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CHEBI:6149 - levobupivacaine
| Formula | C18H28N2O |
| Net Charge | 0 |
| Average Mass | 288.435 |
| Monoisotopic Mass | 288.22016 |
| SMILES | CCCCN1CCCC[C@H]1C(=O)Nc1c(C)cccc1C |
| 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 |
| 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 3.1.1.8 (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: | 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 (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 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 |
| INN | Source |
|---|---|
| levobupivacaine | ChemIDplus |
| Synonyms | Source |
|---|---|
| L-(-)-1-Butyl-2',6'-pipecoloxylidide | KEGG COMPOUND |
| Levobupivacaine | KEGG COMPOUND |
| (S)-1-butyl-2',6'-pipecoloxylidide | ChemIDplus |
| L-(−)-bupivacaine | ChemIDplus |
| (−)-bupivacaine | ChEBI |
| (S)-bupivacaine | ChEBI |
| Manual Xrefs | Databases |
|---|---|
| C07887 | KEGG COMPOUND |
| D08116 | KEGG DRUG |
| DB01002 | DrugBank |
| Levobupivacaine | Wikipedia |
| HMDB0015137 | HMDB |
| 4 | DrugCentral |
| Registry Numbers | Sources |
|---|---|
| Reaxys:5382240 | Reaxys |
| CAS:27262-47-1 | KEGG COMPOUND |
| CAS:27262-47-1 | ChemIDplus |