levobupivacaine hydrochloride (anhydrous) (CHEBI:31772)

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ChEBI Name	levobupivacaine hydrochloride (anhydrous)

ChEBI ID	CHEBI:31772

Definition	The monohydrochloride salt of levobupivacaine.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

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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/t16-;/m0./s1

InChIKey

SIEYLFHKZGLBNX-NTISSMGPSA-N

SMILES

Cl.CCCCN1CCCC[C@H]1C(=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.

ChEBI Ontology
Outgoing	levobupivacaine hydrochloride (anhydrous) (CHEBI:31772) has part levobupivacaine(1+) (CHEBI:77458) levobupivacaine hydrochloride (anhydrous) (CHEBI:31772) has role adrenergic antagonist (CHEBI:37887) levobupivacaine hydrochloride (anhydrous) (CHEBI:31772) has role amphiphile (CHEBI:59941) levobupivacaine hydrochloride (anhydrous) (CHEBI:31772) has role EC 3.1.1.8 (cholinesterase) inhibitor (CHEBI:37733) levobupivacaine hydrochloride (anhydrous) (CHEBI:31772) has role EC 3.6.3.8 (Ca²⁺-transporting ATPase) inhibitor (CHEBI:60186) levobupivacaine hydrochloride (anhydrous) (CHEBI:31772) has role local anaesthetic (CHEBI:36333) levobupivacaine hydrochloride (anhydrous) (CHEBI:31772) is a 1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide hydrochloride (CHEBI:77441) levobupivacaine hydrochloride (anhydrous) (CHEBI:31772) is enantiomer of dextrobupivacaine hydrochloride (anhydrous) (CHEBI:77442)

Incoming	bupivacaine hydrochloride (anhydrous) (CHEBI:31322) has part levobupivacaine hydrochloride (anhydrous) (CHEBI:31772) levobupivacaine hydrochloride hydrate (CHEBI:77453) has part levobupivacaine hydrochloride (anhydrous) (CHEBI:31772) dextrobupivacaine hydrochloride (anhydrous) (CHEBI:77442) is enantiomer of levobupivacaine hydrochloride (anhydrous) (CHEBI:31772)

IUPAC Names

(2S)-1-butyl-2-[(2,6-dimethylphenyl)carbamoyl]piperidinium chloride

(2S)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide hydrochloride

Synonyms	Sources
(−)-bupivacaine hydrochloride	ChEBI
(S)-1-butyl-2',6'-pipecoloxylidide hydrochloride	ChEBI
(S)-1-butyl-2',6'-pipecoloxylidide monohydrochloride	COMe
levobupivacaine HCl	ChemIDplus
levobupivacaine hydrochloride	ChEBI
levobupivacaine monohydrochloride	ChEBI

Brand Name	Source
Chirocaine	ChEBI

Last Modified

24 February 2014

General Comment
2010-12-10	An amide-type local anaesthetic, levobupivacaine hydrochloride has a longer duration of action and is associated with less vasodilation than racemic bupivacaine, but is approximately 13% less potent (by molarity).