Identification

Name
Benzocaine
Accession Number
DB01086  (APRD00539)
Type
Small Molecule
Groups
Approved, Investigational
Description

A surface anesthetic that acts by preventing transmission of impulses along nerve fibers and at nerve endings. [PubChem]

Structure
Thumb
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
Product Ingredients
IngredientUNIICASInChI Key
Benzocaine hydrochlorideOG625Z9LEO23239-88-5JAADDQHUJDUAKW-UHFFFAOYSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Anal Swabs 20%Stick20 %TopicalEndovations Inc.1988-12-311997-07-15Canada
Endocaine Spray 20%Spray20 %Buccal; OralEndovations Inc.1988-12-311997-07-15Canada
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
20/20 Topical AnestheticStrip10 mg/1DentalAdvanced Dental Anesthetics2012-02-28Not applicableUs
7 Select Oral Pain Maximum Strength ReliefGel200 mg/1gTopical7-ELEVEN, INC.2016-12-08Not applicableUs
Advance Topical Anesthetic GelGel200 mg/1gDentalThe Atlanta Dental Supply Company Dba Advanced Dental Products2017-03-01Not applicableUs
Advance Topical Anesthetic GelGel200 mg/1gDentalThe Atlanta Dental Supply Company Dba Advanced Dental Products2017-03-01Not applicableUs
Advance Topical Anesthetic GelGel200 mg/1gDentalThe Atlanta Dental Supply Company Dba Advanced Dental Products2017-03-01Not applicableUs
Advance Topical Anesthetic GelGel200 mg/1gDentalThe Atlanta Dental Supply Company Dba Advanced Dental Products2017-03-01Not applicableUs
Advance Topical Anesthetic GelGel200 mg/1gDentalThe Atlanta Dental Supply Company Dba Advanced Dental Products2017-03-01Not applicableUs
Advance Topical Anesthetic GelGel200 mg/1gDentalThe Atlanta Dental Supply Company Dba Advanced Dental Products2017-03-01Not applicableUs
Adventure Medical Kits Dental MedicKit200 mg/1gOral; TopicalTender Corporation2012-09-19Not applicableUs
Aftertest Pain ReliefStick100 mg/1mLTopicalDiabetic Supply Of Suncoast, Inc.2017-01-28Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
10 Person ANSIBenzocaine (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)KitGenuine First Aid2010-04-24Not applicableUs
25 Person ANSIBenzocaine (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)KitGenuine First Aid2010-04-25Not applicableUs
3M Nexcare Cold Sore TreatmentBenzocaine (50 mg/1g) + Allantoin (10 mg/1g)OintmentTopical3M Company2008-02-20Not applicableUs
50 Person ANSIBenzocaine (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 (98.16 mL/100mL)KitGenuine First Aid2010-06-02Not applicableUs
ACME FIRST AID Contains 404 PIECESBenzocaine (6 mL/100mL) + Acetylsalicylic acid (81 mg/1) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Benzalkonium chloride (0.40 mL/100mL) + Ethanol (60 mL/100mL) + Isopropyl Alcohol (70 mL/100mL) + Lidocaine (0.5 g/100g) + Neomycin sulfate (5 mg/1g) + Polymyxin B Sulfate (5000 [iU]/1g) + Water (98.16 mL/100mL)KitAcme United Corporation2010-04-27Not applicableUs
