CICLOPIROX

First approved in 1982

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H17NO2
Molecular Weight	207.2689
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=SCKYRAXSEDYPSA-UHFFFAOYSA-N

InChI=1S/C12H17NO2/c1-9-7-11(13(15)12(14)8-9)10-5-3-2-4-6-10/h7-8,10,15H,2-6H2,1H3

HIDE SMILES / InChI

Molecular Formula	C12H17NO2
Molecular Weight	207.2689
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021159s020lbl.pdf
Curator's Comment: description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21022s004lbl.pdf

Ciclopirox is an antifungal medication indicated for the treatment of seborrheic dermatitis (Loprox trade name) and onychomycosis of fingernails and toenails due to Trichophyton rubrum (Penlac trade name). The drug exerts its action by chelating Fe3+ and Al3+, resulting in the inhibition of the metal-dependent enzymes that are responsible for the degradation of peroxides within the fungal cell.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Aluminium 2 Target ID: CHEMBL2366381 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021159s020lbl.pdf	Chelating Agent 139
Iron 18 Target ID: CHEMBL2363058 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021159s020lbl.pdf	Chelating Agent 139

Conditions

Condition	Modality	Targets	Highest Phase	Product
Seborrheic dermatitis 15 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021159s020lbl.pdf	Curative		Approved 8583	LOPROX Approved Use Loprox Shampoo is an antifungal indicated for the topical treatment of seborrheic dermatitis of the scalp in adults. Launch Date 1982
Onychomycosis of fingernails and toenails due to Trichophyton rubrum 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21022s004lbl.pdf	Curative		Approved 8583	PENALC Approved Use PENLAC NAIL LACQUER (ciclopirox) Topical Solution, 8%, as a component of a comprehensive management program, is indicated as topical treatment in immunocompetent patients with mild to moderate onychomycosis of fingernails and toenails without lunula involvement, due to Trichophyton rubrum. Launch Date 1999

C_max

Value	Dose	Co-administered	Analyte	Population
25.02 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/20519slr005_loprox_lbl.pdf	38.5 mg single, topical dose: 38.5 mg route of administration: Topical experiment type: SINGLE co-administered:		CICLOPIROX blood	Homo sapiens population: HEALTHY age: UNKNOWN sex: MALE food status: UNKNOWN
220 ng/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/24273151/	80 mg/m² 1 times / day multiple, oral dose: 80 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:		CICLOPIROX plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
750 ng × h/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/24273151/	80 mg/m² 1 times / day multiple, oral dose: 80 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:		CICLOPIROX plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.7 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/018748s024,019824s023,020519s016lbl.pdf	9 mg single, topical dose: 9 mg route of administration: Topical experiment type: SINGLE co-administered:		CICLOPIROX unknown	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
2.7 h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/24273151/	80 mg/m² 1 times / day multiple, oral dose: 80 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:		CICLOPIROX plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
8 % 1 times / day multiple, topical Recommended Dose: 8 %, 1 times / day Route: topical Route: multiple Dose: 8 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21022s004lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21022s004lbl.pdf	Disc. AE: Creatine phosphokinase increased... AEs leading to discontinuation/dose reduction: Creatine phosphokinase increased (0.36%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21022s004lbl.pdf

AEs

AE	Significance	Dose	Population
Creatine phosphokinase increased	0.36% Disc. AE	8 % 1 times / day multiple, topical Recommended Dose: 8 %, 1 times / day Route: topical Route: multiple Dose: 8 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21022s004lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21022s004lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			binder 2 activator 14 inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
MATE1 415

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
MATE1 416	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23241029/	no [IC50 >500 uM]

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	activator 14 Sources: https://pubmed.ncbi.nlm.nih.gov/21158687/
hERG 2263	binder 5 Sources: https://pubmed.ncbi.nlm.nih.gov/21158687/
hERG 2263	inhibitor 2237 Sources: https://pubmed.ncbi.nlm.nih.gov/21158687/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:453011	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:453011
ChemicalBook	CB7673863	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7673863
eMolecules	901641	https://www.emolecules.com/cgi-bin/more?vid=901641
MolPort	MolPort-003-845-943	https://www.molport.com/shop/molecule-link/MolPort-003-845-943
Selleck Chemicals	Ciclopirox-Penlac	http://www.selleckchem.com/products/Ciclopirox-Penlac.html
ZINC	ZINC000000001145	http://zinc15.docking.org/substances/ZINC000000001145

