Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR5213)
Drug Name
Benzocaine
Synonyms
Aethoform; Americaine; Anaesthesin; Anaesthesinum; Anaesthin; Anestezin; Anesthesin; Anesthesine; Anesthone; Bensokain; Benzocaina; Benzocainum; Chloraseptic; Dermoplast; Ethoform; Ethoforme; Hurricaine; Identhesin; Keloform; Norcain; Norcaine; Norcainum; Orthesin; Otocain; Outgro; Parathesin; Parathesine; Solarcaine; Topcaine; Aethylium paraminobenzoicum; Amben ethyl ester; Anestezin [Russian]; Baby Anbesol; Benzocaine Acetate; Benzocaine Formate; Benzocaine Hydrobromide; Benzocaine Hydrochloride; Benzocaine Methanesulfonate; Ethyl PABA; Ethyl aminobenzoate; Ethylis aminobenzoas; Solu H; Acetate, Benzocaine; Anaesthan-syngala; Auralgan (TN); Benzocaina [INN-Spanish]; Benzocaine [INN:BAN]; Benzocainum [INN-Latin]; Ethyl 4-aminobenzoate; Ethyl 4-aminobenzoate hydrochloride; Ethyl aminobenzoate (JP15); Ethyl aminobenzoate (VAN); Ethyl p-aminobenzoate; Ethyl p-aminophenylcarboxylate; Ethylaminobenzoate-4; Ethylesterkyseliny p-aminobenzoove; Ethylester kyseliny p-aminobenzoove [Czech]; Formate, Benzocaine; Hydrobromide, Benzocaine; Hydrochloride, Benzocaine; Methanesulfonate, Benzocaine; Ora-jel; P-Aminobenzoic acid ethyl ester; P-Aminobenzoic ethyl ester; P-Carbethoxyaniline; P-Ethoxycarboxylic aniline; Parathesin (TN); AE-562/40377256; Benzocaine (USP/INN); ETHYL-P-AMINOBENZOATE; P-(Ethoxycarbonyl)aniline;P-Aminobenzoic acid, ethyl ester; Benzoic acid, amino-, ethyl ester; H-4-abz-oet; Benzoic acid, 4-amino-, ethyl ester; Benzoic acid, p-amino-, ethyl ester; Benzoic acid, 4-amino-, ethyl ester, hydrochloride; 112909_ALDRICH; 112909_SIAL; 4 Aminobenzoic Acid Ethyl Ester; 4-(Ethoxycarbonyl)aniline; 4-Aminobenzoic acid ethyl ester; 4-Aminobenzoic acid, ethyl ester; 4-Carbethoxyaniline; 4-amino-benzoic acid ethyl ester
Indication Anaesthesia [ICD11: 9A76-9A78] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 165.19 Topological Polar Surface Area 52.3
Heavy Atom Count 12 Rotatable Bond Count 3
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
2337
ChEBI ID
CHEBI:116735
CAS Number
94-09-7
TTD Drug ID
D0Q8ZX
Formula
C9H11NO2
Canonical SMILES
CCOC(=O)C1=CC=C(C=C1)N
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Acetylbenzocaine DM015257
220420
Conjugation - Acetylation 1 [2]
Benzocaine hydroxylamine DM015773
11622443
Oxidation - N-hydroxylation 1 [2]
PABA DM006982
978
Hydrolysis - Esterase hydrolysis 1 [2]
N-acetyl-p-aminobenzoic acid DM003795
19266
Hydrolysis - Esterase hydrolysis 2 [3]
N-acetyl-p-aminobenzoic acid DM003795
19266
Conjugation - Acetylation 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR008754 Benzocaine Aminobenzoic acid Hydrolysis - Esterase hydrolysis Unclear [2]
MR008756 Benzocaine Acetylbenzocaine Conjugation - Acetylation AT [2]
MR008758 Benzocaine Benzocaine hydroxylamine Oxidation - N-hydroxylation CYP1A2 ... [2]
MR008757 Acetylbenzocaine 4-Acetaminobenzoic acid Hydrolysis - Esterase hydrolysis Unclear [3]
MR008755 Aminobenzoic acid 4-Acetaminobenzoic acid Conjugation - Acetylation Unclear [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Acetyltransferase (AT) DMEN253 Bacteroides fragilis Not Available Not Available [2]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
⏷ Show the Full List of 6  DME(s)
References
1 Double-blind, randomized, placebo-controlled clinical trials with non-prescription medications for the treatment of obesity. Obes Res. 1999 Jul;7(4):370-8.
2 More methemoglobin is produced by benzocaine treatment than lidocaine treatment in human in vitro systems
3 Metabolism and elimination of benzocaine by rainbow trout, Oncorhynchus mykiss

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