ActisepBenzocaine (2 g/100mL) + Cetylpyridinium chloride (0.1 g/100mL) + Menthol (0.5 g/100mL)SprayTopicalActipharma, Inc2015-12-28Not applicableUs
ActisepBenzocaine (2 g/100mL) + Cetylpyridinium chloride (0.1 g/100mL) + Menthol (0.5 g/100mL)SolutionTopicalActipharma, Inc2015-12-28Not applicableUs
Adventure First Aid .5 TinBenzocaine (0.6 mg/100mL) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Ethanol (60 mL/100mL) + Isopropyl Alcohol (700 mg/1mL) + Neomycin sulfate (5 mg/1g) + Polymyxin B Sulfate (5000 [iU]/1g)KitOral; TopicalTender Corporation2015-10-01Not applicableUs
Adventure First Aid Water ResistantBenzocaine (0.6 mg/100mL) + Benzalkonium chloride (1.3 mg/1mL) + Ethanol (60 mL/100mL) + Isopropyl Alcohol (700 mg/1mL)KitOral; TopicalTender Corporation2015-10-01Not applicableUs
Adventure Medical Kits 1 Person First AidBenzocaine (6 mL/100mL) + Benzalkonium chloride (0.4 mL/100mL) + Ethanol (60 mL/100mL)KitTender Corp Dba Adventure Medical Kits2010-08-25Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Acella Antipyrine and Benzocaine OticBenzocaine (14 mg/1mL) + Antipyrine (54 mg/1mL)SolutionAuricular (otic)Proficient Rx LP2010-11-092015-12-31Us
Acella Antipyrine and Benzocaine OticBenzocaine (14 mg/1mL) + Antipyrine (54 mg/1mL)SolutionAuricular (otic)Acella Pharmaceuticals, LLC2010-11-092016-11-23Us
AdazinBenzocaine (2 g/100g) + Capsaicin (0.035 g/100g) + Lidocaine (2 g/100g) + Methyl salicylate (1.0 g/100g)CreamTopicalSterling Knight Pharmaceuticals, Llc2014-12-03Not applicableUs
Antipyrine and BenzocaineBenzocaine (14 mg/1mL) + Antipyrine (54 mg/1mL)LiquidTopicalVirtus Pharmaceuticals2012-09-122015-07-01Us
Antipyrine and BenzocaineBenzocaine (14 mg/1mL) + Antipyrine (54 mg/1mL)SolutionAuricular (otic)Aidarex Pharmaceuticals LLC2009-04-302016-04-08Us
Antipyrine and BenzocaineBenzocaine (14 mg/1mL) + Antipyrine (54 mg/1mL)SolutionAuricular (otic)A S Medication Solutions2009-04-302016-10-01Us
Antipyrine and BenzocaineBenzocaine (14 mg/1mL) + Antipyrine (54 mg/1mL)LiquidTopicalDirectrx2014-01-012014-12-31Us
Antipyrine and BenzocaineBenzocaine (14 mg/1mL) + Antipyrine (54 mg/1mL)SolutionAuricular (otic)Sda Laboratories2000-01-012015-08-31Us
Antipyrine and BenzocaineBenzocaine (14 mg/1mL) + Antipyrine (54 mg/1mL)SolutionAuricular (otic)Stratus Pharmaceuticals2014-06-152015-04-09Us
Antipyrine and BenzocaineBenzocaine (14 mg/1mL) + Antipyrine (55 mg/1mL)SolutionAuricular (otic)Virtus Pharmaceuticals2012-09-122015-07-01Us
International/Other Brands
Anacaine / Anaesthesin / Anbesol Baby / Dermoplast
Categories
UNII
U3RSY48JW5
CAS number
94-09-7
Weight
Average: 165.1891
Monoisotopic: 165.078978601
Chemical Formula
C9H11NO2
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

