Identification

Summary

Bupivacaine is a local anesthetic used in a wide variety of superficial and invasive procedures.

Brand Names
Exparel, Kenalog, Marbeta, Marcaine, Marcaine With Epinephrine, Marvona Suik, P-Care M, P-Care MG, P-care, Posimir, Readysharp Anesthetics Plus Ketorolac, Readysharp-A, Readysharp-p40, Readysharp-p80, Sensorcaine, Sensorcaine With Epinephrine, Vivacaine, Xaracoll
Generic Name
Bupivacaine
DrugBank Accession Number
DB00297
Background

Bupivacaine is a widely used local anesthetic agent.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 288.4277
Monoisotopic: 288.220163528
Chemical Formula
C18H28N2O
Synonyms
  • (±)-bupivacaine
  • (RS)-bupivacaine
  • 1-Butyl-2',6'-pipecoloxylidide
  • 1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide
  • Bupivacaina
  • Bupivacaine
  • Bupivacainum
  • dl-1-Butyl-2',6'-pipecoloxylidide
  • DL-Bupivacaine
  • Racemic bupivacaine
External IDs
  • AH 250
  • DUR-843
  • LAC-43
  • SKY 0402
  • SKY-0402
  • SKY0402
  • Win 11318

Pharmacology

Indication

As an implant, bupivacaine is indicated in adults for placement into the surgical site to produce postsurgical analgesia for up to 24 hours following open inguinal hernia repair.8

Bupivacaine, in liposome suspension, is indicated in patients aged 6 years and older for single-dose infiltration to produce postsurgical local analgesia. In adults, it is also indicated as an interscalene brachial plexus nerve block to produce postsurgical regional analgesia.11

Bupivacaine, in combination with meloxicam, is indicated for postsurgical analgesia in adult patients for up to 72 hours following foot and ankle, small-to-medium open abdominal, and lower extremity total joint arthroplasty surgical procedures.7

Bupivacaine, alone or in combination with epinephrine, is indicated in adults for the production of local or regional anesthesia or analgesia for surgery, dental and oral surgery procedures, diagnostic and therapeutic procedures, and for obstetrical procedures. Specific concentrations and presentations are recommended for each type of block indicated to produce local or regional anesthesia or analgesia. Finally, its use is not indicated in all blocks given clinically significant risks associated with use.10

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Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

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.

Mechanism of action

Like lidocaine, bupivacaine is an amide local anesthetic that provides local anesthesia through blockade of nerve impulse generation and conduction.10 These impulses, also known as action potentials, critically depend on membrane depolarization produced by the influx of sodium ions into the neuron through voltage-gated sodium channels.12 Bupivacaine crosses the neuronal membrane and exerts its anesthetic action through blockade of these channels at the intracellular portion of their pore-forming transmembrane segments.3 The block is use-dependent, where repetitive or prolonged depolarization increases sodium channel blockade.5,3 Without sodium ions passing through the channel’s pore, bupivacaine stabilizes the membrane at rest and therefore prevents neurotransmission.

In general, the progression of anesthesia is related to the diameter, myelination and conduction velocity of affected nerve fibers.10 Clinically, the order of loss of nerve function is as follows: (1) pain, (2) temperature, (3) touch, (4) proprioception, and (5) skeletal muscle tone.10

While it is well-established that the main action of bupivacaine is through sodium channel block, additional analgesic effects of bupivacaine 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.3,4

TargetActionsOrganism
ASodium channel protein type 10 subunit alpha
inhibitor
Humans
UProstaglandin E2 receptor EP1 subtype
other/unknown
Humans
Absorption

Systemic absorption of local anesthetics is dose- and concentration-dependendent on the total drug administered. Other factors that affect the rate of systemic absorption include the route of administration, blood flow at the administration site, and the presence or absence of epinephrine in the anesthetic solution.

Bupivacaine formulated for instillation with meloxicam produced varied systemic measures following a single dose of varying strength. In patients undergoing bunionectomy, 60 mg of bupivacaine produced a Cmax of 54 ± 33 ng/mL, a median Tmax of 3 h, and an AUC of 1718 ± 1211 ng*h/mL. For a 300 mg dose used in herniorrhaphy, the corresponding values were 271 ± 147 ng/mL, 18 h, and 15,524 ± 8921 ng*h/mL. Lastly, a 400 mg dose used in total knee arthroplasty produced values of 695 ± 411 ng/mL, 21 h, and 38,173 ± 29,400 ng*h/mL.7

Volume of distribution

Not Available

Protein binding

Bupivacaine is ~95% protein bound.7

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.

