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Details

Stereochemistry ACHIRAL
Molecular Formula C14H30N2O4.2Cl.2H2O
Molecular Weight 397.336
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SUCCINYLCHOLINE CHLORIDE DIHYDRATE

SMILES

C[N+](C)(C)CCOC(=O)CCC(=O)OCC[N+](C)(C)C.[Cl-].[Cl-].O.O

InChI

InChIKey=FFSBEIRFVXGRPR-UHFFFAOYSA-L
InChI=1S/C14H30N2O4.2ClH.2H2O/c1-15(2,3)9-11-19-13(17)7-8-14(18)20-12-10-16(4,5)6;;;;/h7-12H2,1-6H3;2*1H;2*1H2/q+2;;;;/p-2

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula HO
Molecular Weight 17.0073
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C14H30N2O4
Molecular Weight 290.3996
Charge 2
Count
Stereochemistry MIXED
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Succinylcholine also known as suxamethonium is a quaternary skeletal muscle relaxant usually used in the form of its halogen salt. It is is indicated under brand name anectine as an adjunct to general anesthesia, to facilitate tracheal intubation, and to provide skeletal muscle relaxation during surgery or mechanical ventilation. Succinylcholine activates the muscle-type nicotinic acetylcholine receptor followed by desensitization. Succinylcholine does not inhibit the presynaptic alpha3beta2 autoreceptor at clinically relevant concentrations, that provides a possible mechanistic explanation for the typical lack of tetanic fade in succinylcholine-induced neuromuscular blockade. Finally, was explored, that cardiovascular side effects (e.g., tachyarrhythmias) of succinylcholine were not mediated via direct activation of the autonomic ganglionic alpha3beta4 subtype because succinylcholine didn’t not activate the neuronal nicotinic acetylcholine receptor (nAChR) subtypes.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
ANECTINE

Approved Use

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.

Launch Date

-5.48035199E11
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
18.5 μg × min/mL
1 mg/kg bw single, intravenous
dose: 1 mg/kg bw
route of administration: Intravenous
experiment type: SINGLE
co-administered:
SUCCINYLCHOLINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
58.6 μg × min/mL
2 mg/kg bw single, intravenous
dose: 2 mg/kg bw
route of administration: Intravenous
experiment type: SINGLE
co-administered:
SUCCINYLCHOLINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
25.4 s
1 mg/kg bw single, intravenous
dose: 1 mg/kg bw
route of administration: Intravenous
experiment type: SINGLE
co-administered:
SUCCINYLCHOLINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
26.3 s
2 mg/kg bw single, intravenous
dose: 2 mg/kg bw
route of administration: Intravenous
experiment type: SINGLE
co-administered:
SUCCINYLCHOLINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1.5 mg/kg single, intravenous
Higher than recommended
Dose: 1.5 mg/kg
Route: intravenous
Route: single
Dose: 1.5 mg/kg
Sources: Page: p.866
healthy, 31
n = 22
Health Status: healthy
Condition: General anesthesia
Age Group: 31
Sex: F
Population Size: 22
Sources: Page: p.866
1.1 mg/kg single, intravenous (max)
Recommended
Dose: 1.1 mg/kg
Route: intravenous
Route: single
Dose: 1.1 mg/kg
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: General anesthesia|Skeletal muscle relaxation
Sources: Page: p.1
Disc. AE: Rhabdomyolysis, Ventricular arrhythmia...
AEs leading to
discontinuation/dose reduction:
Rhabdomyolysis (acute, rare)
Ventricular arrhythmia (rare)
Cardiac arrest (grade 5, rare)
Sources: Page: p.1
AEs

AEs

AESignificanceDosePopulation
Rhabdomyolysis acute, rare
Disc. AE
1.1 mg/kg single, intravenous (max)
Recommended
Dose: 1.1 mg/kg
Route: intravenous
Route: single
Dose: 1.1 mg/kg
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: General anesthesia|Skeletal muscle relaxation
Sources: Page: p.1
Cardiac arrest grade 5, rare
Disc. AE
1.1 mg/kg single, intravenous (max)
Recommended
Dose: 1.1 mg/kg
Route: intravenous
Route: single
Dose: 1.1 mg/kg
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: General anesthesia|Skeletal muscle relaxation
Sources: Page: p.1
Ventricular arrhythmia rare
Disc. AE
1.1 mg/kg single, intravenous (max)
Recommended
Dose: 1.1 mg/kg
Route: intravenous
Route: single
Dose: 1.1 mg/kg
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: General anesthesia|Skeletal muscle relaxation
Sources: Page: p.1
PubMed

