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Ciclopirox

drug
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Also known as CyclopiroxHOE 296BHOE-296BLoproxPenlacCicloproxCiclopirox ethanolamineC0088433CICLOPIROX OLAMINE

Summary

Ciclopirox (CHEMBL1413) is an approved small-molecule antibacterial agent (ATC D01AE14) targeting PARP1; indicated across 5 conditions including seborrheic dermatitis and tinea pedis.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: D01AE14 (+1 more)
  • Targets: 1 (PARP1)
  • Indications: 5 conditions
  • Clinical trials: 9
  • Chemistry: 207.27 Da · C12H17NO2

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL1413
NameCiclopirox
TypeSmall molecule
Max phase4
FDA approvedyes
PubChem CID2749
ChEBICHEBI:453011
ATCD01AE14, G01AX12
Molecular formulaC12H17NO2
Molecular weight207.27
InChIKeySCKYRAXSEDYPSA-UHFFFAOYSA-N

SMILES: CC1=CC(=O)N(C(=C1)C2CCCCC2)O

IUPAC name: 6-cyclohexyl-1-hydroxy-4-methylpyridin-2-one

ChEBI definition: A cyclic hydroxamic acid that is 1-hydroxypyridin-2(1H)-one in which the hydrogens at positions 4 and 6 are substituted by methyl and cyclohexyl groups, respectively. A broad spectrum antigfungal agent, it also exhibits antibacterial activity against many Gram-positive and Gram-negative bacteria, and has anti-inflammatory properties. It is used a a topical treatment of fungal skin and nail infections.

Pharmacological roles (ChEBI): antibacterial agent, antiseborrheic.

Also known as: Ciclopirox, Cyclopirox, HOE 296B, HOE-296B, Loprox, Penlac, ciclopirox, CICLOPIROX, Cicloprox, Ciclopirox ethanolamine, C0088433, CICLOPIROX OLAMINE

Parent form; salt/anhydrous children: CHEMBL242580

Patent coverage: 4,124 distinct patent families (14,782 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

GeneTargetActionpAffinityCancer dependencyUniProt
PARP1poly(ADP-ribose) polymerase 1Inhibition6.84.1%P09874

Broader ChEMBL bioactivity targets: 6 (assay-derived). Sample: Thromboxane A2 receptor, Muscarinic acetylcholine receptor M1, Alpha-1A adrenergic receptor, Lysine-specific demethylase 4B, Nuclear receptor subfamily 1 group I member 2, Deoxyhypusine hydroxylase.

Bioactivity

ChEMBL activities: 2 potent at pChembl ≥ 5 of 6 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
KDM4B5.42IC503800nMCHEMBL_ACT_24824605
DOHH5.3IC505000nMCHEMBL_ACT_19246887

Target pathways

Aggregated over 1 target gene(s): PARP1.

Top Reactome pathways

8 total, by targets touching each:

PathwayTargetsGenes
POLB-Dependent Long Patch Base Excision Repair1PARP1
vRNA Synthesis1PARP1
Downregulation of SMAD2/3:SMAD4 transcriptional activity1PARP1
SUMOylation of DNA damage response and repair proteins1PARP1
HDR through MMEJ (alt-NHEJ)1PARP1
DNA Damage Recognition in GG-NER1PARP1
Formation of Incision Complex in GG-NER1PARP1
Dual Incision in GG-NER1PARP1

Dominant GO biological processes

GO termTargets
negative regulation of transcription by RNA polymerase II1
telomere maintenance1
DNA repair1
double-strand break repair1
transcription by RNA polymerase II1
apoptotic process1
DNA damage response1
mitochondrion organization1
transforming growth factor beta receptor signaling pathway1
response to gamma radiation1
positive regulation of cardiac muscle hypertrophy1
carbohydrate biosynthetic process1
protein autoprocessing1
signal transduction involved in regulation of gene expression1
macrophage differentiation1

Indications & clinical

Indications

5 indications (5 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

IndicationTrial phaseMONDOEFO
seborrheic dermatitis4MONDO:0006608EFO:1000764
tinea pedis4MONDO:0005984EFO:0007512
tinea infection4MONDO:0005982EFO:0007510
candidiasis4MONDO:0002026MONDO:0002026
tinea unguium4MONDO:0001628MONDO:0001628

Clinical trials

Total trials: 9.