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Route of elimination

Only 6% of bupivacaine is excreted unchanged in the urine.

Half-life

2.7 hours in adults and 8.1 hours in neonates.

Bupivacaine applied together with meloxicam for postsurgical analgesia had a median half-life of 15-17 hours, depending on dose and application site.7

Clearance

Not Available

Adverse Effects
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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.

Pathways
PathwayCategory
Bupivacaine Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Bupivacaine is combined with 1,2-Benzodiazepine.
AbametapirThe serum concentration of Bupivacaine can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Bupivacaine can be increased when combined with Abatacept.
AbemaciclibThe risk or severity of methemoglobinemia can be increased when Abemaciclib is combined with Bupivacaine.
AbirateroneThe metabolism of Bupivacaine can be decreased when combined with Abiraterone.
AcebutololThe serum concentration of Bupivacaine can be increased when it is combined with Acebutolol.
AcetaminophenThe risk or severity of methemoglobinemia can be increased when Acetaminophen is combined with Bupivacaine.
AcetazolamideThe risk or severity of methemoglobinemia can be increased when Acetazolamide is combined with Bupivacaine.
Acetic acidThe risk or severity of methemoglobinemia can be increased when Acetic acid is combined with Bupivacaine.
AcetophenazineThe risk or severity of adverse effects can be increased when Bupivacaine is combined with Acetophenazine.
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Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Bupivacaine hydrochloride7TQO7W3VT873360-54-0HUCIWBPMHXGLFM-UHFFFAOYSA-N
Bupivacaine hydrochloride anhydrousAKA908P8J118010-40-7SIEYLFHKZGLBNX-UHFFFAOYSA-N
International/Other Brands
Bupivan (Sun) / Carbostesin (AstraZeneca) / Marcain (AstraZeneca) / Marcaina (AstraZeneca) / Posimir (Durect) / Sensorcaine-MPF (Astra Zeneca) / Xaracoll (Innocoll Holdings Limited)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
BUPIVACAINE HClInjection, solution5 mg/1mLPerineuralHF Acquisition Co LLC, DBA HealthFirst2022-07-11Not applicableUS flag
Bupivacaine HClInjection, solution1.25 mg/1mLEpiduralCantrell Drug Company2011-08-012015-01-14US flag
BUPIVACAINE HClInjection, solution2.5 mg/1mLInfiltration; PerineuralHF Acquisition Co LLC, DBA HealthFirst2022-07-13Not applicableUS flag
Bupivacaine HClInjection, solution2.5 mg/1mLEpiduralCantrell Drug Company2012-05-182015-01-14US flag
Bupivacaine Heavy Injection BPSolution15 mg / 2 mLIntraspinalAuro Pharma IncNot applicableNot applicableCanada flag
Bupivacaine HydrochlorideInjection, solution5 mg/1mLEpidural; InfiltrationHospira, Inc.2007-03-312007-05-31US flag
Bupivacaine HydrochlorideInjection, solution5 mg/1mLEpidural; Infiltration; IntracaudalHospira, Inc.2010-05-192010-05-19US flag
Bupivacaine HydrochlorideInjection, solution7.5 mg/1mLEpidural; RetrobulbarHospira, Inc.2007-03-312007-05-31US flag
Bupivacaine HydrochlorideInjection, solution2.5 mg/1mLEpidural; InfiltrationHospira, Inc.2007-03-31Not applicableUS flag
Bupivacaine HydrochlorideInjection, solution5 mg/1mLEpidural; InfiltrationHospira, Inc.2006-05-232006-05-23US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
0.25% BUPIVACAINE HClInjection, solution2.5 mg/1mLInfiltration; PerineuralHF Acquisition Co LLC, DBA HealthFirst2022-08-01Not applicableUS flag
Bupivacaine HciInjection, solution2.5 mg/1mLInfiltration; PerineuralHF Acquisition Co LLC, DBA HealthFirst2022-07-10Not applicableUS flag
Bupivacaine HydrochlorideInjection, solution5 mg/1mLEpidural; IntracaudalRemedy Repack2016-06-072016-06-09US flag
Bupivacaine HydrochlorideInjection, solution7.5 mg/1mLIntraspinalBaxter Healthcare Corporation2016-08-08Not applicableUS flag
Bupivacaine HydrochlorideInjection7.5 mg/1mLIntravenousHuons Co., Ltd.2019-12-30Not applicableUS flag
Bupivacaine HydrochlorideInjection, solution7.5 mg/1mLEpidural; RetrobulbarHikma Pharmaceuticals USA Inc.2021-02-11Not applicableUS flag
Bupivacaine HydrochlorideInjection, solution2.5 mg/1mLEpidural; Infiltration; Intracaudal; PerineuralSagent Pharmaceuticals2015-04-012015-04-01US flag
Bupivacaine HydrochlorideInjection, solution7.5 mg/1mLEpidural; RetrobulbarAuroMedics Pharma LLC2013-11-05Not applicableUS flag