PubMed

TitleDatePubMed
Influence of tetrahydro-aminacrine on muscle pains after suxamethonium.
1975 Jan 18
Comparison of gallamine with d-tubocurarine effects on fasciculations after succinylcholine.
1975 Jan-Feb
"Precurarization" using pancuronium.
1975 Jan-Feb
Cardiac arrest related to anesthesia. Contributing factors in infants and children.
1975 Jul 21
Out-of-hospital succinylcholine-assisted endotracheal intubation by paramedics.
2000 Jun
[Anesthetic complications. The incidence of severe anesthetic complications in patients and families with progressive muscular dystrophy of the Duchenne and Becker types].
2000 Mar
Choice of the hypnotic and the opioid for rapid-sequence induction.
2001
Muscle relaxants in paediatric day case surgery.
2001
Muscle relaxants suitable for day case surgery.
2001
[Clinical administration of muscle relaxants for intubation].
2001
Difficult airway management of a child impaled through the neck.
2001
Malignant hyperthermia in a patient with Graves' disease during subtotal thyroidectomy.
2001 Apr
Giant multimodal heart motoneurons of Achatina fulica: a new cardioregulatory input in pulmonates.
2001 Aug
Effects of combined methohexitone-remifentanil anaesthesia in electroconvulsive therapy.
2001 Aug
Why do we still use suxamethonium for caesarean section?
2001 Dec
Analysis of mutations in the plasma cholinesterase gene of patients with a history of prolonged neuromuscular block during anesthesia.
2001 Dec
The laryngeal mask airway is effective (and probably safe) in selected healthy parturients for elective Cesarean section: a prospective study of 1067 cases.
2001 Dec
Intubating trauma patients before reaching hospital -- revisited.
2001 Dec
B-lymphocytes from malignant hyperthermia-susceptible patients have an increased sensitivity to skeletal muscle ryanodine receptor activators.
2001 Dec 21
Military and civilian penetrating eye trauma: anesthetic implications.
2001 Feb
Frequency of haemoglobin desaturation with the use of succinylcholine during rapid sequence induction of anaesthesia.
2001 Jul
[Short-term anesthesia to stop persistent hiccups].
2001 Jun 22
EEG-bispectral index changes with ketamine versus thiamylal induction of anesthesia.
2001 Mar
Hemoglobin desaturation after succinylcholine-induced apnea: a study of the recovery of spontaneous ventilation in healthy volunteers.
2001 May
Maternal anaphylactic reaction to a general anaesthetic at emergency caesarean section for fetal bradycardia.
2001 May
Rapid sequence induction: a national survey of practice.
2001 Nov
Is succinylcholine appropriate or obsolete in the intensive care unit?
2001 Oct
Goal oriented general anesthesia for Cesarean section in a parturient with a large intracranial epidermoid cyst.
2001 Oct
[Anesthesia for electroconvulsive therapy during pregnancy--a case report].
2001 Sep
Autosomal dominant canine malignant hyperthermia is caused by a mutation in the gene encoding the skeletal muscle calcium release channel (RYR1).
2001 Sep
In patients with head injuries who undergo rapid sequence intubation using succinylcholine, does pretreatment with a competitive neuromuscular blocking agent improve outcome? A literature review.
2001 Sep
Succinylcholine in the intensive care unit.
2002 Jan
Patents

