CHEBI:6149 - levobupivacaine

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ChEBI Name levobupivacaine
ChEBI ID CHEBI:6149
Definition The (S)-(−)-enantiomer of bupivacaine.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C18H28N2O
Net Charge 0
Average Mass 288.42770
Monoisotopic Mass 288.22016
InChI InChI=1S/C18H28N2O/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)/t16-/m0/s1
InChIKey LEBVLXFERQHONN-INIZCTEOSA-N
SMILES CCCCN1CCCC[C@H]1C(=O)Nc1c(C)cccc1C
Roles Classification
Chemical Role(s): amphiphile
A surfactant molecule possessing both hydrophilic and lipophilic properties.
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
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 levobupivacaine (CHEBI:6149) has role adrenergic antagonist (CHEBI:37887)
levobupivacaine (CHEBI:6149) has role amphiphile (CHEBI:59941)
levobupivacaine (CHEBI:6149) has role EC 3.1.1.8 (cholinesterase) inhibitor (CHEBI:37733)
levobupivacaine (CHEBI:6149) has role EC 3.6.3.8 (Ca2+-transporting ATPase) inhibitor (CHEBI:60186)
levobupivacaine (CHEBI:6149) has role local anaesthetic (CHEBI:36333)
levobupivacaine (CHEBI:6149) is a 1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide (CHEBI:77431)
levobupivacaine (CHEBI:6149) is conjugate base of levobupivacaine(1+) (CHEBI:77458)
levobupivacaine (CHEBI:6149) is enantiomer of dextrobupivacaine (CHEBI:60790)
Incoming bupivacaine (CHEBI:3215) has part levobupivacaine (CHEBI:6149)
levobupivacaine(1+) (CHEBI:77458) is conjugate acid of levobupivacaine (CHEBI:6149)
dextrobupivacaine (CHEBI:60790) is enantiomer of levobupivacaine (CHEBI:6149)
IUPAC Name
(2S)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
INN Source
levobupivacaine ChemIDplus
Synonyms Sources
(−)-bupivacaine ChEBI
(S)-1-butyl-2',6'-pipecoloxylidide ChemIDplus
(S)-bupivacaine ChEBI
L-(−)-bupivacaine ChemIDplus
L-(-)-1-Butyl-2',6'-pipecoloxylidide KEGG COMPOUND
Levobupivacaine KEGG COMPOUND
Manual Xrefs Databases
4 DrugCentral
C07887 KEGG COMPOUND
D08116 KEGG DRUG
DB01002 DrugBank
HMDB0015137 HMDB
Levobupivacaine Wikipedia
View more database links
Registry Numbers Types Sources
27262-47-1 CAS Registry Number ChemIDplus
5382240 Reaxys Registry Number Reaxys
Last Modified
22 February 2017
General Comment
2010-12-10 An amide-type local anaesthetic, levobupivacaine has a longer duration of action and is associated with less vasodilation than racemic bupivacaine, but is approximately 13% less potent (by molarity). It is commonly used as the hydrochloride salt.