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
Usefulness of histological examination for the diagnosis of onychomycosis.	2001	11455138
A multicenter, open-label study of the efficacy and safety of ciclopirox nail lacquer solution 8% for the treatment of onychomycosis in patients with diabetes.	2001 Aug	11665724
Ciclopirox nail lacquer: a brush with onychomycosis.	2001 Aug	11665723
Role of oral antifungal agents for the treatment of superficial fungal infections in immunocompromised patients.	2001 Jul	11499333
[Treatment of therapy refractory verrucae vulgares with a ciclopirox-containing lacquer].	2001 Jun	11428076
Allergic contact dermatitis from ciclopirox olamine.	2001 May	11309043
[Batrafen in the treatment of fungal diseases of the skin and nails].	2002 Aug	12379027
Ciclopiroxolamine cream for treating seborrheic dermatitis: a double-blind parallel group comparison.	2002 Dec	12478328
A randomised, single-blind, single-centre clinical trial to evaluate comparative clinical efficacy of shampoos containing ciclopirox olamine (1.5%) and salicylic acid (3%), or ketoconazole (2%, Nizoral) for the treatment of dandruff/seborrhoeic dermatitis.	2002 Jun	12060502
Treatment of dermatophyte toenail onychomycosis in the United States. A pharmacoeconomic analysis.	2002 May	12015408
Randomized, open-labeled, non-inferiority study between ciclopiroxolamine 1% cream and ketoconazole 2% foaming gel in mild to moderate facial seborrheic dermatitis.	2003	12673081
Ciclopirox olamine: head to foot.	2003 Jan	12852382
Permeation of ciclopirox across porcine hoof membrane: effect of pressure sensitive adhesives and vehicles.	2003 Nov	14592697
Ciclopirox gel in the treatment of patients with interdigital tinea pedis.	2003 Sep	14567368
Ciclopirox gel for seborrheic dermatitis of the scalp.	2003 Sep	12895183
Evaluation of the drug treatment and persistence of onychomycosis.	2004 Aug 31	15349516
Onychomycosis: review of recurrence rates, poor prognostic factors, and strategies to prevent disease recurrence.	2004 Jul	15287395
Management of onychomycosis: examining the role of monotherapy and dual, triple, or quadruple therapies.	2004 Jul	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 Jul	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 Jul	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 Jul	15271194
Ciclopirox: a broad-spectrum antifungal with antibacterial and anti-inflammatory properties.	2004 Jul	15271193
Eukaryotic initiation factor 5A-1 (eIF5A-1) as a diagnostic marker for aberrant proliferation in intraepithelial neoplasia of the vulva.	2004 Jul	15262146
Tinea capitis favosa in Poland.	2004 Jun	15189196
Agar sublimation test for the in vitro determination of the antifungal activity of morpholine derivatives.	2004 Jun	15189181
Ciclopirox shampoo for treating seborrheic dermatitis.	2004 Jun-Jul	15334279
[Chronic favus caused by infection with Trichophyton schönleinii].	2004 Oct	16281590
Pharmacotherapy of onychomycosis.	2005 Apr	15934887
Physicochemical studies on Ciclopirox olamine complexes with divalent metal ions.	2005 Jan 31	15652210
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 Jul	15985032
In vitro susceptibility of 15 strains of zygomycetes to nine antifungal agents as determined by the NCCLS M38-A microdilution method.	2005 Jul	15982206
Ciclopirox topical solution, 8% combined with oral terbinafine to treat onychomycosis: a randomized, evaluator-blinded study.	2005 Jul-Aug	16004022
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
Ciclopirox protects mitochondria from hydrogen peroxide toxicity.	2005 Jun	15806112
The safety and efficacy of ciclopirox olamine for the treatment of seborrheic dermatitis.	2005 Mar	15794716
Genome-wide expression profiling of the response to ciclopirox olamine in Candida albicans.	2005 May	15814599
Oxygen accessibility and iron levels are critical factors for the antifungal action of ciclopirox against Candida albicans.	2005 May	15790671
Ciclopirox nail lacquer 8% for the treatment of onychomycosis: a Canadian perspective.	2005 Sep	16292454

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