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Compound Detail

CHEMBL79

LIDOCAINE
💊 Approved Drug
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💊 Approved Drug
CCN(CC)CC(=O)Nc1c(C)cccc1C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL79
Name LIDOCAINE
Phase Approved
Structure Type MOL
InChI Key NNJVILVZKWQKPM-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

ALGRX 3268 ALGRX-3268 Alphacaine Dentipatch Embolex Iontocaine Lidocaina Lidocaine Lidocaine component of emla Lidocaine component of fortacin Lidocaine component of lanabiotic Lidocaine component of oraqix +17 more
7
Targets
26
Activities
2
Assay Types
30
PK Parameters
20
Publications
29
Known Names
20
Indications
1
Mechanisms

Molecular Properties

234.3
MW (Da)
2.58
ALogP
2
HBA
1
HBD
32.3
PSA (Ų)
0.85
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1948
Availability Prescription
Chirality Achiral

Routes of Administration

Oral Parenteral Topical

Flags

Black Box Warning Natural Product
USAN Stem -caine

Extended Properties

Molecular Formula C14H22N2O
MW 234.34
Aromatic Rings 1
Heavy Atoms 17
NP-Likeness -1.69

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Sodium channel alpha subunit blocker BLOCKER Sodium channel alpha subunit ✓ ✓

Indications

Arrhythmias, Cardiac Arrhythmias, Cardiac Arthritis Back Pain Burns Bursitis Hemorrhoids Inflammation Insect Bites and Stings Muscle Cramp Muscle Cramp Myalgia Neuralgia Neuralgia Neuralgia, Postherpetic Neuralgia, Postherpetic Osteoarthritis Pain Premature Ejaculation Pruritus

ATC Classification

C01BB01
lidocaine
Level 1: CARDIOVASCULAR SYSTEM
Level 2: CARDIAC THERAPY
C05AD01
lidocaine
Level 1: CARDIOVASCULAR SYSTEM
Level 2: VASOPROTECTIVES
D04AB01
lidocaine
Level 1: DERMATOLOGICALS
Level 2: ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.
N01BB02
lidocaine
Level 1: NERVOUS SYSTEM
Level 2: ANESTHETICS
N01BB52
lidocaine, combinations
Level 1: NERVOUS SYSTEM
Level 2: ANESTHETICS
R02AD02
lidocaine
Level 1: RESPIRATORY SYSTEM
Level 2: THROAT PREPARATIONS
S01HA07
lidocaine
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS
S02DA01
lidocaine
Level 1: SENSORY ORGANS
Level 2: OTOLOGICALS

Activity Summary

IC50 23 meas. best 5.7
EC50 3 meas. best 7.77

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 7.77 7.77 17.0 3
Sodium channel protein type 4 subunit alpha
CHEMBL2072
 IC50 5.7 5.7 2000.0 1
Sodium channel protein type 3 subunit alpha
CHEMBL5163
 IC50 4.98 4.98 10500.0 1
Sodium channel protein type 9 subunit alpha
CHEMBL4296
 IC50 4.8 4.67 16000.0 2
Sodium channel protein type 5 subunit alpha
CHEMBL1980
 IC50 4.3 4.3 50000.0 1
Sodium channel alpha subunits; brain (Types I, II, III)
CHEMBL2095171
 IC50 4.25 4.25 56000.0 1
Unchecked
CHEMBL612545
 IC50 4.01 4.01 97000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 61.32 ng.hr.mL-1 Homo sapiens
AUC 35.17 ng.hr.mL-1 Homo sapiens
C 2.5 ng/mL Homo sapiens
C 148.0 ng/mL Homo sapiens
CL 15.0 mL.min-1.kg-1 Homo sapiens
CL 16.0 mL.min-1.kg-1 Homo sapiens
CL 47.0 mL.min-1.kg-1 Rattus norvegicus
CL 66.0 mL.min-1.kg-1 Macaca
CL 9.2 mL.min-1.kg-1 Homo sapiens
CL 16.0 mL.min-1.kg-1 Homo sapiens
CL 37.0 mL.min-1.kg-1 Canis lupus familiaris
CL 78.4 mL.min-1.kg-1 Homo sapiens
CL 21.3 uL.min-1.(10^6cells)-1 Homo sapiens
CL 12.1 uL.min-1.(10^6cells)-1 Homo sapiens
CL 11.5 mL.min-1.kg-1 Homo sapiens
CL 13.0 mL.min-1.kg-1 Homo sapiens
Cmax 512.08 nM Homo sapiens
Cmax 1194.85 nM Homo sapiens
Cmax 116.07 nM Homo sapiens
Cmax 134.42 nM Homo sapiens
Cmax 94.73 nM Homo sapiens
Cmax 70.41 nM Homo sapiens
F 49.0 % Homo sapiens
Fu 0.3 - -
Fu 0.118 - -
Fu 0.3 - Homo sapiens
Fu 0.33 - Homo sapiens
Fu 0.998 - Homo sapiens
Fu 0.303 - Homo sapiens
Fu 0.239 - Macaca fascicularis

