Identification
- Summary
Benzocaine is a topical local anesthetic used for the temporary relief of pain and itching associated with minor burns, sunburn, scrapes and insect bites or minor skin irritations.
- Brand Names
- Anbesol Cold Sore Therapy, Cepacol Sore Throat Plus Cough, Cetacaine, Chloraseptic Sore Throat, Chloraseptic Sore Throat + Cough, Diphen, Docusol Plus, Enemeez Plus, Medicaine Sting and Bite, One Touch Reformulated Apr 2009, Orasep Reformulated Dec 2013, Rectogel, Salinocaine, Topex, Vagisil Original Formula, Zap, Zilactin-B
- Generic Name
- Benzocaine
- DrugBank Accession Number
- DB01086
- Background
Benzocaine is an ester local anesthetic that acts by preventing transmission of impulses along nerve fibers and at nerve endings.4 It is commonly used for local anesthesia in many over the counter products.13,14,15 Benzocaine was first used for local anesthesia in dentistry.10
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Benzocaine (DB01086)
- Weight
- Average: 165.1891
Monoisotopic: 165.078978601 - Chemical Formula
- C9H11NO2
- Synonyms
- 4-aminobenzoic acid ethyl ester
- Amben ethyl ester
- Benzocaina
- Benzocaine
- Benzocainum
- Ethyl aminobenzoate
- Ethyl p-aminobenzoate
- Ethyl p-aminophenylcarboxylate
- p-(Ethoxycarbonyl)aniline
- p-Carbethoxyaniline
- p-Ethoxycarboxylic aniline
- External IDs
- AR-01
- AR01
- NSC-41531
- NSC-4688
Pharmacology
- Indication
Benzocaine is indicated for local anesthesia in dentistry, minor trauma, and as preparation for infiltrative anesthesia.4 Benzocaine products are indicated for topical anesthesia in a wide variety of conditions including skin irritation,13 oral pain,14 and hemorrhoids.15
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Acute sore throat pain Combination Product in combination with: Chlorhexidine (DB00878) •••••••••••• ••••••• Used in combination to treat Dental pain Combination Product in combination with: Chlorhexidine (DB00878) •••••••••••• ••••••• Used in combination to prevent Gangrene stomatitis Combination Product in combination with: Chlorhexidine (DB00878) •••••••••••• ••••••• Used in combination to prevent Gingivitis Combination Product in combination with: Chlorhexidine (DB00878) •••••••••••• ••••••• Symptomatic treatment of Hemorrhoid ••• ••• - Associated Therapies
- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Benzocaine is indicated for use as a topical anesthetic.4 It has a duration of action of approximately 10 minutes9 and a wide therapeutic window.4 Patients should be counselled regarding the risks of methemoglobinemia.4,5,6,8
- Mechanism of action
Benzocaine diffuses into nerve cells where it binds to sodium channels, preventing the channels from opening, and blocking the influx of sodium ions.2,3,4 Nerve cells unable to allow sodium into cells cannot depolarize and conduct nerve impulses.3,4
Target Actions Organism ASodium channel protein type 10 subunit alpha inhibitorHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Benzocaine binds to both serum albumin and alpha-1-acid glycoprotein.7
- Metabolism
Benzocaine undergoes ester hydrolysis to form 4-aminobenzoic acid, acetylation to form acetylbenzocaine, or N-hydroxylation to form benzocaine hydroxide.1 4-aminobenzoic acid can be acetylated or acetylbenzocaine can undergo ester hydrolysis to form 4-acetaminobenzoic acid.1
Hover over products below to view reaction partners
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Patients experiencing an overdose may present with local anesthetic systemic toxicity syndrome, decreased cardiovascular function, decreased central nervous system function, cardiac arrest, bradycardia, hypotension, cardiac arrhythmias, syncope, and seizures.4 Patients should be treated with symptomatic and supportive measures which include airway maintenance, controlling seizures, and hemodynamic stabilization.4
- Pathways
Pathway Category Benzocaine Action Pathway Drug action - Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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 CNS depression can be increased when Benzocaine is combined with 1,2-Benzodiazepine. Abametapir The serum concentration of Benzocaine can be increased when it is combined with Abametapir. Abatacept The metabolism of Benzocaine can be increased when combined with Abatacept. Abemaciclib The risk or severity of methemoglobinemia can be increased when Abemaciclib is combined with Benzocaine. Abiraterone The serum concentration of Benzocaine can be increased when it is combined with Abiraterone. - Food Interactions
- 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 Benzocaine hydrochloride OG625Z9LEO 23239-88-5 JAADDQHUJDUAKW-UHFFFAOYSA-N - International/Other Brands
- Anacaine / Anaesthesin / Anbesol Baby / Dermoplast
