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CHEBI:77453 - levobupivacaine hydrochloride hydrate

Default Structure
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:
adrenergic antagonist  An agent that binds to but does not activate adrenergic receptors thereby blocking the actions of endogenous or exogenous adrenergic agonists.
EC 3.6.3.8 (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).
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).
Applications:
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 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-2-[(2,6-dimethylphenyl)carbamoyl]piperidinium chloride—water (1/1)
(2S)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide hydrochloride—water (1/1)
Synonyms  Source
(S)-1-butyl-2',6'-pipecoloxylidide hydrochloride hydrateChEBI
levobupivacaine.HCl.H2OChEBI
levobupivacaine monohydrochloride monohydrateChEBI