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    Chemistry

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    Also known as: Ethyl 4-aminobenzoate, 94-09-7, Ethyl aminobenzoate, Ethyl p-aminobenzoate, Americaine, Anaesthesin
    Molecular Formula
    C9H11NO2
    Molecular Weight
    165.19  g/mol
    InChI Key
    BLFLLBZGZJTVJG-UHFFFAOYSA-N
    FDA UNII
    U3RSY48JW5
    Benzocaine
    A surface anesthetic that acts by preventing transmission of impulses along nerve fibers and at nerve endings.
    Benzocaine is a Standardized Chemical Allergen. The physiologic effect of benzocaine is by means of Increased Histamine Release, and Cell-mediated Immunity.
    1 2D Structure

    Benzocaine

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    ethyl 4-aminobenzoate
    2.1.2 InChI
    InChI=1S/C9H11NO2/c1-2-12-9(11)7-3-5-8(10)6-4-7/h3-6H,2,10H2,1H3
    2.1.3 InChI Key
    BLFLLBZGZJTVJG-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CCOC(=O)C1=CC=C(C=C1)N
    2.2 Other Identifiers
    2.2.1 UNII
    U3RSY48JW5
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 4-aminobenzoic Acid Ethyl Ester

    2. Acetate, Benzocaine

    3. Americaine

    4. Anaesthesin

    5. Anesthesin

    6. Bensokain

    7. Benzocaine Acetate

    8. Benzocaine Formate

    9. Benzocaine Hydrobromide

    10. Benzocaine Hydrochloride

    11. Benzocaine Methanesulfonate

    12. Ethoform

    13. Ethyl Aminobenzoate

    14. Formate, Benzocaine

    15. Hydrobromide, Benzocaine

    16. Hydrochloride, Benzocaine

    17. Methanesulfonate, Benzocaine

    2.3.2 Depositor-Supplied Synonyms

    1. Ethyl 4-aminobenzoate

    2. 94-09-7

    3. Ethyl Aminobenzoate

    4. Ethyl P-aminobenzoate

    5. Americaine

    6. Anaesthesin

    7. Parathesin

    8. Norcaine

    9. Parathesine

    10. Anesthesin

    11. 4-aminobenzoic Acid Ethyl Ester

    12. Ethoform

    13. Orthesin

    14. Amben Ethyl Ester

    15. P-carbethoxyaniline

    16. Anaesthin

    17. Anestezin

    18. Anesthesine

    19. Anesthone

    20. Dermoplast

    21. Hurricaine

    22. Identhesin

    23. Keloform

    24. Norcain

    25. Topcaine

    26. Baby Anbesol

    27. Anaesthan-syngala

    28. Ora-jel

    29. Benzocainum

    30. Solu H

    31. P-ethoxycarboxylic Aniline

    32. 4-carbethoxyaniline

    33. Benzoic Acid, 4-amino-, Ethyl Ester

    34. P-(ethoxycarbonyl)aniline

    35. Ethyl P-aminophenylcarboxylate

    36. Dextran Sulfate Sodium

    37. 9011-18-1

    38. Benzocaina

    39. Ethyl Paba

    40. 4-(ethoxycarbonyl)aniline

    41. P-aminobenzoic Acid Ethyl Ester

    42. Aethoform

    43. Benzoic Acid, P-amino-, Ethyl Ester

    44. Ethyl4-aminobenzoate

    45. 4-aminobenzoic Acid, Ethyl Ester

    46. 4-amino-benzoic Acid Ethyl Ester

    47. Ethylester Kyseliny P-aminobenzoove

