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Compound Detail

CHEMBL1413

CICLOPIROX
💊 Approved Drug
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💊 Approved Drug
Cc1cc(C2CCCCC2)n(O)c(=O)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1413
Name CICLOPIROX
Phase Approved
Structure Type MOL
InChI Key SCKYRAXSEDYPSA-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Ciclopirox Cyclopirox HOE 296B HOE-296B Loprox Penlac
9
Targets
10
Activities
2
Assay Types
0
PK Parameters
20
Publications
6
Known Names
5
Indications
2
Mechanisms

Molecular Properties

207.3
MW (Da)
2.44
ALogP
3
HBA
1
HBD
42.2
PSA (Ų)
0.72
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1982
Availability Prescription
Chirality Achiral

Routes of Administration

Topical

Flags

Natural Product
USAN Stem -pirox
USAN Year 1975

Extended Properties

Molecular Formula C12H17NO2
MW 207.27
Aromatic Rings 1
Heavy Atoms 15
NP-Likeness 0.30

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Iron chelating agent CHELATING AGENT Iron ✓ ✓
Aluminium chelating agent CHELATING AGENT Aluminium ✓ ✓

Indications

Candidiasis Dermatitis, Seborrheic Onychomycosis Onychomycosis Tinea Pedis

ATC Classification

D01AE14
ciclopirox
Level 1: DERMATOLOGICALS
Level 2: ANTIFUNGALS FOR DERMATOLOGICAL USE
G01AX12
ciclopirox
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS

Activity Summary

IC50 6 meas. best 6.7
EC50 4 meas. best 6.57

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 6.7 6.7 200.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 6.6 6.6 249.9 1
Human alphaherpesvirus 1
CHEMBL377
 EC50 6.57 6.57 270.0 1
Astrocyte
CHEMBL614871
 IC50 6.48 6.48 330.0 1
Human alphaherpesvirus 2
CHEMBL370
 EC50 6.3 6.3 500.0 1
Lysine-specific demethylase 4B
CHEMBL3313832
 IC50 5.42 5.42 3800.0 1
Aspergillus fumigatus
CHEMBL363
 IC50 5.38 5.38 4220.0 1
Deoxyhypusine hydroxylase
CHEMBL4523441
 IC50 5.3 5.3 5000.0 1
Vaccinia virus
CHEMBL613493
 EC50 5.24 5.2 5800.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 200.0 nM 6.7 Antiproliferative activity against human neuroblastoma cells after 3 days by Pre... 35838529
NON-PROTEIN TARGET IC50 = 249.9 nM 6.6 Cytoprotective activity in Sprague-Dawley rat primary astrocytes assessed as inh... 28089588
Human alphaherpesvirus 1 EC50 = 270.0 nM 6.57 Antiviral activity against HSV-1 infected in African green monkey Vero cells ass... 35635945
Astrocyte IC50 = 330.0 nM 6.48 Inhibition of H2O2-induced mitochondrial metabolic dysfunction in Sprague-Dawley... 28089588
Human alphaherpesvirus 2 EC50 = 500.0 nM 6.3 Antiviral activity against HSV-2 infected in African green monkey Vero cells ass... 35635945
Lysine-specific demethylase 4B IC50 = 3800.0 nM 5.42 Inhibition of GST-tagged KDM4B (unknown origin) using H3K9(me3)-biotin peptide a... 35838529
Aspergillus fumigatus IC50 = 4220.0 nM 5.38 Antifungal activity against Aspergillus fumigatus B5233 conidia after 16 hrs by ... 19307370
Deoxyhypusine hydroxylase IC50 = 5000.0 nM 5.3 Inhibition of DOHH (unknown origin) 30684796
Vaccinia virus EC50 = 5800.0 nM 5.24 Antiviral activity against Vaccinia virus infected in African green monkey BSC-1... 36961984
Vaccinia virus EC50 = 6900.0 nM 5.16 Antiviral activity against Vaccinia virus VG9 infected in African green monkey B... 36961984

Literature References

PubMed DOI Target Context # Activities
16472241 10.2174/1570163043334794 Hepatotoxicity 18
39018123 10.1021/acs.jmedchem.4c01183 U2OS 17
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
31910018 10.1021/acs.jmedchem.9b01338 No relevant target 10
39018123 10.1021/acs.jmedchem.4c01183 Unchecked 9
35635945 10.1016/j.ejmech.2022.114443 Human alphaherpesvirus 2 5
28089588 10.1016/j.bmc.2016.12.052 Astrocyte 3
31910018 10.1021/acs.jmedchem.9b01338 SH-SY5Y 3
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
35635945 10.1016/j.ejmech.2022.114443 Human alphaherpesvirus 1 3
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 3
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 3
35635945 10.1016/j.ejmech.2022.114443 ADMET 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 Adenosine receptor A3 2
37468498 10.1038/s41467-023-40064-9 Sodium-dependent noradrenaline transporter 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
28089588 10.1016/j.bmc.2016.12.052 NON-PROTEIN TARGET 2

Data from ChEMBL 36 via Core Engine