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
Structure for Bupivacaine (DB00297)
- 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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- Acute Gouty Arthritis
- Adrenal cortical hypofunctions
- Alopecia Areata (AA)
- Ankylosing Spondylitis (AS)
- Berylliosis
- Bullous dermatitis herpetiformis
- Congenital Adrenal Hyperplasia (CAH)
- Congenital Hypoplastic Anemia
- Dermatomyositis (DM)
- Discoid Lupus Erythematosus (DLE)
- Edema of the cerebrum
- Epicondylitis
- Hemolytic Anemia
- Hypercalcemia caused by Cancer
- Keloids Scars
- Leukemias
- Mycosis Fungoides (MF)
- Necrobiosis lipoidica diabeticorum
- Ocular Inflammation
- Ophthalmia, Sympathetic
- Osteoarthritis (OA)
- Pain, Labor
- Polymyositis
- Postoperative pain
- Psoriatic Arthritis
- Psoriatic plaque
- Pure Red Cell Aplasia
- Regional Enteritis
- Rheumatoid Arthritis
- Secondary thrombocytopenia
- Stevens-Johnson Syndrome
- Synovitis
- Systemic Lupus Erythematosus (SLE)
- Temporal Arteritis
- Trichinosis
- Tuberculous Meningitis
- Ulcerative Colitis
- Uveitis
- Acute Bursitis
- Acute Idiopathic Nephrotic Syndrome
- Acute Lupus Erythematosus
- Acute Multiple sclerosis
- Acute Rheumatic heart disease, unspecified
- Acute nonspecific tenosynovitis
- Cystic tumors of aponeurosis
- Cystic tumors of tendon
- Disseminated Pulmonary Tuberculosis (TB)
- Exfoliative erythroderma
- Inflammatory lesions of granuloma annulare
- Inflammatory lesions of lichen planus
- Inflammatory lesions of lichen simplex
- Non-suppurative Thyroiditis
- Permphigus
- Severe Allergic Reactions
- Associated Therapies
- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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
Target Actions Organism ASodium channel protein type 10 subunit alpha inhibitorHumans UProstaglandin E2 receptor EP1 subtype other/unknownHumans - 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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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
Pathway Category Bupivacaine Action Pathway Drug 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of adverse effects can be increased when Bupivacaine is combined with 1,2-Benzodiazepine. Abametapir The serum concentration of Bupivacaine can be increased when it is combined with Abametapir. Abatacept The metabolism of Bupivacaine can be increased when combined with Abatacept. Abiraterone The metabolism of Bupivacaine can be decreased when combined with Abiraterone. Acebutolol The serum concentration of Bupivacaine can be increased when it is combined with Acebutolol. Acetaminophen The risk or severity of methemoglobinemia can be increased when Bupivacaine is combined with Acetaminophen. Acetazolamide The risk or severity of adverse effects can be increased when Bupivacaine is combined with Acetazolamide. Acetophenazine The risk or severity of adverse effects can be increased when Bupivacaine is combined with Acetophenazine. Aclidinium Bupivacaine may increase the central nervous system depressant (CNS depressant) activities of Aclidinium. Adalimumab The metabolism of Bupivacaine can be increased when combined with Adalimumab. 
