Active Ingredient History

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Bupivacaine is a widely used local anesthetic agent. Bupivacaine is often administered by spinal injection prior to total hip arthroplasty. It is also commonly injected into surgical wound sites to reduce pain for up to 20 hours after surgery. In comparison to other local anesthetics it has a long duration of action. It is also the most toxic to the heart when administered in large doses. Bupivacaine blocks the generation and the conduction of nerve impulses, presumably by increasing the threshold for electrical excitation in the nerve, by slowing the propagation of the nerve impulse, and by reducing the rate of rise of the action potential. Bupivacaine binds to the intracellular portion of sodium channels and blocks sodium influx into nerve cells, which prevents depolarization. In general, the progression of anesthesia is related to the diameter, myelination and conduction velocity of affected nerve fibers. The analgesic effects of bupivicaine are thought to potentially be due to its binding to the prostaglandin E2 receptors, subtype EP1 (PGE2EP1), which inhibits the production of prostaglandins, thereby reducing fever, inflammation, and hyperalgesia. Bupivacaine sometimes used in combination with epinephrine to prevent systemic absorption and extend the duration of action.   NCATS

  • SMILES: CCCCN1CCCCC1C(=O)NC2=C(C)C=CC=C2C
  • InChIKey: LEBVLXFERQHONN-UHFFFAOYSA-N
  • Mol. Mass: 288.4277
  • ALogP: 3.9
  • ChEMBL Molecule:
More Chemistry
  • Mechanisms of Action: Missing data
  • Multi-specific: Missing data
  • Black Box: Yes
  • Availability: Prescription Only
  • Delivery Methods: Parenteral
  • Pro Drug: No

Drug Pricing (per unit)

United States

$131.7690 - $303.2525
More Pricing Detail

Note: This drug pricing data is preliminary, incomplete, and may contain errors.

exparel | liposomal bupivacaine | liposomal bupivicaine | liposome bupivacaine

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