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Anal Swabs 20% Stick 20 % Topical Endovations Inc. 1988-12-31 1997-07-15 Canada 
BeeGentle Topical Anesthetic Gel 210 mg/1g Topical Cao Group, Inc. 2010-09-01 2018-10-11 US 
Benzo-Jel Gel 200 mg/1g Topical Henry Schein, Inc. 2015-07-03 Not applicable US Benzo-Jel Gel 200 mg/1g Topical Henry Schein, Inc. 2015-07-03 Not applicable US Benzo-Jel Gel 200 mg/1g Topical Henry Schein, Inc. 2015-07-03 Not applicable US - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image 20/20 Topical Anesthetic Strip 10 mg/1 Dental Advanced Dental Anesthetics 2012-02-28 Not applicable US 7 Select Oral Pain Maximum Strength Relief Gel 200 mg/1g Topical 7-ELEVEN, INC. 2016-12-08 Not applicable US Advance Topical Anesthetic Gel Gel 200 mg/1g Dental The Atlanta Dental Supply Company Dba Advanced Dental Products 2017-03-01 Not applicable US Advance Topical Anesthetic Gel Gel 200 mg/1g Dental The Atlanta Dental Supply Company Dba Advanced Dental Products 2017-03-01 Not applicable US Advance Topical Anesthetic Gel Gel 200 mg/1g Dental The Atlanta Dental Supply Company Dba Advanced Dental Products 2017-03-01 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image 10 Person ANSI Benzocaine (6 mL/100mL) + Acetaminophen (325 mg/1) + Acetylsalicylic acid (325 mg/1) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Benzalkonium chloride (0.40 mL/100mL) + Ethanol (60 mL/100mL) + Ibuprofen (200 mg/1) + Lidocaine (0.5 1/100g) + Neomycin sulfate (5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL) Kit Ophthalmic; Oral; Topical Genuine First Aid 2010-04-24 Not applicable US 25 Person ANSI Benzocaine (6 mL/100mL) + Acetaminophen (325 mg/1) + Acetylsalicylic acid (325 mg/1) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Benzalkonium chloride (0.40 mL/100mL) + Ethanol (60 mL/100mL) + Ethanol (62 g/100g) + Ibuprofen (200 mg/1) + Isopropyl alcohol (70 mL/100mL) + Lidocaine (0.5 g/100g) + Neomycin sulfate (5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL) Kit Ophthalmic; Oral; Topical Genuine First Aid 2010-04-25 Not applicable US 2x Med Liq Benzocaine (20 mg/100mL) + Menthol (0.1 mg/100mL) Liquid Oral Lornamead 2021-09-01 Not applicable US 2x Med Liq Benzocaine (20 mg/100mL) + Menthol (0.1 mg/100mL) Liquid Oral CSR Cosmetic Solutions 2021-09-01 Not applicable US 3M Nexcare Cold Sore Treatment Benzocaine (50 mg/1g) + Allantoin (10 mg/1g) Ointment Topical 3M Company 2008-02-20 2015-09-30 US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image 4125 First Aid Kit Benzocaine (10 g/100g) + Benzocaine (10 g/100g) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Benzethonium chloride (0.2 g/100g) + Benzethonium chloride (0.2 g/100g) + Isopropyl alcohol (0.7 mL/1mL) + Menthol (0.33 g/100g) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL) Inhalant; Kit; Liquid; Ointment; Spray; Swab Ophthalmic; Respiratory (inhalation); Topical Honeywell Safety Products USA, Inc 2018-10-18 Not applicable US 4125 First Aid Kit Benzocaine (10 g/100g) + Benzocaine (10 g/100g) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Benzethonium chloride (0.2 g/100g) + Benzethonium chloride (0.2 g/100g) + Isopropyl alcohol (0.7 mL/1mL) + Menthol (0.33 g/100g) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL) Inhalant; Kit; Liquid; Ointment; Spray; Swab Ophthalmic; Respiratory (inhalation); Topical Honeywell Safety Products USA, Inc 2018-10-18 Not applicable US 4129 First Aid Kit Benzocaine (20 g/100g) + Ammonia (0.045 g/0.3mL) + Benzalkonium chloride (1.3 mg/1mL) + Benzethonium chloride (0.2 g/100g) + Ethanol (0.5 mL/1mL) + Hydrocortisone acetate (1 g/100g) + Hydrocortisone acetate (1 g/100g) + Isopropyl alcohol (0.7 mL/1mL) + Lidocaine hydrochloride (20 mg/1mL) + Povidone-iodine (10 mg/1mL) Kit Respiratory (inhalation); Topical Honeywell Safety Products USA, Inc 2018-10-18 Not applicable US 4142 First Aid Kit Benzocaine (10 g/100g) + Acetylsalicylic acid (325 mg/1) + Ammonia (0.045 g/0.3mL) + Benzalkonium chloride (1.3 mg/1mL) + Benzethonium chloride (0.2 g/100g) + Lidocaine hydrochloride (2 g/100g) + Water (98.6 mL/100mL) Kit Ophthalmic; Oral; Respiratory (inhalation); Topical Honeywell Safety Products USA, Inc 2018-10-18 Not applicable US 4209 First Aid Kit Benzocaine (20 g/100g) + Acetylsalicylic acid (325 mg/1) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Benzethonium chloride (0.2 g/100g) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL) Kit Ophthalmic; Oral; Respiratory (inhalation); Topical Honeywell Safety Products USA, Inc 2018-10-18 Not applicable US
Categories
- ATC Codes
- C05AD03 — Benzocaine
- C05AD — Local anesthetics
- C05A — AGENTS FOR TREATMENT OF HEMORRHOIDS AND ANAL FISSURES FOR TOPICAL USE
- C05 — VASOPROTECTIVES
- C — CARDIOVASCULAR SYSTEM
- D04AB — Anesthetics for topical use
- D04A — ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.