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- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Bupivacaine hydrochloride 7TQO7W3VT8 73360-54-0 HUCIWBPMHXGLFM-UHFFFAOYSA-N Bupivacaine hydrochloride anhydrous AKA908P8J1 18010-40-7 SIEYLFHKZGLBNX-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
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Bupivacaine HCl Injection, solution 2.5 mg/1mL Epidural Cantrell Drug Company 2012-05-18 2015-01-14 US 
Bupivacaine HCl Injection, solution 1.25 mg/1mL Epidural Cantrell Drug Company 2011-08-01 2015-01-14 US Bupivacaine Heavy Injection BP Solution 15 mg / 2 mL Intraspinal Auro Pharma Inc Not applicable Not applicable Canada 
Bupivacaine Hydrochloride Injection 2.5 mg/1mL Epidural; Intracaudal; Perineural Areva Pharmaceuticals 2019-07-12 Not applicable US Bupivacaine Hydrochloride Injection, solution 7.5 mg/1mL Epidural; Retrobulbar Hospira, Inc. 2007-03-31 2007-05-31 US Bupivacaine Hydrochloride Injection, solution 5 mg/1mL Epidural Hospira, Inc. 2006-08-09 2006-08-09 US Bupivacaine Hydrochloride Injection, solution 7.5 mg/1mL Epidural; Retrobulbar Hospira, Inc. 2007-03-31 2007-05-31 US Bupivacaine Hydrochloride Injection, solution 2.5 mg/1mL Epidural; Infiltration Hospira, Inc. 2006-05-23 2006-05-23 US Bupivacaine Hydrochloride Injection 5 mg/1mL Epidural; Intracaudal; Perineural Areva Pharmaceuticals 2019-07-12 Not applicable US Bupivacaine Hydrochloride Injection 2.5 mg/1mL Epidural; Intracaudal; Perineural Areva Pharmaceuticals 2019-07-12 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Bupivacaine Hydrochloride Injection, solution 2.5 mg/1mL Infiltration; Perineural AuroMedics Pharma LLC 2016-05-13 Not applicable US Bupivacaine Hydrochloride Injection, solution 5 mg/1mL Epidural; Intracaudal Asclemed Usa, Inc. 2013-11-05 Not applicable US Bupivacaine Hydrochloride Injection, solution 5 mg/1mL Epidural; Intracaudal; Perineural Hospira, Inc. 2005-11-22 Not applicable US Bupivacaine Hydrochloride Injection, solution 7.5 mg/1mL Epidural; Retrobulbar Sagent Pharmaceuticals 2015-04-01 2015-04-01 US Bupivacaine Hydrochloride Injection, solution 5 mg/1mL Epidural; Intracaudal AuroMedics Pharma LLC 2013-11-05 Not applicable US Bupivacaine Hydrochloride Injection, solution 7.5 mg/1mL Epidural; Retrobulbar Hikma Pharmaceuticals USA Inc. 2021-02-11 Not applicable US Bupivacaine Hydrochloride Injection, solution 5 mg/1mL Perineural Sagent Pharmaceuticals 2015-04-01 2015-04-01 US Bupivacaine Hydrochloride Injection, solution 5 mg/1mL Epidural; Intracaudal REMEDYREPACK INC. 2019-10-10 Not applicable US Bupivacaine Hydrochloride Injection, solution 5 mg/1mL Perineural Hospira, Inc. 2005-03-31 Not applicable US Bupivacaine Hydrochloride Injection, solution 2.5 mg/1mL Epidural; Infiltration; Intracaudal; Perineural Hikma Pharmaceuticals USA Inc. 2021-02-11 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Bl Bupivacaine hydrochloride (5 mg/1mL) + Isopropyl alcohol (0.7 mL/1) + Lidocaine hydrochloride (20 mg/1mL) + Povidone-iodine (0.10 g/1) Kit Epidural; Infiltration; Topical Sa3, Llc 2015-07-01 2017-12-01 US Bt Bupivacaine hydrochloride (5 mg/1mL) + Isopropyl alcohol (0.7 mL/1) + Povidone-iodine (0.10 g/1) + Triamcinolone acetonide (40 mg/1mL) Epidural; Infiltration; Intra-articular; Intramuscular; Topical Sa3, Llc 2015-07-01 2017-12-01 US BUPITROY® HEAVY 5 MG/ML Bupivacaine hydrochloride anhydrous (20 mg) + D-glucose monohydrate (320 mg) Solution Intraspinal DISTRIBUIDORA SICMAFARMA S.A.S. 2013-10-09 Not applicable Colombia 
