General Information of Drug (ID: DR0953)
Drug Name
Lidocaine
Synonyms
Leostesin; Lida-Mantle; Lidocaine (VAN); Lidoderm; Lignocaine; Lignocainum; Maricaine; Octocaine; Remicaine; Rucaina; Solcain; Xilina; Alphacaine; Anestacon; Cappicaine; Cito optadren; Cuivasil; Dalcaine; Dentipatch; Duncaine; Esracaine; Gravocain; Isicaina; Isicaine; Jetocaine; L-Caine; Xilocaina; Xllina; Xycaine; Xylestesin; Xylocain; Xylocaine; Xylocitin; Xyloneural (free base); Xylotox; lidocaine; 137-58-6; 2-(Diethylamino)-2',6'-acetoxylidide; 2-(Diethylamino)-N-(2,6-dimethylphenyl)acetamide; 2-Diethylamino-N-(2,6-dimethylphenyl)acetamide
Indication Anaesthesia [ICD11: 8E22] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 234.34 Topological Polar Surface Area 32.299
Heavy Atom Count 17 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
3676
PubChem SID
9284 ; 95410 ; 855682 ; 3134587 ; 5152743 ; 7847424 ; 7979776 ; 8152322 ; 10507335 ; 11110520 ; 11111384 ; 11111385 ; 11120259 ; 11120747 ; 11121235 ; 11121424 ; 11121904 ; 11335349 ; 11336498 ; 11360588 ; 11362493 ; 11364012 ; 11365055 ; 11366574 ; 11367617 ; 11369136 ; 11370257 ; 11370258 ; 11372323 ; 11373218 ; 11373738 ; 11375779 ; 11377298 ; 11380842 ; 11461560 ; 11466078 ; 11467198 ; 11485261 ; 11485836 ; 11489159 ; 11491207 ; 11491885 ; 11494932 ; 11511857 ; 15196283 ; 24896272 ; 24896480 ; 26719632 ; 26744219 ; 26751483
ChEBI ID
ChEBI:6456
CAS Number
137-58-6
TTD Drug ID
D0X4RN
Formula
C14H22N2O
Canonical SMILES
CCN(CC)CC(=O)NC1=C(C=CC=C1C)C
InChI
1S/C14H22N2O/c1-5-16(6-2)10-13(17)15-14-11(3)8-7-9-12(14)4/h7-9H,5-6,10H2,1-4H3,(H,15,17)
InChIKey
NNJVILVZKWQKPM-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
2,6-xylidine DM000340
6896
Unclear 1 [8] , [9] , [10]
3-hydroxylidocaine DM000344
161824
Oxidation - Hydroxylation 1 [11]
Monoethylglycinexylidide DM000339
24415
Oxidation - N-De-Ethylation 1 [5] , [11]
N-hydroxy-lidocaine DM000346
148591
Oxidation - Hydroxylation 1 [11]
NL-Ethyl-2-methyl-Nj-(2,6-dimethylphenyl)-4-imidazolidin DM000345
3082362
Unclear 1 [11]
Unclear DM009999 N. A. Unclear 1 [5]
Unclear DM009999 N. A. Unclear 1 [4]
Unclear DM009999 N. A. Unclear 1 [3]
2,6-xylidine DM000340
6896
Hydrolysis - Hydrolysis 2 [11]
3-hydroxymonoethylglycinexylidide DM000343
3015693
Unclear 2 [11]
4-hydroxy-2,6-xylidine DM000341
76543
Conjugation - Methylation 2 [8]
Glycinexylidide DM000342
87833
Oxidation - Deamination 2 [11]
4-hydroxy-2,6-xylidine DM000341
76543
Conjugation - Methylation 3 [11]
⏷ Show the Full List of 13  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001550 Lidocaine Monoethylglycinexylidide Oxidation - N-De-Ethylation CYP1A2 ... [5], [11]
MR001551 Lidocaine 2,6-xylidine Unclear Unclear [8], [9], [10]
MR001552 Lidocaine 3-hydroxylidocaine Oxidation - Hydroxylation CYP1A2 ... [11]
MR001553 Lidocaine NL-Ethyl-2-methyl-Nj-(2,6-dimethylphenyl)-4-imidazolidin Unclear Unclear [11]
MR001554 Lidocaine N-hydroxy-lidocaine Oxidation - Hydroxylation Unclear [11]
MR001555 Lidocaine . Unclear CYP2D6 [5]
MR001548 2,6-xylidine 4-hydroxy-2,6-xylidine Conjugation - Methylation Unclear [8]
MR001549 3-hydroxylidocaine 3-hydroxymonoethylglycinexylidide Unclear Unclear [11]
MR001545 Monoethylglycinexylidide 2,6-xylidine Hydrolysis - Hydrolysis Unclear [11]
MR001546 Monoethylglycinexylidide Glycinexylidide Oxidation - Deamination CYP3A4 [11]
MR001547 Monoethylglycinexylidide 3-hydroxymonoethylglycinexylidide Unclear Unclear [11]
⏷ Show the Full List of 11 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2A6 (CYP2A6) DME0005 Homo sapiens
CP2A6_HUMAN
1.14.14.1
[3]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[4]
Cytochrome P450 2C18 (CYP2C18) DME0017 Homo sapiens
CP2CI_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[3]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[5]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[6]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[7]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[7]
⏷ Show the Full List of 10  DME(s)
References
1 Sufentanil was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem. 2009;16(31):4066-218.
3 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
4 Insights into CYP2B6-mediated drug-drug interactions. Acta Pharm Sin B. 2016 Sep;6(5):413-425.
5 Involvement of CYP1A2 and CYP3A4 in lidocaine N-deethylation and 3-hydroxylation in humans. Drug Metab Dispos. 2000 Aug;28(8):959-65.
6 Pharmacokinetics of lidocaine hydrochloride metabolized by CYP3A4 in Chinese Han volunteers living at low altitude and in native Han and Tibetan Chinese volunteers living at high altitude. Pharmacology. 2016;97(3-4):107-13.
7 Drug Interactions Flockhart Table
8 Quantification of lidocaine and several metabolites utilizing chemical-ionization mass spectrometry and stable isotope labeling J Pharm Sci. 1977 Aug;66(8):1180-90. doi: 10.1002/jps.2600660834.
9 An innovative nanoparticle-modified carbon paste sensor for ultrasensitive detection of lignocaine and its extremely carcinogenic metabolite residues in bovine food samples: Application of NEMI, ESA, AGREE, ComplexGAPI, and RGB12 algorithms. Food Chem. 2023 Jun 12;426:136579. doi: 10.1016/j.foodchem.2023.136579.
10 In vitro metabolism of lidocaine in subcellular post-mitochondrial fractions and precision cut slices from cattle liver. Toxicol In Vitro. 2021 Oct;76:105228. doi: 10.1016/j.tiv.2021.105228.
11 The Use and Method of Action of Intravenous Lidocaine and Its Metabolite in Headache Disorders Headache. 2018 May;58(5):783-789. doi: 10.1111/head.13298.

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