CICLOPIROX OLAMINE

First approved in 1982

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H17NO2.C2H7NO
Molecular Weight	268.352
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=MBRHNTMUYWQHMR-UHFFFAOYSA-N

InChI=1S/C12H17NO2.C2H7NO/c1-9-7-11(13(15)12(14)8-9)10-5-3-2-4-6-10;3-1-2-4/h7-8,10,15H,2-6H2,1H3;4H,1-3H2

HIDE SMILES / InChI

Molecular Formula	C2H7NO
Molecular Weight	61.0831
Charge	0
Count

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

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
Role of oral antifungal agents for the treatment of superficial fungal infections in immunocompromised patients.	2001 Jul	11499333
[Mode of action of ciclopiroxolamine on Candida albicans].	2002	12073566
Six novel antimycotics.	2002	11893219
[Batrafen in the treatment of fungal diseases of the skin and nails].	2002 Aug	12379027
The antifungal drug ciclopirox inhibits deoxyhypusine and proline hydroxylation, endothelial cell growth and angiogenesis in vitro.	2002 Aug 1	12115536
Homologous recombination induced by replication inhibition, is stimulated by expression of mutant p53.	2002 Jan 17	11821962
[Tinea].	2002 Jul	12162167
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
Ciclopirox prevents peroxynitrite toxicity in astrocytes by maintaining their mitochondrial function: a novel mechanism for cytoprotection by ciclopirox.	2002 Sep	12243770
Evaluation of in vitro resistance in patients with onychomycosis who fail antifungal therapy.	2003	14657630
Successful treatment of dandruff with 1.5% ciclopirox olamine shampoo in Korea.	2003 Dec	14660265
Action mechanisms of modern antifungal agents and resulting problems in the management of onychomycosis.	2003 Dec	14641625
Polarographic determination of ciclopirox olamine in pure substance and in different pharmaceutical preparations.	2003 Dec	14630245
Effects of hypoxia and intracellular iron chelation on hypoxia-inducible factor-1alpha and -1beta in the rat carotid body and glomus cells.	2003 Nov	14600837
Ciclopirox gel in the treatment of patients with interdigital tinea pedis.	2003 Sep	14567368
[Onychomycosis].	2004 Feb	14968324
Managing simple chronic paronychia and onycholysis with ciclopirox 0.77% and an irritant-avoidance regimen.	2004 Jan	14964637
Fungus-free versus disease-free nails.	2004 Jan	14699392
Ciclopirox: a broad-spectrum antifungal with antibacterial and anti-inflammatory properties.	2004 Jul	15271193
Activation of HIF-1alpha mRNA by hypoxia and iron chelator in isolated rat carotid body.	2004 Jun 17	15182949
The use of 40% urea cream in the treatment of moccasin tinea pedis.	2004 May	15186053
[Chronic favus caused by infection with Trichophyton schönleinii].	2004 Oct	16281590
Pharmacotherapy of onychomycosis.	2005 Apr	15934887
Treatment and prophylaxis of seborrheic dermatitis of the scalp with antipityrosporal 1% ciclopirox shampoo.	2005 Jan	15655141
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 Jan-Feb	15696982
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
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
Trichophyton rubrum isolated from aids and human immunodeficiency virus-infected patients in São Paulo, Brazil: antifungal susceptibility and extracellular enzyme production.	2005 Mar	15722629
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 17:52:04 GMT 2025` Edited by `admin` on `Mon Mar 31 17:52:04 GMT 2025`
Record UNII	50MD4SB4AP
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CICLOPIROX OLAMINE

Official Name

English

BATRAFEN

Preferred Name

English

CICLOPIROX OLAMINE [EP IMPURITY]

Common Name

English

CICLOPIROX OLAMINE [USP-RS]

Common Name

English

CICLOPIROX OLAMINE [JAN]

Common Name

English

2(1H)-PYRIDINONE, 6-CYCLOHEXYL-1-HYDROXY-4-METHYL-, COMPOUND WITH 2-AMINOETHANOL (1:1)

Systematic Name

English

HOE 296

Code

English

CICLOCHEM

Brand Name

English

MICOXOLAMINA

Brand Name

English

HOE-296

Code

English

DAFNEGIN

Brand Name

English

NSC-336278

Code

English

BRUMIXOL

Brand Name

English

CICLOPIROX OLAMINE [VANDF]

Common Name

English

CICLOPIROX ETHANOLAMINE SALT (1:1) [MI]

Common Name

English

Ciclopirox olamine [WHO-DD]

Common Name

English

CICLOPIROX OLAMINE [MART.]

Common Name

English

CICLOPIROX OLAMINE [EP MONOGRAPH]

Common Name

English

CICLOPIROX OLAMINE [USAN]

Common Name

English

CICLOPIROX OLAMINE [USP MONOGRAPH]

Common Name

English

6-CYCLOHEXYL-1-HYDROXY-4-METHYL-2(1H)-PYRIDONE COMPOUND WITH 2-AMINOETHANOL

Systematic Name

English

MYCOSTER

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C514