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CHEBI:77453 - levobupivacaine hydrochloride hydrate

ChEBI IDCHEBI:77453
ChEBI Namelevobupivacaine hydrochloride hydrate
Stars
DefinitionThe monohydrate form of levobupivacaine hydrochloride. A piperidinecarboxamide-based local anaesthetic, it has a slow onset and long duration of action.
Last Modified24 February 2014
SubmitterSteve
DownloadsMolfile
FormulaC18H28N2O.H2O.HCl
Net Charge0
Average Mass342.911
Monoisotopic Mass342.20741
SMILESCCCCN1CCCC[C@H]1C(=O)Nc1c(C)cccc1C.Cl.O
InChIInChI=1S/C18H28N2O.ClH.H2O/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;1H2/t16-;;/m0../s1
InChIKeyHUCIWBPMHXGLFM-SQKCAUCHSA-N
Roles Classification
Chemical Role:
amphiphile  A surfactant molecule possessing both hydrophilic and lipophilic properties.
Biological Roles:
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).
adrenergic antagonist  An agent that binds to but does not activate adrenergic receptors thereby blocking the actions of endogenous or exogenous adrenergic agonists.
Applications:
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 Relation(s)
levobupivacaine hydrochloride hydrate (CHEBI:77453) has part levobupivacaine hydrochloride (anhydrous) (CHEBI:31772)
levobupivacaine hydrochloride hydrate (CHEBI:77453) has role adrenergic antagonist (CHEBI:37887)
levobupivacaine hydrochloride hydrate (CHEBI:77453) has role amphiphile (CHEBI:59941)
levobupivacaine hydrochloride hydrate (CHEBI:77453) has role EC 3.1.1.8 (cholinesterase) inhibitor (CHEBI:37733)
levobupivacaine hydrochloride hydrate (CHEBI:77453) has role EC 3.6.3.8 (Ca2+-transporting ATPase) inhibitor (CHEBI:60186)
levobupivacaine hydrochloride hydrate (CHEBI:77453) has role local anaesthetic (CHEBI:36333)
levobupivacaine hydrochloride hydrate (CHEBI:77453) is a 1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide hydrochloride hydrate (CHEBI:77449)
levobupivacaine hydrochloride hydrate (CHEBI:77453) is enantiomer of dextrobupivacaine hydrochloride hydrate (CHEBI:77454)
Incoming Relation(s)
bupivacaine hydrochloride hydrate (CHEBI:60789) has part levobupivacaine hydrochloride hydrate (CHEBI:77453)
dextrobupivacaine hydrochloride hydrate (CHEBI:77454) is enantiomer of levobupivacaine hydrochloride hydrate (CHEBI:77453)
IUPAC Names 
(2S)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide hydrochloride—water (1/1)
(2S)-1-butyl-2-[(2,6-dimethylphenyl)carbamoyl]piperidinium chloride—water (1/1)
Synonyms  Source
levobupivacaine monohydrochloride monohydrateChEBI
levobupivacaine.HCl.H2OChEBI
(S)-1-butyl-2',6'-pipecoloxylidide hydrochloride hydrateChEBI