StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
Huagongshe Open Project：[email protected]KI-Anbindung: llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.7.8
  1. Startseite
  2. /Verbindung

Cisatracurium

HCID 62887
NotizenReaktionen
GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
TeilstruktursucheÄhnliche Strukturen suchen

Grundinformationen

CAS
96946-41-7
Standard-SMILES
COc1ccc(C[C@@H]2c3cc(OC)c(OC)cc3CC[N@+]2(C)CCC(=O)OCCCCCOC(=O)CC[N@@+]2(C)CCc3cc(OC)c(OC)cc3[C@H]2Cc2ccc(OC)c(OC)c2)cc1OC
InChIKey
YXSLJKQTIDHPOT-LJCJQEJUSA-N
Summenformel
C53H72N2O12+2
Durchschnittliche Molmasse
929,1 g/mol
Monoisotopische Masse
928,50852574

Überblick

Cisatracurium is a diester that is the (1R,1'R,2R,2'R)-diastereoisomer of atracurium, a quaternary ammonium ion consisting of pentane-1,5-diol with both hydroxy functions bearing 3-[1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methyl-3,4-dihydroisoquinolinium-2(1H)-yl]propanoyl groups. The active species in the skeletal muscle relaxant cisatracurium besylate. It has a role as a nicotinic antagonist and a muscle relaxant. It is a quaternary ammonium ion and a diester.

Namen und Bezeichner

Bevorzugter Name
Cisatracurium
IUPAC
5-[3-[(1R,2R)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-2-ium-2-yl]propanoyloxy]pentyl 3-[(1R,2R)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-2-ium-2-yl]propanoate

Namen und Synonyme

Cisatracurium96946-41-7Cisatracurium cationCisatracurium ionQX62KLI41NCHEBI:140621DTXSID60873212(1R,2R,1'R,2'R)-2,2'-(PENTANE-1,5-DIYLBIS(OXY(3-OXOPROPANE-3,1-DIYL)))BIS(1-(3,4-DIMETHOXYBENZYL)-6,7-DIMETHOXY-2-METHYL-1,2,3,4-TETRAHYDROISOQUINOLINIUM)(1r,2r,1'r,2'r)-2,2'-{pentane-1,5-diylbis[oxy(3-oxopropane-3,1-diyl)]}bis[1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolinium]5-[3-[(1R,2R)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-2-ium-2-yl]propanoyloxy]pentyl 3-[(1R,2R)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-2-ium-2-yl]propanoateISOQUINOLINIUM, 2,2'-(1,5-PENTANEDIYLBIS(OXY(3-OXO-3,1-PROPANEDIYL)))BIS(1-((3,4-DIMETHOXYPHENYL)METHYL)-1,2,3,4-TETRAHYDRO-6,7-DIMETHOXY-2-METHYL-, (1R,2R,1'R,2'R)-5-(3-((1R,2R)-1-((3,4-dimethoxyphenyl)methyl)-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-2-ium-2-yl)propanoyloxy)pentyl 3-((1R,2R)-1-((3,4-dimethoxyphenyl)methyl)-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-2-ium-2-yl)propanoate
Weitere Namen anzeigen
RefChem:56878DTXCID90820714Isoquinolinium, 2,2'-[1,5-pentanediylbis[oxy(3-oxo-3,1-propanediyl)]]bis[1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-, (1R,1'R,2R,2'R)-UNII-QX62KLI41NAtracurium Impurity 20SKE79AOA7LCISATRACURIUM [VANDF]CISATRACURIUM [WHO-DD]

Eigenschaften

Berechnete Struktureigenschaften

XLogP
7,9
Polarare Oberfläche (TPSA)
126 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
12
Frei drehbare Bindungen
26
Schwere Atome
67
Formalladung
2
Komplexität
1.390

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
Human DrugsBreast Feeding; Lactation; Milk, Human; Muscle Relaxants; Neuromuscular Nondepolarizing Agents

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

Toxikologische Informationen

Adverse EffectsAdverse effects are uncommon with the use of cisatracurium. Adverse reactions occurred at a rate of less than 1% and included bradycardia, hypotension, bronchospasm, rash, anaphylaxis, prolonged neuromuscular blockade, and myopathy.
Toxicity Summary · 1 Eintrag

Overdose with cisatracurium may result in neuromuscular blockade beyond the time needed for surgery and anesthesia. The primary treatment is maintaining sedation, a patent airway, and controlled ventilation until recovery of neuromuscular function is assured. There should be no attempt at reversal if there is evidence or suspicion of complete neuromuscular blockade.

