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Bupivacaine
Identification
- Name
- Bupivacaine
- Accession Number
- DB00297
- Description
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
- DUR-843
- LAC-43
- SKY-0402
- SKY0402
Pharmacology
- Indication
For the production of local or regional anesthesia or analgesia for surgery, for oral surgery procedures, for diagnostic and therapeutic procedures, and for obstetrical procedures.
- Associated Conditions
- Acute Gouty Arthritis
- Adrenal cortical hypofunctions
- Alopecia Areata (AA)
- Ankylosing Spondylitis (AS)
- Berylliosis
- Bullous dermatitis herpetiformis
- Congenital Adrenal Hyperplasia (CAH)
- Congenital Hypoplastic Anemia
- Dermatomyositis
- Discoid Lupus Erythematosus (DLE)
- Edema of the cerebrum
- Epicondylitis
- Eye inflammation
- Hemolytic Anemia
- Keloid Scars
- Leukemias
- Mycosis Fungoides (MF)
- Necrobiosis lipoidica diabeticorum
- Ophthalmia, Sympathetic
- Osteoarthritis (OA)
- Polymyositis
- 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
- Cancer-associated hypercalcemia
- Cystic tumors of aponeurosis
- Cystic tumors of tendon
- Disseminated Pulmonary Tuberculosis
- 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
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- 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
Local 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 prevents depolarization by bindng to the intracellular portion of sodium channels and blocking sodium ion influx into neurons. 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.
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.
- Volume of distribution
- Not Available
- Protein binding
95%
- 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.
Hover over products below to view reaction partners
- 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
- Clearance
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
The mean seizure dosage of bupivacaine in rhesus monkeys was found to be 4.4 mg/kg with mean arterial plasma concentration of 4.5 mcg/mL. The intravenous and subcutaneous LD 50 in mice is 6 to 8 mg/kg and 38 to 54 mg/kg respectively. Recent clinical data from patients experiencing local anesthetic induced convulsions demonstrated rapid development of hypoxia, hypercarbia, and acidosis with bupivacaine within a minute of the onset of convulsions. These observations suggest that oxygen consumption and carbon dioxide production are greatly increased during local anesthetic convulsions and emphasize the importance of immediate and effective ventilation with oxygen which may avoid cardiac arrest.
- Affected organisms
- Humans and other mammals
- 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 Unlock Additional DataAbametapir 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 metabolism of Acetaminophen can be decreased when combined with Bupivacaine. Acetazolamide The therapeutic efficacy of Acetazolamide can be decreased when used in combination with Bupivacaine. Adalimumab The metabolism of Bupivacaine can be increased when combined with Adalimumab. Aldesleukin The risk or severity of adverse effects can be increased when Aldesleukin is combined with Bupivacaine. Aliskiren The risk or severity of adverse effects can be increased when Bupivacaine is combined with Aliskiren. Almotriptan The metabolism of Almotriptan can be decreased when combined with Bupivacaine. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- No interactions found.