Bupivacaine HydrochlorideInjection, solution5 mg/1mLEpidural; Intracaudal; PerineuralREMEDYREPACK INC.2019-04-26Not applicableUS flag
Bupivacaine HydrochlorideInjection, solution7.5 mg/1mLEpidural; RetrobulbarHospira, Inc.2005-06-08Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
BlBupivacaine hydrochloride (5 mg/1mL) + Isopropyl alcohol (0.7 mL/1) + Lidocaine hydrochloride (20 mg/1mL) + Povidone-iodine (0.10 g/1)KitEpidural; Infiltration; TopicalSa3, Llc2015-07-012017-12-01US flag
BtBupivacaine hydrochloride (5 mg/1mL) + Isopropyl alcohol (0.7 mL/1) + Povidone-iodine (0.10 g/1) + Triamcinolone acetonide (40 mg/1mL)Cloth; Injection, solution; Kit; SolutionEpidural; Infiltration; Intra-articular; Intramuscular; TopicalSa3, Llc2015-07-012017-12-01US flag
BUPITROY® HEAVY 5 MG/MLBupivacaine hydrochloride anhydrous (20 mg) + D-glucose monohydrate (320 mg)SolutionIntraspinalDISTRIBUIDORA SICMAFARMA S.A.S.2013-10-09Not applicableColombia flag
BUPIVACAINA 0.5 % EPINEFRINA 1:200.000 AMPOLLASBupivacaine hydrochloride (50 mg) + Epinephrine bitartrate (50 mcg)SolutionEpiduralROPSOHN LABORATORIOSS.A.S. (PLANTA INYECTABLES)2006-11-102018-10-01Colombia flag
BUPIVACAINA CLORHIDRATO 5MG/ML + DEXTROSA80 MG/ML AMPOLLABupivacaine hydrochloride anhydrous (20 mg) + Dextrose, unspecified form (320 mg)SolutionIntraspinalSETAA PHARMA S.A.S.2019-08-27Not applicableColombia flag
Bupivacaine Hci and EpinephrineBupivacaine hydrochloride (5 mg/1mL) + Epinephrine bitartrate (0.005 mg/1mL)Injection, solutionPerineuralHF Acquisition Co LLC, DBA HealthFirst2019-12-09Not applicableUS flag
Bupivacaine HCl 0.5% and Epinephrine 1:200,000 InjectionBupivacaine hydrochloride (5 mg / mL) + Epinephrine bitartrate (0.0091 mg / mL)SolutionInfiltrationNovocol Inc.2012-05-07Not applicableCanada flag
Bupivacaine Hydrochloride and EpinephrineBupivacaine hydrochloride (2.5 mg/1mL) + Epinephrine bitartrate (5 ug/1mL)Injection, solutionEpidural; Infiltration; Intracaudal; PerineuralHenry Schein, Inc.2022-01-09Not applicableUS flag
Bupivacaine Hydrochloride and EpinephrineBupivacaine hydrochloride (2.5 mg/1mL) + Epinephrine bitartrate (5 ug/1mL)Injection, solutionEpidural; Infiltration; IntracaudalCardinal Health1988-06-162017-10-31US flag
Bupivacaine Hydrochloride and EpinephrineBupivacaine hydrochloride (5 mg/1mL) + Epinephrine bitartrate (5 ug/1mL)Injection, solutionPerineuralHospira, Inc.2005-07-26Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Bupivacaine HClBupivacaine hydrochloride (1.25 mg/1mL)Injection, solutionEpiduralCantrell Drug Company2011-08-012015-01-14US flag
Bupivacaine HClBupivacaine hydrochloride (2.5 mg/1mL)Injection, solutionEpiduralCantrell Drug Company2012-05-182015-01-14US flag
Bupivacaine HydrochlorideBupivacaine hydrochloride anhydrous (5 mg/1mL)InjectionEpidural; Intracaudal; PerineuralAreva Pharmaceuticals2019-07-12Not applicableUS flag
Bupivacaine HydrochlorideBupivacaine hydrochloride anhydrous (2.5 mg/1mL)InjectionEpidural; Intracaudal; PerineuralAreva Pharmaceuticals2019-07-12Not applicableUS flag
Bupivacaine HydrochlorideBupivacaine hydrochloride anhydrous (5 mg/1mL)InjectionEpidural; Intracaudal; PerineuralAreva Pharmaceuticals2019-07-12Not applicableUS flag
Bupivacaine HydrochlorideBupivacaine hydrochloride anhydrous (2.5 mg/1mL)InjectionEpidural; Intracaudal; PerineuralAreva Pharmaceuticals2019-07-12Not applicableUS flag
Bupivilog KitBupivacaine hydrochloride (5 mg/1mL) + Povidone-iodine (10 mg/1mL) + Triamcinolone acetonide (40 mg/1mL)KitEpidural; Intra-articular; Intramuscular; TopicalAsclemed Usa, Inc.2014-02-04Not applicableUS flag
Chi-Myst Resolve TopicalBupivacaine hydrochloride (0.09 g/30mL) + Chitosan low molecular weight (20-200 mpa.s) (0.03 g/30mL) + Ketorolac tromethamine (0.09 g/30mL) + Lidocaine hydrochloride (50 g/30mL)Spray, meteredTopicalPrescription Care Llc2016-06-01Not applicableUS flag
Chi-Myst Resolve TopicalBupivacaine hydrochloride (0.3 g/100mL) + Chitosan low molecular weight (20-200 mpa.s) (0.1 g/100mL) + Ketorolac tromethamine (0.3 g/100mL) + Lidocaine hydrochloride (5 g/100mL)Spray, meteredTopicalPrescription Care Llc2016-06-01Not applicableUS flag
Chi-Myst Synergy TopicalBupivacaine hydrochloride (0.09 g/30mL) + Chitosan low molecular weight (20-200 mpa.s) (0.03 g/30mL) + Ketorolac tromethamine (0.45 g/30mL) + Lidocaine hydrochloride (1.5 g/30mL)Spray, meteredTopicalPrescription Care Llc2016-06-01Not applicableUS flag

