Bupivacaine

Bupivacaine
Systematic (IUPAC) name
(RS)-1-butyl-N-(2,6-dimethylphenyl)
piperidine-2-carboxamide
Clinical data
AHFS/Drugs.com monograph
Pregnancy cat. A(AU)
Legal status Prescription Only (S4) (AU)
Routes parenteral, topical
Pharmacokinetic data
Bioavailability n/a
Metabolism hepatic
Half-life 3.5 hours (adults)
8.1 hours (neonates)
Excretion Renal, 4–10%
Identifiers
ATC code N01BB01
PubChem CID 2474
IUPHAR ligand 2397
DrugBank APRD00247
ChemSpider 2380 YesY
UNII Y8335394RO YesY
KEGG D07552 YesY
ChEBI CHEBI:60789 YesY
ChEMBL CHEMBL1098 YesY
Chemical data
Formula C18H28N2O 
Mol. mass 288.43 g/mol
SMILES eMolecules & PubChem
 YesY(what is this?)  (verify)

Bupivacaine (rINN) (play /bjuːˈpɪvəkn/) is a local anaesthetic drug belonging to the amino amide group. AstraZeneca commonly markets it under various trade names, including Marcain, Marcaine, Sensorcaine and Vivacaine.

Contents

Indications

Bupivacaine is indicated for local anaesthesia including infiltration, nerve block, epidural, and intrathecal anaesthesia. Bupivacaine often is administered by epidural injection before total hip arthroplasty. It also is commonly injected to surgical wound sites to reduce pain for up to 20 hours after the surgery. Sometimes, bupivacaine is co-administered with epinephrine to prolong the duration of its action, fentanyl for epidural analgesia, or glucose.

Contraindications

Bupivacaine is contraindicated for IV regional anaesthesia (IVRA) because of potential risk of tourniquet failure and systemic absorption of the drug.

Adverse effects

Compared to other local anaesthetic, bupivacaine is markedly cardiotoxic. However, adverse drug reactions (ADRs) are rare when it is administered correctly. Most ADRs relate to administration technique (resulting in systemic exposure) or pharmacological effects of anesthesia, however allergic reactions can rarely occur.

Systemic exposure to excessive quantities of bupivacaine mainly result in central nervous system (CNS) and cardiovascular effects – CNS effects usually occur at lower blood plasma concentrations and additional cardiovascular effects present at higher concentrations, though cardiovascular collapse may also occur with low concentrations. CNS effects may include CNS excitation (nervousness, tingling around the mouth, tinnitus, tremor, dizziness, blurred vision, seizures) followed by depression (drowsiness, loss of consciousness, respiratory depression and apnea). Cardiovascular effects include hypotension, bradycardia, arrhythmias, and/or cardiac arrest – some of which may be due to hypoxemia secondary to respiratory depression.[1]

Bupivacaine has caused several deaths when the epidural anaesthetic has been administered intravenously accidentally.[2]

Treatment of overdose: lipid rescue

There is animal evidence[3][4] that Intralipid, a commonly available intravenous lipid emulsion, can be effective in treating severe cardiotoxicity secondary to local anaesthetic overdose, and human case reports of successful use in this way.[5][6] Schemes to publicise this use more widely have been published.[7]

Mechanism of action

Bupivacaine binds to the intracellular portion of sodium channels and blocks sodium influx into nerve cells, which prevents depolarization. Since pain transmitting nerve fibres tend to be thinner and either unmyelinated or lightly myelinated, the agent can diffuse more readily into them than into thicker and more heavily myelinated nerve fibres like touch, proprioception, etc. (Myelin is non-polar / lipophilic).It should be noted, however, that bupivacaine also blocks specific potassium channels, an effect contributing to resting membrane potential depolarization.

