CHEBI:31322 - bupivacaine hydrochloride (anhydrous)

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ChEBI Name bupivacaine hydrochloride (anhydrous)
ChEBI ID CHEBI:31322
Definition A racemate composed of equimolar amounts of dextrobupivacaine hydrochloride and levobupivacaine hydrochloride. The monohydrate form is commonly used as a local anaesthetic.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C18H29ClN2O
Net Charge 0
Average Mass 324.88900
Monoisotopic Mass 324.19684
InChI InChI=1S/C18H28N2O.ClH/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
InChIKey SIEYLFHKZGLBNX-UHFFFAOYSA-N
SMILES 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): 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 hydrochloride (anhydrous) (CHEBI:31322) has part bupivacaine(1+) (CHEBI:77455)
bupivacaine hydrochloride (anhydrous) (CHEBI:31322) has part dextrobupivacaine hydrochloride (anhydrous) (CHEBI:77442)
bupivacaine hydrochloride (anhydrous) (CHEBI:31322) has part levobupivacaine hydrochloride (anhydrous) (CHEBI:31772)
bupivacaine hydrochloride (anhydrous) (CHEBI:31322) has role adrenergic antagonist (CHEBI:37887)
bupivacaine hydrochloride (anhydrous) (CHEBI:31322) has role amphiphile (CHEBI:59941)
bupivacaine hydrochloride (anhydrous) (CHEBI:31322) has role EC 3.1.1.8 (cholinesterase) inhibitor (CHEBI:37733)
bupivacaine hydrochloride (anhydrous) (CHEBI:31322) has role EC 3.6.3.8 (Ca2+-transporting ATPase) inhibitor (CHEBI:60186)
bupivacaine hydrochloride (anhydrous) (CHEBI:31322) has role local anaesthetic (CHEBI:36333)
bupivacaine hydrochloride (anhydrous) (CHEBI:31322) is a racemate (CHEBI:60911)
Incoming bupivacaine hydrochloride hydrate (CHEBI:60789) has part bupivacaine hydrochloride (anhydrous) (CHEBI:31322)
IUPAC Names
rac-1-butyl-2-[(2,6-dimethylphenyl)carbamoyl]piperidinium chloride
rac-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide hydrochloride
Synonyms Sources
1-butyl-2-piperidylformo-2',6'-xylidide hydrochloride ChEBI
1-butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide monohydrochloride ChemIDplus
bupivacaine HCl ChemIDplus
bupivacaine hydrochloride ChemIDplus
bupivacaine monohydrochloride ChEBI
Registry Numbers Types Sources
18010-40-7 CAS Registry Number ChemIDplus
4048737 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
22285545 PubMed citation Europe PMC
22374474 PubMed citation Europe PMC
22900785 PubMed citation Europe PMC
23229686 PubMed citation Europe PMC
23446090 PubMed citation Europe PMC
23453403 PubMed citation Europe PMC
23458225 PubMed citation Europe PMC
23487596 PubMed citation Europe PMC
7069125 PubMed citation Europe PMC
Last Modified
24 February 2014