BUPIVACAINA 0.5 % EPINEFRINA 1:200.000 AMPOLLAS Bupivacaine hydrochloride (50 mg) + Epinephrine bitartrate (50 mcg) Solution Epidural ROPSOHN LABORATORIOSS.A.S. (PLANTA INYECTABLES) 2006-11-10 2018-10-01 Colombia BUPIVACAINA CLORHIDRATO 5MG/ML + DEXTROSA80 MG/ML AMPOLLA Bupivacaine hydrochloride anhydrous (20 mg) + Dextrose, unspecified form (320 mg) Solution Intraspinal SETAA PHARMA S.A.S. 2019-08-27 Not applicable Colombia Bupivacaine Hci and Epinephrine Bupivacaine hydrochloride (5 mg/1mL) + Epinephrine bitartrate (0.005 mg/1mL) Injection, solution Perineural HF Acquisition Co LLC, DBA HealthFirst 2019-12-09 Not applicable US Bupivacaine HCl 0.5% and Epinephrine 1:200,000 Injection Bupivacaine hydrochloride (5 mg / mL) + Epinephrine bitartrate (0.0091 mg / mL) Solution Infiltration Novocol Inc. 2012-05-07 Not applicable Canada Bupivacaine Hydrochloride and Epinephrine Bupivacaine hydrochloride (5 mg/1mL) + Epinephrine bitartrate (5 ug/1mL) Injection, solution Perineural Hospira, Inc. 2005-07-26 Not applicable US Bupivacaine Hydrochloride and Epinephrine Bupivacaine hydrochloride (5 mg/1mL) + Epinephrine bitartrate (0.0091 mg/1mL) Injection, solution Dental; Infiltration Hospira, Inc. 2006-04-25 2012-07-01 US Bupivacaine Hydrochloride and Epinephrine Bupivacaine hydrochloride (2.5 mg/1mL) + Epinephrine bitartrate (5 ug/1mL) Injection, solution Epidural; Infiltration; Intracaudal; Perineural Hospira, Inc. 2005-06-15 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Bupivacaine HCl Bupivacaine hydrochloride (1.25 mg/1mL) Injection, solution Epidural Cantrell Drug Company 2011-08-01 2015-01-14 US Bupivacaine HCl Bupivacaine hydrochloride (2.5 mg/1mL) Injection, solution Epidural Cantrell Drug Company 2012-05-18 2015-01-14 US Bupivacaine Hydrochloride Bupivacaine hydrochloride anhydrous (5 mg/1mL) Injection Epidural; Intracaudal; Perineural Areva Pharmaceuticals 2019-07-12 Not applicable US Bupivacaine Hydrochloride Bupivacaine hydrochloride anhydrous (2.5 mg/1mL) Injection Epidural; Intracaudal; Perineural Areva Pharmaceuticals 2019-07-12 Not applicable US Bupivacaine Hydrochloride Bupivacaine hydrochloride anhydrous (5 mg/1mL) Injection Epidural; Intracaudal; Perineural Areva Pharmaceuticals 2019-07-12 Not applicable US Bupivacaine Hydrochloride Bupivacaine hydrochloride anhydrous (2.5 mg/1mL) Injection Epidural; Intracaudal; Perineural Areva Pharmaceuticals 2019-07-12 Not applicable US Bupivilog Kit Bupivacaine hydrochloride (5 mg/1mL) + Povidone-iodine (10 mg/1mL) + Triamcinolone acetonide (40 mg/1mL) Kit Epidural; Intra-articular; Intramuscular; Topical Asclemed Usa, Inc. 2014-02-04 Not applicable US Chi-Myst Resolve Topical Bupivacaine 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, metered Topical Prescription Care Llc 2016-06-01 Not applicable US Chi-Myst Resolve Topical Bupivacaine 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, metered Topical Prescription Care Llc 2016-06-01 Not applicable US Chi-Myst Synergy Topical Bupivacaine 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, metered Topical Prescription Care Llc 2016-06-01 Not applicable US
Categories
- ATC Codes
- N01BB01 — BupivacaineN01BB51 — Bupivacaine, combinations
- Drug Categories
- Agents that reduce seizure threshold
- Amides
- Amines
- Anesthetics
- Anesthetics, Local
- Anilides
- Aniline Compounds
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Hypotensive Agents
- Local Anesthesia
- Local Anesthetics (Amide)
- Methemoglobinemia Associated Agents
- Nervous System
- Neuraxial Anesthetics
- Peripheral Nervous System Agents
- Sensory System Agents
