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Compound Detail

CHEMBL1196

PROPARACAINE
💊 Approved Drug
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💊 Approved Drug
CCCOc1ccc(C(=O)OCCN(CC)CC)cc1N
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1196
Name PROPARACAINE
Phase Approved
Structure Type MOL
InChI Key KCLANYCVBBTKTO-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Proparacaine Proximetacaina Proxymetacaine
4
Targets
8
Activities
2
Assay Types
0
PK Parameters
20
Publications
3
Known Names
1
Indications

Molecular Properties

294.4
MW (Da)
2.56
ALogP
5
HBA
1
HBD
64.8
PSA (Ų)
0.56
QED
0
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1953
Availability Prescription
Chirality Achiral

Routes of Administration

Topical

Flags

Natural Product
USAN Stem -caine

Extended Properties

Molecular Formula C16H26N2O3
MW 294.39
Aromatic Rings 1
Heavy Atoms 21
NP-Likeness -0.94

Indications

Pain

ATC Classification

S01HA04
proxymetacaine
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS

Activity Summary

IC50 6 meas. best 6.62
Ki 2 meas. best 7.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sigma non-opioid intracellular receptor 1
CHEMBL287
 Ki 7.0 7.0 100.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
 IC50 6.62 6.62 238.0 1
Unchecked
CHEMBL612545
 Ki 5.89 5.89 1283.0 1
Unchecked
CHEMBL612545
 IC50 5.85 5.7567 1407.0 3
Amine oxidase [flavin-containing] A
CHEMBL1951
 IC50 5.75 5.75 1777.0 1
Sodium channel alpha subunits; brain (Types I, II, III)
CHEMBL2096682
 IC50 5.72 5.72 1900.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sigma non-opioid intracellular receptor 1 Ki = 100.0 nM 7.0 DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol) -
Sigma non-opioid intracellular receptor 1 IC50 = 238.0 nM 6.62 DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol) -
Unchecked Ki = 1283.0 nM 5.89 DRUGMATRIX: Sodium Channel, Site 2 radioligand binding (ligand: [3H] Batrachotox... -
Unchecked IC50 = 1407.0 nM 5.85 DRUGMATRIX: Sodium Channel, Site 2 radioligand binding (ligand: [3H] Batrachotox... -
Amine oxidase [flavin-containing] A IC50 = 1777.0 nM 5.75 DRUGMATRIX: Monoamine Oxidase MAO-A enzyme inhibition (substrate: Kynuramine) -
Sodium channel alpha subunits; brain (Types I, II, III) IC50 = 1900.0 nM 5.72 Inhibition of binding of Batrachotoxinin [3H]BTX-B to high affinity sites on vol... 2579237
Unchecked IC50 = 1905.46 nM 5.72 Displacement of [3H]-BTX-B from neuronal voltage-gated sodium channel in rat cer... 19346132
Unchecked IC50 = 2000.0 nM 5.7 Displacement of [3H]-BTX-B from neuronal voltage-gated sodium channel in rat cer... 19346132

Literature References

PubMed DOI Target Context # Activities
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 3
19346132 10.1016/j.bmc.2008.10.031 Unchecked 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 2
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 2
37468498 10.1038/s41467-023-40064-9 Androgen receptor 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 2
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1/alpha-2/beta-2/gamma-2 2
37468498 10.1038/s41467-023-40064-9 Peroxisome proliferator-activated receptor gamma 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 2
2579237 10.1021/jm00381a019 Sodium channel alpha subunits; brain (Types I, II, III) 2
37468498 10.1038/s41467-023-40064-9 Sodium-dependent dopamine transporter 1
37468498 10.1038/s41467-023-40064-9 Neuronal acetylcholine receptor subunit alpha-4 1
37468498 10.1038/s41467-023-40064-9 Kappa-type opioid receptor 1
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 1

Data from ChEMBL 36 via Core Engine