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Identification
NameBupivacaine
Accession NumberDB00297  (APRD00247)
TypeSmall Molecule
GroupsApproved, Investigational
Description

A widely used local anesthetic agent. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
(+-)-BupivacaineNot AvailableNot Available
(RS)-bupivacaineNot AvailableNot Available
1-Butyl-2',6'-pipecoloxylidideNot AvailableNot Available
1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamideNot AvailableNot Available
BupivacainaSpanishINN
BupivacaineNot AvailableNot Available
BupivacainumLatinINN
CarbostesinNot AvailableNot Available
dl-1-Butyl-2',6'-pipecoloxylidideNot AvailableNot Available
DL-BupivacaineNot AvailableNot Available
Racemic bupivacaineNot AvailableNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Marcaineinjection, solution2.5 mg/mLepidural; infiltrationHospira, Inc.2009-09-08Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Marcaineinjection, solution5 mg/mLepidural; infiltrationHospira, Inc.2010-05-04Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Marcaineinjection, solution7.5 mg/mLepidural; retrobulbarHospira, Inc.2009-09-09Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Marcaineinjection, solution2.5 mg/mLinfiltrationHospira, Inc.2009-09-08Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Marcaineinjection, solution5 mg/mLinfiltrationHospira, Inc.2009-09-09Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Marcaine Spinalinjection, solution7.5 mg/mLsubarachnoidHospira, Inc.1984-05-04Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Bupivacaine Hydrochlorideinjection, solution2.5 mg/mLepidural; infiltration; intracaudalHospira, Inc.1978-04-17Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Bupivacaine Hydrochlorideinjection, solution5 mg/mLepidural; intracaudalHospira, Inc.1978-04-17Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Bupivacaine Hydrochlorideinjection, solution7.5 mg/mLepidural; retrobulbarHospira, Inc.1978-04-17Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Bupivacaine Hydrochlorideinjection, solution2.5 mg/mLepidural; infiltration; intracaudalHospira, Inc.1978-04-17Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Bupivacaine Hydrochlorideinjection, solution7.5 mg/mLepidural; retrobulbarHospira, Inc.1978-04-17Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Bupivacaine Hydrochlorideinjection, solution5 mg/mLepidural; infiltration; intracaudalHospira, Inc.1978-04-17Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Bupivacaine Hydrochlorideinjection, solution5 mg/mLepidural; infiltration; intracaudalHospira, Inc.1978-04-17Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Marcaineinjection, solution5 mg/mLepiduralREMEDYREPACK INC.2013-11-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Marcaineinjection, solution5 mg/mLepiduralREMEDYREPACK INC.2013-06-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Marcaineinjection, solution5 mg/mLinfiltrationREMEDYREPACK INC.2013-11-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Marcaineinjection, solution5 mg/mLinfiltrationREMEDYREPACK INC.2013-06-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Marcaineinjection, solution2.5 mg/mLepidural; infiltrationGeneral Injectables & Vaccines, Inc2010-08-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Marcaineinjection, solution5 mg/mLepiduralGeneral Injectables & Vaccines, Inc2010-08-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Marcaineinjection, solution5 mg/mLepidural; infiltrationGeneral Injectables & Vaccines, Inc2010-03-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Marcaineinjection, solution7.5 mg/mLepidural; retrobulbarA S Medication Solutions Llc2009-09-09Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Marcaineinjection, solution5 mg/mLinfiltrationPhysicians Total Care, Inc.2009-09-09Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Marcaineinjection, solution2.5 mg/mLinfiltrationPhysicians Total Care, Inc.2009-09-08Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Marcaineinjection, solution2.5 mg/mLepidural; infiltrationCardinal Health2009-09-08Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sensorcaineinjection, solution2.5 mg/mLinfiltration; perineuralFresenius Kabi USA, LLC2010-11-19Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sensorcaineinjection, solution5 mg/mLperineuralFresenius Kabi USA, LLC2010-11-19Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Exparelinjection, suspension, liposomal13.3 mg/mLinfiltrationPacira Pharmaceuticals Inc.2012-01-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Vivacaineinjection, solution5; .005 mg/mL; mg/mLsubcutaneousSeptodont, Inc.2013-06-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Vivacaineinjection, solution5; .0091 mg/mL; mg/mLsubcutaneousSeptodont Inc.2009-12-17Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Bupivacaine Hydrochlorideinjection, solution2.5 mg/mLepidural; infiltration; intracaudalHospira, Inc.1987-03-03Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Bupivacaine Hydrochlorideinjection, solution2.5 mg/mLepidural; infiltration; intracaudalHospira, Inc.1987-02-17Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Bupivacaine Hydrochlorideinjection, solution2.5 mg/mLinfiltrationHospira, Inc.1987-02-17Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Bupivacaine Hydrochlorideinjection, solution5 mg/mLepidural; intracaudalHospira, Inc.1987-03-03Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Bupivacaine Hydrochlorideinjection, solution5 mg/mLepidural; intracaudalHospira, Inc.1987-02-17Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Bupivacaine