EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:6149 - levobupivacaine

Default Structure
ChEBI IDCHEBI:6149
ChEBI Namelevobupivacaine
Stars
DefinitionThe (S)-(−)-enantiomer of bupivacaine.
Last Modified22 February 2017
DownloadsMolfile
FormulaC18H28N2O
Net Charge0
Average Mass288.435
Monoisotopic Mass288.22016
SMILESCCCCN1CCCC[C@H]1C(=O)Nc1c(C)cccc1C
InChIInChI=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
InChIKeyLEBVLXFERQHONN-INIZCTEOSA-N
Wikipedia
Roles Classification
Chemical Roles:
amphiphile  A surfactant molecule possessing both hydrophilic and lipophilic properties.
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
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).
analgesic  An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
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).
adrenergic antagonist  An agent that binds to but does not activate adrenergic receptors thereby blocking the actions of endogenous or exogenous adrenergic agonists.
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.
analgesic  An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
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 (CHEBI:6149) has role adrenergic antagonist (CHEBI:37887)
levobupivacaine (CHEBI:6149) has role amphiphile (CHEBI:59941)
levobupivacaine (CHEBI:6149) has role analgesic (CHEBI:35480)
levobupivacaine (CHEBI:6149) has role antineoplastic agent (CHEBI:35610)
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 Relation(s)
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
INNs  Source
levobupivacainaWHO MedNet
levobupivacaineChemIDplus
Synonyms  Source
(−)-bupivacaineChEBI
Bupivacaine, (-)-ChEMBL
Bupivacaine (-)-formChEMBL
Bupivacaine, (s)-ChEMBL
(S)-1-butyl-2',6'-pipecoloxylidideChemIDplus
(S)-bupivacaineChEBI
Manual XrefsDatabases
4DrugCentral
C07887KEGG COMPOUND
D08116KEGG DRUG
DB01002DrugBank
HMDB0015137HMDB
LevobupivacaineWikipedia
Registry NumbersSources
Reaxys:5382240Reaxys
CAS:27262-47-1KEGG COMPOUND
CAS:27262-47-1ChemIDplus
Citations