    48. Ethyl-p-aminobenzoate

    49. Flavamed

    50. Subcutin

    51. P-aminobenzoic Acid, Ethyl Ester

    52. Chebi:116735

    53. Nsc-4688

    54. Mfcd00007892

    55. Nsc-41531

    56. U3rsy48jw5

    57. Ar01

    58. 4-aminobenzoic Acid-ethyl Ester

    59. Anaesthesinum

    60. Ethoforme

    61. Norcainum

    62. Ar-01

    63. Ethylis Aminobenzoas

    64. Cas-94-09-7

    65. Ncgc00016352-01

    66. Anestezin [russian]

    67. Chloraseptic

    68. Dextran Sulfate Sodium Salt

    69. Otocain

    70. Outgro

    71. Dsstox_cid_1804

    72. Wln: Zr Dvo2

    73. Dsstox_rid_76338

    74. Aethylium Paraminobenzoicum

    75. Benzocainum [inn-latin]

    76. Dsstox_gsid_21804

    77. Benzocaina [inn-spanish]

    78. Ethyl Aminobenzoate (van)

    79. Caswell No. 430a

    80. Finafta

    81. Parathesin (tn)

    82. Smr000059025

    83. Ethylaminobenzoate-4

    84. H-4-abz-oet

    85. Hsdb 7225

    86. Ethylester Kyseliny P-aminobenzoove [czech]

    87. Benzocaine (usp/inn)

    88. Sr-05000001573

    89. Einecs 202-303-5

    90. Nsc 41531

    91. P-aminobenzoic Ethyl Ester

    92. Unii-u3rsy48jw5

    93. Epa Pesticide Chemical Code 097001

    94. Brn 0638434

    95. Benzoak

    96. Benzocaine [usp:inn:ban]

    97. Vagisil

    98. Ai3-02081

    99. Benzocaine Usp

    100. Diet Ayds

    101. Orabase-b

    102. Slim Mint Gum

    103. Prestwick_991

    104. 4-carboethoxyaniline

    105. Ethyl 4aminobenzoate

    106. Ethyl 4-aminobenzate

    107. Ethyl 4-aminobezoate

    108. Outgro (salt/mix)

    109. Anbesol (salt/mix)

    110. Vagisil (salt/mix)

    111. Ethyl-4-aminobenzoate

    112. P-ethoxycarbonylaniline

    113. 4-ethoxycarbonylaniline

    114. Ethyl P-amino-benzoate

    115. Ethyl-p-amino-benzoate

    116. Ethyl Aminobenzoic Acid

    117. Cough-x (salt/mix)

    118. Spectrum_000074

    119. Ethyl 4-amino-benzoate

    120. Benzocaine [mi]

    121. Ethyl 4-(amino)benzoate

    122. Benzocaine [inn]

    123. Ethyl P-aminobenzoic Acid

    124. Prestwick0_000712

    125. Prestwick1_000712

    126. Prestwick2_000712

    127. Prestwick3_000712

    128. Spectrum2_000117

    129. Spectrum3_000314

    130. Spectrum4_000249

    131. Spectrum5_000860

    132. Benzocaine [hsdb]

    133. Ethyl 4-aminobenzoic Acid

    134. Benzocaine [vandf]

    135. Epitope Id:114084

    136. Ethyl Paba [inci]

    137. Benzocaine [mart.]

    138. Benzocaine [usp-rs]

    139. Benzocaine [who-dd]

    140. Benzocaine [who-ip]

    141. Sampl3, G4

    142. Ethyl Aminobenzoate (jp17)

    143. Oprea1_750694

    144. Oprea1_827402

    145. Schembl25100

    146. Bspbio_000923

    147. Bspbio_001908

    148. Kbiogr_000658

    149. Kbioss_000474

    150. 4-(ethoxycarbonyl)phenylamine

    151. 4-14-00-01129 (beilstein Handbook Reference)

