 Non-Human Toxicity Excerpts

DEATHS FROM SUCCINYLCHOLINE CHLORIDE HAVE BEEN RECORDED IN THE HORSE. THESE WERE ASSUMED ... TO BE DUE TO ... DEPRESSION OF RESPIRATION BUT ARE MORE PROBABLY ASSOCIATED WITH CARDIAC ARREST. /CHLORIDE/
Humphreys, D.J. Veterinary Toxicology. 3rd ed. London, England: Bailliere Tindell, 1988., p. 114
MUSCLE RELAXANTS CAN ACT AS TRIGGERING AGENTS IN GENETICALLY SUSCEPTIBLE PIGS WHICH DEVELOP HYPERMETABOLIC STATE, CHARACTERIZED BY RAPID RISE IN BODY TEMP, MUSCLE RIGIDITY, TACHYCARDIA & TACHYPNEA, CYANOSIS & SEVERE RESP & METABOLIC ACIDOSIS.
DEMEYERE R; ACTA ANAESTHESIOL BERG 29(1) 101 (1978)

12.1.7 Non-Human Toxicity Values

LD50 Mouse oral 125 mg/kg
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 851
LD50 Mouse ip 2140 ug/kg
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 851
LD50 Mouse sc 7500 ug/kg
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 851
LD50 Mouse iv 280 ug/kg
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 851
LD50 rabbit iv 800 ug/kg
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 851

12.1.8 Populations at Special Risk

All neuromuscular blocking agents should be used with caution in patients with renal, hepatic, or pulmonary impairment, or respiratory depression, and in geriatric or debilitated patients. The drugs should be used with extreme caution, if at all, in patients with myasthenia gravis. Other conditions that are associated with increased response to the neuromuscular blocking agents are the myasthenic syndrome associated with lung cancer, dehydration, thyroid disorder, collagen diseases, porphyria, and familial periodic paralysis. Potent inhalation anesthetics and neuromuscular blocking agents should be avoided if possible in patients who have experienced malignant hyperthermia and in members of their families, and the possibility that this reaction could occur in any patient undergoing general anesthesia should be considered. During the first month of life, neonates are particularly sensitive to the action of most nondepolarizing agents and respond with prolonged neuromuscular blockade to usual doses of the drugs. /Neuromuscular blocking agents/
McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 1999. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1999 (Plus Supplements)., p. 1172

13 Associated Disorders and Diseases

14 Literature

14.1 Consolidated References

14.2 NLM Curated PubMed Citations

14.3 Springer Nature References

14.4 Chemical Co-Occurrences in Literature

14.5 Chemical-Gene Co-Occurrences in Literature

14.6 Chemical-Disease Co-Occurrences in Literature

15 Patents

15.1 Depositor-Supplied Patent Identifiers

15.2 WIPO PATENTSCOPE

15.3 Chemical Co-Occurrences in Patents

15.4 Chemical-Disease Co-Occurrences in Patents

15.5 Chemical-Gene Co-Occurrences in Patents

16 Interactions and Pathways

16.1 Protein Bound 3D Structures

16.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

16.2 Chemical-Target Interactions

16.3 Drug-Drug Interactions

17 Biological Test Results

17.1 BioAssay Results

18 Classification

18.1 MeSH Tree

18.2 NCI Thesaurus Tree

18.3 ChEBI Ontology

18.4 KEGG: ATC

18.5 KEGG: Drug Groups

18.6 WHO ATC Classification System

18.7 FDA Pharm Classes

18.8 ChemIDplus

18.9 IUPHAR / BPS Guide to PHARMACOLOGY Target Classification

18.10 ChEMBL Target Tree

18.11 UN GHS Classification

18.12 NORMAN Suspect List Exchange Classification

18.13 EPA DSSTox Classification

18.14 MolGenie Organic Chemistry Ontology

19 Information Sources

  1. CAS Common Chemistry
    LICENSE
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    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. DrugBank
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    https://www.drugbank.ca/legal/terms_of_use
  4. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. European Chemicals Agency (ECHA)
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    https://echa.europa.eu/web/guest/legal-notice
  6. FDA Global Substance Registration System (GSRS)
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  7. Hazardous Substances Data Bank (HSDB)
  8. Human Metabolome Database (HMDB)
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    http://www.hmdb.ca/citing
  9. ChEBI
  10. FDA Pharm Classes
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  11. NCI Thesaurus (NCIt)
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    https://www.cancer.gov/policies/copyright-reuse
  12. Open Targets
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    https://platform-docs.opentargets.org/licence
  13. ChEMBL
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    http://www.ebi.ac.uk/Information/termsofuse.html
  14. ClinicalTrials.gov
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    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  15. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  16. Drug Gene Interaction database (DGIdb)
    LICENSE
    The data used in DGIdb is all open access and where possible made available as raw data dumps in the downloads section.
    http://www.dgidb.org/downloads
  17. IUPHAR/BPS Guide to PHARMACOLOGY
    LICENSE
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    https://www.guidetopharmacology.org/about.jsp#license
    Guide to Pharmacology Target Classification
    https://www.guidetopharmacology.org/targets.jsp
  18. Therapeutic Target Database (TTD)
  19. Crystallography Open Database (COD)
    LICENSE
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    https://creativecommons.org/publicdomain/zero/1.0/
  20. DailyMed
  21. Drug Induced Liver Injury Rank (DILIrank) Dataset
    LICENSE
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  22. Drugs and Lactation Database (LactMed)
  23. Drugs@FDA
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  24. WHO Model Lists of Essential Medicines
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    https://www.who.int/about/policies/publishing/copyright
  25. EU Clinical Trials Register
  26. National Drug Code (NDC) Directory
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  27. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    SUXAMETHONIUM
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  28. Japan Chemical Substance Dictionary (Nikkaji)
  29. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
    Anatomical Therapeutic Chemical (ATC) classification
    http://www.genome.jp/kegg-bin/get_htext?br08303.keg
  30. MassBank Europe
  31. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  32. Metabolomics Workbench
  33. NIPH Clinical Trials Search of Japan
  34. NLM RxNorm Terminology
    LICENSE
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    https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.html
  35. NMRShiftDB
  36. WHO Anatomical Therapeutic Chemical (ATC) Classification
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    https://www.whocc.no/copyright_disclaimer/
  37. PharmGKB
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    https://www.pharmgkb.org/page/policies
  38. Pharos
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    https://pharos.nih.gov/about
  39. Protein Data Bank in Europe (PDBe)
  40. RCSB Protein Data Bank (RCSB PDB)
    LICENSE
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    https://www.rcsb.org/pages/policies
  41. Springer Nature
  42. Wikidata
  43. Wikipedia
  44. Medical Subject Headings (MeSH)
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    https://www.nlm.nih.gov/copyright.html
    Neuromuscular Depolarizing Agents
    https://www.ncbi.nlm.nih.gov/mesh/68009467
  45. PubChem
  46. GHS Classification (UNECE)
  47. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  48. PATENTSCOPE (WIPO)
  49. NCBI
CONTENTS