CHEBI:3215 - bupivacaine

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ChEBI Name bupivacaine
ChEBI ID CHEBI:3215
Definition A racemate composed of equimolar amounts of dextrobupivacaine and levobupivacaine. Used (in the form of its hydrochloride hydrate) as a local anaesthetic.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:250882
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Formula C18H28N2O
Net Charge 0
Average Mass 288.42770
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): adrenergic antagonist
An agent that binds to but does not activate adrenergic receptors thereby blocking the actions of endogenous or exogenous adrenergic agonists.
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.
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ChEBI Ontology
Outgoing bupivacaine (CHEBI:3215) has part dextrobupivacaine (CHEBI:60790)
bupivacaine (CHEBI:3215) has part levobupivacaine (CHEBI:6149)
bupivacaine (CHEBI:3215) has role adrenergic antagonist (CHEBI:37887)
bupivacaine (CHEBI:3215) has role amphiphile (CHEBI:59941)
bupivacaine (CHEBI:3215) has role EC 3.1.1.8 (cholinesterase) inhibitor (CHEBI:37733)
bupivacaine (CHEBI:3215) has role EC 3.6.3.8 (Ca2+-transporting ATPase) inhibitor (CHEBI:60186)
bupivacaine (CHEBI:3215) has role local anaesthetic (CHEBI:36333)
bupivacaine (CHEBI:3215) is a racemate (CHEBI:60911)
bupivacaine (CHEBI:3215) is conjugate base of bupivacaine(1+) (CHEBI:77455)
Incoming bupivacaine(1+) (CHEBI:77455) is conjugate acid of bupivacaine (CHEBI:3215)
IUPAC Name
rac-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
INNs Sources
bupivacaina ChemIDplus
bupivacaine ChemIDplus
bupivacainum ChemIDplus
Synonyms Sources
(±)-bupivacaine ChEBI
(+-)-Bupivacaine ChemIDplus
(RS)-bupivacaine ChEBI
1-Butyl-2',6'-pipecoloxylidide ChemIDplus
1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide NIST Chemistry WebBook
Bupivacaine KEGG COMPOUND
Carbostesin NIST Chemistry WebBook
dl-1-Butyl-2',6'-pipecoloxylidide ChemIDplus
DL-Bupivacaine ChemIDplus
racemic bupivacaine ChEBI
Database Links Databases
Bupivacaine Wikipedia
C07529 KEGG COMPOUND
D07552 KEGG DRUG
DB00297 DrugBank
HMDB0014442 HMDB
US2955111 Patent
View more database links
Registry Numbers Types Sources
2180-92-9 CAS Registry Number NIST Chemistry WebBook
280794 Reaxys Registry Number Reaxys
38396-39-3 CAS Registry Number KEGG COMPOUND
38396-39-3 CAS Registry Number ChemIDplus
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Last Modified
22 February 2017
General Comment
2010-12-13 Commonly used as the hydrochloride monohydrate, bupivacaine has a slow onset and long duration of action. The (S)-(−)-isomer, levobupivacaine, is also used.