- 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
- 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]
- 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]
- 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]
- 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]
- 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]
- Link [Link]
- FDA Approved Drug Products: ZYNRELEF (bupivacaine and meloxicam) extended-release solution for injection [Link]
- FDA Approved Drug Products: Xaracoll (bupivacaine hydrochloride) for inguinal implantation [Link]
- FDA Approved Drug Products: Sensorcaine (bupivacaine hydrochloride, or bupivacaine hydrochloride and epinephrine) solution for injection use [Link]
- FDA Approved Products: MARCAINE (bupivacaine hydrochloride) injection, for infiltration, perineural, caudal, epidural, or retrobulbar use [Link]
- FDA Approved Drug Products: EXPAREL (bupivacaine liposome) injectable suspension, for local infiltration [Link]
- StatPearls Internet: Bupivacaine Profile [Link]
- External Links
- Human Metabolome Database
- HMDB0014442
- KEGG Compound
- C07529
- PubChem Compound
- 2474
- PubChem Substance
- 46506768
- ChemSpider
- 2380
- BindingDB
- 50350790
- 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
Phase Status Purpose Conditions Count 4 Active Not Recruiting Treatment Anterior Cruciate Ligament Injury 1 4 Active Not Recruiting Treatment Immunosuppression / Neoplasms, Lung / Pain 1 4 Active Not Recruiting Treatment Modified Radical Mastectomy 1 4 Active Not Recruiting Treatment Opioids Use / Post Operative Nausea and Vomiting (PONV) / Postoperative pain 1 4 Active Not Recruiting Treatment Pain 1 4 Completed Not Available Haemorrhoids / Peri-anal Fistulas 1 4 Completed Not Available Pain 1 4 Completed Not Available Postoperative pain 1 4 Completed Basic Science Pain 1 4 Completed Basic Science Periarticular Block / Serum Bupivacaine Level / Total Knee Arthroplasty (TKA) 1
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
Form Route Strength Kit Epidural; Infiltration; Topical Injection, solution Parenteral Injection 0.5 % Injection, solution Parenteral Solution Intraspinal Solution Parenteral 7.5 mg Solution Epidural 50 mg Solution Subcutaneous 5 mg Solution Epidural Solution Parenteral 5 mg Solution Intramuscular 5 mg Solution Epidural; Intrathecal 50 mg Injection, solution 5 MG/ML Injection, solution Injection, solution 0.25 % Injection, solution 0.50 % Injection, solution Epidural 1.25 mg/1mL Injection, solution Epidural 2.5 mg/1mL Injection Parenteral 250 mg Injection Epidural; Intracaudal; Perineural 2.5 mg/1mL Injection Epidural; Intracaudal; Perineural 5 mg/1mL Injection Intravenous 7.5 mg/1mL Injection, solution Enteral; Epidural; Intracaudal 5 mg/1mL Injection, solution Epidural; Infiltration 2.5 mg/1mL Injection, solution Epidural; Infiltration 5 mg/1mL Injection, solution Epidural; Infiltration; Intracaudal 2.5 mg/1mL Injection, solution Epidural; Infiltration; Intracaudal 5 mg/1mL Injection, solution Epidural; Infiltration; Intracaudal; Perineural 2.5 mg/1mL Injection, solution Epidural; Intracaudal 5 mg/1mL Injection, solution Epidural; Intracaudal; Perineural 5 mg/1mL Injection, solution Epidural; Retrobulbar 7.5 mg/1mL Injection, solution Infiltration; Perineural 2.5 mg/1mL Injection, solution Intraspinal 7.5 mg/1mL Injection, solution Perineural 5 mg/1mL Solution Parenteral 0.0025 g Solution Parenteral 100 mg Injection, solution Dental; Infiltration Injection, solution Epidural; Infiltration; Intracaudal Injection, solution