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NON-PROTEIN TARGET EC50 = 17.0 nM 7.77 Negative inotropic activity assessed as decrease in developed tension in isolate... 17228875
NON-PROTEIN TARGET EC50 = 17.0 nM 7.77 Negative inotropic activity against potassium-induced contraction in guinea pig ... 20509610
NON-PROTEIN TARGET EC50 = 17.0 nM 7.77 Negative inotropic activity in guinea pig left atria assessed as decrease of 1 H... 22191686
Sodium channel protein type 4 subunit alpha IC50 = 2000.0 nM 5.7 Modulation of human Nav1.4 in open-inactivated state assessed as inhibition of i... 24440379
Sodium channel protein type 3 subunit alpha IC50 = 10500.0 nM 4.98 Modulation of human Nav1.3 in open-inactivated state assessed as inhibition of i... 24440379
Sodium channel protein type 9 subunit alpha IC50 = 16000.0 nM 4.8 Inhibition of human Nav1.7 in inactivated condition by automated patch-clamp ass... 36092147
Sodium channel protein type 9 subunit alpha IC50 = 29000.0 nM 4.54 Modulation of human Nav1.7 in open-inactivated state assessed as inhibition of i... 24440379
Sodium channel protein type 5 subunit alpha IC50 = 50000.0 nM 4.3 Inhibition of human Nav1.5 in inactivated condition by automated patch-clamp ass... 36092147
Sodium channel alpha subunits; brain (Types I, II, III) IC50 = 56000.0 nM 4.25 Concentration required to inhibit [3H]BTX binding to Sodium channel of rat brain 15177465
Unchecked IC50 = 97000.0 nM 4.01 Inhibition of veratridine-induced guanidine flux in cardiac voltage-gated sodium... 11170622

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 332
3681896 10.1021/jm00395a014 Canis familiaris 29
3572967 10.1021/jm00388a006 Canis familiaris 21
845875 10.1021/jm00213a021 Canis familiaris 16
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
36796127 10.1016/j.bmc.2023.117203 No relevant target 12
8691454 10.1021/jm950772j Canis familiaris 12
690997 10.1021/jm00206a001 ADMET 11
16789751 10.1021/jm060230+ ADMET 11
1263207 10.1021/jm00226a019 Rattus norvegicus 9
6167716 10.1021/jm00135a006 ADMET 8
15920768 10.1002/jps.20373 ADMET 8
7205874 10.1021/jm00133a011 Mus musculus 7
513066 10.1021/jm00196a007 Mus musculus 7
513065 10.1021/jm00196a006 Mus musculus 7
7359531 10.1021/jm00176a014 Canis familiaris 7
18534720 10.1016/j.ejmech.2008.04.006 NON-PROTEIN TARGET 6
17506538 10.1021/jm0604528 Rattus norvegicus 6
874964 10.1021/jm00217a005 Mus musculus 6
12061889 10.1021/jm0200409 ADMET 5

Data from ChEMBL 36 via Core Engine