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

A widely used local anesthetic agent. [PubChem]

Structure
Thumb
Synonyms
(+-)-Bupivacaine
(RS)-bupivacaine
1-Butyl-2',6'-pipecoloxylidide
1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide
Bupivacaina
Bupivacaine
Bupivacainum
Carbostesin
dl-1-Butyl-2',6'-pipecoloxylidide
DL-Bupivacaine
Racemic bupivacaine
External Identifiers
  • DUR-843
  • LAC-43
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Bupivacaine Hydrochlorideinjection, solution7.5 mg/mLepidural; retrobulbarHospira, Inc.1978-04-172016-04-23Us
Bupivacaine Hydrochlorideinjection, solution5 mg/mLepidural; intracaudalHospira, Inc.1978-04-172016-04-23Us
Bupivacaine Hydrochlorideinjection, solution2.5 mg/mLepidural; infiltration; intracaudalHospira, Inc.1978-04-172016-04-23Us
Bupivacaine Hydrochlorideinjection, solution5 mg/mLepidural; infiltration; intracaudalHospira, Inc.1978-04-172016-04-23Us
Bupivacaine Hydrochlorideinjection, solution5 mg/mLepidural; infiltration; intracaudalHospira, Inc.1978-04-172016-04-23Us
Bupivacaine Hydrochlorideinjection, solution7.5 mg/mLepidural; retrobulbarHospira, Inc.1978-04-172016-04-23Us
Bupivacaine Hydrochlorideinjection, solution2.5 mg/mLepidural; infiltration; intracaudalHospira, Inc.1978-04-172016-04-23Us
Bupivacaine Hydrochloride Injection USPsolution2.5 mgblock/infiltrationMylan Pharmaceuticals UlcNot applicableNot applicableCanada
Bupivacaine Hydrochloride Injection USPsolution5 mgblock/infiltrationMylan Pharmaceuticals UlcNot applicableNot applicableCanada
Bupivacaine Hydrochloride Injection USPsolution7.5 mgretrobulbar; epiduralMylan Pharmaceuticals UlcNot applicableNot applicableCanada
Bupivacaine Hydrochloride Injection USPsolution5 mgblock/infiltration; epiduralMylan Pharmaceuticals UlcNot applicableNot applicableCanada
Bupivacaine Hydrochloride Injection USPsolution2.5 mgblock/infiltration; epiduralMylan Pharmaceuticals UlcNot applicableNot applicableCanada
Bupivacaine Hydrochloride Injection USP .25%solution2.5 mgblock/infiltration; intracaudal; epiduralHospira Healthcare Corporation1996-07-302011-08-05Canada
Bupivacaine Hydrochloride Injection USP .50%solution5 mgblock/infiltration; intracaudal; epiduralHospira Healthcare Corporation1996-07-302011-08-05Canada
Bupivacaine Hydrochloride Injection USP .75%solution7.5 mgblock/infiltration; intracaudal; epiduralHospira Healthcare Corporation1996-07-302011-08-05Canada
Bupivacaine Injection BPsolution5 mgblock/infiltration; epiduralSterimax IncNot applicableNot applicableCanada
Bupivacaine Injection BPsolution2.5 mgblock/infiltration; epiduralSterimax IncNot applicableNot applicableCanada
Exparelinjection, suspension, liposomal13.3 mg/mLinfiltrationPacira Pharmaceuticals Inc.2016-01-012016-04-01Us
Exparelinjection, suspension, liposomal13.3 mg/mLinfiltrationPacira Pharmaceuticals Inc.2012-01-012016-04-05Us
Jamp-bupivacainesolution5 mgblock/infiltrationJamp Pharma CorporationNot applicableNot applicableCanada
Jamp-bupivacainesolution5 mgblock/infiltration; epiduralJamp Pharma CorporationNot applicableNot applicableCanada
Jamp-bupivacainesolution2.5 mgblock/infiltrationJamp Pharma CorporationNot applicableNot applicableCanada
Jamp-bupivacainesolution2.5 mgblock/infiltration; epiduralJamp Pharma CorporationNot applicableNot applicableCanada