- D04 — ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.
- D — DERMATOLOGICALS
- Drug Categories
- Acids, Carbocyclic
- Agents for Treatment of Hemorrhoids and Anal Fissures for Topical Use
- Aminobenzoates
- Anesthetics
- Anesthetics for Topical Use
- Anesthetics, Local
- Antipruritics and Local Anesthetics
- Antipruritics, Incl. Antihistamines, Anesthetics, Etc.
- Benzene Derivatives
- Benzoates
- Cell-mediated Immunity
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP1A2 Substrates
- Cytochrome P-450 CYP2B6 Substrates
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 CYP2E1 Substrates
- Cytochrome P-450 Substrates
- Dermatologicals
- Esters of Aminobenzoic Acid
- Increased Histamine Release
- Local Anesthetics (Ester)
- Methemoglobinemia Associated Agents
- Nervous System
- P-glycoprotein inhibitors
- para-Aminobenzoates
- Peripheral Nervous System Agents
- Sensory System Agents
- Standardized Chemical Allergen
- Throat Preparations
- Vasoprotectives
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Benzoic acids and derivatives
- Direct Parent
- Benzoic acid esters
- Alternative Parents
- Aminobenzoic acids and derivatives / Benzoyl derivatives / Aniline and substituted anilines / Carboxylic acid esters / Amino acids and derivatives / Monocarboxylic acids and derivatives / Primary amines / Organopnictogen compounds / Organooxygen compounds / Organic oxides show 1 more
- Substituents
- Amine / Amino acid or derivatives / Aminobenzoic acid or derivatives / Aniline or substituted anilines / Aromatic homomonocyclic compound / Benzoate ester / Benzoyl / Carboxylic acid derivative / Carboxylic acid ester / Hydrocarbon derivative show 8 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- substituted aniline, benzoate ester (CHEBI:116735)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- U3RSY48JW5
- CAS number
- 94-09-7
- InChI Key
- BLFLLBZGZJTVJG-UHFFFAOYSA-N
- InChI
- InChI=1S/C9H11NO2/c1-2-12-9(11)7-3-5-8(10)6-4-7/h3-6H,2,10H2,1H3
- IUPAC Name
- ethyl 4-aminobenzoate
- SMILES
- CCOC(=O)C1=CC=C(N)C=C1
References
- General References
- Hartman NR, Mao JJ, Zhou H, Boyne MT 2nd, Wasserman AM, Taylor K, Racoosin JA, Patel V, Colatsky T: More methemoglobin is produced by benzocaine treatment than lidocaine treatment in human in vitro systems. Regul Toxicol Pharmacol. 2014 Oct;70(1):182-8. doi: 10.1016/j.yrtph.2014.07.002. Epub 2014 Jul 8. [Article]
- Becker DE, Reed KL: Essentials of local anesthetic pharmacology. Anesth Prog. 2006 Fall;53(3):98-108; quiz 109-10. doi: 10.2344/0003-3006(2006)53[98:EOLAP]2.0.CO;2. [Article]
- Hanck DA, Nikitina E, McNulty MM, Fozzard HA, Lipkind GM, Sheets MF: Using lidocaine and benzocaine to link sodium channel molecular conformations to state-dependent antiarrhythmic drug affinity. Circ Res. 2009 Aug 28;105(5):492-9. doi: 10.1161/CIRCRESAHA.109.198572. Epub 2009 Aug 6. [Article]
- Singh R, Al Khalili Y: Benzocaine . [Article]
- Moore TJ, Walsh CS, Cohen MR: Reported adverse event cases of methemoglobinemia associated with benzocaine products. Arch Intern Med. 2004 Jun 14;164(11):1192-6. doi: 10.1001/archinte.164.11.1192. [Article]
- de Freiras GC, Pozzobon RT, Blaya DS, Moreira CH: Efficacy of Benzocaine 20% Topical Anesthetic Compared to Placebo Prior to Administration of Local Anesthesia in the Oral Cavity: A Randomized Controlled Trial. Anesth Prog. 2015 Summer;62(2):46-50. doi: 10.2344/0003-3006-62.2.46. [Article]
