Details
Stereochemistry | ACHIRAL |
Molecular Formula | C14H30N2O4 |
Molecular Weight | 290.399 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 2 |
E/Z Centers | 0 |
Charge | 2 |
SHOW SMILES / InChI
SMILES
C[N+](C)(C)CCOC(=O)CCC(=O)OCC[N+](C)(C)C
InChI
InChIKey=AXOIZCJOOAYSMI-UHFFFAOYSA-N
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
Molecular Formula | C14H30N2O4 |
Molecular Weight | 290.399 |
Charge | 2 |
Count |
|
Stereochemistry | MIXED |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 2 |
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2362997 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16571968 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | ANECTINE Approved UseSuccinylcholine 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 Date1952 |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
18.5 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14564614/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14564614/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
25.4 s EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14564614/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14564614/ |
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
Dose | Population | Adverse 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: |
healthy, 31 |
|
1.1 mg/kg single, intravenous Recommended Dose: 1.1 mg/kg Route: intravenous Route: single Dose: 1.1 mg/kg Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Rhabdomyolysis, Ventricular arrhythmia... AEs leading to discontinuation/dose reduction: Rhabdomyolysis (acute, rare) Sources: Ventricular arrhythmia (rare) Cardiac arrest (grade 5, rare) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Rhabdomyolysis | acute, rare Disc. AE |
1.1 mg/kg single, intravenous Recommended Dose: 1.1 mg/kg Route: intravenous Route: single Dose: 1.1 mg/kg Sources: |
unhealthy Health Status: unhealthy Sources: |
Cardiac arrest | grade 5, rare Disc. AE |
1.1 mg/kg single, intravenous Recommended Dose: 1.1 mg/kg Route: intravenous Route: single Dose: 1.1 mg/kg Sources: |
unhealthy Health Status: unhealthy Sources: |
Ventricular arrhythmia | rare Disc. AE |
1.1 mg/kg single, intravenous Recommended Dose: 1.1 mg/kg Route: intravenous Route: single Dose: 1.1 mg/kg Sources: |
unhealthy Health Status: unhealthy Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Comparison of gallamine with d-tubocurarine effects on fasciculations after succinylcholine. | 1975 Jan-Feb |
|
"Precurarization" using pancuronium. | 1975 Jan-Feb |
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Cardiac arrest related to anesthesia. Contributing factors in infants and children. | 1975 Jul 21 |
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Survey of local anesthetic toxicity in the families of patients with atypical plasma cholinesterase. | 1975 Nov |
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Anaphylaxis due to suxamethonium--manifested at induction of anaesthesia by bradycardia and cardiac arrest. | 1999 Apr-Jun |
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Effects of pretreatment with cisatracurium, rocuronium, and d-tubocurarine on succinylcholine-induced fasciculations and myalgia: a comparison with placebo. | 1999 Dec |
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Choice of the hypnotic and the opioid for rapid-sequence induction. | 2001 |
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Difficult airway management of a child impaled through the neck. | 2001 |
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Newer neuromuscular blocking agents: how do they compare with established agents? | 2001 |
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Tracheal intubation without muscle relaxant--a technique using sevoflurane vital capacity induction and alfentanil. | 2001 Aug |
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Safety and efficacy of rocuronium for controlled intubation with paralytics in the pediatric emergency department. | 2001 Aug |
|
The influence of fentanyl vs. s-ketamine on intubating conditions during induction of anaesthesia with etomidate and rocuronium. | 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 |
|
Military and civilian penetrating eye trauma: anesthetic implications. | 2001 Feb |
|
Sore throat following tracheal intubation. | 2001 Feb |
|
Assessment of depth of anesthesia and postoperative respiratory recovery after remifentanil- versus alfentanil-based total intravenous anesthesia in patients undergoing ear-nose-throat surgery. | 2001 Feb |
|
Endotracheal intubation with thiopental/succinylcholine or sevoflurane-nitrous oxide anesthesia in adults: a comparative study. | 2001 Feb |
|
The use of esmolol as an alternative to remifentanil during desflurane anesthesia for fast-track outpatient gynecologic laparoscopic surgery. | 2001 Feb |
|
Use of a multidisciplinary continuous-quality-improvement process to investigate succinylcholine treatment failures. | 2001 Feb 1 |
|
[Concerning the new presentation of Celocurine]. | 2001 Jan |
|
An evaluation of Automode, a computer-controlled ventilator mode, with the Siemens Servo 300A ventilator, using a porcine model. | 2001 Jan |
|
Unplanned administration of atropine, succinylcholine and lidocaine. | 2001 Jan |
|
Adrenocortical dysfunction following etomidate induction in emergency department patients. | 2001 Jan |
|
Effectiveness of continuous positive airway pressure to enhance pre-oxygenation in morbidly obese women. | 2001 Jul |
|
Asystole during electroconvulsive therapy: a case report. | 2001 Jun |
|
Succinylcholine pretreatment using gallamine or mivacurium during rapid sequence induction in children: a randomized, controlled study. | 2001 Jun |
|
Cardiac arrest after succinylcholine: mortality greater with rhabdomyolysis than receptor upregulation. | 2001 Mar |
|
Conquer difficult airways. Strategies to help you identify & control a problem airway. | 2001 Mar |
|
Measurement of succinylcholine concentration in human plasma by electrospray tandem mass spectrometry. | 2001 Mar |
|
Cost identification analysis for succinylcholine. | 2001 Mar |
|
Succinylcholine-assisted endotracheal intubation by paramedics. | 2001 Mar |
|
The intubating laryngeal mask airway after induction of general anesthesia versus awake fiberoptic intubation in patients with difficult airways. | 2001 May |
|
Duration of action of vecuronium after an intubating dose of rapacuronium, vecuronium, or succinylcholine. | 2001 May |
|
Intramuscular succinylcholine and laryngospasm. | 2001 Oct |
|
[Anesthesia for electroconvulsive therapy during pregnancy--a case report]. | 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
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3790394
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
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Edited
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Record UNII |
J2R869A8YF
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Record Status |
Validated (UNII)
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Record Version |
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NDF-RT |
N0000175733
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M03AB01
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QM03AB01
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WHO-ESSENTIAL MEDICINES LIST |
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NCI_THESAURUS |
C29696
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Succinylcholine
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Succinylcholine
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