Marcaineinjection, solution7.5 mg/mLepidural; retrobulbarA S Medication Solutions Llc2009-09-092016-04-05Us
Marcaineinjection, solution2.5 mg/mLepidural; infiltrationHospira, Inc.1972-10-032016-04-23Us
Marcaineinjection, solution2.5 mg/mLinfiltrationPhysicians Total Care, Inc.2009-09-082016-04-05Us
Marcaineinjection, solution5 mg/mLepiduralGeneral Injectables & Vaccines, Inc2010-03-012016-04-05Us
Marcaineinjection, solution2.5 mg/mLepidural; infiltrationGeneral Injectables & Vaccines, Inc2010-08-012016-04-05Us
Marcaineinjection, solution5 mg/mLepiduralREMEDYREPACK INC.2013-06-122016-04-05Us
Marcaineinjection, solution5 mg/mLinfiltrationHospira, Inc.1972-10-032016-04-23Us
Marcaineinjection, solution2.5 mg/mLinfiltrationHospira, Inc.1972-10-032016-04-23Us
Marcaineinjection, solution5 mg/mLepiduralREMEDYREPACK INC.2015-03-072016-04-05Us
Marcaineinjection, solution7.5 mg/mLepidural; retrobulbarHospira, Inc.1972-10-032016-04-23Us
Marcaineinjection, solution5 mg/mLepidural; infiltrationHospira, Inc.1972-10-032016-04-23Us
Marcaineinjection, solution2.5 mg/mLepidural; infiltrationCardinal Health2009-09-082016-04-05Us
Marcaine 0.25%solution2.5 mgblock/infiltrationHospira Healthcare Corporation2008-10-08Not applicableCanada
Marcaine 0.25% Liq Prt 2.5mg/mlliquid2.5 mgblock/infiltration; epiduralSanofi Canada, Inc.1973-12-312001-08-10Canada
Marcaine 0.50%solution5.0 mgblock/infiltrationHospira Healthcare Corporation2008-09-17Not applicableCanada
Marcaine 0.50% Liq Bin 5mg/mlliquid5 mgblock/infiltration; epiduralSanofi Canada, Inc.1973-12-312001-08-10Canada
Marcaine 0.75% Liq Prt 7.5mg/mlliquid7.5 mgretrobulbar; epiduralSanofi Canada, Inc.1974-12-312001-08-10Canada
Marcaine 0.75% Liq Spinal 7.5mg/mlliquid7.5 mgintraspinalSanofi Canada, Inc.1979-12-312001-08-10Canada
Marcaine 2.5 mg/mlsolution2.5 mgblock/infiltration; epiduralHospira Healthcare Corporation2000-12-01Not applicableCanada
Marcaine 5 mg/mlsolution5.0 mgblock/infiltration; epiduralHospira Healthcare Corporation2000-12-01Not applicableCanada
Marcaine 7.5 mg/mlsolution7.5 mgretrobulbar; epiduralHospira Healthcare Corporation2001-09-15Not applicableCanada
Marcaine Spinalinjection, solution7.5 mg/mLsubarachnoidHospira, Inc.1984-05-042016-04-23Us
Marcaine Spinal 7.5 mg/mlsolution7.5 mgintraspinalHospira Healthcare Corporation2000-12-01Not applicableCanada
Sensorcaineinjection, solution5 mg/mLperineuralFresenius Kabi USA, LLC2010-11-192016-04-05Us
Sensorcaineinjection, solution2.5 mg/mLinfiltration; perineuralFresenius Kabi USA, LLC2010-11-192016-04-05Us
Sensorcaine 0.25%liquid2.5 mgblock/infiltration; epiduralAstrazeneca Canada Inc1994-12-31Not applicableCanada
Sensorcaine 0.5%liquid5 mgblock/infiltration; epiduralAstrazeneca Canada Inc1994-12-31Not applicableCanada
Sensorcaine Mpfinjection, solution5 mg/mLepidural; intracaudal; perineuralFresenius Kabi USA, LLC2010-11-192016-04-05Us
Sensorcaine Mpfinjection, solution2.5 mg/mLepidural; infiltration; intracaudal; perineuralFresenius Kabi USA, LLC2010-11-192016-04-05Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Bupivacaineinjection, solution7.5 mg/mLsubarachnoidHospira, Inc.1987-12-112016-04-23Us
Bupivacaine Hydrochlorideinjection, solution7.5 mg/mLepidural; retrobulbarAuro Medics Pharma Llc2013-11-052016-04-05Us