Hydrochlorideinjection, solution5 mg/mLinfiltrationHospira, Inc.1987-03-03Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Bupivacaine Hydrochlorideinjection, solution7.5 mg/mLepidural; retrobulbarHospira, Inc.1987-03-03Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Bupivacaineinjection, solution7.5 mg/mLsubarachnoidHospira, Inc.1987-12-11Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Marcaineinjection, solution5; .005 mg/mL; mg/mLsubcutaneousCarestream Health Inc.2013-06-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Bupivacaine Hydrochlorideinjection2.5 mg/mLinfiltrationGeneral Injectables & Vaccines, Inc2010-07-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Bupivacaine Hydrochlorideinjection5 mg/mLinfiltrationGeneral Injectables & Vaccines, Inc2010-07-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sensorcaineinjection, solution2.5 mg/mLinfiltration; perineuralGeneral Injectables & Vaccines, Inc2011-10-17Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sensorcaineinjection, solution5 mg/mLperineuralGeneral Injectables & Vaccines, Inc2011-10-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Bupivacaine Hydrochlorideinjection, solution2.5 mg/mLepidural; infiltration; intracaudalAuro Medics Pharma Llc2013-11-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Bupivacaine Hydrochlorideinjection, solution2.5 mg/mLepidural; infiltration; intracaudalAuro Medics Pharma Llc2013-11-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Bupivacaine Hydrochlorideinjection, solution5 mg/mLepidural; intracaudalAuro Medics Pharma Llc2013-11-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Bupivacaine Hydrochlorideinjection, solution5 mg/mLepidural; intracaudalAuro Medics Pharma Llc2013-11-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Bupivacaine Hydrochlorideinjection, solution7.5 mg/mLepidural; retrobulbarAuro Medics Pharma Llc2013-11-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Bupivacaine Hydrochlorideinjection, solution7.5 mg/mLepidural; retrobulbarAuro Medics Pharma Llc2013-11-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Bupivacaine Hydrochlorideinjection, solution5 mg/mLepidural; infiltration; intracaudalCardinal Health2010-01-07Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Bupivacaine Hydrochlorideinjection, solution5 mg/mLepidural; infiltration; intracaudalCardinal Health2010-01-07Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Bupivacaine Hydrochlorideinjection, solution2.5 mg/mLepidural; infiltration; intracaudalCardinal Health2010-01-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Bupivacaine Hydrochlorideinjection, solution2.5 mg/mLepidural; infiltration; intracaudalCardinal Health2010-01-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sensorcaineinjection, solution2.5; .005 mg/mL; mg/mLinfiltration; perineuralFresenius Kabi USA, LLC2010-11-19Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sensorcaineinjection, solution5; .005 mg/mL; mg/mLperineuralFresenius Kabi USA, LLC2010-11-19Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International Brands
NameCompany
BupivanSun
CarbostesinAstraZeneca
MarcainAstraZeneca
MarcainaAstraZeneca
Sensorcaine-MPFAstra Zeneca
Brand mixtures
Brand NameIngredients
Marcaine EBupivacaine Hydrochloride + Epinephrine Bitartrate
Sensorcaine ForteBupivacaine Hydrochloride + Epinephrine Bitartrate
Salts
Name/CASStructureProperties
Bupivacaine Hydrochloride
14252-80-3
Thumb
  • InChI Key: SIEYLFHKZGLBNX-UHFFFAOYNA-N
  • Monoisotopic Mass: 324.196841267
  • Average Mass: 324.889
DBSALT000202
Categories
CAS number2180-92-9
WeightAverage: 288.4277
Monoisotopic: 288.220163528
Chemical FormulaC18H28N2O
InChI KeyLEBVLXFERQHONN-UHFFFAOYSA-N
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)
IUPAC Name
1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
SMILES
CCCCN1CCCCC1C(=O)NC1=C(C)C=CC=C1C
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acid amides
Alternative Parents
Substituents
  • Alpha-amino acid amide
  • N-arylamide
  • Piperidinecarboxylic acid
  • Piperidinecarboxamide
  • 2-piperidinecarboxamide
  • Benzenoid
  • Piperidine
  • Monocyclic benzene moiety
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the production of local or regional anesthesia or analgesia for surgery, for oral surgery procedures, for diagnostic and therapeutic procedures, and for obstetrical procedures.
PharmacodynamicsBupivacaine 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.
Mechanism of actionLocal anesthetics such as bupivacaine block the generation and the conduction of nerve impulses, presumably by increasing the threshold for electrical excitation in the nerve, by slowing the propagation of the nerve impulse, and by reducing the rate of rise of the action potential. Bupivacaine binds to the intracellular portion of sodium channels and blocks sodium influx into nerve cells, which prevents depolarization. In general, the progression of anesthesia is related to the diameter, myelination and conduction velocity of affected nerve fibers. Clinically, the order of loss of nerve function is as follows: (1) pain, (2) temperature, (3) touch, (4) proprioception, and (5) skeletal muscle tone. The analgesic effects of Bupivicaine are thought to potentially be due to its binding to the prostaglandin E2 receptors, subtype EP1 (PGE2EP1), which inhibits the production of prostaglandins, thereby reducing fever, inflammation, and hyperalgesia.
AbsorptionThe 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.
Volume of distributionNot Available
Protein binding95%
Metabolism