Epidural; Infiltration; Intracaudal; Perineural Solution Intraspinal 7.5 mg / mL Solution Infiltration 2.5 mg / mL Solution Epidural; Infiltration; Intracaudal 2.5 mg / mL Solution Epidural; Infiltration; Intracaudal 5 mg / mL Solution Epidural; Infiltration; Intracaudal 7.5 mg / mL Solution Epidural; Infiltration 2.5 mg / mL Solution Epidural; Infiltration 5 mg / mL Solution Epidural; Retrobulbar 7.5 mg / mL Solution Infiltration 5 mg / mL Injection Subarachnoid 7.5 mg/1mL Solution Parenteral 125 mg Injection, solution Epidural; Infiltration 2.5 mg/mL Injection, solution Epidural; Infiltration 5 mg/mL Kit Epidural; Intra-articular; Intramuscular; Topical Solution Epidural 7.5 mg Solution Parenteral Solution Parenteral 50 mg Injection Intraspinal Solution Parenteral Spray, metered Topical Injection Epidural; Intracaudal 5 mg/ml Kit Epidural; Infiltration; Intramuscular; Intravenous; Topical Kit Epidural; Infiltration; Intracaudal; Subcutaneous; Topical Injection Retrobulbar Kit Intra-articular; Intralesional; Intramuscular; Soft tissue; Topical Kit Epidural; Infiltration; Intra-articular; Intralesional; Intramuscular; Intravenous; Soft tissue; Subcutaneous; Topical Kit Epidural; Infiltration; Intra-articular; Intralesional; Intramuscular; Soft tissue; Topical Injection, suspension, liposomal Infiltration 13.3 mg/1mL Injection 133 MG/10ML Injection 266 MG/20ML Injection, solution Epidural Solution Epidural 75 mg Kit Epidural; Infiltration; Intra-articular; Intralesional; Intramuscular; Topical Injection Epidural Injection Epidural 5 mg/ml Injection Intrathecal 5 mg/ml Injection, solution Epidural Injection, solution Epidural; Infiltration Injection, solution Epidural 5 mg/1mL Injection, solution Infiltration 2.5 mg/1mL Injection, solution Infiltration 5 mg/1mL Injection, solution Subcutaneous Solution Epidural; Retrobulbar 150 mg / 20 mL Solution Infiltration 125 mg / 50 mL Solution Infiltration 250 mg / 50 mL Liquid Epidural; Infiltration 2.5 mg / mL Liquid Infiltration Injection Epidural Liquid Epidural; Infiltration 5 mg / mL Liquid Epidural; Retrobulbar 7.5 mg / mL Liquid Intraspinal 7.5 mg / mL Liquid Epidural; Infiltration Injection, solution Subarachnoid 7.5 mg/1mL Solution Intraspinal 15 mg / 2 mL Injection, solution Infiltration Kit Intravenous Kit Epidural; Infiltration; Intra-articular; Intramuscular Kit Epidural; Infiltration; Intra-articular; Intramuscular; Topical Kit Epidural; Infiltration; Intramuscular; Intrasynovial; Soft tissue; Topical Kit Epidural; Infiltration; Intracaudal; Perineural Solution Infiltration 660 mg/5mL Kit Topical Injection 5 mg/ml Kit Intra-articular; Intralesional; Intramuscular Kit Intramuscular; Intravenous Kit Epidural; Infiltration Solution Injection Injection Infiltration; Parenteral 2.5 mg/1mL Injection Parenteral 5 mg/1mL Injection, solution Infiltration; Perineural Injection, solution Perineural Injection Epidural; Infiltration; Parenteral 2.5 mg/1mL Injection Epidural; Parenteral 5 mg/1mL Injection Epidural; Parenteral; Retrobulbar 7.5 mg/1mL Injection, solution Epidural; Intracaudal; Perineural Injection, solution Epidural; Retrobulbar Injection Epidural; Parenteral Injection Epidural; Parenteral; Retrobulbar Solution Epidural; Infiltration Injection Dental 5 mg Implant Parenteral 100 mg/1 Solution Infiltration Solution Intralesional Solution, gel forming, extended release Solution 2.5 mg/1ml Solution 5 mg/1ml Injection, solution 5 mg/1ml - Prices
