CHEBI:60789 - bupivacaine hydrochloride hydrate

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ChEBI Name bupivacaine hydrochloride hydrate
ChEBI ID CHEBI:60789
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C18H31ClN2O2
Net Charge 0
Average Mass 342.90400
Monoisotopic Mass 342.207
InChI InChI=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
InChIKey HUCIWBPMHXGLFM-UHFFFAOYSA-N
SMILES O.Cl.CCCCN1CCCCC1C(=O)Nc1c(C)cccc1C
Roles Classification
Chemical Role(s): amphiphile
A surfactant molecule possessing both hydrophilic and lipophilic properties.
Biological Role(s): 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).
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).
Application(s): 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.
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ChEBI Ontology
Outgoing 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 Sources
(+/-)-1-Butyl-2',6'-pipecoloxylidide monohydrochloride, monohydrate ChemIDplus
1-butyl-2',6'-pipecoloxylidide monohydrochloride monohydrate ChEBI
1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide hydrochloride hydrate ChEBI
bupivacaine hydrochloride ChemIDplus
bupivacaine hydrochloride monohydrate ChEBI
bupivacaine monohydrochloride monohydrate ChEBI
Brand Name Source
Marcaine KEGG DRUG
Manual Xrefs Databases
D01450 KEGG DRUG
DB00297 DrugBank
View more database links
Registry Numbers Types Sources
13856665 Reaxys Registry Number Reaxys
73360-54-0 CAS Registry Number ChemIDplus
Last Modified
24 February 2014