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CHEBI:3215 - bupivacaine
| ChEBI ID | CHEBI:3215 |
| ChEBI Name | bupivacaine |
| Stars | |
| Definition | A racemate composed of equimolar amounts of dextrobupivacaine and levobupivacaine. Used (in the form of its hydrochloride hydrate) as a local anaesthetic. |
| Secondary ChEBI ID | CHEBI:250882 |
| Last Modified | 29 September 2025 |
| Formula | C18H28N2O |
| Net Charge | 0 |
| Average Mass | 288.435 |
| Monoisotopic Mass | 288.22016 |
| Wikipedia |
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| Roles Classification |
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| Chemical Role: | amphiphile A surfactant molecule possessing both hydrophilic and lipophilic properties. |
| Biological Roles: | drug allergen Any drug which causes the onset of an allergic reaction. 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: | drug allergen Any drug which causes the onset of an allergic reaction. 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 |
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| Outgoing Relation(s) |
| bupivacaine (CHEBI:3215) has part dextrobupivacaine (CHEBI:60790) |
| bupivacaine (CHEBI:3215) has part levobupivacaine (CHEBI:6149) |
| bupivacaine (CHEBI:3215) has role adrenergic antagonist (CHEBI:37887) |
| bupivacaine (CHEBI:3215) has role amphiphile (CHEBI:59941) |
| bupivacaine (CHEBI:3215) has role drug allergen (CHEBI:88188) |
| bupivacaine (CHEBI:3215) has role EC 3.1.1.8 (cholinesterase) inhibitor (CHEBI:37733) |
| bupivacaine (CHEBI:3215) has role EC 3.6.3.8 (Ca2+-transporting ATPase) inhibitor (CHEBI:60186) |
| bupivacaine (CHEBI:3215) has role local anaesthetic (CHEBI:36333) |
| bupivacaine (CHEBI:3215) is a racemate (CHEBI:60911) |
| bupivacaine (CHEBI:3215) is conjugate base of bupivacaine(1+) (CHEBI:77455) |
| Incoming Relation(s) |
| bupivacaine(1+) (CHEBI:77455) is conjugate acid of bupivacaine (CHEBI:3215) |
| IUPAC Name |
|---|
| rac-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide |
| INNs | Source |
|---|---|
| bupivacaina | ChemIDplus |
| bupivacainum | ChemIDplus |
| bupivacaine | ChemIDplus |
| Synonyms | Source |
|---|---|
| Bupivacaine | KEGG COMPOUND |
| 1-Butyl-2',6'-pipecoloxylidide | ChemIDplus |
| DL-Bupivacaine | ChemIDplus |
| dl-1-Butyl-2',6'-pipecoloxylidide | ChemIDplus |
| (+-)-Bupivacaine | ChemIDplus |
| Carbostesin | NIST Chemistry WebBook |
| Manual Xrefs | Databases |
|---|---|
| C07529 | KEGG COMPOUND |
| D07552 | KEGG DRUG |
| DB00297 | DrugBank |
| US2955111 | Patent |
| Bupivacaine | Wikipedia |
| HMDB0014442 | HMDB |
| Registry Numbers | Sources |
|---|---|
| Reaxys:280794 | Reaxys |
| CAS:38396-39-3 | KEGG COMPOUND |
| CAS:38396-39-3 | NIST Chemistry WebBook |
| CAS:38396-39-3 | ChemIDplus |
| Citations |
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