Categories

ATC Codes
N01BB01 — BupivacaineN01BB59 — Bupivacaine and meloxicamN01BB51 — Bupivacaine, combinations
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acid amides
Alternative Parents
Piperidinecarboxamides / Anilides / m-Xylenes / N-arylamides / Trialkylamines / Secondary carboxylic acid amides / Azacyclic compounds / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
2-piperidinecarboxamide / Alpha-amino acid amide / Amine / Anilide / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxamide group / Hydrocarbon derivative
show 16 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
piperidinecarboxamide, tertiary amino compound, aromatic amide (CHEBI:77431)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
Y8335394RO
CAS number
38396-39-3
InChI Key
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

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. [Article]
  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. [Article]
  3. Zhang H, Ji H, Liu Z, Ji Y, You X, Ding G, Cheng Z: Voltage-dependent blockade by bupivacaine of cardiac sodium channels expressed in Xenopus oocytes. Neurosci Bull. 2014 Aug;30(4):697-710. doi: 10.1007/s12264-013-1449-1. Epub 2014 Jul 9. [Article]
  4. Honemann CW, Heyse TJ, Mollhoff T, Hahnenkamp K, Berning S, Hinder F, Linck B, Schmitz W, van Aken H: The inhibitory effect of bupivacaine on prostaglandin E(2) (EP(1)) receptor functioning: mechanism of action. Anesth Analg. 2001 Sep;93(3):628-34. doi: 10.1097/00000539-200109000-00019. [Article]
  5. 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. [Article]
  6. Link [Link]
  7. FDA Approved Drug Products: ZYNRELEF (bupivacaine and meloxicam) extended-release solution for injection [Link]
  8. FDA Approved Drug Products: Xaracoll (bupivacaine hydrochloride) for inguinal implantation [Link]
  9. FDA Approved Drug Products: Sensorcaine (bupivacaine hydrochloride, or bupivacaine hydrochloride and epinephrine) solution for injection use [Link]
  10. FDA Approved Products: MARCAINE (bupivacaine hydrochloride) injection, for infiltration, perineural, caudal, epidural, or retrobulbar use [Link]
  11. FDA Approved Drug Products: EXPAREL (bupivacaine liposome) injectable suspension, for local infiltration [Link]
  12. StatPearls Internet: Bupivacaine Profile [Link]
Human Metabolome Database
HMDB0014442
KEGG Compound
C07529
PubChem Compound
2474
PubChem Substance
46506768
ChemSpider
2380
BindingDB
50350790
RxNav
1815
ChEBI
77431
ChEMBL
CHEMBL1098
Therapeutic Targets Database
DAP001229
PharmGKB
PA135057240
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Bupivacaine
FDA label
Download (147 KB)
MSDS
Download (73.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentAnterior Cruciate Ligament Injury1
4Active Not RecruitingTreatmentComplications; Cesarean Section / Opioids Use / Pain1
4Active Not RecruitingTreatmentImmunosuppression / Neoplasms, Lung / Pain1
4Active Not RecruitingTreatmentModified Radical Mastectomy1
4Active Not RecruitingTreatmentOpioids Use / Post Operative Nausea and Vomiting (PONV) / Postoperative pain1
4Active Not RecruitingTreatmentPain1
4CompletedNot AvailableHaemorrhoids / Peri-anal Fistulas1
4CompletedNot AvailablePain1
4CompletedNot AvailablePostoperative pain1
4CompletedBasic SciencePain1

