Bupivacaine

Bupivacaine
Clinical data
Pronunciation	/bjuːˈpɪvəkeɪn/
Trade names	Marcaine, Sensorcaine, Posimir, others
AHFS/Drugs.com	Monograph
License data	US DailyMed: Bupivacaine;
Pregnancy; category	AU: A;
Routes of; administration	Parenteral, topical, implant
ATC code	N01BB01 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	n/a
Protein binding	95%
Metabolism	Liver
Onset of action	Within 15 min
Elimination half-life	3.1 hours (adults); 8.1 hours (neonates)
Duration of action	2 to 8 hr
Excretion	Kidney, 4–10%
Identifiers
	IUPAC name (RS)-1-Butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide;
CAS Number	38396-39-3 ; HCl: 73360-54-0 ;
PubChem CID	2474; HCl: 5282419;
IUPHAR/BPS	2397;
DrugBank	DB00297 ;
ChemSpider	2380 ; HCl: 58277;
UNII	Y8335394RO; HCl: 7TQO7W3VT8;
KEGG	D07552 ; HCl: D01450;
ChEBI	CHEBI:60789 ; HCl: CHEBI:31322;
ChEMBL	ChEMBL1098 ; HCl: ChEMBL1200396;
CompTox Dashboard (EPA)	DTXSID2022703 ;
ECHA InfoCard	100.048.993
Chemical and physical data
Formula	C18H28N2O
Molar mass	288.435 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	107 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) ; Key:LEBVLXFERQHONN-UHFFFAOYSA-N ;
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Bupivacaine, marketed under the brand name Marcaine among others, is a medication used to decrease sensation in a specific small area. In nerve blocks, it is injected around a nerve that supplies the area, or into the spinal canal's epidural space. It is available mixed with a small amount of epinephrine to increase the duration of its action. It typically begins working within 15 minutes and lasts for 2 to 8 hours.

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

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