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.[Br-]- InChIKey
VEPSYABRBFXYIB-PWXDFCLTSA-M- Molecular formula
- C34H57BrN2O4
- Average molar mass
- 637.7 g/mol
- Monoisotopic mass
- 636.35017
Overview
Vecuronium bromide is the organic bromide salt of a 5alpha-androstane compound having 3alpha-acetoxy-, 17beta-acetoxy-, 2beta-piperidinino- and 16beta-N-methylpiperidinium substituents. It has a role as a nicotinic antagonist, a muscle relaxant and a neuromuscular agent. It is a quaternary ammonium salt and an organic bromide salt. It contains a vecuronium. It is functionally related to a 5alpha-androstane.
Names & identifiers
- Preferred name
- Vecuronium Bromide
- 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 bromide
- English name
- Vecuronium bromide
- Molecular formula
- C34H57BrN2O4
- Molecular weight
- 637.73138
Names & synonyms
VECURONIUM BROMIDE50700-72-6NorcuronBromuro de vecuronioBromure de vecuroniumVecuronii bromidumORG NC 45MusculaxORG-NC 45Vecuronium HydrobromideVercuroniumDTXSID1023736
Show more names
vecuroniumVecuronim BromideVBMCorgnc45Muscuratemide,diacetateVECRONIUM BROMIDE
vecuronio bromuroNC-457E4PHP5N1DBromide, VecuroniumNSC-759184CHEBI:9940DTXCID003736Piperidinium, 1-((2beta,3alpha,5alpha,16beta,17beta)-3,17-bis(acetyloxy)-2-(1-piperidinyl)androstan-16-yl)-1-methyl-, bromide
Database identifiers
- CAS
50700-72-6- PubChem CID
- 39764
- DTXSID
DTXSID1023736- ChEMBL
CHEMBL1200629- ChEBI
CHEBI:9940
Properties
Computed structural properties
- Topological polar surface area
- 55.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 6
- Heavy atoms
- 41
- Formal charge
- 0
- Complexity
- 958
Experimental & physicochemical properties
Human Drugs
Breast Feeding; Lactation; Muscle Relaxants; Neuromuscular Nondepolarizing Agents
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Collision Cross Section248.4 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 227 · 227-229°C
- alpha
- 30.5 · +30.5~+35.0゜(D/20℃)(c=0.5,dil.HCl)
- storage temp.
- -20 °C · Inert atmosphere,Store in freezer, under -20°C
- solubility
- Slightly soluble in water, freely soluble in methylene chloride, sparingly soluble in acetonitrile and in anhydrous ethanol.
- form
- Solid
- color
- White
- biological source
- synthetic
- Merck
- 14 · 14,9941
- BRN
- 4837308 · 4837308
- Stability
- Hygroscopic
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H302 (98.4%): Harmful if swallowed [Warning Acute toxicity, oral]
P260, P264, P270, P271, P280, P284, P301+P317, P302+P352, P304+P340, P316, P317, P320, P321, P330, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 62 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (98.4%)
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Vecuronium bromide
vNo-DILI-concern
0
No match
DOI:10.1016/j.drudis.2016.02.015
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 3
- rtecs
- TN4875000
- hs_code
- 2933399090
- Toxicity
- LD50 in mice: 0.061 mg/kg i.v. (Buckett)
- risk_code
- 36/37/38-22
- Signal word
- Warning
Chemistry & industry
Pharmacology
FDA Pharmacological Classification
VECURONIUM BROMIDE
Neuromuscular Nondepolarizing Blockade [PE]; Nondepolarizing Neuromuscular Blocker [EPC]
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.
Applications
DescriptionVecuronium bromide (Brand name: Norcuron) is a drug which can be supplied to general anesthesia to keep skeletal muscle relaxation during the surgery or mechanical ventilation. It can also be used to help with endotracheal intubation. It has rapid onset (within 4 minutes) and has its effect last for 4 hour. Its mechanism of action is through competitively binding to the nicotinic cholinergic receptors, further antagonizing the opportunity for acetylcholine from binding to the nicotinic receptor at the postjunctional membrane of the myoneural junction. This process prevents the depolarization and the release of calcium ions, stopping muscle contraction and help muscle relaxation.
DescriptionVecuronium, 1-[(2β,3α,5α,16β,17β,)-3,17-bis(acetyloxy)-2-(1-piperidinyl) androstan-16-yl]-1-methylpiperidinium bromide (15.1.9), differs from panuronium only in the extent of alkylation. Only the piperidine substituent on C16 of the steroid skeleton is transformed into a quaternary salt.
DescriptionVecuronium is a non-depolarizing muscle relaxant derived from the aminosteroid pancuronium and used adjunctively to general anesthesia. It competitively blocks cholinergic receptors at the motor end plate of the neuromuscular junction, inducing temporary paralysis. In humans, it has been shown to reduce muscle twitch tension with an ED50 value of 0.15 mg/kg for a duration of 27 minutes without inducing cardiovascular effects.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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