Pharmacoeconomics

Manufacturers
  • Hospira inc
  • International medicated systems ltd
  • App pharmaceuticals llc
Packagers
  • APP Pharmaceuticals
  • A-S Medication Solutions LLC
  • AstraZeneca Inc.
  • Cardinal Health
  • General Injectables and Vaccines Inc.
  • Hospira Inc.
  • Medisca Inc.
  • Pharmakon
  • Pharmedium
  • Physicians Total Care Inc.
  • Prescript Pharmaceuticals
Dosage Forms
FormRouteStrength
KitEpidural; Infiltration; Topical
Cloth; injection, solution; kit; solutionEpidural; Infiltration; Intra-articular; Intramuscular; Topical
Injection, solutionParenteral
Injection0.5 %
Injection, solutionParenteral
SolutionIntraspinal
SolutionParenteral7.5 mg
SolutionEpidural50 mg
SolutionSubcutaneous5 mg
SolutionEpidural
SolutionParenteral5 mg
SolutionIntramuscular5 mg
SolutionEpidural; Intrathecal50 mg
Injection, solution5 MG/ML
Injection, solution
Injection, solution0.25 %
Injection, solution0.50 %
Injection, solutionEpidural1.25 mg/1mL
Injection, solutionEpidural2.5 mg/1mL
InjectionParenteral250 mg
InjectionEpidural; Intracaudal; Perineural2.5 mg/1mL
InjectionEpidural; Intracaudal; Perineural5 mg/1mL
InjectionIntravenous7.5 mg/1mL
Injection, solutionEnteral; Epidural; Intracaudal5 mg/1mL
Injection, solutionEpidural; Infiltration2.5 mg/1mL
Injection, solutionEpidural; Infiltration5 mg/1mL
Injection, solutionEpidural; Infiltration; Intracaudal2.5 mg/1mL
Injection, solutionEpidural; Infiltration; Intracaudal5 mg/1mL
Injection, solutionEpidural; Infiltration; Intracaudal; Perineural2.5 mg/1mL
Injection, solutionEpidural; Intracaudal5 mg/1mL
Injection, solutionEpidural; Intracaudal; Perineural5 mg/1mL
Injection, solutionEpidural; Retrobulbar7.5 mg/1mL
Injection, solutionInfiltration; Perineural2.5 mg/1mL
Injection, solutionIntraspinal7.5 mg/1mL
Injection, solutionPerineural5 mg/1mL
SolutionParenteral0.0025 g
SolutionParenteral100 mg
Injection, solutionDental; Infiltration
Injection, solutionEpidural; Infiltration; Intracaudal
Injection, solutionEpidural; Infiltration; Intracaudal; Perineural
SolutionIntraspinal7.5 mg / mL
SolutionInfiltration2.5 mg / mL
SolutionEpidural; Infiltration; Intracaudal2.5 mg / mL
SolutionEpidural; Infiltration; Intracaudal5 mg / mL
SolutionEpidural; Infiltration; Intracaudal7.5 mg / mL
SolutionEpidural; Infiltration2.5 mg / mL
SolutionEpidural; Infiltration5 mg / mL
SolutionEpidural; Retrobulbar7.5 mg / mL
SolutionInfiltration5 mg / mL
InjectionSubarachnoid7.5 mg/1mL
SolutionParenteral125 mg
Injection, solutionEpidural; Infiltration2.5 mg/mL
Injection, solutionEpidural; Infiltration5 mg/mL
KitEpidural; Intra-articular; Intramuscular; Topical
SolutionEpidural7.5 mg
SolutionParenteral
SolutionParenteral50 mg
InjectionIntraspinal
SolutionParenteral
Spray, meteredTopical
Injection, solution; injection, suspension; kitEpidural; Intra-articular; Intracaudal; Intramuscular; Intravenous; Perineural; Topical
InjectionEpidural; Intracaudal5 mg/ml
KitEpidural; Infiltration; Intramuscular; Intravenous; Topical
KitEpidural; Infiltration; Intracaudal; Subcutaneous; Topical
InjectionRetrobulbar
KitIntra-articular; Intralesional; Intramuscular; Soft tissue; Topical
KitEpidural; Infiltration; Intra-articular; Intralesional; Intramuscular; Intravenous; Soft tissue; Subcutaneous; Topical
KitEpidural; Infiltration; Intra-articular; Intralesional; Intramuscular; Soft tissue; Topical
Injection, suspension, liposomalInfiltration13.3 mg/1mL
