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: WARNINGRx-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 ;
	(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. 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.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.