Pharmacology

Indication

For general use as a lubricant and topical anesthetic on esophagus, larynx, mouth, nasal cavity, rectum, respiratory tract or trachea, urinary tract, vagina. It is also used to suppress gag reflex.

Associated Conditions
Pharmacodynamics

Benzocaine is a local anesthetic commonly used as a topical pain reliever. It is the active ingredient in many over-the-counter analgesic ointments. It is also indicated for general use as a lubricant and topical anesthetic on intratracheal catheters and pharyngeal and nasal airways to obtund the pharyngeal and tracheal reflexes; on nasogastric and endoscopic tubes; urinary catheters; laryngoscopes; proctoscopes; sigmoidoscopes and vaginal specula.

Mechanism of action

Benzocaine binds to sodium channels and reversibly stabilizes the neuronal membrane which decreases its permeability to sodium ions. Depolarization of the neuronal membrane is inhibited thereby blocking the initiation and conduction of nerve impulses.

TargetActionsOrganism
ASodium channel protein type 10 subunit alpha
inhibitor
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

LD50=3040 mg/kg (rat, oral)

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Benzocaine Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
Amyl NitriteThe risk or severity of methemoglobinemia can be increased when Benzocaine is combined with Amyl Nitrite.
ButalbitalThe risk or severity of methemoglobinemia can be increased when Butalbital is combined with Benzocaine.
CelecoxibThe risk or severity of methemoglobinemia can be increased when Celecoxib is combined with Benzocaine.
ChloroquineThe risk or severity of methemoglobinemia can be increased when Chloroquine is combined with Benzocaine.
CyclophosphamideThe risk or severity of methemoglobinemia can be increased when Cyclophosphamide is combined with Benzocaine.
DapsoneThe risk or severity of methemoglobinemia can be increased when Dapsone is combined with Benzocaine.
FlutamideThe risk or severity of methemoglobinemia can be increased when Flutamide is combined with Benzocaine.
HyaluronidaseHyaluronidase can cause an increase in the absorption of Benzocaine resulting in an increased serum concentration and potentially a worsening of adverse effects.
IfosfamideThe risk or severity of methemoglobinemia can be increased when Benzocaine is combined with Ifosfamide.
IsomethepteneThe risk or severity of methemoglobinemia can be increased when Benzocaine is combined with Isometheptene.
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0004992
KEGG Drug
D00552
KEGG Compound
C07527
PubChem Compound
2337
PubChem Substance
46508891
ChemSpider
13854242
ChEBI
116735
ChEMBL
CHEMBL278172
Therapeutic Targets Database
DAP001234
PharmGKB
PA448576
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Benzocaine
ATC Codes
R02AD01 — BenzocaineD04AB04 — BenzocaineN01BA05 — BenzocaineC05AD03 — Benzocaine
AHFS Codes
  • 84:08.00 — Antipruritics and Local Anesthetics
  • 52:16.00 — Local Anesthetics
MSDS
Download (73.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Enrolling by InvitationBasic ScienceBMI >30 kg/m21
1, 2TerminatedTreatmentMaternal Nipple Pain Upon Breastfeeding / Neonatal Latch Difficulties / Neonatal Tongue-tie1
2CompletedPreventionAnaesthesia therapy1
2CompletedPreventionNo Disease State or Condition1
2CompletedSupportive CareOtitis Media (OM) / Pain NOS1
2CompletedTreatmentAcute Otitis Media1
2CompletedTreatmentAcute Otitis Media / Pain NOS1
2Enrolling by InvitationPreventionNormal Pulp/ Pulpitis1
3CompletedTreatmentAcute Otitis Media1
3CompletedTreatmentAcute Otitis Media / Pain NOS1
3CompletedTreatmentDrug Reaction to Analgesic Nos1
3CompletedTreatmentPharyngitis1
3CompletedTreatmentThroat Pain1
3TerminatedTreatmentAcute Otitis Media1
4CompletedPreventionAnesthesia of Mucous Membrane1
4CompletedPreventionNeonatal Infections1
4CompletedTreatmentAnalgesia / Pain Relief1
4CompletedTreatmentToothache1
4Not Yet RecruitingTreatmentAcute-On-Chronic Liver Failure / Viral Hepatitis B / Virus Diseases1
4RecruitingTreatmentRadial Artery Spasm1
4Unknown StatusTreatmentDental Pain / Postoperative pain1
Not AvailableActive Not RecruitingPreventionArterial Hypotension1
Not AvailableActive Not RecruitingTreatmentSpondyloarthritis1
Not AvailableCompletedBasic ScienceDepression1
Not AvailableCompletedTreatmentAge-Related Macular Degeneration (ARMD) / Central Retinal Vein Occlusion (CRVO) / Diabetic Macular Edema (DME)1
Not AvailableCompletedTreatmentAging / Pain NOS1
Not AvailableCompletedTreatmentLocal Anesthesia / Postoperative pain / Self-Perception1
Not AvailableNot Yet RecruitingBasic ScienceBack Pain Lower Back Chronic1
Not AvailableRecruitingTreatmentAnaesthesia therapy / Surgery--Complications1
Not AvailableUnknown StatusTreatmentPain NOS1
Not AvailableWithdrawnTreatmentPain NOS1