Patents

Sample Use Guides

Adults: For Short Surgical Procedures: the average dose required to produce neuromuscular blockade and to facilitate tracheal intubation is 0.6 mg/kg ANECTINE (Succinylcholine Chloride Injection) given intravenously. The optimum dose will vary among individuals and may be from 0.3 to 1.1 mg/kg for adults. Following administration of doses in this range, neuromuscular blockade develops in about 1 minute; maximum blockade may persist for about 2 minutes, after which recovery takes place within 4 to 6 minutes. However, very large doses may result in more prolonged blockade. A 5- to 10-mg test dose may be used to determine the sensitivity of the patient and the individual recovery time (see PRECAUTIONS). For Long Surgical Procedures The dose of succinylcholine administered by infusion depends upon the duration of the surgical procedure and the need for muscle relaxation. The average rate for an adult ranges between 2.5 and 4.3 mg per minute. Solutions containing from 1 to 2 mg per mL succinylcholine have commonly been used for continuous infusion. The more dilute solution (1 mg per mL) is probably preferable from the standpoint of ease of control of the rate of administration of the drug and, hence, of relaxation. This IV solution containing 1 mg per mL may be administered at a rate of 0.5 mg (0.5 mL) to 10 mg (10 mL) per minute to obtain the required amount of relaxation. Intermittent IV injections of succinylcholine may also be used to provide muscle relaxation for long procedures. An IV injection of 0.3 to 1.1 mg/kg may be given initially, followed, at appropriate intervals, by further injections of 0.04 to 0.07 mg/kg to maintain the degree of relaxation required. Pediatrics: for emergency tracheal intubation or in instances where immediate securing of the airway is necessary, the IV dose of succinylcholine is 2 mg/kg for infants and small children; for older children and adolescents the dose is 1 mg/kg. Rarely, IV bolus administration of succinylcholine in infants and children may result in malignant ventricular arrhythmias and cardiac arrest secondary to acute rhabdomyolysis with hyperkalemia. In such situations, an underlying myopathy should be suspected. Intravenous bolus administration of succinylcholine in infants or children may result in profound bradycardia or, rarely, asystole. As in adults, the incidence of bradycardia in children is higher Intramuscular Use: If necessary, succinylcholine may be given intramuscularly to infants, older children, or adults when a suitable vein is inaccessible. A dose of up to 3 to 4 mg/kg may be given, but not more than 150 mg total dose should be administered by this route. The onset of effect of succinylcholine given intramuscularly is usually observed in about 2 to 3 minutes.
Route of Administration: Other
In Vitro Use Guide
The rat diaphragm was used as an in vitro model for studies of contractures synergistically-induced by halothane and suxamethonium (succinylcholine). The effects of three agents reported to inhibit phospholipase A2 activity (quinacrine, spermine and indomethacin), tubocurarine and dantrolene were examined on these contractures. Contractures induced by 1% halothane (0.26 +/- 0.02 g) (mean +/- SEM) were increased (0.60 +/- 0.04 g) if suxamethonium 50 mmol litre-1 was also in the bathing medium. Suxamethonium-induced contractures (0.22 +/- 0.03 g) were also enhanced when halothane was present (0.51 +/- 0.03 g). Spermine, indomethacin and dantrolene antagonized both halothane- and suxamethonium-induced contractures. Quinacrine potentiated contractures induced by either halothane or suxamethonium. Contractures induced by suxamethonium were antagonized by tubocurarine; however, contractures induced by halothane were not antagonized by tubocurarine. These results suggest that free fatty acids may be involved in contractures induced synergistically by halothane and suxamethonium. Different mechanisms are involved in the induction of contractures by suxamethonium than by halothane.
Substance Class Chemical
Created
by admin
on Sat Jun 26 13:38:17 UTC 2021
Edited
by admin
on Sat Jun 26 13:38:17 UTC 2021
Record UNII
8L0S1G435E
Record Status Validated (UNII)
Record Version
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Name Type Language
SUCCINYLCHOLINE CHLORIDE DIHYDRATE
Common Name English
SUXAMETHONIUM CHLORIDE HYDRATE
JAN  
Common Name English
SUXAMETHONII CHLORIDUM [WHO-IP LATIN]
Common Name English
SUXAMETHONIUM CHLORIDE [WHO-IP]
Common Name English
SUXAMETHONIUM CHLORIDE DIHYDRATE
WHO-DD  
Common Name English
SUXAMETHONIUM CHLORIDE HYDRATE [JAN]
Common Name English
ETHANAMINIUM, 2,2'-((1,4-DIOXO-1,4-BUTANEDIYL)BIS(OXY))BIS(N,N,N-TRIMETHYL-), DICHLORIDE, DIHYDRATE
Common Name English
2,2'-SUCCINYLDIOXYBIS(ETHYLTRIMETHYLAMMONIUM) DICHLORIDE, DIHYDRATE [WHO-IP]
Common Name English
SUXAMETHONIUM CHLORIDE DIHYDRATE [WHO-DD]
Common Name English
SUCCINYLCHOLINE CHLORIDE [WHO-IP]
Common Name English
Code System Code Type Description
EVMPD
SUB71135
Created by admin on Sat Jun 26 13:38:17 UTC 2021 , Edited by admin on Sat Jun 26 13:38:17 UTC 2021
PRIMARY
CAS
6101-15-1
Created by admin on Sat Jun 26 13:38:17 UTC 2021 , Edited by admin on Sat Jun 26 13:38:17 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
SUCCINYLCHOLINE CHLORIDE DIHYDRATE
Created by admin on Sat Jun 26 13:38:17 UTC 2021 , Edited by admin on Sat Jun 26 13:38:17 UTC 2021
PRIMARY Description: A white or almost white, crystalline powder; odourless or almost odourless. Solubility: Soluble in 1 pan of water; slightly soluble in ethanol (~750 g/l) TS; practically insoluble in ether R. Category: Muscle relaxant. Storage: Suxamethonium chloride should be kept in a tightly closed container, protected from light. Additional information: Suxamethonium chloride is hygroscopic. Even in the absence of light, it is gradually degraded on exposure to a humid atmosphere, the decomposition being faster at higher temperatures. Definition: Suxamethonium chloride contains not less than 98.0% and not more than 101.0% of C14H30Cl2N2O4, calculated with reference to the anhydrous substance.
RXCUI
2397714
Created by admin on Sat Jun 26 13:38:17 UTC 2021 , Edited by admin on Sat Jun 26 13:38:17 UTC 2021
PRIMARY
FDA UNII
8L0S1G435E
Created by admin on Sat Jun 26 13:38:17 UTC 2021 , Edited by admin on Sat Jun 26 13:38:17 UTC 2021
PRIMARY
PUBCHEM
656867
Created by admin on Sat Jun 26 13:38:17 UTC 2021 , Edited by admin on Sat Jun 26 13:38:17 UTC 2021
PRIMARY
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