Injection133 MG/10ML
Injection266 MG/20ML
Injection, solutionEpidural
Injection, solution; kitInfiltration; Perineural; Topical
Injection, solution; kitPerineural; Retrobulbar; Topical
Injection, solution; injection, suspension; kitInfiltration; Intra-articular; Intralesional; Intramuscular; Perineural; Topical
SolutionEpidural75 mg
Injection, solution; kitIntra-articular; Intralesional; Intramuscular; Intravenous; Perineural; Soft tissue
KitEpidural; Infiltration; Intra-articular; Intralesional; Intramuscular; Topical
InjectionEpidural
InjectionEpidural5 mg/ml
InjectionIntrathecal5 mg/ml
Injection, solutionEpidural
Injection, solutionEpidural; Infiltration
Injection, solutionEpidural5 mg/1mL
Injection, solutionInfiltration2.5 mg/1mL
Injection, solutionInfiltration5 mg/1mL
Injection, solutionSubcutaneous
SolutionEpidural; Retrobulbar150 mg / 20 mL
SolutionInfiltration125 mg / 50 mL
SolutionInfiltration250 mg / 50 mL
LiquidEpidural; Infiltration2.5 mg / mL
LiquidInfiltration
InjectionEpidural
LiquidEpidural; Infiltration5 mg / mL
LiquidEpidural; Retrobulbar7.5 mg / mL
LiquidIntraspinal7.5 mg / mL
LiquidEpidural; Infiltration
Injection, solutionSubarachnoid7.5 mg/1mL
SolutionIntraspinal15 mg / 2 mL
Injection, solutionInfiltration
KitIntravenous
KitEpidural; Infiltration; Intra-articular; Intramuscular
KitEpidural; Infiltration; Intra-articular; Intramuscular; Topical
Injection, solution; kitEpidural; Intracaudal; Intramuscular; Intravenous; Perineural; Topical
Injection, solution; kit; solutionEpidural; Infiltration; Intracaudal; Intravenous; Perineural; Topical
Injection, solution; injection, suspension; kit; solutionEpidural; Infiltration; Intra-articular; Intracaudal; Intralesional; Intramuscular; Intravenous; Perineural; Soft tissue; Topical
Injection, solution; injection, suspension; kit; solutionEpidural; Infiltration; Intra-articular; Intracaudal; Intramuscular; Intravenous; Perineural; Topical
Injection; injection, solution; kit; solutionEpidural; Intracaudal; Intravenous; Perineural; Topical
Injection, solution; kit; solutionEpidural; Intracaudal; Intravenous; Perineural; Topical
KitEpidural; Infiltration; Intramuscular; Intrasynovial; Soft tissue; Topical
KitEpidural; Infiltration; Intracaudal; Perineural
SolutionInfiltration660 mg/5mL
KitTopical
Injection5 mg/ml
KitIntra-articular; Intralesional; Intramuscular
KitIntramuscular; Intravenous
KitEpidural; Infiltration
Solution
Injection
InjectionInfiltration; Parenteral2.5 mg/1mL
InjectionParenteral5 mg/1mL
Injection, solutionInfiltration; Perineural
Injection, solutionPerineural
InjectionEpidural; Infiltration; Parenteral2.5 mg/1mL
InjectionEpidural; Parenteral5 mg/1mL
InjectionEpidural; Parenteral; Retrobulbar7.5 mg/1mL
Injection, solutionEpidural; Intracaudal; Perineural
Injection, solutionEpidural; Retrobulbar
InjectionEpidural; Parenteral
InjectionEpidural; Parenteral; Retrobulbar
SolutionEpidural; Infiltration
InjectionDental5 mg
ImplantParenteral100 mg/1
SolutionInfiltration
SolutionIntralesional
Solution, gel forming, extended release
Solution2.5 mg/1ml
Solution5 mg/1ml
Injection, solution5 mg/1ml
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)Region
US8182835No2012-05-222018-09-18US flag
US8834921No2014-09-162018-09-18US flag
US9205052No2015-12-082018-09-18US flag
US9585838No2017-03-072021-12-24US flag
USRE47826No2020-01-282029-05-20US flag
