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Bupivacaine

Catalog No. DB00297 Name DrugBank
CAS Number 2180-92-9 Website http://www.ualberta.ca/
M. F. C18H28N2O Telephone (780) 492-3111
M. W. 288.42772 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 182

SYNONYMS

IUPAC name
1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
IUPAC Traditional name
bupivacaine
Brand Name
Sensorcaine-MPF Spinal
DepoBupivacaine
Anekain
Bupivan
Carbostesin
Chirocaine
Marcaina
Marcaine
Marcaine HCL
Transdur-Bupivacaine
Marcaine Spinal
Sensorcaine
Sensorcaine-MPF
Synonyms
Bupivacaine HCL
Bupivacaine HCL KIT
Bupivacaina [INN-Spanish]
cBupivacaine
(+-)-Bupivacaine
Bloqueina
LAC-43
bupivacaine
DL-Bupivacaine
Bupivacainum [INN-Latin]
DUR-843

DATABASE IDS

PubChem SID 46506768
CAS Number 2180-92-9
PubChem CID 2474

PROPERTIES

Hydrophobicity(logP) 3.6
Solubility 2400 mg/L

DETAILS

Description (English)
Item Information
Drug Groups approved; investigational
Description A widely used local anesthetic agent. [PubChem]
Indication For the production of local or regional anesthesia or analgesia for surgery, for oral surgery procedures, for diagnostic and therapeutic procedures, and for obstetrical procedures.
Pharmacology Bupivacaine is a widely used local anesthetic agent. Bupivacaine is often administered by spinal injection prior to total hip arthroplasty. It is also commonly injected into surgical wound sites to reduce pain for up to 20 hours after surgery. In comparison to other local anesthetics it has a long duration of action. It is also the most toxic to the heart when administered in large doses. This problem has led to the use of other long-acting local anaesthetics:ropivacaine and levobupivacaine. Levobupivacaine is a derivative, specifically an enantiomer, of bupivacaine. Systemic absorption of local anesthetics produces effects on the cardiovascular and central nervous systems. At blood concentrations achieved with therapeutic doses, changes in cardiac conduction, excitability, refractoriness, contractility, and peripheral vascular resistance are minimal. However, toxic blood concentrations depress cardiac conduction and excitability, which may lead to atrioventricular block, ventricular arrhythmias and to cardiac arrest, sometimes resulting in fatalities. In addition, myocardial contractility is depressed and peripheral vasodilation occurs, leading to decreased cardiac output and arterial blood pressure. Following systemic absorption, local anesthetics can produce central nervous system stimulation, depression or both.
Toxicity The mean seizure dosage of bupivacaine in rhesus monkeys was found to be 4.4 mg/kg with mean arterial plasma concentration of 4.5 mcg/mL. The intravenous and subcutaneous LD 50 in mice is 6 to 8 mg/kg and 38 to 54 mg/kg respectively. Recent clinical data from patients experiencing local anesthetic induced convulsions demonstrated rapid development of hypoxia, hypercarbia, and acidosis with bupivacaine within a minute of the onset of convulsions. These observations suggest that oxygen consumption and carbon dioxide production are greatly increased during local anesthetic convulsions and emphasize the importance of immediate and effective ventilation with oxygen which may avoid cardiac arrest.
Affected Organisms
Humans and other mammals
Biotransformation Amide-type local anesthetics such as bupivacaine are metabolized primarily in the liver via conjugation with glucuronic acid. The major metabolite of bupivacaine is 2,6-pipecoloxylidine, which is mainly catalyzed via cytochrome P450 3A4.
Absorption The rate of systemic absorption of local anesthetics is dependent upon the total dose and concentration of drug administered, the route of administration, the vascularity of the administration site, and the presence or absence of epinephrine in the anesthetic solution.
Half Life 2.7 hours in adults and 8.1 hours in neonates
Protein Binding 95%
Elimination Only 6% of bupivacaine is excreted unchanged in the urine.
References
[Link]
Rosenblatt MA, Abel M, Fischer GW, Itzkovich CJ, Eisenkraft JB: Successful use of a 20% lipid emulsion to resuscitate a patient after a presumed bupivacaine-related cardiac arrest. Anesthesiology. 2006 Jul;105(1):217-8. [Pubmed]
Picard J, Meek T: Lipid emulsion to treat overdose of local anaesthetic: the gift of the glob. Anaesthesia. 2006 Feb;61(2):107-9. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

  • Link
  • Rosenblatt MA, Abel M, Fischer GW, Itzkovich CJ, Eisenkraft JB: Successful use of a 20% lipid emulsion to resuscitate a patient after a presumed bupivacaine-related cardiac arrest. Anesthesiology. 2006 Jul;105(1):217-8. Pubmed
  • Picard J, Meek T: Lipid emulsion to treat overdose of local anaesthetic: the gift of the glob. Anaesthesia. 2006 Feb;61(2):107-9. Pubmed