基本情報
- CAS
50700-72-6- 標準SMILES
CC(=O)O[C@H]1C[C@@H]2CC[C@@H]3[C@H](CC[C@@]4(C)[C@H]3C[C@H]([N+]3(C)CCCCC3)[C@@H]4OC(C)=O)[C@@]2(C)C[C@@H]1N1CCCCC1- InChIKey
BGSZAXLLHYERSY-XQIGCQGXSA-N- 分子式
- C34H57N2O4+
- 平均分子量
- 557.8 g/mol
- 単同位体質量
- 557.4318333
概要
Vecuronium is a 5alpha-androstane compound having 3alpha-acetoxy-, 17beta-acetoxy-, 2beta-piperidino- and 16beta-N-methylpiperidinium substituents. It has a role as a nicotinic antagonist, a muscle relaxant, a neuromuscular agent and a drug allergen. It is a quaternary ammonium ion, an androstane and an acetate ester. It derives from a hydride of a 5alpha-androstane.
名称と識別子
- 優先名称
- Vecuronium
- IUPAC
- [(2S,3S,5S,8R,9S,10S,13S,14S,16S,17R)-17-acetyloxy-10,13-dimethyl-16-(1-methylpiperidin-1-ium-1-yl)-2-piperidin-1-yl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
- 現地名
- 1-[3α,17β-ビス(アセチルオキシ)-2β-(1-ピペリジニル)-5α-アンドロスタン-16β-イル]-1-メチルピペリジニウム
- 英語名
- Androstane, piperidinium deriv.
- 分子式
- C34H57N2O4+
- 分子量
- 557.82738
名称と別名
Vecuronium86029-43-8Vecuronium cationVecuronium ionCHEBI:9939[(2S,3S,5S,8R,9S,10S,13S,14S,16S,17R)-17-acetyloxy-10,13-dimethyl-16-(1-methylpiperidin-1-ium-1-yl)-2-piperidin-1-yl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetatePiperidinium, 1-((2beta,3alpha,5alpha,16beta,17beta)-3,17-bis(acetyloxy)-2-(1-piperidinyl)androstan-16-yl)-1-methyl-DTXSID10441461-[(1S,2S,4S,5S,7S,10R,11S,13S,14R,15S)-5,14-bis(acetyloxy)-2,15-dimethyl-4-(piperidin-1-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-13-yl]-1-methylpiperidin-1-iumPiperidinium, 1-[(2beta,3alpha,5alpha,16beta,17beta)-3,17-bis(acetyloxy)-2-(1-piperidinyl)androstan-16-yl]-1-methyl-((2S,3S,5S,8R,9S,10S,13S,14S,16S,17R)-17-acetyloxy-10,13-dimethyl-16-(1-methylpiperidin-1-ium-1-yl)-2-piperidin-1-yl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta(a)phenanthren-3-yl) acetate1-((1S,2S,4S,5S,7S,10R,11S,13S,14R,15S)-5,14-bis(acetyloxy)-2,15-dimethyl-4-(piperidin-1-yl)tetracyclo(8.7.0.0^(2,7).0^(11,15))heptadecan-13-yl)-1-methylpiperidin-1-ium
物性
構造計算による物性
- XLogP
- 6.5
- 極性表面積
- 55.8 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 5
- 回転可能結合数
- 6
- 重原子数
- 40
- 形式電荷
- 1
- 複雑度
- 958
実験および物理化学的性質
DrugsPharmaceuticals -> Listed in ZINC15
Solubility1.86e-05 g/L
Human Drugs
Breast Feeding; Lactation; Muscle Relaxants; Neuromuscular Nondepolarizing Agents
Muscle relaxants (peripherally-acting) and cholinesterase inhibitors
Physical DescriptionSolid
Collision Cross Section246.83 Ų [M]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
毒性情報
Adverse Effects
The primary adverse event associated with all nondepolarizing neuromuscular agents is the extension of the drug's pharmacological effect past the needed time of use, resulting in adverse effects ranging from skeletal muscle weakness to extended muscular paralysis leading to respiratory insufficiency or apnea.
Toxicity Summary
The risk of iatrogenic overdosage can be reduced by closely monitoring muscle twitch responses using peripheral nerve stimulation. Anticholinesterases antagonize neuromuscular blockade action; therefore, acetylcholinesterase inhibitors such as neostigmine are useful to reverse rocuronium and vecuronium's effect on muscle paralysis.
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
vecuronium
DILI Negative
Intravenous
DOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
化学と産業
薬理情報
ATC Code
M - Musculo-skeletal system
QM - Musculo-skeletal system
M03AC03
Pharmacodynamics
The principal pharmacologic effects demonstrated by vecuronium revolve around its competitive binding of cholinergic receptors located at motor end plates. This competitive binding results in muscle relaxant effects that are typically employed as an adjunct to general anesthesia.
Mechanism of Action
Vecuronium is a bisquaternary nitrogen compound that acts by competitively binding to nicotinic cholinergic receptors. The binding of vecuronium decreases the opportunity for acetylcholine to bind to the nicotinic receptor at the postjunctional membrane of the myoneural junction. As a result, depolarization is prevented, calcium ions are not released and muscle contraction does not occur.
Biological Half-Life51–80 minutes
Metabolism/Metabolites100%
FDA Pharmacological Classification
5438723848
VECURONIUM
Physiologic Effects [PE] - Neuromuscular Nondepolarizing Blockade
Established Pharmacologic Class [EPC] - Nondepolarizing Neuromuscular Blocker
Vecuronium is a Nondepolarizing Neuromuscular Blocker. The physiologic effect of vecuronium is by means of Neuromuscular Nondepolarizing Blockade.
MeSH Pharmacological Classification
Drugs that interrupt transmission at the skeletal neuromuscular junction without causing depolarization of the motor end plate. They prevent acetylcholine from triggering muscle contraction and are used as muscle relaxants during electroshock treatments, in convulsive states, and as anesthesia adjuvants.
Drugs that bind to nicotinic cholinergic receptors (RECEPTORS, NICOTINIC) and block the actions of acetylcholine or cholinergic agonists. Nicotinic antagonists block synaptic transmission at autonomic ganglia, the skeletal neuromuscular junction, and at central nervous system nicotinic synapses.
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