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
FormRouteStrength
StripDental10 mg/1
KitOral; Topical
Kit
KitTopical
KitOral; Topical200 mg/1g
StickTopical100 mg/1mL
SwabTopical
CreamTopical7.5 g/100g
Aerosol, sprayTopical11.4 g/57g
OintmentTopical5.6 g/28g
GelTopical2833 mg/60mL
StickTopical20 %
GelOral7.5 %
GelTopical20 %
GelOral
LiquidBuccal
SolutionTopical200 mg/1mL
LiquidOral
SolutionTopical100 mg/1mL
GelOral0.2 g/100g
LiquidTopical0.2 mg/2mL
GelTopical200.0 mg/1g
LiquidTopical20 g/100mL
GelOral10 g/100g
Solution / dropsAuricular (otic)
SolutionAuricular (otic)
LiquidTopical2.1 mg/30mL
GelTopical75 mg/1g
LiquidTopical.075 mL/1mL
GelTopical10 g/100g
GelTopical7.5 g/100g
LozengeOral15 mg/1
GelTopical210 mg/1g
SprayTopical11.8 g/59mL
SprayTopical20 mL/100mL
Spray, meteredDental11.4 g/57g
GelDental230 mg/1mL
GelTopical200 mg/1mL
SwabTopical0.12 mL/1
SwabTopical60 mg/1mL
CreamTopical0.2 g/1g
LiquidTopical5 g/100g
CreamTopical5 g/100g
SprayTopical5 g/100g
LiquidTopical
CreamTopical5 g/100mL
BeadOral3 mg/1
OintmentTopical20 g/100g
OintmentTopical20 %
CreamTopical71.9395789 mg/1mL
CreamTopical73.9395789 mg/1mL
CreamTopical34.05 g/454g
GelOral9 mg/1mL
GelTopical0.2 g/1g
LotionTopical
LiquidOral20 g/100mL
CreamTopical10 g/100g
Tablet, orally disintegratingOral6 mg/1
LozengeOral3 mg/1
LozengeOral4 mg/1
SprayOral
SwabTopical0.06 mL/1mL
AerosolTopical
OintmentTopical10 g/100g
LiquidAuricular (otic)
GelTopical0.075 g/1g
SpongeTopical
Paste, dentifriceTopical200 mg/1g
PasteDental
GelOral75 mg/1g
LotionTopical50 mg/1mL
Paste, dentifriceTopical20 g/100g
LiquidOral200 mg/1mL
Gel, dentifriceDental20.00 g/100g
Gel, dentifriceOral20.0 g/100g
Gel, dentifriceDental
Gel, dentifriceDental10.00 g/100g
LiquidDental; Topical200 mg/1mL
GelDental
OintmentDental0.2 g/1mL
OintmentDental0.20 g/1mL
GelBuccal; Topical
OintmentTopical
LotionTopical0.05 g/1g
GelTopical7.5 %
GelTopical2410 mg/50mL
GelTopical50 mg/1mL
SprayBuccal; Oral20 %
Aerosol, meteredTopical
LiquidRectal
LiquidOral7.5 mg/100mg
SprayOral7.5 mg/100mL
PatchTopical6 g/100g
PatchTopical
GelDental6 g/30g
GelDental20 %
GelDental; Oral; Periodontal200 mg/1
LiquidDental20 %
LiquidDental; Oral; Periodontal200 mg/1
LiquidOral50 mg/1mL
SolutionOral
SuppositoryRectal
CreamTopical4.5 g/100g
SprayDental; Periodontal183 mg/1g
LiquidTopical20 %
GelDental; Periodontal200 mg/1g
SprayDental; Oral; Periodontal200 mg/1g
GelDental; Oral; Periodontal200 mg/1g
LiquidDental; Oral; Periodontal200 mg/1g
AerosolDental; Topical21.9 %
LiquidTopical15 mg/1mL
SolutionTopical150 mg/1mL
GelDental; Oral6.4 g/100g
LiquidTopical6 g/100g
LiquidDental
CreamTopical5 %
LiquidBuccal; Topical
LiquidBuccal200 mg/1mL
CreamDental
GelTopical7 g/100mL
LozengeBuccal
GelOral20 g/100g
GelOral200 mg/1g
GranuleOral6 mg/1
Aerosol, sprayTopical
LiquidTopical1417 mg/30mL
LiquidTopical50 mg/1mL
GelTopical3.00 g/100mL
GelTopical2.13 g/28.35g
SwabTopical0.12 g/1g
SwabTopical0.12 g/0.6mL
ClothTopical
OintmentTopical1.27 g/100g
SprayTopical11.4 g/57g
LiquidOral200 mg/1g
CreamTopical200 mg/1mL
Powder, for solutionOral90 mg/1
GelBuccal
Spray, meteredDental; Oral; Topical12 g/60g
GelDental; Oral6.4 g/32g
Paste, dentifriceDental19.8 mg/1g
LiquidDental205 mg
StripDental
GelDental200 mg
SwabTopical0.2 mL/1mL
GelTopical100 mg/1g
SwabTopical.075 mL/1mL
GelDental; Topical
Film, solubleOral
GelTopical200 mg/1g
LiquidTopical0.2 mL/1mL
PasteTopical
GelOral0.2 mL/1mL
GelTopical20 g/100g
OintmentTopical5.00 mg/1g
LiquidTopical.009 mg/1mL
LiquidTopical18.6 g/100mL
CreamTopical20 mg/100mg
LiquidTopical200 mg/1g
GelOral; Topical
Solution / dropsAuricular (otic)200 mg/1mL