    152. Ae-562/40377256

    153. Mls001331704

    154. Mls002153970

    155. Divk1c_000932

    156. Ethyl 4-aminobenzoate, 98%

    157. Spectrum1500139

    158. (p-(ethoxycarbonyl)phenylamine

    159. Ethyl P-aminobenzenecarboxylate

    160. Spbio_000134

    161. Spbio_002844

    162. Bpbio1_001017

    163. Chembl278172

    164. Dtxsid8021804

    165. Dextran Sulfate Sodium (dst-h)

    166. Ethyl Para Amino Benzoate

    167. Hms502o14

    168. Kbio1_000932

    169. Kbio2_000474

    170. Kbio2_003042

    171. Kbio2_005610

    172. Kbio3_001408

    173. P-amino Benzoic Acid Ethyl Ester

    174. 4-amino Benzoic Acid Ethyl Ester

    175. Benzocaine [ep Monograph]

    176. Ethyl Aminobenzoate [jan]

    177. Nsc4688

    178. Dextran Sulfate Sodium (kmds-h)

    179. Ninds_000932

    180. Bdbm197282

    181. Benzocaine [usp Monograph]

    182. Dextran Sulfate Sodium (ds-m-1)

    183. Hms1570o05

    184. Hms1920g09

    185. Hms2091m11

    186. Hms2097o05

    187. Hms2233h21

    188. Hms3371d08

    189. Hms3652h13

    190. Hms3714o05

    191. Hms3885b11

    192. Pharmakon1600-01500139

    193. Benzocainum [who-ip Latin]

    194. Component Of Tympagesic (salt/mix)

    195. Cs-b0934

    196. Hy-y0258

    197. Nsc41531

    198. Str01509

    199. Tox21_110391

    200. Tox21_301149

    201. Ccg-38918

    202. Nsc755909

    203. S4210

    204. Stk043620

    205. Zinc12358719

    206. Akos000119763

    207. Benzocaine 1.0 Mg/ml In Acetonitrile

    208. Benzocaine 100 Microg/ml In Methanol

    209. Tox21_110391_1

    210. Ac-8127

    211. Db01086

    212. Dextran, Hydrogen Sulfate, Sodium Salt

    213. Nsc-755909

    214. Idi1_000932

    215. Benzocaine, Purum, >=99.0% (hplc)

    216. Benzocaine, Tested According To Ph.eur.

    217. Ncgc00016352-02

    218. Ncgc00016352-03

    219. Ncgc00016352-04

    220. Ncgc00016352-07

    221. Ncgc00094598-01

    222. Ncgc00094598-02

    223. Ncgc00255047-01

    224. Ethyl 4-aminobenzoate, 98.0-101.0%

    225. Sbi-0051293.p003

    226. Component Of Solarcaine Aerosol (salt/mix)

    227. A0271

    228. Ab00051923

    229. Bb 0258778

    230. Ft-0624536

    231. Ft-0625762

    232. Ft-0662548

    233. Sw197074-3

    234. A14560

    235. C07527

    236. D00552

    237. Ab00051923_09

    238. Ab00051923_10

    239. Component Of Anbesol Maximum Strength (salt/mix)

    240. A860898

    241. A930377

    242. Aminobenzoic Acid Impurity B [ep Impurity]

    243. Q422745

    244. Ethyl 4-aminobenzoate, Saj First Grade, >=99.0%

    245. Q-200688

    246. Sr-05000001573-1

    247. Sr-05000001573-3

    248. Brd-k75466013-001-05-2

    249. Brd-k75466013-001-08-6

    250. Ethyl 4-aminobenzoate, Vetec(tm) Reagent Grade, 98%

    251. F2190-0448

    252. 4-aminobenzoic Acid-ethyl Ester 1000 Microg/ml In Methanol

    253. Benzocaine, European Pharmacopoeia (ep) Reference Standard

    254. Benzocaine, United States Pharmacopeia (usp) Reference Standard

    255. Benzocaine, Pharmaceutical Secondary Standard; Certified Reference Material

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 165.19 g/mol
    Molecular Formula C9H11NO2
    XLogP31.9
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count3
    Exact Mass165.078978594 g/mol
    Monoisotopic Mass165.078978594 g/mol
    Topological Polar Surface Area52.3 Ų
    Heavy Atom Count12
    Formal Charge0
    Complexity151
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Therapeutic Uses

    Indicated for the relief of: canker sores, cold sores, or fever blisters: benzocaine (gel and topical solution); gingival or oral mucosal pain (i.e., pain caused by mouth or gum irritation, inflammation, lesions, or minor dental procedures): benzocaine (gel, dental paste, lozenges, and topical solution); dental prosthetic pain (i.e., pain or irritation caused by dentures or other dental or orthodontic appliances): benzocaine (dental paste, gel ointment, and topical solution); teething pain: benzocaine (7.5% and 10% gel); and toothache: benzocaine (10% and 20% gel and topical solution).

    Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 153

    Indicated to suppress the gag reflex and/or other laryngeal and esophageal reflexes to facilitate dental examination or procedures (including oral surgery), endoscopy, or intubation: benzocaine (gel, topical aerosol, and topical solution). /Included in US product labeling/

    Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 153

    Indicated to provide topical anesthesia of accessible mucous membranes prior to examination, endoscopy or instrumentation, or other procedures involving the: esophagus: benzocaine (gel and topical solution)); larynx: benzocaine (gel and topical solution); mouth, In dental procedures and oral surgery: benzocaine (gel, topical aerosol, and topical solution); nasal cavity: benzocaine (gel); pharynx or throat: benzocaine (gel, topical aerosol, and topical solution); rectum: benzocaine (gel); respiratory tract or trachea: benzocaine (gel, topical aerosol, and topical solution); urinary tract: benzocaine (gel); and vagina: benzocaine (gel).

    Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 153

    Anesthetic (local).

    O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 186

    (VET): Local (usually surface) anesthetic.

    O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 186

    4.2 Drug Warning

    Infants and the elderly were more likely to develop toxic methemoglobinemia after benzocaine exposure. Other risk factors included genetic reductase deficiencies, exposure to high doses of anesthetic, and presence of denuded skin and mucous membranes. Because of the potential for severe complications, methemoglobinemia should be corrected promptly in compromised patients and those with toxic benzocaine concentrations. The possibility of masking symptoms during general anesthesia carries special risk of use of this agent in the preanesthesia setting.

    PMID:8069004 Rodriguez LF et al; Ann Pharmacother 28 (5): 643-9 (1994)

    Use of otic anesthetics may mask symptoms of a fulminating middle ear infection (acute otitis media). Otic solutions containing benzocaine should not be used in the presence of a perforated tympanic membrane.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2004. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2004 (Plus Supplements)., p. 2695

    When applied topically as recommended, benzocaine is relatively nontoxic, however, sensitization may occur.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2004. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2004 (Plus Supplements)., p. 3411

    When used as a male genital desensitizer, benzocaine generally does not adversely affect orgasm in female sexual partners and does not appear to anesthetize the clitoris or vagina.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2004. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2004 (Plus Supplements)., p. 3411

    For more Drug Warnings (Complete) data for BENZOCAINE (9 total), please visit the HSDB record page.

    4.3 Drug Indication

    Benzocaine is indicated for local anesthesia in dentistry, minor trauma, and as preparation for infiltrative anesthesia. Benzocaine products are indicated for topical anesthesia in a wide variety of conditions including skin irritation, oral pain, and hemorrhoids.

    Treatment of oropharyngeal pain

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Benzocaine is indicated for use as a topical anesthetic. It has a duration of action of approximately 10 minutes and a wide therapeutic window. Patients should be counselled regarding the risks of methemoglobinemia.

    5.2 MeSH Pharmacological Classification

    Anesthetics, Local

    Drugs that block nerve conduction when applied locally to nerve tissue in appropriate concentrations. They act on any part of the nervous system and on every type of nerve fiber. In contact with a nerve trunk, these anesthetics can cause both sensory and motor paralysis in the innervated area. Their action is completely reversible. (From Gilman AG, et. al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed) Nearly all local anesthetics act by reducing the tendency of voltage-dependent sodium channels to activate. (See all compounds classified as Anesthetics, Local.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    BENZOCAINE
    5.3.2 FDA UNII
    U3RSY48JW5
    5.3.3 Pharmacological Classes
    Cell-mediated Immunity [PE]; Copper Absorption Inhibitor [EPC]; Decreased Copper Ion Absorption [PE]; Increased Histamine Release [PE]; Sigma-1 Agonist [EPC]; Sigma-1 Receptor Agonists [MoA]; Skin Barrier Activity [PE]; Standardized Chemical Allergen [EPC]; Uncompetitive N-methyl-D-aspartate Receptor Antagonist [EPC]; Uncompetitive NMDA Receptor Antagonists [MoA]; Allergens [CS]
    5.4 ATC Code

    C05AD03

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    C - Cardiovascular system

    C05 - Vasoprotectives

    C05A - Agents for treatment of hemorrhoids and anal fissures for topical use

    C05AD - Local anesthetics

    C05AD03 - Benzocaine

    D - Dermatologicals

    D04 - Antipruritics, incl. antihistamines, anesthetics, etc.

