Compound Detail

CHEMBL698

TETRACAINE

💊 Approved Drug

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💊 Approved Drug

CCCCNc1ccc(C(=O)OCCN(C)C)cc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL698
Name	TETRACAINE
Phase	Approved
Structure Type	MOL
InChI Key	GKCBAIGFKIBETG-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Ametop Dicaine Tetracaina Tetracaine Tetracaine component of pliaglis Tetracaine component of synera

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

264.4

MW (Da)

2.62

ALogP

HBA

HBD

41.6

PSA (Å²)

0.58

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	2005
Availability	Prescription
Chirality	Achiral

Routes of Administration

Topical

Flags

Natural Product First in Class

USAN Stem

-caine

Extended Properties

Molecular Formula	C15H24N2O2
MW	264.37
Aromatic Rings	1
Heavy Atoms	19
NP-Likeness	-0.97

Mechanism of Action

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

Indications

Hemorrhoids Pain Pruritus Cataract Carpal Tunnel Syndrome Myofascial Pain Syndromes Neuralgia, Postherpetic Shoulder Impingement Syndrome Skin Diseases Tendinopathy Wounds and Injuries Osteoarthritis, Knee

ATC Classification

C05AD02

tetracaine

Level 1: CARDIOVASCULAR SYSTEM

Level 2: VASOPROTECTIVES

D04AB06

tetracaine

Level 1: DERMATOLOGICALS

Level 2: ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.

N01BA03

tetracaine

Level 1: NERVOUS SYSTEM

Level 2: ANESTHETICS

S01HA03

tetracaine

Level 1: SENSORY ORGANS

Level 2: OPHTHALMOLOGICALS

Activity Summary

IC50 28 meas. best 7.25

Kd 9 meas. best 5.31

Ki 6 meas. best 6.3

EC50 1 meas.

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Sodium channel protein type 9 subunit alpha CHEMBL4296	IC50	7.25	6.4567	56.0	6
Sodium channel protein type 7 subunit alpha CHEMBL3585	IC50	7.25	7.25	56.0	1
Sodium channel protein type 5 subunit alpha CHEMBL1980	IC50	6.7	6.34	200.0	4
Amine oxidase [flavin-containing] A CHEMBL1951	IC50	6.5	6.5	317.0	1
Sodium channel alpha subunits; brain (Types I, II, III) CHEMBL2096682	IC50	6.4	5.935	400.0	2
Sodium channel protein type 2 subunit alpha CHEMBL4187	IC50	6.31	6.135	490.0	2
Sodium channel protein type 9 subunit alpha CHEMBL4296	Ki	6.3	5.61	500.0	2
Sodium channel protein type 8 subunit alpha CHEMBL5202	IC50	6.28	6.28	520.0	1
Sigma non-opioid intracellular receptor 1 CHEMBL287	Ki	6.15	6.15	703.0	1
Sodium channel protein type 3 subunit alpha CHEMBL5163	IC50	6.13	6.13	740.0	1
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	6.01	6.01	976.0	1
Unchecked CHEMBL612545	Ki	5.81	5.81	1551.0	1
Sigma non-opioid intracellular receptor 1 CHEMBL287	IC50	5.78	5.78	1673.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	5.77	5.77	1712.0	1
Unchecked CHEMBL612545	IC50	5.77	5.2975	1700.0	4
5-hydroxytryptamine receptor 2C CHEMBL225	IC50	5.49	5.49	3268.0	1
5-hydroxytryptamine receptor 2A CHEMBL224	IC50	5.47	5.47	3415.0	1
Unchecked CHEMBL612545	Kd	5.31	5.0643	4900.0	7
Sodium channel alpha subunits; brain (Types I, II, III) CHEMBL2095171	IC50	5.22	5.22	6000.0	1
Cyclic nucleotide-gated channel alpha-1 CHEMBL4907	Kd	5.17	5.045	6800.0	2