TabletOral
GelTopical5 g/100mL
LiquidTopical4 g/100mL
GelDental221 mg/1g
GelDental; Topical20 %
GelTopical20 1/100g
CreamTopical4.2 g/56g
LiquidAuricular (otic)200 mg/1mL
OintmentRectal
OintmentTopical200 mg/1g
LiquidTopical200 mg/1mL
Gel, dentifriceOral7.5 g/100g
GelOral200 mg/1mL
Gel, dentifriceOral
LiquidDental20.00 g/100g
SwabTopical15 %
Powder, for solutionOral150 mg/3000mg
KitTopical0.05 g/1g
ClothTopical0.0543 g/1
KitTopical6 g/1
KitTopical0.0543 g/1
LiquidOral20 g/100g
Aerosol, sprayTopical1.125 g/15g
GelTopical5.06 g/67.50g
GelTopical5.07 g/67.5g
GelTopical5.07 g/67.50g
SyrupDental1.8 %
Gum, chewingOral
CreamTopical
LozengeOral
SwabTopical6 g/100mL
SolutionTopical
SwabTopical0.06 mg/1
SwabOral20 %
LiquidOral1.3 mg/13mL
OintmentTopical3.5 g/100g
GelDental200 mg/1g
Gel, dentifriceDental220 mg/1g
Spray, meteredPeriodontal220 mg/1g
GelOral; Topical20 %
GelOral; Topical200 mg
GelDental220 mg/1g
GelDental200 mg/1mL
EnemaRectal
CreamTopical125 mg/1
SprayTopical7.5 g/100mL
Spray, meteredTopical
GelTopical
SprayTopical
AerosolOral
GelTopical10 %
SwabTopical20 %
GelTopical0.1 g/1g
GelDental20 g/100g
Prices
Unit descriptionCostUnit
Americaine Anesthetic 20% Gel 28 gm Tube22.99USD tube
Americaine 20% ear drops1.26USD ml
Oticaine 20% ear drops0.83USD ml
Americaine lubricant0.71USD g
Hurricaine 20% liquid swab0.6USD swab
Hurricaine 20% spray0.52USD ml
Anbesol baby 7.5% gel0.41USD g
Cepacol 6 mg fizzlers tablet0.39USD tablet
Benzocaine powder0.09USD g
Dermoplast pain relieving spry0.07USD ml
Dermoplast spray0.07USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)92 °CPhysProp
boiling point (°C)310 °CPhysProp
water solubility1310 mg/L (at 30 °C)YALKOWSKY,SH & HE,Y (2003)
logP1.86HANSCH,C ET AL. (1995)
pKa2.51 (at 25 °C)PERRIN,DD (1965)
Predicted Properties
PropertyValueSource
Water Solubility2.85 mg/mLALOGPS
logP2.2ALOGPS
logP1.5ChemAxon
logS-1.8ALOGPS
pKa (Strongest Basic)2.78ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area52.32 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.53 m3·mol-1ChemAxon
Polarizability17.46 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9963
Blood Brain Barrier+0.9609
Caco-2 permeable+0.7814
P-glycoprotein substrateNon-substrate0.8329
P-glycoprotein inhibitor INon-inhibitor0.9589
P-glycoprotein inhibitor IINon-inhibitor0.9612
Renal organic cation transporterNon-inhibitor0.8818
CYP450 2C9 substrateNon-substrate0.8426
CYP450 2D6 substrateNon-substrate0.7934
CYP450 3A4 substrateNon-substrate0.7513
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.937
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7883
Ames testNon AMES toxic0.8825
CarcinogenicityCarcinogens 0.513
BiodegradationReady biodegradable0.7718
Rat acute toxicity1.7665 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9721
hERG inhibition (predictor II)Non-inhibitor0.9668
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (7.74 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)GC-MSsplash10-00dl-0980000000-9bd6d020be04ce49bd3e
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-00di-4900000000-9341302295e361a20bfd
GC-MS Spectrum - EI-BGC-MSsplash10-0109-9400000000-8e31c925b871e0f0299e
GC-MS Spectrum - EI-BGC-MSsplash10-0109-9400000000-c755b4e5336a2867357e
GC-MS Spectrum - EI-BGC-MSsplash10-01b9-1900000000-a811093acfd0672fece6
GC-MS Spectrum - CI-BGC-MSsplash10-014i-0900000000-49302e8e4fd5158a36da
GC-MS Spectrum - EI-BGC-MSsplash10-00di-5900000000-dcd2847110af7c87bf18
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00dl-0980000000-9bd6d020be04ce49bd3e
Mass Spectrum (Electron Ionization)MSsplash10-00xr-6900000000-0594451f3b181ab3c883