Developments

Levobupivacaine is the (S)-(–)-enantiomer of bupivacaine, with a longer duration of action and produces less vasodilation. Durect Corporation is developing a biodegradable controlled-release drug delivery system for post surgery. It is currently in Phase II.[citation needed]

References

  1. ^ Rossi S, editor. Australian Medicines Handbook 2006. Adelaide: Australian Medicines Handbook; 2006. ISBN 0-9757919-2-3
  2. ^ ABS-CBN Interactive: Filipino nurse dies in UK due to wrong use of anaesthetic
  3. ^ Weinberg GL, VadeBoncouer T, Ramaraju GA, Garcia-Amaro MF, Cwik MJ. (1998). "Pretreatment or resuscitation with a lipid infusion shifts the dose-response to bupivacaine-induced asystole in rats". Anesthesiology 88 (4): 1071–5. doi:10.1097/00000542-199804000-00028. PMID 9579517. 
  4. ^ Weinberg G, Ripper R, Feinstein DL, Hoffman W. (2003). "Lipid emulsion infusion rescues dogs from bupivacaine-induced cardiac toxicity". Regional Anesthesia and Pain Medicine 28 (3): 198–202. doi:10.1053/rapm.2003.50041. PMID 12772136. 
  5. ^ Rosenblatt MA, Abel M, Fischer GW, Itzkovich CJ, Eisenkraft JB (July 2006). "Successful use of a 20% lipid emulsion to resuscitate a patient after a presumed bupivacaine-related cardiac arrest.". Anesthesiology 105 (1): 217–8. doi:10.1097/00000542-200607000-00033. PMID 16810015. 
  6. ^ Litz, RJ; Popp, M; Stehr, S N; Koch, T. (2006). "Successful resuscitation of a patient with ropivacaine-induced asystole after axillary plexus block using lipid infusion". Anaesthesia 61 (8): 800–1. doi:10.1111/j.1365-2044.2006.04740.x. PMID 16867094. 
  7. ^ Picard J, Meek T (February 2006). "Lipid emulsion to treat overdose of local anaesthetic: the gift of the glob.". Anaesthesia 61 (2): 107–9. doi:10.1111/j.1365-2044.2005.04494.x. PMID 16430560. 

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Look at other dictionaries:

  • Bupivacaïne — Énantiomère R de la bupivacaïne (en haut) et S bupivacaïne (en bas) Général …   Wikipédia en Français

  • Bupivacaine — Bupivacaïne Bupivacaïne Général Nom IUPAC (RS) 1 butyl N (2,6 dimethylphenyl) piperidine 2 carboxamide …   Wikipédia en Français

  • bupivacaine — /byooh piv euh kayn /, n. Pharm. a white, crystalline powder, C18H28N2O, used as a local anesthetic. [perh. BU(TYL) + pi(pecoloxylidide) its chemical components + vacaine, irreg. for (NO)VOCAINE; see PROCAINE] * * * …   Universalium

  • bupivacaine — noun A local anesthetic drug of the amino amide group …   Wiktionary

  • bupivacaine — A potent, long acting local anesthetic used in regional anesthesia, joint and trigger point injections. * * * bu·piv·a·caine byü piv ə .kān n a local anesthetic C18H28N2O that is like lidocaine in its action but is longer acting * * * …   Medical dictionary

  • bupivacaine — n. a potent local anaesthetic, used mainly for regional nerve block. It is significantly longer acting than many other local anaesthetics. It has been used in childbirth, but may cause slowing of the baby s heart, with a risk of death. Trade… …   The new mediacal dictionary

  • bupivacaine — /byooh piv euh kayn /, n. Pharm. a white, crystalline powder, C18H28N2O, used as a local anesthetic. [perh. BU(TYL) + pi(pecoloxylidide) its chemical components + vacaine, irreg. for (NO)VOCAINE; see PROCAINE] …   Useful english dictionary

  • Bupivacaine hydrochloride — БУПИВАКАИНА ГИДРОХЛОРИД ( Bupivacainе hydrochloride )*. 1 Бутил 2 ,6 диметилфенил 2 пиперидинкарбоксамида гидрохлорид. Синонимы: Маркаин, Саrbostesin, Duracain, Маrcain, Narcain, Sensorcain, Svedocain. По химической структуре близок к лидокаину.… …   Словарь медицинских препаратов

  • bupivacaine hydrochloride — bu·piv·a·caine hy·dro·chlo·ride (bu pivґə kān) [USP] a homologue of mepivacaine, chemically related to lidocaine, used as a local anesthetic for infiltration, peripheral nerve block, retrobulbar block, subarachnoid block, sympathetic… …   Medical dictionary

  • Бупивакаин (Bupivacaine) — сильнодействующий местный анестетик, применяемый в основном для проводниковой анестезии. Действует значительно дольше, чем большинство других местных анестетиков. Применяется при родах, однако может вызвать замедление частоты сердечных сокращений …   Медицинские термины

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