{"ATC Code":"C05AD03","Abbreviation":"","Aliases":["Ethyl 4-aminobenzoate","Ethyl p-aminobenzoate","Parathesin","Norcaine","Anesthesin","Parathesine","Amben ethyl ester","p-Carbethoxyaniline","Anaesthin","Anesthesine"],"Boiling Point":"310 °C","CAS":"94-09-7","ChEBI":"CHEBI:116735","ChEMBL":"CHEMBL278172","ChemicalClasses":["alcohol"],"Chirality":"achiral","Classes":["Sodium channel blocker"],"Color/Form":"Rhombohedra from ether","Dosing Info":[{"Method":"Sublingual","Tiers":{"Common":{"Lower":20,"Upper":20},"Heavy":{"Lower":20,"Upper":20},"Light":{"Lower":20,"Upper":20},"Strong":{"Lower":20,"Upper":20},"Threshold":{"Lower":20,"Upper":20}},"Unit":"mg"}],"Drug Classes":"Breast Feeding; Lactation; Anesthetics, Local","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.","Drug Warnings":"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.","DrugClasses":[],"EINECS":"202-303-5","EliminationHalfLife":"","European Community (EC) Number":"202-303-5","FDA Pharmacological Classification":"U3RSY48JW5","FullSalts":["Benzocaine hydrochloride"],"HMDB ID":"HMDB0004992","HeavyAtomCount":12,"Human Drugs":"Breast Feeding; Lactation; Anesthetics, Local","IUPACName":"ethyl 4-aminobenzoate","Impurities":["aminobenzoic acid","ethyl p-nitrobenzoate"],"InChI":"InChI=1S/C9H11NO2/c1-2-12-9(11)7-3-5-8(10)6-4-7/h3-6H,2,10H2,1H3","InChIKey":"BLFLLBZGZJTVJG-UHFFFAOYSA-N","MeSH Pharmacological Classification":"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\u0026apos;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.)","Melting Point":"92 °C","MolecularFormula":"C\u003csub\u003e9\u003c/sub\u003eH\u003csub\u003e11\u003c/sub\u003eNO\u003csub\u003e2\u003c/sub\u003e","MolecularWeight":"165.19 g/mol","Pharmacodynamics":"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.","Physical Description":"Solid","PrevSalts":["hydrochloride"],"PubChemId":2337,"Record Description":["Benzocaine is a benzoate ester having 4-aminobenzoic acid as the acid component and ethanol as the alcohol component. A surface anaesthetic, it is used to suppress the gag reflex, and as a lubricant and topical anaesthetic on the larynx, mouth, nasal cavity, respiratory tract, oesophagus, rectum, urinary tract, and vagina. It has a role as a topical anaesthetic, an antipruritic drug, an allergen and a sensitiser. It is a benzoate ester and a substituted aniline.","Benzocaine is an ester local anesthetic that acts by preventing transmission of impulses along nerve fibers and at nerve endings. It is commonly used for local anesthesia in many over the counter products. Benzocaine was first used for local anesthesia in dentistry.","Benzocaine is a Standardized Chemical Allergen. The physiologic effect of benzocaine is by means of Increased Histamine Release, and Cell-mediated Immunity.","Benzocaine is an ester of paraaminobenzoic acid, lacking the terminal diethylamino group of procaine, with anesthetic activity. Benzocaine binds to the sodium channel 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.","BENZOCAINE is a small molecule drug with a maximum clinical trial phase of IV (across all indications) and has 9 approved and 5 investigational indications.","Benzocaine is a surface anesthetic that acts by preventing transmission of impulses along nerve fibers and at nerve endings. Benzocaine is a local anesthetic commonly used as a topical pain reliever. It is the active ingredient in many over-the-counter analgesic ointments. Benzocaine is an ester, a compound made from the organic acid PABA (para-aminobenzoic acid) and ethanol. The process in which this ester is created is known as Fischer esterification.","A surface anesthetic that acts by preventing transmission of impulses along nerve fibers and at nerve endings.","See also: Benzocaine Hydrochloride (has salt form); Alcohol; Benzocaine (component of); Benzocaine; white petrolatum (active moiety of) ... View More ...","Benzocaine is a benzoate ester having 4-aminobenzoic acid as the acid component and ethanol as the alcohol component. A surface anaesthetic, it is used to suppress the gag reflex, and as a lubricant and topical anaesthetic on the larynx, mouth, nasal cavity, respiratory tract, oesophagus, rectum, urinary tract, and vagina. It has a role as a topical anaesthetic, an antipruritic drug, an allergen and a sensitiser. It is a benzoate ester and a substituted aniline."],"References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Benzocaine","Name":"Benzocaine","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q422745","Name":"Benzocaine","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/drugs/DB01086","Name":"Benzocaine","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/2337","Name":"Benzocaine","Sub":false}]},{"Name":"ChEMBL","Urls":[{"Link":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL278172","Name":"Benzocaine","Sub":false}]},{"Name":"ChEBI","Urls":[{"Link":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:116735","Name":"Benzocaine","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=94-09-7","Name":"Benzocaine","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0004992","Name":"Benzocaine","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/C07527","Name":"Benzocaine","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/U3RSY48JW5","Name":"Benzocaine","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID8021804","Name":"Benzocaine","Sub":false}]}],"SMILES":"CCOC(=O)C1=CC=C(C=C1)N","Salts":["hydrochloride"],"SaltsAcidCount":[1],"SaltsAmineCount":[1],"SaltsUNII":["OG625Z9LEO"],"Scheduling":[{"gov":"United States","schedule":"OTC substance"},{"gov":"United Kingdom","schedule":"GSL, P substance"}],"Solubility":"\u003e24.8 [ug/mL] (The mean of the results at pH 7.4)","Stability/Shelf Life":"Stable in air.","StoreUNII":["U3RSY48JW5"],"StructureBase64":"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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).","Title":"Benzocaine","UNII":"U3RSY48JW5","Wikidata":"Q422745","Wikipedia":"Benzocaine","XLogP":1.9}