- Kitamura K, Omran AA, Takegami S, Tanaka R, Kitade T: (19)F NMR spectroscopic characterization of the interaction of niflumic acid with human serum albumin. Anal Bioanal Chem. 2007 Apr;387(8):2843-8. doi: 10.1007/s00216-007-1162-x. Epub 2007 Feb 14. [Article]
- Hieger MA, Afeld JL, Cumpston KL, Wills BK: Topical Benzocaine and Methemoglobinemia. Am J Ther. 2017 Sep/Oct;24(5):e596-e598. doi: 10.1097/MJT.0000000000000521. [Article]
- Lee HS: Recent advances in topical anesthesia. J Dent Anesth Pain Med. 2016 Dec;16(4):237-244. doi: 10.17245/jdapm.2016.16.4.237. Epub 2016 Dec 31. [Article]
- CORNFELD S: The use of ethyl aminobenzoate. Dent Surv. 1946 Jun;22(6):1101. [Article]
- INVIMA Product Authorization: Aldrifress (benzocaine/cetylpyridinium chloride) chewable tablets [Link]
- BASG Product Information: Herposicc (benzocaine/zinc oxide) lip ointment [Link]
- Dailymed: Dermoplast First Aid (Benzocaine and Benzethonium) Topical Spray [Link]
- Dailymed: Rite Aid Maximum Toothache Reliever (Benzocaine and Menthol) Oral Gel [Link]
- Dailymed: Americaine (Benzocaine) Topical Ointment [Link]
- External Links
- Human Metabolome Database
- HMDB0004992
- KEGG Drug
- D00552
- KEGG Compound
- C07527
- PubChem Compound
- 2337
- PubChem Substance
- 46508891
- ChemSpider
- 13854242
- BindingDB
- 197282
- 1399
- ChEBI
- 116735
- ChEMBL
- CHEMBL278172
- ZINC
- ZINC000012358719
- Therapeutic Targets Database
- DAP001234
- PharmGKB
- PA448576
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Benzocaine
- MSDS
- Download (73.3 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Health Services Research Pain 1 4 Completed Prevention Anesthesia of Mucous Membrane 1 4 Completed Treatment Analgesia / Pain Relief 1 4 Completed Treatment Pharyngitis 1 4 Completed Treatment Toothache 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Advanced Pharmaceutical Services Inc.
- Aidarex Pharmacuticals LLC
- Alba Pharmacal
- American Dental Cooperative Inc.
- AR Medicom Inc.
- Assured Packaging Inc.
- Ballay Pharmaceuticals
- Bausch & Lomb Inc.
- Belport Co. Inc.
- Benco Dental Co.
- Beutlich Pharmaceuticals LP
- Bio Pharm Inc.
- Boca Pharmacal
- Burkhart Dental Supply Inc.
- Cao Group Inc.
- Combe Inc.
- County Line Pharmaceuticals LLC
- Cross Country Paper Products Corp.
- Crosstex International
- Deepak Products Inc.
- Dental Resources Inc.
- Dental Technologies Inc.
- DENTSPLY International
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- DSHealthcare Inc.
- Essence Dental LLC
- Foremost Dental LLC
- Germiphene Corp.
- Great Southern Laboratories
- Henry Schein Inc.
- Hi Tech Pharmacal Co. Inc.
- Irisys Inc.
- Laboratorios Zeyco SA De CV
- Major Pharmaceuticals
- Mallinckrodt Inc.
- Marlop Pharmaceuticals Inc.
- Medical Products Laboratories Inc.
- Medtech Labs
- Palmetto Pharmaceuticals Inc.
- Patterson Dental Supply Inc.
- Perrigo Co.
- Pharmedix
- Physicians Total Care Inc.
- Preferred Pharmaceuticals Inc.
- Prescript Pharmaceuticals
- PruGen Inc. Pharmaceuticals
- Puretek Corp.
- Qualitest
- Rebel Distributors Corp.
- Redpharm Drug
- River's Edge Pharmaceuticals
- Sciarra Laboratories Inc.
- SDA Laboratories Inc.
- Sonar Products Inc.
- Sunstar Pharmaceutical Inc.
- Taro Pharmaceuticals USA
- Taylor Pharmaceuticals
- Trigen Laboratories Inc.
- UCB Pharma
- Vintage Pharmaceuticals Inc.
