bupivacaine hydrochloride (anhydrous) (CHEBI:31322)

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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	ChemicalBook:CB3920826, ChemicalBook:CB1386202, eMolecules:535231, Selleckchem:Bupivacaine-hydrochloride(Marcain)

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Formula

C18H29ClN2O

Net Charge

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.

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

Citations

Last Modified

24 February 2014