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-00kr-0900000000-b54aebb77e7a69ada07c
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-014i-5900000000-ce90658bd0fc66df820d
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-03xu-9100000000-5179b7804d2c59e71aa4
MS/MS Spectrum - EI-B (HITACHI RMU-7M) , PositiveLC-MS/MSsplash10-00di-4900000000-9341302295e361a20bfd
MS/MS Spectrum - EI-B (HITACHI RMU-7) , PositiveLC-MS/MSsplash10-0109-9400000000-8e31c925b871e0f0299e
MS/MS Spectrum - EI-B (HITACHI RMU-6D) , PositiveLC-MS/MSsplash10-0109-9400000000-c755b4e5336a2867357e
MS/MS Spectrum - EI-B (HITACHI M-60) , PositiveLC-MS/MSsplash10-01b9-1900000000-57d39b512bc5bdbb4987
MS/MS Spectrum - CI-B (HITACHI M-60) , PositiveLC-MS/MSsplash10-014i-0900000000-49302e8e4fd5158a36da
MS/MS Spectrum - EI-B (JEOL JMS-DX-300) , PositiveLC-MS/MSsplash10-00di-5900000000-dcd2847110af7c87bf18
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-014i-0900000000-a0f10abbe67842c2c958
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-00du-5900000000-43a89461a4d9cc5d1409
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-00dl-9600000000-049e2653cbbf24aaf010
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-002f-9100000000-6fbc7720b326773643af
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-00ou-9000000000-d7f7622c3a270c5ffcbb
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-0900000000-e061a0f4172b47a8bd22
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00du-5900000000-54757e57c91d3eaa1976
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00dl-9600000000-049e2653cbbf24aaf010
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-002f-9100000000-e16fc2db7a632fc6f4da
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00ou-9000000000-d7f7622c3a270c5ffcbb
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-5900100000-72ac4bcb64db0d25261e
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-000i-2900000000-89639c79865df34d7081
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-000i-2900000000-2132ea2de3c0db3e47fa
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

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
Aminobenzoic acid or derivatives / Benzoate ester / Benzoyl / Aniline or substituted anilines / Amino acid or derivatives / Carboxylic acid ester / Carboxylic acid derivative / Monocarboxylic acid or derivatives / Amine / Organonitrogen compound
show 8 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
substituted aniline, benzoate ester (CHEBI:116735)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Voltage-gated sodium channel activity
Specific Function
Tetrodotoxin-resistant channel that mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference acro...
Gene Name
SCN10A
Uniprot ID
Q9Y5Y9
Uniprot Name
Sodium channel protein type 10 subunit alpha
Molecular Weight
220623.605 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. 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. [PubMed:17967784]
  4. 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. [PubMed:19661462]
  5. 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. [PubMed:16174788]

Enzymes

Kind
Protein
Organism
Human
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
  1. 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. [PubMed:7470208]

Transporters

Kind
Protein
Organism
Human
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
  1. 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. [PubMed:14985103]

Drug created on June 13, 2005 07:24 / Updated on November 12, 2018 07:26