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Bupivacaine information


Bupivacaine
Clinical data
Pronunciation/bjuːˈpɪvəkn/
Trade namesMarcaine, Sensorcaine, Posimir, others
AHFS/Drugs.comMonograph
License data
  • US DailyMed: Bupivacaine
Pregnancy
category
  • AU: A[1]
Routes of
administration
Parenteral, topical, implant
ATC code
  • N01BB01 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • US: WARNING[2]Rx-only[3][4]
  • EU: Rx-only
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
IUPAC name
  • (RS)-1-Butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
CAS Number
  • 38396-39-3 checkY
  • HCl: 73360-54-0 checkY
PubChem CID
  • 2474
  • HCl: 5282419
IUPHAR/BPS
  • 2397
DrugBank
  • DB00297 checkY
ChemSpider
  • 2380 checkY
  • HCl: 58277
UNII
  • Y8335394RO
  • HCl: 7TQO7W3VT8
KEGG
  • D07552 checkY
  • HCl: D01450
ChEBI
  • CHEBI:60789 ☒N
  • HCl: CHEBI:31322
ChEMBL
  • ChEMBL1098 checkY
  • HCl: ChEMBL1200396
CompTox Dashboard (EPA)
  • DTXSID2022703 Edit this at Wikidata
ECHA InfoCard100.048.993 Edit this at Wikidata
Chemical and physical data
FormulaC18H28N2O
Molar mass288.435 g·mol−1
3D model (JSmol)
  • Interactive image
Melting point107 to 108 °C (225 to 226 °F)
SMILES
  • O=C(C1N(CCCC1)CCCC)NC2=C(C)C=CC=C2C
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) 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).

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Bupivacaine

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into the nerve cells. Levobupivacaine is the S-enantiomer of racemic bupivacaine and therefore similar in pharmacological effects. The drug typically...

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AstraZeneca under the brand name Naropin. Ropivacaine was developed after bupivacaine was noted to be associated with cardiac arrest, particularly in pregnant...

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Local anesthetic

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Potency Lidocaine Prilocaine High Duration and High Potency Tetracaine Bupivacaine Cinchocaine Ropivacaine Local anesthetics may be used to prevent and/or...

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Management of strabismus

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Spinal anaesthesia

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spinal must be injected below L2 to avoid piercing the spinal cord. Bupivacaine (Marcaine) is the local anaesthetic most commonly used, although lidocaine...

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Anesthetic

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Cocaine (historical) Procaine Tetracaine (sometimes called Amethocaine) Bupivacaine Cinchocaine(INN/BAN)/Dibucaine(USAN) Etidocaine Levobupivacaine Lidocaine...

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Botulinum toxin therapy of strabismus

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repeatedly. It is also under investigation whether the injection of bupivacaine into extraocular muscles is of possible therapeutic use for treating...

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ATC code N01

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N01BA52 Procaine, combinations N01BA53 Tetracaine, combinations N01BB01 Bupivacaine N01BB02 Lidocaine N01BB03 Mepivacaine N01BB04 Prilocaine N01BB05 Butanilicaine...

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Cardiotoxicity

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stimulants such as cocaine; or an incorrectly administered drug such as bupivacaine. One of the ways to detect cardiotoxicity at early stages when there...

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Myofascial trigger point

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bupivacaine (Marcaine) is often used. A mixture of 1 part 2% lidocaine with 3 parts 0.5% bupivacaine provides 0.5% lidocaine and 0.375% bupivacaine....

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Epidural administration

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fascial plane blocks that may be provided instead of an epidural. If bupivacaine, a medication commonly administered via epidural, is inadvertently administered...

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Lidocaine

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infiltration, block, and surface anaesthesia. Longer-acting substances such as bupivacaine are sometimes given preference for spinal and epidural anaesthesias;...

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Cocaine

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Valpromide Zonisamide Local anesthetics: pFBT Amylocaine Articaine Benzocaine Bupivacaine (Levobupivacaine, Ropivacaine) Butacaine Butamben Chloroprocaine Cinchocaine...

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Uncoupler

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following compounds are known to be pseudo-uncouplers: Azide Biguanides Bupivacaine Calcimycin (A23187) Dodecyltriphenylphosphonium (C12TPP) Lasalocid (X537A)...

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Ketamine

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Valpromide Zonisamide Local anesthetics: pFBT Amylocaine Articaine Benzocaine Bupivacaine (Levobupivacaine, Ropivacaine) Butacaine Butamben Chloroprocaine Cinchocaine...

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Amino esters

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(primarily sodium channel blockers) (N01B) Esters by acid Amides Articaine Bupivacaine#/Levobupivacaine/Ropivacaine Butanilicaine Carticaine Cinchocaine (Dibucaine)...

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Lipid emulsion

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cardiotoxicity from intravenous overdose of local anaesthetic drugs such as bupivacaine. They have been effective in people unresponsive to the usual resuscitation...

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Nerve block

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from an injection of bupivacaine or had a history of difficulty getting numb at the dentist.  Skin testing with lidocaine, bupivacaine, and mepivacaine was...

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Chondrolysis

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Intra-articular infusions of certain local anesthetic agents such as bupivacaine, lidocaine, ropivacaine and levobupivacaine can also lead to this effect...

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Combined spinal and epidural anaesthesia

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rapid onset of analgesia in labour. It further recommends the use of bupivacaine and fentanyl to establish the block. Combined spinal-epidural anaesthesia...

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Domperidone

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Valpromide Zonisamide Local anesthetics: pFBT Amylocaine Articaine Benzocaine Bupivacaine (Levobupivacaine, Ropivacaine) Butacaine Butamben Chloroprocaine Cinchocaine...

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WHO Model List of Essential Medicines

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Isoflurane Nitrous oxide Oxygen Sevoflurane Ketamine Propofol Thiopental Bupivacaine Lidocaine Lidocaine/epinephrine (lidocaine + epinephrine) Complementary:...

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Uterine myomectomy

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tranexamic acid, infusion of vitamin C, infiltration of a mixture of bupivacaine and epinephrine into the uterine muscles, or the use of a fibrin sealant...

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Notalgia paresthetica

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One patient has been treated with "paravertebral nerve blocks, with bupivacaine and methylprednisolone acetate injected into the T3–T4 and T5–T6 intervertebral...

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