Basic information
- CAS
50700-72-6- Standard 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- Molecular formula
- C34H57N2O4+
- Average molar mass
- 557.8 g/mol
- Monoisotopic mass
- 557.4318333
Overview
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.
Names & identifiers
- Preferred name
- 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
- English name
- Androstane, piperidinium deriv.
- Molecular formula
- C34H57N2O4+
- Molecular weight
- 557.82738
Names & synonyms
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
Properties
Computed structural properties
- XLogP
- 6.5
- Topological polar surface area
- 55.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 6
- Heavy atoms
- 40
- Formal charge
- 1
- Complexity
- 958
Experimental & physicochemical properties
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]
Physicochemical properties
- FDA UNII
- 5438723848 · 5438723848
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
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
Chemistry & industry
Pharmacology
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.
Related reactions
0 records
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Compound notes
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