Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00061)
Name
Benzocaine
Synonyms    Click to Show/Hide the Synonyms of This API
benzocaine; Ethyl 4-aminobenzoate; Ethyl aminobenzoate; Ethyl p-aminobenzoate; Americaine; Anesthesin; 4-Aminobenzoic acid ethyl ester; Anaesthesin; Ethoform; Norcaine; Orthesin; Parathesin; Amben ethyl ester; p-Carbethoxyaniline; Anaesthin; Anestezin; Anesthesine; Anesthone; Dermoplast; Hurricaine; Identhesin; Parathesine; Keloform; Norcain; Topcaine; Anaesthan-syngala; Ora-jel; Solarcaine; Solu H; p-Ethoxycarboxylic aniline; 4-Carbethoxyaniline; Baby Anbesol; Benzoic acid, 4-amino-, ethyl ester; Benzocainum; p-(Ethoxycarbonyl)aniline; Ethyl p-aminophenylcarboxylate; Benzocaina; 4-(Ethoxycarbonyl)aniline; p-Aminobenzoic acid ethyl ester; Aethoform; Benzoic acid, p-amino-, ethyl ester; Ethyl PABA; 4-Aminobenzoic acid, ethyl ester; 4-amino-benzoic acid ethyl ester; ETHYL4-AMINOBENZOATE; h-4-abz-oet; Ethylester kyseliny p-aminobenzoove; ETHYL-P-AMINOBENZOATE; 9011-18-1; p-Aminobenzoic acid, ethyl ester; UNII-U3RSY48JW5; CHEBI:116735; MFCD00007892; U3RSY48JW5; Ethyl 4-aminobenzoate, 98%; 4-aminobenzoic acid-ethyl ester; Anaesthesinum; Ethoforme; Norcainum; NSC-4688; NSC-41531; Ethylis aminobenzoas; CAS-94-09-7; NCGC00016352-01; Anestezin [Russian]; Chloraseptic; Otocain; Outgro; DSSTox_CID_1804; WLN: ZR DVO2; DSSTox_RID_76338; Aethylium paraminobenzoicum; Benzocainum [INN-Latin]; DSSTox_GSID_21804; Benzocaina [INN-Spanish]; Ethyl aminobenzoate (VAN); Caswell No. 430A; Finafta; Parathesin (TN); SMR000059025; ethylaminobenzoate-4; HSDB 7225; Ethylester kyseliny p-aminobenzoove [Czech]; Benzocaine (USP/INN); SR-05000001573; EINECS 202-303-5; NSC 41531; Dextran sulfate sodium salt, approx. M.W. 500,000; p-Aminobenzoic ethyl ester; EPA Pesticide Chemical Code 097001; BRN 0638434; Benzoak; Benzocaine [USP:INN:BAN]; Vagisil; Dextran sulfate sodium salt, approx. M.W. 6,500 - 10,000; AI3-02081; Benzocaine USP; Diet Ayds; Orabase-B; Slim Mint Gum; Prestwick_991; 4-carboethoxyaniline; ethyl 4aminobenzoate; ethyl 4-aminobenzate; ethyl 4-aminobezoate; Outgro (Salt/Mix); Anbesol (Salt/Mix); Vagisil (Salt/Mix); ethyl-4-aminobenzoate; p-ethoxycarbonylaniline; 4-ethoxycarbonylaniline; ethyl p-amino-benzoate; ethyl-p-amino-benzoate; Ethyl aminobenzoic acid; Cough-X (Salt/Mix); Spectrum_000074; Ethyl 4-amino-benzoate; ethyl 4-(amino)benzoate; H-(4)Abz-OEt; Ethyl p-aminobenzoic acid; Prestwick0_000712; Prestwick1_000712; Prestwick2_000712; Prestwick3_000712; Spectrum2_000117; Spectrum3_000314; Spectrum4_000249; Spectrum5_000860; ethyl 4-aminobenzoic acid; Epitope ID:114084; SAMPL3, G4; Ethyl aminobenzoate (JP17); Oprea1_750694; Oprea1_827402; SCHEMBL25100; BSPBio_000923; BSPBio_001908; KBioGR_000658; KBioSS_000474; 4-(Ethoxycarbonyl)phenylamine; 4-14-00-01129 (Beilstein Handbook Reference); AE-562/40377256; MLS001331704; MLS002153970; ARONIS27057; DivK1c_000932; SPECTRUM1500139; (p-(Ethoxycarbonyl)phenylamine; Ethyl p-aminobenzenecarboxylate; SPBio_000134; SPBio_002844; ACMC-20978l; BPBio1_001017; CHEMBL278172; DTXSID8021804; ETHYL PARA AMINO BENZOATE; HMS502O14; KBio1_000932; KBio2_000474; KBio2_003042; KBio2_005610; KBio3_001408; p-amino benzoic acid ethyl ester; 4-amino benzoic acid ethyl