    D04A - Antipruritics, incl. antihistamines, anesthetics, etc.

    D04AB - Anesthetics for topical use

    D04AB04 - Benzocaine

    N - Nervous system

    N01 - Anesthetics

    N01B - Anesthetics, local

    N01BA - Esters of aminobenzoic acid

    N01BA05 - Benzocaine

    R - Respiratory system

    R02 - Throat preparations

    R02A - Throat preparations

    R02AD - Anesthetics, local

    R02AD01 - Benzocaine

    5.5 Absorption, Distribution and Excretion

    Branchial and urinary elimination of benzocaine residues was evaluated in adult rainbow trout, Oncorhynchus mykiss, given a single dorsal aortic dose of 14(C)-benzocaine hydrochloride. Branchial elimination of benzocaine residues was rapid and accounted for 59.2% of the dose during the first 3 h after dosing. Renal elimination of radioactivity was considerably slower; the kidney excreted 2.7% dose within 3 h and 9.0% within 24 hr. Gallbladder bile contained 2.0% dose 24 hr after injection. Of the radioactivity in radiochromatograms from water taken 3 min after injection, 87.3% was benzocaine and 12.7% was N-acetylated benzocaine. After 60 min, 32.7% was benzocaine and 67.3% was N-acetylated benzocaine. Of the radioactivity in radiochromatograms from urine taken 1 hr after dosing, 7.6% was para-aminobenzoic acid, 59.7% was N-acetylated para-aminobenzoic acid, 19.5% was benzocaine, and 8.0% was N-acetylated benzocaine. The proportion of the radioactivity in urine changed with time so that by 20 hr, 1.0% was para-aminobenzoic acid and 96.6% was N-acetylated para-aminobenzoic acid. Benzocaine and a more hydrophobic metabolite, N-acetylated benzocaine, were eliminated primarily through the gills; renal and biliary pathways were less significant elimination routes for benzocaine residues.

    PMID:1897251 Meinertz JR et al; Xenobiotica 21 (4): 525-33 (1991)

    5.6 Metabolism/Metabolites

    Benzocaine undergoes ester hydrolysis to form 4-aminobenzoic acid, acetylation to form acetylbenzocaine, or N-hydroxylation to form benzocaine hydroxide. 4-aminobenzoic acid can be acetylated or acetylbenzocaine can undergo ester hydrolysis to form 4-acetaminobenzoic acid.

    The effect of dose and enzymatic inhibition on the percutaneous absorption and metabolism of benzocaine was studied in vitro in the hairless guinea pig. At the dose level of 2 ug/sq cm, benzocaine was rapidly absorbed and extensively metabolized (80%) by acetyltransferase. As the applied dose of benzocaine was increased to 40 and 200 ug/sq cm, N-acetylation of benzocaine decreased to 44 and 34%, respectively, suggesting saturation of the acetyltransferase system. Total 14(C) absorption after benzocaine application was not significantly different between control and enzyme-inhibited skin and therefore does not appear to be affected by the extent of benzocaine metabolism during percutaneous penetration. Skin provides a significant first-pass metabolic effect for therapeutic doses of percutaneously absorbed benzocaine, and the primary metabolite formed, acetylbenzocaine, is biologically active.

    PMID:8737920 Kraeling ME et al; Skin Pharmacol 9 (3): 221-30 (1996)

    5.7 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. Nerve cells unable to allow sodium into cells cannot depolarize and conduct nerve impulses.

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

    Physicians Desk Reference. 58th ed. Thomson PDR. Montvale, NJ 2004., p. 1130

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    05-Jan-2021
    22-Aug-2024
    KGS
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