Phase distribution

PhaseTrials
PHASE43
PHASE32
PHASE12
PHASE21
Not specified1

Top trials by phase / activity

NCTPhaseStatusTitle
NCT01139749PHASE4UNKNOWNEfficacy and Safety of Low-dose Oral Isotretinoin for Seborrhea
NCT01419847PHASE4COMPLETEDTopical Penlac Nail Lacquer for Onychomycosis in Children
NCT01646580PHASE4TERMINATEDSafety Study of Ciclopirox Olamine Cream for Dermatomycoses in Children
NCT02866032PHASE3COMPLETEDStudy to Evaluate the Efficacy and Safety of Topical MOB015B in the Treatment of Mild to Moderate Distal Subungual Onychomycosis (DSO)
NCT02961634PHASE3UNKNOWNStudy Efficacy and Safety in Comparative Use of Investigational Product Adjuvant Treatment in Onychomycosis
NCT02644551PHASE2UNKNOWNThe Efficacy of CELEXT07 in the Treatment of Toenail Onychomycosis
NCT00990587PHASE1COMPLETEDStudy Evaluating the Tolerance and Biologic Activity of Oral Ciclopirox Olamine in Patients With Relapsed or Refractory Hematologic Malignancy
NCT05647343PHASE1COMPLETEDStudy to Assess the Safety and Pharmacokinetics of ATL-001 (Ciclopirox Olamine) in Healthy Volunteers
NCT00382330Not specifiedWITHDRAWNChemoprevention of Cancer in the Lower Female Genital Tract: The Antineoplastic Activity of the Fungicide Ciclopirox.

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

55 molecules share ≥1 primary target. Top 55 by shared-target count:

MoleculeSourceStatusShared targets
AMITRIPTYLINEChEMBLPhase 4 (approved)PARP1
NIRAPARIBChEMBLPhase 4 (approved)PARP1
OLAPARIBChEMBLPhase 4 (approved)PARP1
PALBOCICLIBChEMBLPhase 4 (approved)PARP1
RUCAPARIBChEMBLPhase 4 (approved)PARP1
RUCAPARIB CAMSYLATEChEMBLPhase 4 (approved)PARP1
TALAZOPARIBChEMBLPhase 4 (approved)PARP1
FLUZOPARIBChEMBLPhase 3PARP1
INIPARIBChEMBLPhase 3PARP1
PAMIPARIBChEMBLPhase 3PARP1
SARUPARIBChEMBLPhase 3PARP1
VELIPARIBChEMBLPhase 3PARP1
2X-121ChEMBLPhase 2PARP1
AMELPARIBChEMBLPhase 2PARP1
CHLORTHENOXAZINEChEMBLPhase 2PARP1
E-7016ChEMBLPhase 2PARP1
FLAVONEChEMBLPhase 2PARP1
LUTEOLINChEMBLPhase 2PARP1
NESUPARIBChEMBLPhase 2PARP1
AfatinibPubChemApprovedPARP1
ApixabanPubChemApprovedPARP1
belumosudilPubChemApprovedPARP1
BinimetinibPubChemApprovedPARP1
CarfilzomibPubChemApprovedPARP1
chenodiolPubChemApprovedPARP1
ClascoteronePubChemApprovedPARP1
ClofarabinePubChemApprovedPARP1
CrizotinibPubChemApprovedPARP1
cytisiniclinePubChemApprovedPARP1
dacomitinibPubChemApprovedPARP1
ElagolixPubChemApprovedPARP1
EribulinPubChemApprovedPARP1
FingolimodPubChemApprovedPARP1
IdelalisibPubChemApprovedPARP1
LactulosePubChemApprovedPARP1
LinagliptinPubChemApprovedPARP1
MavacamtenPubChemApprovedPARP1
MegestrolPubChemApprovedPARP1
NitisinonePubChemApprovedPARP1
PazopanibPubChemApprovedPARP1
podofiloxPubChemApprovedPARP1
PramipexolePubChemApprovedPARP1
PyrazinamidePubChemApprovedPARP1
regorafenibPubChemApprovedPARP1
RelugolixPubChemApprovedPARP1
RiociguatPubChemApprovedPARP1
RitlecitinibPubChemApprovedPARP1
RolapitantPubChemApprovedPARP1
saxagliptinPubChemApprovedPARP1
SelumetinibPubChemApprovedPARP1
TadalafilPubChemApprovedPARP1
TaurinePubChemApprovedPARP1
TrabectedinPubChemApprovedPARP1
TrametinibPubChemApprovedPARP1
VorapaxarPubChemApprovedPARP1

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
Atlas version
v1.1.2
BioBTree
v2.0.2

Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot