Bupivacaine

Bupivacaine

Clinical data
Pronunciation	/bjuːˈpɪvəkeɪn/
Trade names	Marcaine, Marcain, Sensorcaine, and Vivacaine
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)
Pharmacokinetic data
Bioavailability	n/a
Protein binding	95%
Metabolism	Liver
Onset of action	Within 15 min
Biological half-life	3.5 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 N 2180-92-9
PubChem (CID)	2474 CID 5282419
IUPHAR/BPS	2397
DrugBank	DB00297 Y
ChemSpider	2380 Y
UNII	Y8335394RO Y
KEGG	D07552 Y
ChEBI	CHEBI:60789 N
ChEMBL	CHEMBL1098 Y
ECHA InfoCard	100.016.867
Chemical and physical data
Formula	C18H28N2O
Molar mass	288.43 g/mol
3D model (Jmol)	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) Y Key:LEBVLXFERQHONN-UHFFFAOYSA-N Y
NY (what is this?)

Bupivacaine, marketed under the brand name Marcaine among others, is a medication used to decrease feeling in a specific area. It is used by injecting it into the area, 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 make it last longer. 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, the most effective and safe medicines needed in a health system. Bupivacaine is available as a generic medication and is not very expensive. The wholesale cost in the developing world of a vial is about US$2.10.

Bupivacaine is indicated for local infiltration, peripheral nerve block, sympathetic nerve block, and epidural and caudal blocks. It is sometimes used in combination with epinephrine to prevent systemic absorption and extend the duration of action. The 0.75% (most concentrated) formulation is used in retrobulbar block. It is the most commonly used local anesthetic in epidural anesthesia during labor, as well as in postoperative pain management.