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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: | 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). |
| 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 (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 |
|---|---|
| (−)-bupivacaine | ChEBI |
| (S)-1-butyl-2',6'-pipecoloxylidide | ChemIDplus |
| (S)-bupivacaine | ChEBI |
| L-(-)-1-Butyl-2',6'-pipecoloxylidide | KEGG COMPOUND |
| Levobupivacaine | KEGG COMPOUND |
| L-(−)-bupivacaine | ChemIDplus |
| Manual Xrefs | Databases |
|---|---|
| 4 | DrugCentral |
| C07887 | KEGG COMPOUND |
| D08116 | KEGG DRUG |
| DB01002 | DrugBank |
| HMDB0015137 | HMDB |
| Levobupivacaine | Wikipedia |
| Registry Numbers | Sources |
|---|---|
| Reaxys:5382240 | Reaxys |
| CAS:27262-47-1 | KEGG COMPOUND |
| CAS:27262-47-1 | ChemIDplus |