Products
- 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) / Sensorcaine-MPF (Astra Zeneca) / Xaracoll (Innocoll Holdings Limited)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataBupivacaine 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 Intraspinal Auro Pharma Inc Not applicable Not applicable Canada 
Bupivacaine Hydrochloride Injection, solution 5 mg/1mL Epidural; Infiltration Hospira, Inc. 2006-05-23 2006-05-23 US Bupivacaine Hydrochloride Injection, solution 2.5 mg/1mL Epidural; Infiltration Hospira, Inc. 2007-03-31 2007-05-31 US Bupivacaine Hydrochloride Injection 5 mg/1mL Epidural; Intracaudal; Perineural Areva Pharmaceuticals 2019-07-12 Not applicable US Bupivacaine Hydrochloride Injection, solution 5 mg/1mL Epidural; Infiltration; Intracaudal Hospira, Inc. 2010-05-19 2010-05-19 US Bupivacaine Hydrochloride Injection, solution 2.5 mg/1mL Epidural; Infiltration 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, solution 5 mg/1mL Epidural; Infiltration Hospira, Inc. 2007-03-31 2007-05-31 US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataBupivacaine Hydrochloride Injection, solution 2.5 mg/1mL Epidural; Infiltration; Intracaudal AuroMedics Pharma LLC 2013-11-05 Not applicable US Bupivacaine Hydrochloride Injection, solution 5 mg/1mL Epidural; Infiltration; Intracaudal Cardinal Health 2010-01-07 2016-05-31 US Bupivacaine Hydrochloride Injection, solution 2.5 mg/1mL Epidural; Infiltration; Intracaudal A-S Medication Solutions 2013-11-05 2018-11-01 US Bupivacaine Hydrochloride Injection, solution 5 mg/1mL Epidural; Intracaudal Remedy Repack 2016-06-15 2016-06-15 US Bupivacaine Hydrochloride Injection, solution 2.5 mg/1mL Infiltration; Perineural General Injectables & Vaccines, Inc 2010-07-01 Not applicable US Bupivacaine Hydrochloride Injection, solution 5 mg/1mL Epidural; Intracaudal; Perineural Sagent Pharmaceuticals 2015-04-01 2015-04-01 US Bupivacaine Hydrochloride Injection, solution 2.5 mg/1mL Epidural; Infiltration; Intracaudal; Perineural Hospira, Inc. 2015-08-11 Not applicable US Bupivacaine Hydrochloride Injection, solution 2.5 mg/1mL Infiltration; Perineural AuroMedics Pharma LLC 2016-05-13 Not applicable US Bupivacaine Hydrochloride Injection, solution 7.5 mg/1mL Intraspinal Baxter Healthcare Corporation 2016-08-08 Not applicable US Bupivacaine Hydrochloride Injection, solution 2.5 mg/1mL Infiltration; Perineural Sagent Pharmaceuticals 2015-04-01 2015-04-01 US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- 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 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 anhydrous (5 mg) + Epinephrine bitartrate (0.0091 mg) Solution Infiltration Novocol Inc. 2012-05-07 Not applicable Canada Bupivacaine Hydrochloride and Epinephrine Bupivacaine hydrochloride (2.5 mg/1mL) + Epinephrine bitartrate (5 ug/1mL) Injection, solution Epidural; Infiltration; Intracaudal Cardinal Health 1988-06-16 2017-10-31 US 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. 2015-10-07 2018-05-01 US Bupivacaine Hydrochloride and Epinephrine Bupivacaine hydrochloride (2.5 mg/1mL) + Epinephrine bitartrate (5 ug/1mL) Injection, solution Infiltration; Perineural Hospira, Inc. 2005-11-29 Not applicable US Bupivacaine Hydrochloride and Epinephrine Bupivacaine hydrochloride (2.5 mg/1mL) + Epinephrine bitartrate (5 ug/1mL) Injection, solution Epidural; Infiltration; Intracaudal Cardinal Health 1988-06-16 2016-04-30 US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Bupivacaine HCl Bupivacaine hydrochloride (2.5 mg/1mL) Injection, solution Epidural Cantrell Drug Company 2012-05-18 2015-01-14 US Bupivacaine HCl Bupivacaine hydrochloride (1.25 mg/1mL) Injection, solution Epidural Cantrell Drug Company 2011-08-01 2015-01-14 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 (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 (0.3 g/100mL) + Chitosan low molecular weight (20-200 mpa.s) (0.1 g/100mL) + Ketorolac tromethamine (1.5 g/100mL) + Lidocaine hydrochloride (5 g/100mL) 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)
- 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)
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. [PubMed:16810015]
- 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]
- Link [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
- AHFS Codes
- 72:00.00 — Local Anesthetics
- FDA label
- Download (147 KB)
- MSDS