- Wyeth Pharmaceuticals
- Dosage Forms
Form Route Strength Strip Dental 10 mg/1 Kit Respiratory (inhalation); Topical Kit Ophthalmic; Oral; Respiratory (inhalation); Topical Inhalant; kit; liquid; ointment; spray; swab; tablet Ophthalmic; Oral; Respiratory (inhalation); Topical Inhalant; kit; liquid; ointment; spray; swab Ophthalmic; Respiratory (inhalation); Topical Kit; liquid; ointment; spray; swab Ophthalmic; Topical Kit Ophthalmic; Respiratory (inhalation); Topical Cream; kit; liquid; ointment; spray; tablet Ophthalmic; Oral; Topical Cream; gel; kit; liquid; ointment; spray; swab Ophthalmic; Topical Gel; kit; liquid; ointment; swab; tablet Oral; Topical Cream Oral Kit Oral; Topical Kit Topical Kit Oral; Topical 200 mg/1g Stick Topical 100 mg/1mL Swab Topical Tablet, chewable Oral Cream Topical 7.5 g/100g Gel Dental; Periodontal 200 mg/1g Aerosol, spray Topical 11.4 g/57g Ointment Topical 5.6 g/28g Ointment Topical 10 % Powder, for solution Topical 6 % Gel Topical 2833 mg/60mL Stick Topical 20 % Cream Topical 7.5 g/100mL Gel Oral 7.5 % Gel Topical 20 % Solution Topical 200 mg/1mL Liquid Oral Solution Topical 100 mg/1mL Gel Oral 0.2 g/100g Liquid Topical 0.2 mg/2mL Solution / drops Auricular (otic) Cream Cutaneous Liquid Topical Liquid Topical 20 g/100mL Gel Oral 10 g/100g Solution Auricular (otic) 0.02 g Gel Dental 6.4 g/100g Gel Buccal; Topical 7.5 g Gel Buccal; Topical 7.5 % Liquid Topical 2.1 mg/30mL Gel Topical 0.100 g Gel Topical 75 mg/1g Gel Topical 100 mg/1g Liquid Topical .075 mL/1mL Swab Topical .075 mL/1mL Gel Buccal; Oral 7.5 g Gel Topical 10 g/100g Gel Topical 7.5 g/100g Lozenge Oral 15 mg/1 Gel Topical 210 mg/1g Spray Topical 11.8 g/59mL Spray Topical 20 mL/100mL Gel Dental 230 mg/1mL Gel Dental 200 mg/1g Tablet, chewable Oral 10 mg Gel Topical 200 mg/1mL Powder Not applicable 1 g/1g Swab Topical 0.12 mL/1 Swab Topical 60 mg/1mL Cream Topical Ointment Topical Cream Topical 0.2 g/1g Liquid Topical 5 g/100g Cream Topical 5 g/100g Spray Topical 5 g/100g Cream Topical 5 g/100mL Bead Oral 3 mg/1 Gel Buccal 10 g/100g Liquid Buccal Gel Buccal 20 g/100mL Ointment Topical 20 % Cream Topical 71.9395789 mg/1mL Cream Topical 73.9395789 mg/1mL Cream Topical 34.05 g/454g Gel Oral 9 mg/1mL Tablet Buccal; Oral 10 mg Gel Topical 0.2 g/1g Kit Electro-osmosis Lotion Topical Liquid Oral 20 g/100mL Gel Topical 0.1000 g Cream Topical 10 g/100g Spray Oral Tablet, orally disintegrating Oral 6 mg/1 Lozenge Oral 3 mg/1 Lozenge Oral 4 mg/1 Lozenge Oral Swab Topical 0.06 mL/1mL Aerosol Topical Lotion Topical 50 mg/1mL Cream Topical 0.1 g/1g Ointment Topical 10 g/100g Liquid Auricular (otic) Gel Topical 0.075 g/1g Sponge Topical Paste, dentifrice Topical 200 mg/1g Solution Paste Dental Gel; kit; lipstick; liquid; lotion; swab Topical Gel Oral 75 mg/1g Paste, dentifrice Topical 20 g/100g Liquid Oral 200 mg/1mL Gel, dentifrice Dental 20 g/100g Gel, dentifrice Oral 20 g/100g Liquid Dental 20 g/100g Gel, dentifrice Dental 10 g/100g Gel, dentifrice Dental Swab Oral Strip Topical 10 g/100g Liquid Dental Liquid Dental 200 mg/1mL Liquid Dental; Topical 200 mg/1mL Gel Dental Ointment Dental 0.2 g/1mL Gel Buccal; Topical Ointment Topical 1.27 g/100g Lotion Topical 0.05 g/1g Gel Topical 7.5 % Cream; kit; liquid; ointment; tablet; tablet, chewable; tablet, film coated Oral; Topical Solution Buccal; Oral Cloth Topical 7 g/100mL Gel Topical 2410 mg/50mL Gel Topical 50 mg/1mL Spray Buccal; Oral 20 % Aerosol, metered Topical Liquid Rectal Aerosol, spray Topical Liquid Oral 7.5 mg/100mg Spray Oral 7.5 mg/100mL Patch Topical 6 g/100g Solution Cutaneous Spray Topical 20 G Cream Topical 20 g/100mL Gel Topical 20 % w/w Patch Topical Gel Dental 2.4 g/12g Gel Dental 6 g/30g Spray, metered Dental 11.4 g/57g Spray Oral; Topical Gel Dental; Topical 20 g/100g Gel Dental 20 % Gel Dental; Oral; Periodontal 200 mg/1 Liquid Dental 20 % Liquid Dental; Oral; Periodontal 200 mg/1 Spray Transmucosal Kit Ophthalmic; Oral; Topical Liquid Oral 50 mg/1mL Lozenge Oral 10 mg Solution Oral Cream Topical 4.5 g/100g Spray Dental; Periodontal 200 mg/1g Gel Dental; Periodontal Spray Dental; Periodontal Liquid Topical 20 % Spray Topical 20 % Gel Dental; Oral; Periodontal 200 mg/1g Spray Dental; Oral; Periodontal 200 mg/1g Liquid Dental; Oral; Periodontal 200 mg/1g Aerosol Dental; Topical 21.9 % Liquid Topical 15 mg/1mL Solution Topical 150 mg/1mL Gel Dental; Oral 6.4 g/100g Liquid Topical 6 g/100g Cream Topical 5 % Liquid Buccal; Topical Solution 20.000 g Liquid Buccal 200 mg/1mL Kit; liquid; ointment Buccal; Topical Gel Oral Cream Dental Gel Topical 7 g/100mL Lozenge Buccal Gel Oral 20 g/100g Gel Oral 200 mg/1g Cream Topical; Vaginal Granule Oral 6 mg/1 Gel, dentifrice Dental 200 mg/1g Liquid Topical 1417 mg/30mL Liquid Topical 50 mg/1mL Gel Topical 3.00 g/100mL Gel Topical 2.13 g/28.35g Gel Dental; Oral 6.4 g/32g Gel Topical 7 g/100g Gel Topical 5 g/100g Swab Topical 0.12 g/1g Swab Topical 0.12 g/0.6mL Cloth Topical Cloth Topical 3.5 g/100g Liquid Topical 5 g/100mL Spray Topical 11.4 g/57g Liquid Topical 200 mg/1g Liquid Oral 200 mg/1g Gel Dental Ointment Topical 5 g/100g Cream Topical 20 mg/100mg Cream Topical 200 mg/1mL Powder, for solution Oral 90 mg/1 Gel Buccal; Topical 20 g Tablet, soluble Oral 6 mg Tablet Buccal Tablet Buccal; Oral Spray Topical Gel Dental; Topical Gel Buccal Spray, metered Dental; Oral; Topical 12 g/60g Cream Topical 7.5 mg/100mL Paste, dentifrice Dental 19.8 mg/1g Liquid Dental 205 mg / g Strip Dental Gel Dental 200 mg / g Swab Topical 0.2 g/1mL Swab Topical 0.2 mL/1mL Gel Topical Swab Topical 75 mg/1g Gel; kit Topical Gel Topical 10 g Film, soluble Oral Gel Topical 200 mg/1g Liquid Topical 0.2 mL/1mL Paste Topical Gel Oral 0.2 mL/1mL Gel Topical 20 g/100g Ointment Topical 5.00 mg/1g Gel Buccal; Oral 20 g Solution Auricular (otic) Solution Auricular (otic) 20 mg Liquid Topical .009 mg/1mL Liquid Topical 18.6 g/100mL Gel Oral; Topical Solution / drops Auricular (otic) 200 mg/1mL Tablet Oral Gel Topical 5 g/100mL Liquid Topical 4 g/100mL Solution Topical 4 g/100mL Gel Dental 221 mg/1g Gel Dental; Oral; Periodontal 0.2 g/1g Gel Dental; Topical 20 % Cream Rectal Suppository Rectal 5 MG Gel Topical 20 1/100g Cream Topical 4.2 g/56g Dressing Topical 70 g/1000g Solution Buccal 200.000 mg Liquid Auricular (otic) 200 mg/1mL Ointment Rectal Ointment Topical 200 mg/1g Liquid Topical 200 mg/1mL Gel, dentifrice Oral 7.5 g/100g Gel Oral 200 mg/1mL Gel, dentifrice Oral Swab Topical 15 % Powder, for solution Oral 150 mg/3000mg Kit Topical 0.05 g/1g Cloth Topical 0.0543 g/1 Kit Topical 0.0543 g/1 Kit Topical 6 g/1 Gel Dental; Oral 20 g/100g Aerosol, spray Topical 1.125 g/15g Gel Topical 5.06 g/67.50g Gel Topical 5.07 g/67.5g Gel Topical 5.07 g/67.50g Syrup Dental 1.8 % Gum, chewing Oral Solution Topical Swab Topical 0.06 mg/1 Solution Topical 10 g/100g Swab Topical 6 g/100mL Swab Oral 20 % Kit Cutaneous Liquid Oral 1.3 mg/13mL Liquid Oral 10 g/100mL Ointment Topical 3.5 g/100g Dressing Oral Gel, dentifrice Dental 220 mg/1g Spray, metered Periodontal 220 mg/1g Gel Buccal 20.000 g Gel Oral; Topical 20 % Gel Oral; Topical 200 mg / g Gel Dental 220 mg/1g Gel Topical 18 g Gel Topical 20 mg Gel Oral 180 mg/1g Ointment Oral 180 mg/1g Patch Oral 180 mg/1g Gel Topical 180 mg/g Spray Topical 4.5 g/60mL Gel Dental; Periodontal; Topical 200 mg/1g Gel Dental 200 mg/1mL Enema Rectal Spray Topical 7.5 g/100mL Gel Dental 200 mg/g Spray 200 mg/mL Ointment Topical 20 g/100g Liquid Oral 20 g/100g Swab Topical 6 g/1001 Spray, metered Topical Aerosol Oral Gel Topical 10 % Swab Topical 20 % Gel Topical 0.1 g/1g Gel Dental 20 g/100g Suppository Rectal Gel 7.5 %w/w - Prices
