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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: | 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). anti-HIV agent An antiviral agent that destroys or inhibits the replication of the human immunodeficiency virus. 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 3.6.3.8 (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). anti-obesity agent Any substance which is used to reduce or control weight. drug allergen Any drug which causes the onset of an allergic reaction. adrenergic antagonist An agent that binds to but does not activate adrenergic receptors thereby blocking the actions of endogenous or exogenous adrenergic agonists. |
| Applications: | gastrointestinal drug A drug used for its effects on the gastrointestinal system, e.g. controlling gastric acidity, regulating gastrointestinal motility and water flow, and improving digestion. 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. antidepressant Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. antitussive An agent that suppresses cough. Antitussives have a central or a peripheral action on the cough reflex, or a combination of both. Compare with expectorants, which are considered to increase the volume of secretions in the respiratory tract, so facilitating their removal by ciliary action and coughing, and mucolytics, which decrease the viscosity of mucus, facilitating its removal by ciliary action and expectoration. drug allergen Any drug which causes the onset of an allergic reaction. antispasmodic drug A drug that suppresses spasms. These are usually caused by smooth muscle contraction, especially in tubular organs. The effect is to prevent spasms of the stomach, intestine or urinary bladder. vulnerary A drug used in treating and healing of wounds. anti-inflammatory agent Any compound that has anti-inflammatory effects. anti-arrhythmia drug A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres. 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) |
| 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 analgesic (CHEBI:35480) |
| bupivacaine (CHEBI:3215) has role anti-arrhythmia drug (CHEBI:38070) |
| bupivacaine (CHEBI:3215) has role anti-HIV agent (CHEBI:64946) |
| bupivacaine (CHEBI:3215) has role anti-inflammatory agent (CHEBI:67079) |
| bupivacaine (CHEBI:3215) has role anti-obesity agent (CHEBI:74518) |
| bupivacaine (CHEBI:3215) has role antidepressant (CHEBI:35469) |
| bupivacaine (CHEBI:3215) has role antineoplastic agent (CHEBI:35610) |
| bupivacaine (CHEBI:3215) has role antispasmodic drug (CHEBI:53784) |
| bupivacaine (CHEBI:3215) has role antitussive (CHEBI:51177) |
| 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 gastrointestinal drug (CHEBI:55324) |
| bupivacaine (CHEBI:3215) has role local anaesthetic (CHEBI:36333) |
| bupivacaine (CHEBI:3215) has role vulnerary (CHEBI:73336) |
| 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 |
| bupivacaine | ChemIDplus |
| bupivacainum | ChemIDplus |
| Synonyms | Source |
|---|---|
| 1-Butyl-2',6'-pipecoloxylidide | ChemIDplus |
| 1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide | NIST Chemistry WebBook |
| BR-003 | ChEMBL |
| Bucaine | ChEMBL |
| (±)-bupivacaine | ChEBI |
| (+-)-Bupivacaine | ChemIDplus |
| Brand Names | Source |
|---|---|
| Anekain | ChEMBL |
| Bupivacaine component of zynrelef | ChEMBL |
| Exparel | ChEMBL |
| Exparel liposomal | ChEMBL |
| Posimir | ChEMBL |
| Manual Xrefs | Databases |
|---|---|
| Bupivacaine | Wikipedia |
| C07529 | KEGG COMPOUND |
| D07552 | KEGG DRUG |
| DB00297 | DrugBank |
| HMDB0014442 | HMDB |
| US2955111 | Patent |
| 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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