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

M03AC11

M - Musculo-skeletal system

Protein BindingThe binding of cisatracurium to plasma proteins has not been successfully studied due to its rapid degradation at physiologic pH.
Pharmacodynamics · 1 Eintrag

The dose required to produce 95% suppression of twitch response to nerve stimulation (ED<sub>95</sub>) of cisatracurium is 0.05 mg/kg in adults receiving opioid/nitrous oxide/oxygen anesthesia. The degree and duration of the neuromuscular block produced by cisatracurium increases in a dose-dependent manner, while the time to maximum neuromuscular block decreases. Compared to other neuromuscular blocking agents, it is intermediate in its onset and duration of action. Cisatracurium acts on cholinergic receptors, blocking neuromuscular transmission. This action is antagonized by acetylcholinesterase inhibitors such as neostigmine. The use of cisatracurium may lead to residual paralysis, as well as a higher risk of seizure. Medication errors increase the risk of death, and the use of certain drugs may potentiate the neuromuscular blocking action of cisatracurium.

Mechanism of Action · 1 Eintrag

Like other non-depolarising neuromuscular blocking agents, cisatracurium binds competitively to cholinergic receptors in motor end-plate neurons, blocking acetylcholine from accessing the receptors. Therefore, in the presence of cisatracurium, an end-plate potential cannot be developed. Ion channels remain closed, the cell does not depolarize, and an action potential is not transmitted.

Biological Half-LifeCisatracurium has an elimination half-life of 22 minutes.
Metabolism/Metabolites · 1 Eintrag

The degradation of cisatracurium is largely independent of liver metabolism. Cisatracurium undergoes Hofmann elimination (a pH and temperature-dependent chemical process) to form laudanosine and the monoquaternary acrylate metabolite. Non-specific plasma esterases hydrolyze the monoquaternary acrylate metabolite to form the monoquaternary alcohol metabolite (MQA). The MQA can also undergo Hofmann elimination, but the rate of this process is slower than the one detected for cisatracurium. Laudanosine is further metabolized to desmethyl metabolites that are conjugated with glucuronic acid and excreted in the urine. Laudanosine may cause transient hypotension and, in higher doses, cerebral excitatory effects when administered to several animal species; however, the effects of laudanosine in humans have not been established.

Zugehörige Reaktionen

0
Reaktionsaufzeichnung erstellen

Keine Reaktionsaufzeichnungen unter den aktuellen Filterkriterien.

Notizen zur Verbindung

Wird geladen…

Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung

Datenbank-Bezeichner

CAS
96946-41-7
PubChem CID
62887
DTXSID
DTXSID60873212
ChEMBL
CHEMBL1201248
ChEBI
CHEBI:140621
UNII
QX62KLI41N、SKE79AOA7L
Nikkaji
J690.205G
FDA Pharmacological Classification · 5 Einträge

QX62KLI41N

CISATRACURIUM

Physiologic Effects [PE] - Neuromuscular Nondepolarizing Blockade

Established Pharmacologic Class [EPC] - Nondepolarizing Neuromuscular Blocker

Cisatracurium is a Nondepolarizing Neuromuscular Blocker. The physiologic effect of cisatracurium is by means of Neuromuscular Nondepolarizing Blockade.

MeSH Pharmacological Classification · 1 Eintrag

Drugs that interrupt transmission of nerve impulses at the skeletal neuromuscular junction. They can be of two types, competitive, stabilizing blockers (NEUROMUSCULAR NONDEPOLARIZING AGENTS) or noncompetitive, depolarizing agents (NEUROMUSCULAR DEPOLARIZING AGENTS). Both prevent acetylcholine from triggering the muscle contraction and they are used as anesthesia adjuvants, as relaxants during electroshock, in convulsive states, etc.

Absorption, Distribution and Excretion · 4 Einträge

The pharmacokinetics of cisatracurium follow a two-compartment open model. Cisatracurium is metabolized into laudanosine and monoquaternary alcohol metabolite (MQA). Following the IV infusion of cisatracurium, the Cmax of laudanosine and MQA were 6% and 11% of the parent compound, respectively. Compared to young patients, the volume of distribution of cisatracurium is slightly larger in elderly patients, which also leads to longer half-life values. The plasma clearance of cisatracurium was not affected by age. Patients with hepatic impairment have a slightly higher volume of distribution and plasma clearance values; however, these minor pharmacokinetic differences are not considered clinically significant. Additionally, the pharmacokinetic parameters of cisatracurium in patients with end-stage renal disease were similar to those detected in healthy adult patients.

The predominant elimination mechanism of cisatracurium is Hofmann elimination, a chemical process dependent on pH and temperature (approximately 80% in healthy surgical patients). The liver and kidney play a minor role in the elimination of cisatracurium (about 20%); however, they have a significant role in the metabolism of cisatracurium metabolites. In healthy male patients (n=6) given <sup>14</sup>C-cisatracurium, 4% of the recovered dose was found in feces, and 95% was found in urine, mostly as conjugated metabolites. Less than 10% of the cisatracurium dose was excreted as the unchanged patent drug. In another group of patients with Foley catheters for surgical management given non-radiolabeled cisatracurium (n=12), 15% of the cisatracurium dose was excreted unchanged in urine.

Cisatracurium has a volume of distribution at steady state of 145 mL/kg. The volume of distribution of cisatracurium besylate is small due to its relatively large molecular weight and high polarity.

Cisatracurium has a plasma clearance of 4.57 mL/min/kg.