Unit description Cost Unit Americaine Anesthetic 20% Gel 28 gm Tube 22.99USD tube Americaine 20% ear drops 1.26USD ml Oticaine 20% ear drops 0.83USD ml Americaine lubricant 0.71USD g Hurricaine 20% liquid swab 0.6USD swab Hurricaine 20% spray 0.52USD ml Anbesol baby 7.5% gel 0.41USD g Cepacol 6 mg fizzlers tablet 0.39USD tablet Benzocaine powder 0.09USD g Dermoplast pain relieving spry 0.07USD ml Dermoplast spray 0.07USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 92 °C PhysProp boiling point (°C) 310 °C PhysProp water solubility 1310 mg/L (at 30 °C) YALKOWSKY,SH & HE,Y (2003) logP 1.86 HANSCH,C ET AL. (1995) pKa 2.51 (at 25 °C) PERRIN,DD (1965) - Predicted Properties
Property Value Source Water Solubility 2.85 mg/mL ALOGPS logP 2.2 ALOGPS logP 1.5 Chemaxon logS -1.8 ALOGPS pKa (Strongest Basic) 2.78 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 52.32 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 47.53 m3·mol-1 Chemaxon Polarizability 17.46 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9963 Blood Brain Barrier + 0.9609 Caco-2 permeable + 0.7814 P-glycoprotein substrate Non-substrate 0.8329 P-glycoprotein inhibitor I Non-inhibitor 0.9589 P-glycoprotein inhibitor II Non-inhibitor 0.9612 Renal organic cation transporter Non-inhibitor 0.8818 CYP450 2C9 substrate Non-substrate 0.8426 CYP450 2D6 substrate Non-substrate 0.7934 CYP450 3A4 substrate Non-substrate 0.7513 CYP450 1A2 substrate Inhibitor 0.9107 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.937 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7883 Ames test Non AMES toxic 0.8825 Carcinogenicity Carcinogens 0.513 Biodegradation Ready biodegradable 0.7718 Rat acute toxicity 1.7665 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9721 hERG inhibition (predictor II) Non-inhibitor 0.9668
Spectra
- Mass Spec (NIST)
- Download (7.74 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 140.6678691 predictedDarkChem Lite v0.1.0 [M-H]- 140.2837691 predictedDarkChem Lite v0.1.0 [M-H]- 141.2068691 predictedDarkChem Lite v0.1.0 [M-H]- 135.47456 predictedDeepCCS 1.0 (2019) [M+H]+ 142.2715691 predictedDarkChem Lite v0.1.0 [M+H]+ 141.3556691 predictedDarkChem Lite v0.1.0 [M+H]+ 141.8359691 predictedDarkChem Lite v0.1.0 [M+H]+ 139.07393 predictedDeepCCS 1.0 (2019) [M+Na]+ 140.9842691 predictedDarkChem Lite v0.1.0 [M+Na]+ 140.8231691 predictedDarkChem Lite v0.1.0 [M+Na]+ 140.9465691 predictedDarkChem Lite v0.1.0 [M+Na]+ 148.34987 predictedDeepCCS 1.0 (2019)
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]
- Ahern CA, Eastwood AL, Dougherty DA, Horn R: Electrostatic contributions of aromatic residues in the local anesthetic receptor of voltage-gated sodium channels. Circ Res. 2008 Jan 4;102(1):86-94. Epub 2007 Oct 25. [Article]
- Hanck DA, Nikitina E, McNulty MM, Fozzard HA, Lipkind GM, Sheets MF: Using lidocaine and benzocaine to link sodium channel molecular conformations to state-dependent antiarrhythmic drug affinity. Circ Res. 2009 Aug 28;105(5):492-9. doi: 10.1161/CIRCRESAHA.109.198572. Epub 2009 Aug 6. [Article]
- Lipkind GM, Fozzard HA: Molecular modeling of local anesthetic drug binding by voltage-gated sodium channels. Mol Pharmacol. 2005 Dec;68(6):1611-22. Epub 2005 Sep 20. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58293.76 Da
References
- Hartman NR, Mao JJ, Zhou H, Boyne MT 2nd, Wasserman AM, Taylor K, Racoosin JA, Patel V, Colatsky T: More methemoglobin is produced by benzocaine treatment than lidocaine treatment in human in vitro systems. Regul Toxicol Pharmacol. 2014 Oct;70(1):182-8. doi: 10.1016/j.yrtph.2014.07.002. Epub 2014 Jul 8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid 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 oxidizes a variety of structurally un...
