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Bupivacaine

Clinical data
AHFS/Drugs.com	Monograph
Pregnancy category	AU: A
Routes of administration	parenteral, topical
ATC code	N01BB01 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) US: WARNING
Pharmacokinetic data
Bioavailability	n/a
Metabolism	hepatic
Elimination half-life	3.5 hours (adults) 8.1 hours (neonates)
Excretion	Renal, 4–10%
Identifiers
IUPAC name (RS)-1-butyl-N-(2,6-dimethylphenyl) piperidine-2-carboxamide
PubChem CID	2474
IUPHAR/BPS	2397
DrugBank	APRD00247
ChemSpider	2380
UNII	Y8335394RO
KEGG	D07552
ChEBI	CHEBI:60789
ChEMBL	ChEMBL1098
CompTox Dashboard (EPA)	DTXSID2022703
ECHA InfoCard	100.048.993
Chemical and physical data
Formula	C18H28N2O
Molar mass	288.43 g/mol g·mol
3D model (JSmol)	Interactive image
SMILES O=C(Nc1c(cccc1C)C)C2N(CCCC)CCCC2
InChI InChI=1S/C18H28N2O.ClH.H2O/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);1H;1H2 Key:HUCIWBPMHXGLFM-UHFFFAOYSA-N
(verify)

Bupivacaine (rINN) (/bjuːˈpɪvəkeɪn/) 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.

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.

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

Treatment of overdose: lipid rescue

There is animal evidence 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. Schemes to publicise this use more widely have been published.

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.

References

1. "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 Oct 2023.
2. Rossi S, editor. Australian Medicines Handbook 2006. Adelaide: Australian Medicines Handbook; 2006. ISBN 0-9757919-2-3
3. ABS-CBN Interactive: Filipino nurse dies in UK due to wrong use of anaesthetic
4. 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. {{cite journal}}: Cite has empty unknown parameter: |author-name-separator= (help); Unknown parameter |author-separator= ignored (help)
5. 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. {{cite journal}}: Cite has empty unknown parameter: |author-name-separator= (help); Unknown parameter |author-separator= ignored (help)
6. Rosenblatt, MA; Abel, M; Fischer, GW; Itzkovich, CJ; Eisenkraft, JB (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. {{cite journal}}: Cite has empty unknown parameter: |author-name-separator= (help); Unknown parameter |author-separator= ignored (help); Unknown parameter |month= ignored (help)
7. 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.
8. Picard, J; Meek, T (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. {{cite journal}}: Cite has empty unknown parameter: |author-name-separator= (help); Unknown parameter |author-separator= ignored (help); Unknown parameter |month= ignored (help)

External links

• RxList.com
• Drugs.com
• More on lipid rescue

• Ill-formatted IPAc-en transclusions
• Local anesthetics
• Piperidines
• World Health Organization essential medicines
• Acetanilides