ester; NSC4688; NINDS_000932; BDBM197282; HMS1570O05; HMS1920G09; HMS2091M11; HMS2097O05; HMS2233H21; HMS3371D08; HMS3652H13; HMS3714O05; HMS3885B11; Pharmakon1600-01500139; component of Tympagesic (Salt/Mix); CS-B0934; HY-Y0258; NSC41531; STR01509; Tox21_110391; Tox21_301149; ANW-13651; BBL010501; CCG-38918; NSC755909; SBB028356; STK043620; ZINC12358719; AKOS000119763; Benzocaine 1.0 mg/ml in Acetonitrile; Tox21_110391_1; AC-8127; ACN-034789; AS04671; DB01086; EBD2186554; MCULE-6566052626; NSC-755909; IDI1_000932; Benzocaine, purum, >=99.0% (HPLC); Benzocaine, tested according to Ph.Eur.; NCGC00016352-02; NCGC00016352-03; NCGC00016352-04; NCGC00016352-07; NCGC00094598-01; NCGC00094598-02; NCGC00255047-01; AK-46733; Ethyl 4-aminobenzoate, 98.0-101.0%; SBI-0051293.P003; component of Solarcaine aerosol (Salt/Mix); AB00051923; BB 0258778; FT-0624536; FT-0625762; FT-0662548; ST45255315; SW197074-3; 1324-EP2280008A2; 1324-EP2315502A1; A14560; C07527; D00552; M-5932; 66567-EP2284157A1; 66567-EP2308851A1; AB00051923_09; AB00051923_10; component of Anbesol maximum strength (Salt/Mix); Q422745; Ethyl 4-aminobenzoate, SAJ first grade, >=99.0%; Q-200688; SR-05000001573-1; SR-05000001573-3; BRD-K75466013-001-05-2; BRD-K75466013-001-08-6; Ethyl 4-aminobenzoate, Vetec(TM) reagent grade, 98%; F2190-0448; Benzocaine, European Pharmacopoeia (EP) Reference Standard; Benzocaine, United States Pharmacopeia (USP) Reference Standard; Benzocaine, Pharmaceutical Secondary Standard; Certified Reference Material
Clinical Status
Approved
Disease Indication Anaesthesia ICD-11: 8E22 [1]
PubChem CID
2337
Formula
C9H11NO2
Canonical SMILES
CCOC(=O)C1=CC=C(C=C1)N
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
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=2337"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 165.19 Topological Polar Surface Area 52.3
XlogP 1.9 Complexity 151
Heavy Atom Count 12 Rotatable Bond Count 3
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Full List of Drug Formulations (DFMs) Containing This API
          Benzocaine 6 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Citric acid; Sucralose; D&c red no. 27; Magnesium stearate; Mannitol; Sodium bicarbonate; Crospovidone; Cellulose, microcrystalline; Colloidal silicon dioxide; D&c blue no. 1
                   Dosage Form Disintegrating Oral Tablet
                   Company Combe Incorporated
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sucralose DIG Info Carbonic anhydrase II (Ki = 300 nM) [2]
D&C red no. 27 DIG Info Solute carrier SLCO2B1 (Ki = 1 uM) [3]
Kyselina citronova DIG Info Perilipin-1 (IC50 = 3708 nM) [4]
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [5]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [6]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [6]
References
1 Benzocaine.
2 Sweet Binders: Carbonic Anhydrase IX in Complex with Sucralose. ACS Med Chem Lett. 2018 May 10; 9(7):657-661.
3 Bacterial metabolism rescues the inhibition of intestinal drug absorption by food and drug additives. Proc Natl Acad Sci U S A. 2020 Jul 7;117(27):16009-16018.
4 PubChem BioAssay data set.
5 Pharmacological property optimization for allosteric ligands: A medicinal chemistry perspective. Bioorg Med Chem Lett. 2017 Jun 1; 27(11):2239-2258.
6 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.

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