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.

SubstrateEnzymesProduct
Bupivacaine
Not Available
2,6-pipecoloxylidineDetails
Route of eliminationOnly 6% of bupivacaine is excreted unchanged in the urine.
Half life2.7 hours in adults and 8.1 hours in neonates
ClearanceNot Available
ToxicityThe 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
Pathways
PathwayCategorySMPDB ID
Bupivacaine Action PathwayDrug actionSMP00393
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9814
Blood Brain Barrier+0.936
Caco-2 permeable+0.6669
P-glycoprotein substrateSubstrate0.8435
P-glycoprotein inhibitor IInhibitor0.8582
P-glycoprotein inhibitor IINon-inhibitor0.7836
Renal organic cation transporterNon-inhibitor0.6471
CYP450 2C9 substrateNon-substrate0.7957
CYP450 2D6 substrateSubstrate0.8346
CYP450 3A4 substrateSubstrate0.7045
CYP450 1A2 substrateInhibitor0.6863
CYP450 2C9 substrateNon-inhibitor0.9099
CYP450 2D6 substrateInhibitor0.8932
CYP450 2C19 substrateNon-inhibitor0.9026
CYP450 3A4 substrateInhibitor0.6205
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6066
Ames testNon AMES toxic0.8462
CarcinogenicityNon-carcinogens0.8859
BiodegradationNot ready biodegradable0.9729
Rat acute toxicity2.2574 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8283
hERG inhibition (predictor II)Inhibitor0.7851
Pharmacoeconomics
Manufacturers
  • Hospira inc
  • International medicated systems ltd
  • App pharmaceuticals llc
Packagers
Dosage forms
FormRouteStrength
Injectioninfiltration2.5 mg/mL
Injectioninfiltration5 mg/mL
Injection, solutionepidural5 mg/mL
Injection, solutionepidural; infiltration2.5 mg/mL
Injection, solutionepidural; infiltration5 mg/mL
Injection, solutionepidural; infiltration; intracaudal2.5 mg/mL
Injection, solutionepidural; infiltration; intracaudal5 mg/mL
Injection, solutionepidural; intracaudal5 mg/mL
Injection, solutionepidural; retrobulbar7.5 mg/mL
Injection, solutioninfiltration2.5 mg/mL
Injection, solutioninfiltration5 mg/mL
Injection, solutioninfiltration; perineural2.5 mg/mL
Injection, solutioninfiltration; perineural2.5; .005 mg/mL; mg/mL
Injection, solutionperineural5 mg/mL
Injection, solutionperineural5; .005 mg/mL; mg/mL
Injection, solutionsubarachnoid7.5 mg/mL
Injection, solutionsubcutaneous5; .005 mg/mL; mg/mL
Injection, solutionsubcutaneous5; .0091 mg/mL; mg/mL
Injection, suspension, liposomalinfiltration13.3 mg/mL
Prices
Unit descriptionCostUnit
Bupivacaine hcl powder18.36USD g
Sensorcaine-dextr 0.75% amp2.36USD ml
Marcaine spinal ampul0.93USD ml
Bupivacaine 0.5% on-q pump0.63USD ml
Bupivacaine hcl 0.5% on-q pump0.63USD ml
Bupivacaine 0.25% on-q pump0.62USD ml
Marcaine 0.25% vial0.26USD ml
Bupivacaine hcl-ns 0.0625%0.25USD ml
Bupivacaine-ns 0.1% on-q pump0.25USD ml
Sensorcaine 0.25% vial0.2USD ml
Bupivacaine hcl-ns 0.1%0.17USD ml
Bupivacaine hcl-ns 0.2%0.15USD ml
Bupivacaine 0.25% vial0.11USD ml
Bupivacaine 0.25% ampul0.1USD ml
Bupivacaine hcl-ns 0.125% bag0.1USD ml
Bupivacaine hcl-ns 0.25%0.1USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point107-108 °CPhysProp
water solubility2400 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP3.41HANSCH,C ET AL. (1995)
pKa8.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0977 mg/mLALOGPS
logP3.31ALOGPS
logP4.52ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)13.62ChemAxon
pKa (Strongest Basic)8ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area32.34 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity90.19 m3·mol-1ChemAxon
Polarizability34.19 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (8.44 KB)
SpectraNot Available
References
Synthesis Reference