Bupivacaine Hydrochlorideinjection5 mg/mLinfiltrationGeneral Injectables & Vaccines, Inc2010-07-012016-04-05Us
Bupivacaine Hydrochlorideinjection, solution2.5 mg/mLepidural; infiltration; intracaudalHospira, Inc.1987-03-032016-04-23Us
Bupivacaine Hydrochlorideinjection, solution7.5 mg/mLepidural; retrobulbarAuro Medics Pharma Llc2013-11-052016-04-05Us
Bupivacaine Hydrochlorideinjection, solution5 mg/mLepidural; intracaudalAuro Medics Pharma Llc2013-11-052016-04-05Us
Bupivacaine Hydrochlorideinjection2.5 mg/mLinfiltrationGeneral Injectables & Vaccines, Inc2010-07-012016-04-05Us
Bupivacaine Hydrochlorideinjection, solution2.5 mg/mLepidural; infiltration; intracaudalHospira, Inc.1987-02-172016-04-23Us
Bupivacaine Hydrochlorideinjection, solution5 mg/mLepidural; intracaudalAuro Medics Pharma Llc2013-11-052016-04-05Us
Bupivacaine Hydrochlorideinjection, solution2.5 mg/mLepidural; infiltration; intracaudalAuro Medics Pharma Llc2013-11-052016-04-05Us
Bupivacaine Hydrochlorideinjection, solution7.5 mg/mLepidural; retrobulbarHospira, Inc.1987-03-032016-04-23Us
Bupivacaine Hydrochlorideinjection, solution2.5 mg/mLepidural; infiltration; intracaudalAuro Medics Pharma Llc2013-11-052016-04-05Us
Bupivacaine Hydrochlorideinjection, solution5 mg/mLinfiltrationHospira, Inc.1987-03-032016-04-23Us
Bupivacaine Hydrochlorideinjection, solution2.5 mg/mLepidural; infiltration; intracaudalCardinal Health2010-01-062016-04-05Us
Bupivacaine Hydrochlorideinjection, solution5 mg/mLepidural; intracaudalHospira, Inc.1987-02-172016-04-23Us
Bupivacaine Hydrochlorideinjection, solution2.5 mg/mLepidural; infiltration; intracaudalCardinal Health2010-01-062016-04-05Us
Bupivacaine Hydrochlorideinjection, solution5 mg/mLepidural; intracaudalHospira, Inc.1987-03-032016-04-23Us
Bupivacaine Hydrochlorideinjection, solution5 mg/mLepidural; infiltration; intracaudalCardinal Health2010-01-072016-04-05Us
Bupivacaine Hydrochlorideinjection, solution5 mg/mLepidural; infiltration; intracaudalCardinal Health2010-01-072016-04-05Us
Bupivacaine Hydrochlorideinjection, solution2.5 mg/mLinfiltrationHospira, Inc.1987-02-172016-04-23Us
Sensorcaineinjection, solution5 mg/mLperineuralGeneral Injectables & Vaccines, Inc2011-10-182016-04-05Us
Sensorcaineinjection, solution2.5 mg/mLinfiltration; perineuralGeneral Injectables & Vaccines, Inc2011-10-172016-04-05Us
Sensorcaine Mpfinjection, solution7.5 mg/mLsubarachnoidFresenius Kabi USA, LLC2010-05-252016-04-05Us
Sensorcaine Mpfinjection, solution7.5 mg/mLepidural; retrobulbarFresenius Kabi USA, LLC2010-11-192016-04-05Us
Sensorcaine Mpfinjection, solution5 mg/mLepidural; intracaudal; perineuralGeneral Injectables & Vaccines, Inc2011-10-262016-04-05Us
Over the Counter ProductsNot Available
International Brands
NameCompany
BupivanSun
CarbostesinAstraZeneca
MarcainAstraZeneca
MarcainaAstraZeneca
Sensorcaine-MPFAstra Zeneca
Brand mixtures
NameLabellerIngredients
Bupivacaine HCl 0.5% and Epinephrine 1:200,000 InjectionNovocol Pharmaceutical Of Canada Inc
Bupivacaine Hydrochloride and EpinephrineGeneral Injectables & Vaccines, Inc
Disposable Convenience Kit (single Shot Epidural)True Fit Rx Llc
Fentanyl Citrate, Bupivacaine HClCantrell Drug Company
MarcaineCarestream Health Inc.