- Download (73.3 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Active Not Recruiting Other Tonsillectomy 1 4 Active Not Recruiting Prevention Rupture of Anterior Cruciate Ligament 1 4 Active Not Recruiting Supportive Care Arthritis of Hip 1 4 Active Not Recruiting Supportive Care Postoperative pain 1 4 Active Not Recruiting Treatment ACL Surgery 1 4 Active Not Recruiting Treatment Arthritis 1 4 Active Not Recruiting Treatment Arthropathy Shoulder 1 4 Active Not Recruiting Treatment Bariatric Surgery Candidate / Postoperative pain 1 4 Active Not Recruiting Treatment Chest Injury Trauma / Drug Effect / Intercostal Rib / Local Anesthesia / Local Infiltration / Opioid Dependence / Pain, Nerve / Pain; Catheter (Other) / Pneumonia / Rib Fractures / Rib Trauma / Surgical Procedure, Unspecified 1 4 Active Not Recruiting Treatment Colorectal Cancers / Crohn's Disease (CD) / Digestive System Diseases / Gastrointestinal Cancers / Gastrointestinal Diseases / Inflammatory Bowel Diseases (IBD) / Intestinal Diseases / Pain / Pain, Neuropathic / Postoperative pain 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 Solution Intraspinal 30 mg Solution Intraspinal 20 mg Solution Subcutaneous 5 mg Solution Epidural 50 mg Injection, solution 0.25 % Injection, solution 0.50 % Injection, solution 1 % Injection, solution 10 MG/ML Injection, solution 5 MG/ML Injection, solution Epidural 1.25 mg/1mL Injection, solution Epidural 2.5 mg/1mL 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 Injection, solution Dental; Infiltration Injection, solution Epidural; Infiltration; Intracaudal Injection, solution Epidural; Infiltration; Intracaudal; Perineural Solution Intraspinal 7.5 mg Solution Epidural; Infiltration 2.5 mg Solution Epidural; Infiltration 5 mg Solution Epidural; Retrobulbar 7.5 mg Solution Infiltration 2.5 mg Solution Infiltration 5 mg Solution Epidural; Infiltration; Intracaudal 2.5 mg Solution Epidural; Infiltration; Intracaudal 5 mg Solution Epidural; Infiltration; Intracaudal 7.5 mg Solution Epidural; Infiltration Solution Epidural; Retrobulbar Injection Subarachnoid 7.5 mg/1mL Kit Epidural; Intra-articular; Intramuscular; Topical Injection 0.5 % Solution Epidural 7.5 mg Injection Intraspinal 5 mg/ml Injection, solution 0.5 % Spray, metered Topical Kit Epidural; Infiltration; Intramuscular; Intravenous; Topical Kit Epidural; Infiltration; Intracaudal; Subcutaneous; Topical Injection Retrobulbar 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, solution Epidural Solution Epidural 75 mg Kit Epidural; Infiltration; Intra-articular; Intralesional; Intramuscular; Topical 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 Solution Infiltration 125 mg Solution Infiltration 250 mg Liquid Epidural; Infiltration 2.5 mg Liquid Infiltration Liquid Epidural; Infiltration 5 mg Liquid Epidural; Retrobulbar 7.5 mg Liquid Intraspinal 7.5 mg Liquid Epidural; Infiltration Injection, solution Subarachnoid 7.5 mg/1mL Solution Intraspinal 15 mg Injection, solution Infiltration Kit Intravenous Kit Epidural; Infiltration; Intra-articular; Intramuscular; Topical Injection Kit Epidural; Infiltration; Intramuscular; Intrasynovial; Soft tissue; Topical Kit Infiltration; Intramuscular Kit Topical Kit Intra-articular; Intralesional; Intramuscular Kit Intramuscular; Intravenous Kit Epidural; Infiltration Solution Injection Infiltration; Parenteral 2.5 mg/1mL Injection Parenteral 5 mg/1mL Injection, solution Infiltration; Perineural Injection, solution Perineural Solution Infiltration 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 Implant Parenteral 100 mg/1 - 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 Unlock Additional DataUS8182835 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 Additional Data Available- Filed On
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
- 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. [PubMed:17139284]
- 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]
- 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
- 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. [PubMed:17139284]
- 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]
- 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
- 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. [PubMed:10725304]
- 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. [PubMed:10725304]
- 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. [PubMed:10725304]
- Prescriber's digital reference, Marcaine with Epinephrine-bipuvacaine-hydrochloride [Link]
Drug created on June 13, 2005 07:24 / Updated on September 22, 2020 02:11
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