US8753665No2014-06-172025-09-15US flag
US8846072No2014-09-302025-09-15US flag
US8153661No2012-04-102025-09-15US flag
US8153149No2012-04-102025-09-15US flag
US9592227No2017-03-142034-03-13US flag
US9694079No2017-07-042035-04-20US flag
US9801945No2017-10-312035-04-20US flag
US10213510No2019-02-262035-04-20US flag
US9913909No2018-03-132034-03-13US flag
US10098957No2018-10-162035-04-20US flag
US10632199No2020-04-282035-04-20US flag
US10898575No2021-01-262035-04-20US flag
US10980886No2021-04-202035-04-20US flag
US10398686No2019-09-032034-03-13US flag
US9744163No2017-08-292034-03-13US flag
US11033495No2021-06-152041-01-22US flag
US11083797No2021-08-102035-04-20US flag
US11083730No2021-08-102035-04-20US flag
US11179336No2021-11-232041-01-22US flag
US11253504No2014-03-132034-03-13US flag
US11278494No2021-01-222041-01-22US flag
US11311486No2021-01-222041-01-22US flag
US11304904No2021-01-222041-01-22US flag
US11357727No2021-01-222041-01-22US flag
US11426348No2021-01-222041-01-22US flag
US11400019No2021-01-122041-01-12US flag
US11413350No2015-04-202035-04-20US flag
US11452691No2021-01-222041-01-22US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)107-108 °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
Polarizability34.2 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
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)

Spectra

Mass Spec (NIST)
Download (8.44 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-000i-0290000000-c1dbebb634be5e7e1140
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0006-0910000000-ae34de204bcb9a9deb23
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0006-0900000000-7ea7001506aae0c271a0
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0006-2900000000-ef819c5e235d6d524d8c
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0006-7900000000-22d7491053c05d773e93
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001l-9400000000-71357b8186126c5933ce

Targets

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Kind
Protein
Organism
Humans
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 acro...
Gene Name
SCN10A
Uniprot ID
Q9Y5Y9
Uniprot Name
Sodium channel protein type 10 subunit alpha
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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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 importa...
Gene Name
PTGER1
Uniprot ID
P34995
Uniprot Name
Prostaglandin E2 receptor EP1 subtype
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. [Article]
  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. [Article]
  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. [Article]

Enzymes

Kind
Protein
Organism
Humans
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 im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 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. [Article]
Kind
Protein
Organism
Humans
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...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 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. [Article]
  2. Prescriber's digital reference, Marcaine with Epinephrine-bipuvacaine-hydrochloride [Link]
Kind
Protein
Organism
Humans
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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
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. [Article]

Drug created at June 13, 2005 13:24 / Updated at November 26, 2022 07:39