Marcaine 0.5% and Epinephrine 1:200,000 LiqKodak Canada Inc.
Marcaine E 0.25% Liq PrtSanofi Canada, Inc.
Marcaine E 2.5 mg/mlHospira Healthcare Corporation
Marcaine E 5.0 mg/mlHospira Healthcare Corporation
Marcaine E Liq Prt 0.50%Sanofi Canada, Inc.
Marcaine With EpinephrineHospira, Inc.
Physicians Ez Use M-predProficient Rx LP
Readysharp-ATerrain Pharmaceuticals
Readysharp-KTerrain Pharmaceuticals
Readysharp-p40Terrain Pharmaceuticals
Readysharp-p80Terrain Pharmaceuticals
SensorcaineFresenius Kabi USA, LLC
Sensorcaine 0.25% With EpinephrineAstrazeneca Canada Inc
Sensorcaine 0.5% With EpinephrineAstrazeneca Canada Inc
Sensorcaine ForteDentsply Canada Limited
Sensorcaine MpfCardinal Health
VivacaineSeptodont, Inc.
Vivacaine (bupivacaine HCl 0.5% & Epinephrine 1:200,000 Inj, USP)Septodont Inc
Salts
Name/CASStructureProperties
Bupivacaine Hydrochloride
14252-80-3
Thumb
  • InChI Key: SIEYLFHKZGLBNX-UHFFFAOYNA-N
  • Monoisotopic Mass: 324.196841267
  • Average Mass: 324.889
DBSALT000202
Bupivacaine hydrochloride anhydrous
ThumbNot applicableDBSALT001512
Categories
UNIIY8335394RO
CAS number2180-92-9
WeightAverage: 288.4277
Monoisotopic: 288.220163528
Chemical FormulaC18H28N2O
InChI KeyInChIKey=LEBVLXFERQHONN-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.
Related Articles
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 inhibitorNon-inhibitor0.9099
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorInhibitor0.6205
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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Hospira inc
  • International medicated systems ltd
  • App pharmaceuticals llc
Packagers
Dosage forms
FormRouteStrength
Injectioninfiltration2.5 mg/mL
Injectioninfiltration5 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
Injectionepidural; infiltration; intracaudal
Injection, solutiondental; infiltration
Injection, solutionepidural; infiltration; intracaudal
Injection, solutionepidural; intracaudal
Solutionblock/infiltration2.5 mg
Solutionblock/infiltration5 mg
Solutionblock/infiltration; epidural5 mg
Solutionblock/infiltration; intracaudal; epidural2.5 mg
Solutionblock/infiltration; intracaudal; epidural5 mg
Solutionblock/infiltration; intracaudal; epidural7.5 mg
Injection, suspension, liposomalinfiltration13.3 mg/mL
Injection, solutionepidural
Injection, solutionepidural5 mg/mL
Injection, solutionepidural; infiltration2.5 mg/mL
Injection, solutionepidural; infiltration5 mg/mL
Liquidblock/infiltration
Solutionblock/infiltration5.0 mg
Liquidretrobulbar; epidural7.5 mg
Liquidintraspinal7.5 mg
Solutionblock/infiltration; epidural2.5 mg
Solutionblock/infiltration; epidural5.0 mg
Solutionretrobulbar; epidural7.5 mg
Liquidblock/infiltration; epidural
Injection, solutionsubarachnoid7.5 mg/mL
Solutionintraspinal7.5 mg
Injection, solutionepidural; infiltration
Injection, solutioninfiltration
Kit
Kitepidural; infiltration; intramuscular; intrasynovial; soft tissue; topical
Kitepidural; infiltration
Kitepidural; infiltration; intra-articular; intramuscular; topical
Kitepidural; infiltration; intra-articular; intralesional; intramuscular; soft tissue
Injection, solutioninfiltration; perineural
Injection, solutioninfiltration; perineural2.5 mg/mL
Injection, solutionperineural
Injection, solutionperineural5 mg/mL
Liquidblock/infiltration; epidural2.5 mg
Solutionblock/infiltration; epidural
Liquidblock/infiltration; epidural5 mg
Injection, solutionepidural; infiltration; intracaudal; perineural
Injection, solutionepidural; infiltration; intracaudal; perineural2.5 mg/mL
Injection, solutionepidural; intracaudal; perineural
Injection, solutionepidural; intracaudal; perineural5 mg/mL
Injection, solutionepidural; retrobulbar
Injection, solutionsubcutaneous
Solutionblock/infiltration
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.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US8182835 No1998-09-182018-09-18Us
US8834921 No1998-09-182018-09-18Us
US9205052 No1998-09-182018-09-18Us
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 References
  1. 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:16810015 ]
  2. 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:16430560 ]
  3. Link [Link]
External Links
ATC CodesN01BB01N01BB51
AHFS Codes
  • 72:00.00
PDB EntriesNot Available
FDA labelDownload (147 KB)
MSDSDownload (73.3 KB)
Interactions
Drug Interactions
Drug
AcebutololThe serum concentration of Bupivacaine can be increased when it is combined with Acebutolol.