Pharmacokinetic Data

Parameter	Value	Units	Species
T1/2	0.3333	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Sodium channel protein type 7 subunit alpha	IC50	=	56.0	nM	7.25	Inhibition of recombinant human Nav 1.7 expressed in HEK293F cells incubated for...	35436748
Sodium channel protein type 9 subunit alpha	IC50	=	56.0	nM	7.25	Inhibition of recombinant human Nav1.7 expressed in HEK293F cells preincubated f...	27015369
Sodium channel protein type 9 subunit alpha	IC50	=	110.0	nM	6.96	Inhibition of recombinant human NaV1.7 alpha subunit expressed in HEK293 cells a...	22770500
Sodium channel protein type 9 subunit alpha	IC50	=	200.0	nM	6.7	Inhibition of human Nav1.7 expressed in CHO-K1 cells at -120 mV holding potentia...	29037948
Sodium channel protein type 5 subunit alpha	IC50	=	200.0	nM	6.7	Inhibition of human Nav1.5 expressed in HEK293 cells at -120 mV holding potentia...	29037948
Amine oxidase [flavin-containing] A	IC50	=	317.0	nM	6.5	DRUGMATRIX: Monoamine Oxidase MAO-A enzyme inhibition (substrate: Kynuramine)	-
Sodium channel protein type 9 subunit alpha	IC50	=	320.0	nM	6.5	Inhibition of human Nav1.7 expressed in HEK293F cells measured at -65 mV holding...	27015369
Sodium channel alpha subunits; brain (Types I, II, III)	IC50	=	400.0	nM	6.4	Antagonism of batrachotoxin-mediated sodium ion uptake into cultured neuroblasto...	-
Sodium channel protein type 2 subunit alpha	IC50	=	490.0	nM	6.31	Inhibition of recombinant human Nav1.2 expressed in HEK293 cells preincubated fo...	27015369
Sodium channel protein type 9 subunit alpha	Ki	=	500.0	nM	6.3	Displacement of [3H]BTX from human Nav1.7 expressed in human HEK293 cells after ...	21634377
Sodium channel protein type 8 subunit alpha	IC50	=	520.0	nM	6.28	Inhibition of recombinant human Nav1.6 expressed in HEK293 cells preincubated fo...	27015369
Sodium channel protein type 5 subunit alpha	IC50	=	530.0	nM	6.28	Inhibition of human NaV1.5 alpha subunit expressed in CHOK1 cells at -90 mV hold...	22770500
Sodium channel protein type 9 subunit alpha	IC50	=	620.0	nM	6.21	Inhibition of recombinant human NaV1.7 alpha subunit expressed in HEK293 cells a...	22770500
Sodium channel protein type 5 subunit alpha	IC50	=	650.0	nM	6.19	Inhibition of human Nav1.5 expressed in HEK293 cells by whole cell-patch clamp m...	27015369
Sodium channel protein type 5 subunit alpha	IC50	=	650.0	nM	6.19	Inhibition of human Nav 1.5 expressed in HEK293 cells at -90 mV holding potentia...	35436748
Sigma non-opioid intracellular receptor 1	Ki	=	703.0	nM	6.15	DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol)	-
Sodium channel protein type 3 subunit alpha	IC50	=	740.0	nM	6.13	Inhibition of recombinant human Nav1.3 expressed in HEK293 cells preincubated fo...	27015369
5-hydroxytryptamine receptor 2A	Ki	=	976.0	nM	6.01	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ...	-
Sodium channel protein type 2 subunit alpha	IC50	=	1100.0	nM	5.96	Inhibition of human NaV1.2 alpha subunit expressed in CHOK1 cells at -65 mV hold...	22770500
Unchecked	Ki	=	1551.0	nM	5.81	DRUGMATRIX: Sodium Channel, Site 2 radioligand binding (ligand: [3H] Batrachotox...	-

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	332
21634421	10.1021/jm200495g	Unchecked	8
37468498	10.1038/s41467-023-40064-9	Alpha-1A adrenergic receptor	6
7205876	10.1021/jm00133a012	Ovis aries	5
37468498	10.1038/s41467-023-40064-9	5-hydroxytryptamine receptor 2B	4
37468498	10.1038/s41467-023-40064-9	Alpha-2A adrenergic receptor	4
37468498	10.1038/s41467-023-40064-9	Cannabinoid receptor 1	4
37468498	10.1038/s41467-023-40064-9	5-hydroxytryptamine receptor 1A	4
37468498	10.1038/s41467-023-40064-9	Muscarinic acetylcholine receptor M2	4
20014752	10.1021/tx900326k	Hepatotoxicity	3
18262683	10.1016/j.ejmech.2007.12.025	Cavia porcellus	3
37468498	10.1038/s41467-023-40064-9	Gamma-aminobutyric acid receptor subunit alpha-1	3
27015369	10.1021/acs.jmedchem.6b00063	Sodium channel protein type 9 subunit alpha	3
37468498	10.1038/s41467-023-40064-9	Prostaglandin G/H synthase 1	3
37468498	10.1038/s41467-023-40064-9	Thromboxane A2 receptor	3
22770500	10.1021/jm300623u	Unchecked	3
24249037	10.1007/s11095-013-1232-z	No relevant target	3
37468498	10.1038/s41467-023-40064-9	D(1A) dopamine receptor	3
37468498	10.1038/s41467-023-40064-9	Muscarinic acetylcholine receptor M1	3
18189348	10.1021/jm7014809	No relevant target	2

Data from ChEMBL 36 via Core Engine