PubMed

Title	Date	PubMed
Ciclopirox nail lacquer 8% for the treatment of onychomycosis: a Canadian perspective.	2005-09	16292454
Ciclopirox topical solution, 8% combined with oral terbinafine to treat onychomycosis: a randomized, evaluator-blinded study.	2005-07-12	16004022
Evaluation of the efficacy of ciclopirox 0.77% gel in the treatment of tinea pedis interdigitalis (dermatophytosis complex) in a randomized, double-blind, placebo-controlled trial.	2005-07	15985032
In vitro susceptibility of 15 strains of zygomycetes to nine antifungal agents as determined by the NCCLS M38-A microdilution method.	2005-07	15982206
Copper-dependent activation of hypoxia-inducible factor (HIF)-1: implications for ceruloplasmin regulation.	2005-06-15	15741220
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005-06	15962942
Ciclopirox protects mitochondria from hydrogen peroxide toxicity.	2005-06	15806112
Genome-wide expression profiling of the response to ciclopirox olamine in Candida albicans.	2005-05	15814599
Oxygen accessibility and iron levels are critical factors for the antifungal action of ciclopirox against Candida albicans.	2005-05	15790671
Pharmacotherapy of onychomycosis.	2005-04	15934887
The safety and efficacy of ciclopirox olamine for the treatment of seborrheic dermatitis.	2005-03	15794716
Trichophyton rubrum isolated from aids and human immunodeficiency virus-infected patients in São Paulo, Brazil: antifungal susceptibility and extracellular enzyme production.	2005-03	15722629
A multicenter, open-label study to assess the safety and efficacy of ciclopirox topical suspension 0.77% in the treatment of diaper dermatitis due to Candida albicans.	2005-02-09	15696982
Treatment of onychomycosis: pros and cons of antifungal agents.	2005-02-03	15688097
Physicochemical studies on Ciclopirox olamine complexes with divalent metal ions.	2005-01-31	15652210
In vitro transungual permeation of ciclopirox from a hydroxypropyl chitosan-based, water-soluble nail lacquer.	2005-01	15704853
Pharmacoeconomic analysis of sequential treatment pathways in the treatment of onychomycosis.	2005-01	15682633
Treatment and prophylaxis of seborrheic dermatitis of the scalp with antipityrosporal 1% ciclopirox shampoo.	2005-01	15655141
Topical antifungal drugs for the treatment of onychomycosis: an overview of current strategies for monotherapy and combination therapy.	2005-01	15649187
Cutaneous adiaspiromycosis: a distinct dermatologic entity associated with Chrysosporium species.	2004-11	15577766
Cell cycle arrest at the initiation step of human chromosomal DNA replication causes DNA damage.	2004-10-01	15456844
[Chronic favus caused by infection with Trichophyton schönleinii].	2004-10	16281590
Management of onychomycosis with topicals.	2004-10	15450900
Ciclopirox delivery into the human nail plate.	2004-10	15349963
Evaluation of the drug treatment and persistence of onychomycosis.	2004-08-31	15349516
Ciclopirox shampoo for treating seborrheic dermatitis.	2004-08-31	15334279
Ciclopirox (Loprox) gel for superficial fungal infections.	2004-08-31	15334276
Onychomycosis: review of recurrence rates, poor prognostic factors, and strategies to prevent disease recurrence.	2004-07	15287395
Management of onychomycosis: examining the role of monotherapy and dual, triple, or quadruple therapies.	2004-07	15287394
Safety and efficacy of ciclopirox 1% shampoo for the treatment of seborrheic dermatitis of the scalp in the US population: results of a double-blind, vehicle-controlled trial.	2004-07	15271196
Rationale of frequency of use of ciclopirox 1% shampoo in the treatment of seborrheic dermatitis: results of a double-blind, placebo-controlled study comparing the efficacy of once, twice, and three times weekly usage.	2004-07	15271195
Efficacy of different concentrations of ciclopirox shampoo for the treatment of seborrheic dermatitis of the scalp: results of a randomized, double-blind, vehicle-controlled trial.	2004-07	15271194
Ciclopirox: a broad-spectrum antifungal with antibacterial and anti-inflammatory properties.	2004-07	15271193
Eukaryotic initiation factor 5A-1 (eIF5A-1) as a diagnostic marker for aberrant proliferation in intraepithelial neoplasia of the vulva.	2004-07	15262146
Activation of HIF-1alpha mRNA by hypoxia and iron chelator in isolated rat carotid body.	2004-06-17	15182949
Tinea capitis favosa in Poland.	2004-06	15189196
Agar sublimation test for the in vitro determination of the antifungal activity of morpholine derivatives.	2004-06	15189181
The use of 40% urea cream in the treatment of moccasin tinea pedis.	2004-05	15186053
In vitro susceptibility testing of dermatophytes: comparison of disk diffusion and reference broth dilution methods.	2004-04	15062918
Onychomycosis in children: a brief overview with treatment strategies.	2004-02-12	14871333
[Onychomycosis].	2004-02	14968324
Managing simple chronic paronychia and onycholysis with ciclopirox 0.77% and an irritant-avoidance regimen.	2004-01	14964637
Dermacase. Pityriasis rosea.	2004-01	14761101
Fungus-free versus disease-free nails.	2004-01	14699392
A randomized comparison of nail surface remanence of three nail lacquers, containing amorolfine 5%, ciclopirox 8% or tioconazole 28%, in healthy volunteers.	2004	15573688
Assessing treatment outcomes in toenail onychomycosis clinical trials.	2004	15186193
Common fungal infections of the feet in patients with diabetes mellitus.	2004	14960127
Successful treatment of dandruff with 1.5% ciclopirox olamine shampoo in Korea.	2003-12	14660265
Action mechanisms of modern antifungal agents and resulting problems in the management of onychomycosis.	2003-12	14641625
Evaluation of in vitro resistance in patients with onychomycosis who fail antifungal therapy.	2003	14657630