AtenololThe serum concentration of Bupivacaine can be increased when it is combined with Atenolol.
BetaxololThe serum concentration of Bupivacaine can be increased when it is combined with Betaxolol.
BisoprololThe serum concentration of Bupivacaine can be increased when it is combined with Bisoprolol.
CarteololThe serum concentration of Bupivacaine can be increased when it is combined with Carteolol.
CarvedilolThe serum concentration of Bupivacaine can be increased when it is combined with Carvedilol.
EsmololThe serum concentration of Bupivacaine can be increased when it is combined with Esmolol.
HyaluronidaseThe risk or severity of adverse effects can be increased when Hyaluronidase is combined with Bupivacaine.
LabetalolThe serum concentration of Bupivacaine can be increased when it is combined with Labetalol.
LevobunololThe serum concentration of Bupivacaine can be increased when it is combined with Levobunolol.
MetipranololThe serum concentration of Bupivacaine can be increased when it is combined with Metipranolol.
MetoprololThe serum concentration of Bupivacaine can be increased when it is combined with Metoprolol.
NadololThe serum concentration of Bupivacaine can be increased when it is combined with Nadolol.
NebivololThe serum concentration of Bupivacaine can be increased when it is combined with Nebivolol.
PenbutololThe serum concentration of Bupivacaine can be increased when it is combined with Penbutolol.
PindololThe serum concentration of Bupivacaine can be increased when it is combined with Pindolol.
PropranololThe serum concentration of Bupivacaine can be increased when it is combined with Propranolol.
SotalolThe serum concentration of Bupivacaine can be increased when it is combined with Sotalol.
Technetium Tc-99m tilmanoceptBupivacaine may decrease effectiveness of Technetium Tc-99m tilmanocept as a diagnostic agent.
TimololThe serum concentration of Bupivacaine can be increased when it is combined with Timolol.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Voltage-gated sodium channel activity
Specific Function:
Tetrodotoxin-resistant channel that mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which sodium ions may pass in accordance with their electrochemical gradient. Plays a role in neuropathic pain mechanisms.
Gene Name:
SCN10A
Uniprot ID:
Q9Y5Y9
Molecular Weight:
220623.605 Da
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:17139284 ]
  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:17016423 ]
  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. doi: 10.1016/j.tcm.2010.03.002. [PubMed:20685573 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
other/unknown
General Function:
Prostaglandin e receptor activity
Specific Function:
Receptor for prostaglandin E2 (PGE2). The activity of this receptor is mediated by G(q) proteins which activate a phosphatidylinositol-calcium second messenger system. May play a role as an important modulator of renal function. Implicated the smooth muscle contractile response to PGE2 in various tissues.
Gene Name:
PTGER1
Uniprot ID:
P34995
Molecular Weight:
41800.655 Da
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:17139284 ]
  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:17016423 ]
  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. doi: 10.1213/ane.0b013e3181aff25e. [PubMed:19690271 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
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:10725304 ]
  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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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Drug created on June 13, 2005 07:24 / Updated on May 04, 2016 02:30