71-27-2 Usage
Description
Succinylcholine chloride is a potent relaxant of voluntary striated muscle but has little direct effect on smooth muscle. It has no anesthetic or pain-obliterating properties; therefore, immobilized animals remain completely conscious although unable to move. The duration of effect is quite brief because succinylcholine is rapidly destroyed by non-specific cholinesterases in the blood plasma and liver. Immobilization lasts five to 12 minutes in man and horses and somewhat longer in other species,with ruminants generally requiring longest recovery periods (Stowe et al. 1958).Since the discovery of its curariform properties in 1949, succinylcholine has been widely used for immobilization of animals and in human surgical procedures. Several workers have used succinylcholine on bears (Black 1958, Knudsen 1959, Craighead et al. 1960, Troyer et al. 1961,Hornocker 1962, Mundy 1963,Pearson et al. 1968, Jonkel and Cowan 1971 and Mundy and Flook 1973).Succinylcholine chloride is indicated as an adjunct to general anesthesia, to facilitate tracheal intubation, and to provide skeletal muscle relaxation during surgery or mechanical ventilation.
Chemical Properties
Succinylcholine chloride is a white, odorless, slightly bitter powder and very soluble in water. The drug is unstable in alkaline solutions but relatively stable in acid solutions, depending upon the concentration of the solution and the storage temperature. Solutions of succinylcholine chloride should be stored under refrigeration to preserve potency.
Uses
A neuromuscular blocking agent. Muscle relaxant (skeletal).
Definition
ChEBI: A chloride salt in which the negative charge of the chloride ions is balanced by succinylcholine dications.
Brand name
Anectine (Sandoz); Quelicin (Hospira); Sucostrin (Apothecon).
Therapeutic Function
Muscle relaxant
World Health Organization (WHO)
Suxamethonium chloride is a short-acting muscle relaxant. It is
used in surgery. Suxamethonium chloride is listed in the WHO Model List of
Essential Drugs.
Biological Functions
Succinylcholine chloride (Anectine) is the only depolarizing-
type blocker that is in widespread clinical use. It
produces neuromuscular block by overstimulation, so
that the end plate is unable to respond to further stimulation.
Structurally, succinylcholine is equivalent to two
ACh molecules joined back to back. The resulting 10-
carbon atom spacing between the two quaternary ammonium
heads is important for activation of the two
binding sites on the AChR. Because the succinylcholine
molecule is “thin,” binding to the two sites does not sterically
occlude the open channel, and cations are allowed
to flow and depolarize the end plate.
Neuromuscular block with succinylcholine occurs
by two sequential events. An initial depolarization of
the end plate produces muscle action potentials and
fasciculation. Maintained depolarization past the threshold for firing produces Na channel inactivation,
so that muscle action potentials cannot be generated.
This is called phase I, or depolarization block. In the
continued presence of succinylcholine, the membrane
becomes repolarized, Na channel inactivation is reversed,
and muscle membrane excitability is restored.
Nonetheless, the neuromuscular block persists because
of desensitization of the AChR. This is known as phase
II, or desensitization block.
Although the mechanism for phase II block is not
completely understood, a series of allosteric transitions
in the AChR is suspected. One model to describe this
has the AChR in equilibrium among four conformations:
resting, active, inactive, and desensitized. Agonists
stabilize the active and desensitized states, whereas antagonists
tend to stabilize the resting and possibly the
desensitized state.
General Description
Succinylcholine chloride,choline chloride succinate (2:1) (Anectine, Sucostrin),is a white, odorless, crystalline substance that is freely solublein water to give solutions with a pH of about 4. It isstable in acidic solutions but unstable in alkali. Aqueous solutionsshould be refrigerated to ensure stability.Succinylcholine chloride is characterized by a very shortduration of action and a quick recovery because of its rapidhydrolysis after injection. It brings about the typical muscularparalysis caused by blocking nervous transmission at themyoneural junction. Large doses may cause temporary respiratorydepression, as with similar agents. Its action, in contrastwith that of (1)-tubocurarine, is not antagonized byneostigmine, physostigmine, or edrophonium chloride.These anticholinesterase drugs actually prolong the action ofsuccinylcholine chloride, which suggests that the drug isprobably hydrolyzed by cholinesterases. The brief durationof action of this curare-like agent is said to render an antidoteunnecessary if the proper supportive measures are available.Succinylcholine chloride has a disadvantage, however, inthat the usual antidotes cannot terminate its action promptly.
