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CHEBI:60789 - bupivacaine hydrochloride hydrate

Default Structure
ChEBI IDCHEBI:60789
ChEBI Namebupivacaine hydrochloride hydrate
Stars
DefinitionA racemate composed of equimolar amounts of dextrobupivacaine hydrochloride hydrate and levobupivacaine hydrochloride hydrate. A piperidinecarboxamide-based local anaesthetic, it has a slow onset and long duration of action.
Last Modified24 February 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC18H28N2O.H2O.HCl
Net Charge0
Average Mass342.911
Monoisotopic Mass342.20741
SMILESCCCCN1CCCCC1C(=O)Nc1c(C)cccc1C.Cl.O
InChIInChI=1S/C18H28N2O.ClH.H2O/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3;;/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21);1H;1H2
InChIKeyHUCIWBPMHXGLFM-UHFFFAOYSA-N
Roles Classification
Chemical Role:
amphiphile  A surfactant molecule possessing both hydrophilic and lipophilic properties.
Biological Roles:
EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor  An EC 3.6.3.* (acid anhydride hydrolase catalysing transmembrane movement of substances) inhibitor that interferes with the action of Ca2+-transporting ATPase (EC 3.6.3.8).
adrenergic antagonist  An agent that binds to but does not activate adrenergic receptors thereby blocking the actions of endogenous or exogenous adrenergic agonists.
EC 3.1.1.8 (cholinesterase) inhibitor  An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of cholinesterase (EC 3.1.1.8).
Applications:
local anaesthetic  Any member of a group of drugs that reversibly inhibit the propagation of signals along nerves. Wide variations in potency, stability, toxicity, water-solubility and duration of action determine the route used for administration, e.g. topical, intravenous, epidural or spinal block.
adrenergic antagonist  An agent that binds to but does not activate adrenergic receptors thereby blocking the actions of endogenous or exogenous adrenergic agonists.
ChEBI Ontology
Outgoing Relation(s)
bupivacaine hydrochloride hydrate (CHEBI:60789) has part bupivacaine hydrochloride (anhydrous) (CHEBI:31322)
bupivacaine hydrochloride hydrate (CHEBI:60789) has part dextrobupivacaine hydrochloride hydrate (CHEBI:77454)
bupivacaine hydrochloride hydrate (CHEBI:60789) has part levobupivacaine hydrochloride hydrate (CHEBI:77453)
bupivacaine hydrochloride hydrate (CHEBI:60789) has role adrenergic antagonist (CHEBI:37887)
bupivacaine hydrochloride hydrate (CHEBI:60789) has role amphiphile (CHEBI:59941)
bupivacaine hydrochloride hydrate (CHEBI:60789) has role EC 3.1.1.8 (cholinesterase) inhibitor (CHEBI:37733)
bupivacaine hydrochloride hydrate (CHEBI:60789) has role EC 3.6.3.8 (Ca2+-transporting ATPase) inhibitor (CHEBI:60186)
bupivacaine hydrochloride hydrate (CHEBI:60789) has role local anaesthetic (CHEBI:36333)
bupivacaine hydrochloride hydrate (CHEBI:60789) is a racemate (CHEBI:60911)
IUPAC Names 
rac-1-butyl-2-[(2,6-dimethylphenyl)carbamoyl]piperidinium chloride—water (1/1)
rac-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide hydrochloride—water (1/1)
Synonyms  Source
1-butyl-2',6'-pipecoloxylidide monohydrochloride monohydrateChEBI
(+/-)-1-Butyl-2',6'-pipecoloxylidide monohydrochloride, monohydrateChemIDplus
1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide hydrochloride hydrateChEBI
bupivacaine hydrochlorideChemIDplus
bupivacaine hydrochloride monohydrateChEBI
bupivacaine monohydrochloride monohydrateChEBI
Brand Name  Source
MarcaineKEGG DRUG
Manual XrefsDatabases
D01450KEGG DRUG
DB00297DrugBank
Registry NumbersSources
Reaxys:13856665Reaxys
CAS:73360-54-0ChemIDplus