Thuresson, B. and Egner, B.P.H.; U.S. Patent 2,792,399; May 14, 1957; assigned to AB Bofors, Sweden.
Thuresson, B. and Pettersson, B.G.; US. Patent 2,955.1 11; October 4,1960; assigned to AB
Bofors, Sweden.

US2955111
General Reference
  1. Link
  2. 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
  3. 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
ATC CodesN01BB01
AHFS Codes
  • 72:00.00
PDB EntriesNot Available
FDA labelDownload (147 KB)
MSDSDownload (73.3 KB)
Interactions
Drug Interactions
Drug
ConivaptanConivaptan may increase the serum concentration of CYP3A4 Substrates such as bupivacaine. Upon completion/discontinuation of conivaptan, allow at least 7 days before initiating therapy with drugs that are CYP3A4 substrates.
Food InteractionsNot Available

Targets

1. Sodium channel protein type 10 subunit alpha

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Sodium channel protein type 10 subunit alpha Q9Y5Y9 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Sheets MF, Fozzard HA, Lipkind GM, Hanck DA: Sodium channel molecular conformations and antiarrhythmic drug affinity. Trends Cardiovasc Med. 2010 Jan;20(1):16-21. Pubmed

2. Prostaglandin E2 receptor EP1 subtype

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: other/unknown

Components

Name UniProt ID Details
Prostaglandin E2 receptor EP1 subtype P34995 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Beloeil H, Gentili M, Benhamou D, Mazoit JX: The effect of a peripheral block on inflammation-induced prostaglandin E2 and cyclooxygenase expression in rats. Anesth Analg. 2009 Sep;109(3):943-50. Pubmed

Enzymes

1. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Gantenbein M, Attolini L, Bruguerolle B, Villard PH, Puyoou F, Durand A, Lacarelle B, Hardwigsen J, Le-Treut YP: Oxidative metabolism of bupivacaine into pipecolylxylidine in humans is mainly catalyzed by CYP3A. Drug Metab Dispos. 2000 Apr;28(4):383-5. Pubmed
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 1A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

3. Cytochrome P450 2C19

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C19 P33261 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

4. Cytochrome P450 2D6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on April 02, 2014 10:14