Air & Water Reactions
Water soluble.
Fire Hazard
Flash point data for SUCCINYLCHOLINE CHLORIDE are not available. SUCCINYLCHOLINE CHLORIDE is probably combustible.
Clinical Use
Succinylcholine Chloride is used as a muscle relaxant for the same indications asother curare agents. It may be used for either short or longperiods of relaxation, depending on whether one or severalinjections are given. In addition, it is suitable for continuousintravenous drip administration.Succinylcholine chloride should not be used withthiopental sodium because of the high alkalinity of the latter.If used together, they should be administered immediatelyafter mixing; however, separate injection is preferable.
Veterinary Drugs and Treatments
Succinylcholine chloride is indicated for short-term muscle relaxation
needed for surgical or diagnostic procedures, to facilitate endotracheal
intubation in some species, and reducing the intensity
of muscle contractions associated with electro- or pharmacological-
induced convulsions. Dogs, cats, and horses are the primary
veterinary species where succinylcholine chloride has been used.
Drug interactions
Potentially hazardous interactions with other drugs
Anaesthetics: increased risk of myocardial depression
and bradycardia with propofol; enhanced effect with
volatile liquid general anaesthetics.
Anti-arrhythmics: lidocaine and procainamide
enhance muscle relaxant effect.
Antibacterials: effect enhanced by aminoglycosides,
clindamycin, polymyxins, vancomycin and
piperacillin.
Cardiac glycosides: increased risk of ventricular
arrhythmias.
Metabolism
Suxamethonium is rapidly hydrolysed to
succinylmonocholine a weak neuro-muscular blocking
drug. This is metabolised to succinic acid with only a
small amount excreted in the urine.
Check Digit Verification of cas no
The CAS Registry Mumber 71-27-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 1 respectively; the second part has 2 digits, 2 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 71-27:
(4*7)+(3*1)+(2*2)+(1*7)=42
42 % 10 = 2
So 71-27-2 is a valid CAS Registry Number.
InChI:InChI=1/C14H30N2O4.2Cr/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;;
71-27-2Relevant articles and documents
Succinylcholine chloride preparation method
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Paragraph 0063-0073, (2020/02/29)
The invention relates to a succinylcholine chloride preparation method, and specifically discloses a synthetic method for preparing succinylcholine chloride by using succinic acid as a starting raw material through a chlorination reaction and an esterification reaction. According to the invention, the method has advantages of safe production, low production cost, high reaction efficiency and simple product purification, and is suitable for mass production of bulk drugs.
PROCESS FOR PREPARATION OF SUCCINYLCHOLINE CHLORIDE
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Page/Page column, (2014/04/18)
The present invention relates to a process for the preparation of succinylcholine chloride, a pharmaceutically active compound used as skeletal muscle relaxant which comprises condensing succinic anhydride with N,N-diemthylaminoethanol using a catalyst in presence of a solvent to form bis[2-(dimethylamino)ethyl]succinate; in situ purifying the bis[2-(dimethylamino)ethyl]succinate using a base; reacting pure bis[2-(dimethylamino)ethyl]succinate with methyl chloride gas using an alcohol; and purifying the obtained crude succinylcholine chloride using water and alcohol.
Process for the preparation of succinylcholine halides
-
, (2008/06/13)
Preparation of succinylcholine halides of formula I: STR1 by reacting dialkyl succinates with an excess dimethylaminoethanol in the presence of an alkali metal alcoholate or alkali metal amide catalyst and then reacting the resulting bis(2-dimethylaminoethyl) succinates with methyl halides.