Unit description Cost Unit Bupivacaine hcl powder 18.36USD g Sensorcaine-dextr 0.75% amp 2.36USD ml Marcaine spinal ampul 0.93USD ml Bupivacaine 0.5% on-q pump 0.63USD ml Bupivacaine hcl 0.5% on-q pump 0.63USD ml Bupivacaine 0.25% on-q pump 0.62USD ml Marcaine 0.25% vial 0.26USD ml Bupivacaine hcl-ns 0.0625% 0.25USD ml Bupivacaine-ns 0.1% on-q pump 0.25USD ml Sensorcaine 0.25% vial 0.2USD ml Bupivacaine hcl-ns 0.1% 0.17USD ml Bupivacaine hcl-ns 0.2% 0.15USD ml Bupivacaine 0.25% vial 0.11USD ml Bupivacaine 0.25% ampul 0.1USD ml Bupivacaine hcl-ns 0.125% bag 0.1USD 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 Number Pediatric Extension Approved Expires (estimated) Region US8182835 No 2012-05-22 2018-09-18 US US8834921 No 2014-09-16 2018-09-18 US US9205052 No 2015-12-08 2018-09-18 US US9585838 No 2017-03-07 2021-12-24 US USRE47826 No 2020-01-28 2029-05-20 US US8753665 No 2014-06-17 2025-09-15 US US8846072 No 2014-09-30 2025-09-15 US US8153661 No 2012-04-10 2025-09-15 US US8153149 No 2012-04-10 2025-09-15 US US9592227 No 2017-03-14 2034-03-13 US US9694079 No 2017-07-04 2035-04-20 US US9801945 No 2017-10-31 2035-04-20 US US10213510 No 2019-02-26 2035-04-20 US US9913909 No 2018-03-13 2034-03-13 US US10098957 No 2018-10-16 2035-04-20 US US10632199 No 2020-04-28 2035-04-20 US US10898575 No 2021-01-26 2035-04-20 US US10980886 No 2021-04-20 2035-04-20 US US10398686 No 2019-09-03 2034-03-13 US US9744163 No 2017-08-29 2034-03-13 US US11033495 No 2021-06-15 2041-01-22 US US11083797 No 2021-08-10 2035-04-20 US US11083730 No 2021-08-10 2035-04-20 US US11179336 No 2021-11-23 2041-01-22 US US11253504 No 2014-03-13 2034-03-13 US US11278494 No 2021-01-22 2041-01-22 US US11311486 No 2021-01-22 2041-01-22 US US11304904 No 2021-01-22 2041-01-22 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 107-108 °C PhysProp water solubility 2400 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 3.41 HANSCH,C ET AL. (1995) pKa 8.1 Not Available - Predicted Properties
Property Value Source Water Solubility 0.0977 mg/mL ALOGPS logP 3.31 ALOGPS logP 4.52 ChemAxon logS -3.5 ALOGPS pKa (Strongest Acidic) 13.62 ChemAxon pKa (Strongest Basic) 8 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 32.34 Å2 ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 90.19 m3·mol-1 ChemAxon Polarizability 34.2 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9814 Blood Brain Barrier + 0.936 Caco-2 permeable + 0.6669 P-glycoprotein substrate Substrate 0.8435 P-glycoprotein inhibitor I Inhibitor 0.8582 P-glycoprotein inhibitor II Non-inhibitor 0.7836 Renal organic cation transporter Non-inhibitor 0.6471 CYP450 2C9 substrate Non-substrate 0.7957 CYP450 2D6 substrate Substrate 0.8346 CYP450 3A4 substrate Substrate 0.7045 CYP450 1A2 substrate Inhibitor 0.6863 CYP450 2C9 inhibitor Non-inhibitor 0.9099 CYP450 2D6 inhibitor Inhibitor 0.8932 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Inhibitor 0.6205 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6066 Ames test Non AMES toxic 0.8462 Carcinogenicity Non-carcinogens 0.8859 Biodegradation Not ready biodegradable 0.9729 Rat acute toxicity 2.2574 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8283 hERG inhibition (predictor II) Inhibitor 0.7851
Spectra
- Mass Spec (NIST)
- Download (8.44 KB)
- Spectra
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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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
- 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
- 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]
- 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
- 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 June 28, 2022 22:35