Skip to main content
Free research Free research Free compound review with research home and workspace preview
Quick search ChEMBL 36
Compound Detail

CHEMBL1086

DIBUCAINE
💊 Approved Drug
Enter ChEMBL ID:
Free Research Context This compound will appear in recent viewed items on the research home for this browser.
Research home View demo workspace
💊 Approved Drug
CCCCOc1cc(C(=O)NCCN(CC)CC)c2ccccc2n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1086
Name DIBUCAINE
Phase Approved
Structure Type MOL
InChI Key PUFQVTATUTYEAL-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Cinchocaine Cincocaina Dibucaine NSC-159055
5
Targets
17
Activities
3
Assay Types
0
PK Parameters
20
Publications
4
Known Names
3
Indications

Molecular Properties

343.5
MW (Da)
3.49
ALogP
4
HBA
1
HBD
54.5
PSA (Ų)
0.67
QED
0
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1982
Availability Discontinued
Chirality Achiral

Routes of Administration

Parenteral

Flags

Natural Product
USAN Stem -caine

Extended Properties

Molecular Formula C20H29N3O2
MW 343.47
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness -1.53

Indications

Hemorrhoids Pruritus Sunburn

ATC Classification

C05AD04
cinchocaine
Level 1: CARDIOVASCULAR SYSTEM
Level 2: VASOPROTECTIVES
D04AB02
cinchocaine
Level 1: DERMATOLOGICALS
Level 2: ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.
N01BB06
cinchocaine
Level 1: NERVOUS SYSTEM
Level 2: ANESTHETICS
S01HA06
cinchocaine
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS
S02DA04
cinchocaine
Level 1: SENSORY ORGANS
Level 2: OTOLOGICALS

Activity Summary

EC50 10 meas. best 5.77
IC50 6 meas. best 6.21
Ki 1 meas. best 6.26

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Ki 6.26 6.26 550.0 1
Unchecked
CHEMBL612545
 IC50 6.21 5.97 610.0 3
Sodium channel alpha subunits; brain (Types I, II, III)
CHEMBL2096682
 IC50 5.85 5.85 1400.0 1
enterovirus D68
CHEMBL613204
 EC50 5.77 5.5967 1700.0 9
Enterovirus A71
CHEMBL612436
 EC50 5.64 5.64 2275.0 1
Bile salt export pump
CHEMBL6020
 IC50 4.38 4.38 41650.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 550.0 nM 6.26 Displacement of [3H]Batrachotoxin from sodium channel site 2 in Wistar rat brain... 23403082
Unchecked IC50 = 610.0 nM 6.21 Displacement of [3H]Batrachotoxin from sodium channel site 2 in Wistar rat brain... 23403082
Sodium channel alpha subunits; brain (Types I, II, III) IC50 = 1400.0 nM 5.85 Inhibition of binding of Batrachotoxinin [3H]BTX-B to high affinity sites on vol... 2579237
Unchecked IC50 = 1400.0 nM 5.85 Displacement of [3H]-BTX-B from neuronal voltage-gated sodium channel in rat cer... 19346132
Unchecked IC50 = 1412.54 nM 5.85 Displacement of [3H]-BTX-B from neuronal voltage-gated sodium channel in rat cer... 19346132
enterovirus D68 EC50 = 1700.0 nM 5.77 Antiviral activity against Enterovirus D68 US/KY/14-18953 infected in human SH-S... 30912944
enterovirus D68 EC50 = 1800.0 nM 5.75 Antiviral activity against Enterovirus D68 US/IL/14-18956 infected in human RD c... 30912944
enterovirus D68 EC50 = 1900.0 nM 5.72 Antiviral activity against Enterovirus D68 US/MO/14-18947 infected in human SH-S... 30912944
enterovirus D68 EC50 = 1900.0 nM 5.72 Antiviral activity against Enterovirus D68 US/MO/14-18947 infected in human A172... 30912944
enterovirus D68 EC50 = 2000.0 nM 5.7 Antiviral activity against Enterovirus D68 UA/IL/14-18952 infected in human RD c... 30912944
Enterovirus A71 EC50 = 2275.0 nM 5.64 Antiviral activity against Enterovirus A71 infected in human RD cells assessed a... 32619885
enterovirus D68 EC50 = 2900.0 nM 5.54 Antiviral activity against Enterovirus D68 US/MO/14-18949 infected in human RD c... 30912944
enterovirus D68 EC50 = 3500.0 nM 5.46 Antiviral activity against Enterovirus D68 US/MO/14-18947 infected in human RD c... 30912944
enterovirus D68 EC50 = 3700.0 nM 5.43 Antiviral activity against Enterovirus D68 US/KY/14-18953 infected in human A172... 30912944
enterovirus D68 EC50 = 5300.0 nM 5.28 Antiviral activity against Enterovirus D68 US/KY/14-18953 infected in human RD c... 30912944
Bile salt export pump IC50 = 41650.0 nM 4.38 Inhibition of human BSEP expressed in baculovirus transfected fall armyworm Sf21... 22961681

Literature References

PubMed DOI Target Context # Activities
30912944 10.1021/acs.jmedchem.9b00115 Unchecked 14
30912944 10.1021/acs.jmedchem.9b00115 enterovirus D68 9
6167716 10.1021/jm00135a006 ADMET 8
- 10.6019/CHEMBL4651402 SARS-CoV-2 4
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 3
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
23403082 10.1016/j.bmcl.2013.01.025 Unchecked 3
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
2579237 10.1021/jm00381a019 Sodium channel alpha subunits; brain (Types I, II, III) 2
- 10.6019/CHEMBL4651402 Vero C1008 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 2
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 2
22819594 10.1016/j.ejmech.2012.06.049 NON-PROTEIN TARGET 2
38318365 10.1016/j.isci.2024.108907 Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
19346132 10.1016/j.bmc.2008.10.031 Unchecked 2
18189348 10.1021/jm7014809 No relevant target 2
18027916 10.1021/jm070524a No relevant target 2
37468498 10.1038/s41467-023-40064-9 Voltage-dependent L-type calcium channel subunit alpha-1C 2

Data from ChEMBL 36 via Core Engine