Patents

Sample Use Guides

In Vivo Use Guide

Seborrheic dermatitis: Wet hair and apply approximately 1 teaspoon (5 mL) of LOPROX Shampoo to the scalp. Up to 2 teaspoons (10 mL) may be used for long hair. Lather and leave on hair and scalp for 3 minutes. Rinse off. Treatment should be repeated twice per week for 4 weeks, with a minimum of 3 days between application. Onychomycosis:

Route of Administration: Topical

In Vitro Use Guide

Ciclopirox exhibited the best antifungal activity against S. brevicaulis, with MICs ranging from 1 to 8mg/l. Mode, MIC50, and MIC90 amounted to 4mg/l.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:11:08 GMT 2025` Edited by `admin` on `Mon Mar 31 18:11:08 GMT 2025`
Record UNII	19W019ZDRJ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LOPROX

Preferred Name

English

CICLOPIROX

Official Name

English

HOE-296B

Code

English

CICLOPIROX [USP-RS]

Common Name

English

CICLOPIROX [MI]

Common Name

English

2(1H)-PYRIDINONE, 6-CYCLOHEXYL-1-HYDROXY-4-METHYL-

Systematic Name

English

6-CYCLOHEXYL-1-HYDROXY-4-METHYL-2(1H)-PYRIDINONE

Systematic Name

English

CICLOPIROX [MART.]

Common Name

English

CYCLOPIROX

Common Name

English

PENLAC

Brand Name

English

CICLOPIROX [USAN]

Common Name

English

CICLOPIROX [ORANGE BOOK]

Common Name

English

CICLOPIROX [VANDF]

Common Name

English

CICLOPIROX [USP MONOGRAPH]

Common Name

English

Ciclopirox [WHO-DD]

Common Name

English

CICLOPIROX [EP MONOGRAPH]

Common Name

English

ciclopirox [INN]

Common Name

English

HOE 296B

Code

English

Classification Tree Code System Code

FDA ORPHAN DRUG

629718