Bupivacaine

Bupivacaine
Clinical data
Pronunciation/bjuːˈpɪvəkeɪn/
Trade namesMarcaine, Sensorcaine, Posimir, others
AHFS/Drugs.comMonograph
License data
Pregnancy
category
Routes of
administration		Parenteral, topical, implant
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailabilityn/a
Protein binding95%
MetabolismLiver
Onset of actionWithin 15 min[5]
Elimination half-life3.1 hours (adults)[5]
8.1 hours (neonates)[5]
Duration of action2 to 8 hr[6]
ExcretionKidney, 4–10%
Identifiers
  • (RS)-1-Butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.048.993 Edit this at Wikidata
Chemical and physical data
FormulaC18H28N2O
Molar mass288.435 g·mol−1
3D model (JSmol)
Melting point107 to 108 °C (225 to 226 °F)
  • O=C(C1N(CCCC1)CCCC)NC2=C(C)C=CC=C2C
  • 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) checkY
  • Key:LEBVLXFERQHONN-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Bupivacaine, marketed under the brand name Marcaine among others, is a medication used to decrease sensation in a specific small area.[5] In nerve blocks, it is injected around a nerve that supplies the area, or into the spinal canal's epidural space.[5] It is available mixed with a small amount of epinephrine to increase the duration of its action.[5] It typically begins working within 15 minutes and lasts for 2 to 8 hours.[5][6]

Possible side effects include sleepiness, muscle twitching, ringing in the ears, changes in vision, low blood pressure, and an irregular heart rate.[5] Concerns exist that injecting it into a joint can cause problems with the cartilage.[5] Concentrated bupivacaine is not recommended for epidural freezing.[5] Epidural freezing may also increase the length of labor.[5] It is a local anaesthetic of the amide group.[5]

Bupivacaine was discovered in 1957.[7] It is on the World Health Organization's List of Essential Medicines.[8] Bupivacaine is available as a generic medication.[5][9] An implantable formulation of bupivacaine (Xaracoll) was approved for medical use in the United States in August 2020.[10][11][12]

  1. ^ "Bupivacaine Use During Pregnancy". Drugs.com. 13 April 2020. Retrieved 21 September 2020.
  2. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  3. ^ "Marcaine- bupivacaine hydrochloride injection, solution Marcaine with epinephrine- bupivacaine hydrochloride and epinephrine bitartrate injection, solution". DailyMed. Retrieved 13 February 2021.
  4. ^ "Sensorcaine MPF- bupivacaine hydrochloride injection, solution". DailyMed. Retrieved 13 February 2021.
  5. ^ a b c d e f g h i j k l m "Bupivacaine Hydrochloride". The American Society of Health-System Pharmacists. Archived from the original on 30 June 2015. Retrieved 1 August 2015.
  6. ^ a b Whimster DS (1997). Cambridge textbook of accident and emergency medicine. Cambridge: Cambridge University Press. p. 194. ISBN 9780521433792. Archived from the original on 5 October 2015.
  7. ^ Egan TD (2013). Pharmacology and physiology for anesthesia : foundations and clinical application. Philadelphia, PA: Elsevier/Saunders. p. 291. ISBN 9781437716795. Archived from the original on 12 May 2016.
  8. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  9. ^ Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 22. ISBN 9781284057560.
  10. ^ "Xaracoll: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Retrieved 2 September 2020.
  11. ^ Cite error: The named reference FDA Xaracoll approval letter was invoked but never defined (see the help page).
  12. ^ Cite error: The named reference Innocoll PR was invoked but never defined (see the help page).