- Gene Name
- CYP2B6
- Uniprot ID
- P20813
- Uniprot Name
- Cytochrome P450 2B6
- Molecular Weight
- 56277.81 Da
References
- Hartman NR, Mao JJ, Zhou H, Boyne MT 2nd, Wasserman AM, Taylor K, Racoosin JA, Patel V, Colatsky T: More methemoglobin is produced by benzocaine treatment than lidocaine treatment in human in vitro systems. Regul Toxicol Pharmacol. 2014 Oct;70(1):182-8. doi: 10.1016/j.yrtph.2014.07.002. Epub 2014 Jul 8. [Article]
- 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
- Hartman NR, Mao JJ, Zhou H, Boyne MT 2nd, Wasserman AM, Taylor K, Racoosin JA, Patel V, Colatsky T: More methemoglobin is produced by benzocaine treatment than lidocaine treatment in human in vitro systems. Regul Toxicol Pharmacol. 2014 Oct;70(1):182-8. doi: 10.1016/j.yrtph.2014.07.002. Epub 2014 Jul 8. [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
- Hartman NR, Mao JJ, Zhou H, Boyne MT 2nd, Wasserman AM, Taylor K, Racoosin JA, Patel V, Colatsky T: More methemoglobin is produced by benzocaine treatment than lidocaine treatment in human in vitro systems. Regul Toxicol Pharmacol. 2014 Oct;70(1):182-8. doi: 10.1016/j.yrtph.2014.07.002. Epub 2014 Jul 8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
- Gene Name
- CYP2E1
- Uniprot ID
- P05181
- Uniprot Name
- Cytochrome P450 2E1
- Molecular Weight
- 56848.42 Da
References
- Hartman NR, Mao JJ, Zhou H, Boyne MT 2nd, Wasserman AM, Taylor K, Racoosin JA, Patel V, Colatsky T: More methemoglobin is produced by benzocaine treatment than lidocaine treatment in human in vitro systems. Regul Toxicol Pharmacol. 2014 Oct;70(1):182-8. doi: 10.1016/j.yrtph.2014.07.002. Epub 2014 Jul 8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Triglyceride lipase activity
- Specific Function
- Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acy...
- Gene Name
- CES1
- Uniprot ID
- P23141
- Uniprot Name
- Liver carboxylesterase 1
- Molecular Weight
- 62520.62 Da
References
- Bell FP: The effect of local anesthetics on arterial lipid metabolism. Inhibition of sterol esterification in vitro. Atherosclerosis. 1981 Jan-Feb;38(1-2):81-8. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- Kitamura K, Omran AA, Takegami S, Tanaka R, Kitade T: (19)F NMR spectroscopic characterization of the interaction of niflumic acid with human serum albumin. Anal Bioanal Chem. 2007 Apr;387(8):2843-8. doi: 10.1007/s00216-007-1162-x. Epub 2007 Feb 14. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Not Available
- Specific Function
- Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...
Components:
References
- Becker DE, Reed KL: Essentials of local anesthetic pharmacology. Anesth Prog. 2006 Fall;53(3):98-108; quiz 109-10. doi: 10.2344/0003-3006(2006)53[98:EOLAP]2.0.CO;2. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Nagy H, Goda K, Fenyvesi F, Bacso Z, Szilasi M, Kappelmayer J, Lustyik G, Cianfriglia M, Szabo G Jr: Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Biochem Biophys Res Commun. 2004 Mar 19;315(4):942-9. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55