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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 of CICLOPIROX OLAMINE

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
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

1982
105
Targets

Targets

Primary TargetPharmacologyConditionPotency
Chelating Agent
139
Chelating Agent
139
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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

AEs

AESignificanceDosePopulation
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

Overview

CYP3A4CYP2C9CYP2D6hERG
binder
2

activator
14

inhibitor
2217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
MATE1
415
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
MATE1
416
 no [IC50 >500 uM]
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
2263
hERG
2263
hERG
2263
Sourcing

Sourcing

Vendor/AggregatorIDURL
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

PubMed

TitleDatePubMed
Ciclopirox nail lacquer 8% for the treatment of onychomycosis: a Canadian perspective.
2005-09
Ciclopirox topical solution, 8% combined with oral terbinafine to treat onychomycosis: a randomized, evaluator-blinded study.
2005-07-12
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
In vitro susceptibility of 15 strains of zygomycetes to nine antifungal agents as determined by the NCCLS M38-A microdilution method.
2005-07
Copper-dependent activation of hypoxia-inducible factor (HIF)-1: implications for ceruloplasmin regulation.
2005-06-15
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005-06
Ciclopirox protects mitochondria from hydrogen peroxide toxicity.
2005-06
Genome-wide expression profiling of the response to ciclopirox olamine in Candida albicans.
2005-05
Oxygen accessibility and iron levels are critical factors for the antifungal action of ciclopirox against Candida albicans.
2005-05
Pharmacotherapy of onychomycosis.
2005-04
The safety and efficacy of ciclopirox olamine for the treatment of seborrheic dermatitis.
2005-03
Trichophyton rubrum isolated from aids and human immunodeficiency virus-infected patients in São Paulo, Brazil: antifungal susceptibility and extracellular enzyme production.
2005-03
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
Treatment of onychomycosis: pros and cons of antifungal agents.
2005-02-03
Physicochemical studies on Ciclopirox olamine complexes with divalent metal ions.
2005-01-31
In vitro transungual permeation of ciclopirox from a hydroxypropyl chitosan-based, water-soluble nail lacquer.
2005-01
Pharmacoeconomic analysis of sequential treatment pathways in the treatment of onychomycosis.
2005-01
Treatment and prophylaxis of seborrheic dermatitis of the scalp with antipityrosporal 1% ciclopirox shampoo.
2005-01
Topical antifungal drugs for the treatment of onychomycosis: an overview of current strategies for monotherapy and combination therapy.
2005-01
Cutaneous adiaspiromycosis: a distinct dermatologic entity associated with Chrysosporium species.
2004-11
Cell cycle arrest at the initiation step of human chromosomal DNA replication causes DNA damage.
2004-10-01
[Chronic favus caused by infection with Trichophyton schönleinii].
2004-10
Management of onychomycosis with topicals.
2004-10
Ciclopirox delivery into the human nail plate.
2004-10
Evaluation of the drug treatment and persistence of onychomycosis.
2004-08-31
Ciclopirox shampoo for treating seborrheic dermatitis.
2004-08-31
Ciclopirox (Loprox) gel for superficial fungal infections.
2004-08-31
Onychomycosis: review of recurrence rates, poor prognostic factors, and strategies to prevent disease recurrence.
2004-07
Management of onychomycosis: examining the role of monotherapy and dual, triple, or quadruple therapies.
2004-07
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
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
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
Ciclopirox: a broad-spectrum antifungal with antibacterial and anti-inflammatory properties.
2004-07
Eukaryotic initiation factor 5A-1 (eIF5A-1) as a diagnostic marker for aberrant proliferation in intraepithelial neoplasia of the vulva.
2004-07
Activation of HIF-1alpha mRNA by hypoxia and iron chelator in isolated rat carotid body.
2004-06-17
Tinea capitis favosa in Poland.
2004-06
Agar sublimation test for the in vitro determination of the antifungal activity of morpholine derivatives.
2004-06
The use of 40% urea cream in the treatment of moccasin tinea pedis.
2004-05
In vitro susceptibility testing of dermatophytes: comparison of disk diffusion and reference broth dilution methods.
2004-04
Onychomycosis in children: a brief overview with treatment strategies.
2004-02-12
[Onychomycosis].
2004-02
Managing simple chronic paronychia and onycholysis with ciclopirox 0.77% and an irritant-avoidance regimen.
2004-01
Dermacase. Pityriasis rosea.
2004-01
Fungus-free versus disease-free nails.
2004-01
A randomized comparison of nail surface remanence of three nail lacquers, containing amorolfine 5%, ciclopirox 8% or tioconazole 28%, in healthy volunteers.
2004
Assessing treatment outcomes in toenail onychomycosis clinical trials.
2004
Common fungal infections of the feet in patients with diabetes mellitus.
2004
Successful treatment of dandruff with 1.5% ciclopirox olamine shampoo in Korea.
2003-12
Action mechanisms of modern antifungal agents and resulting problems in the management of onychomycosis.
2003-12
Evaluation of in vitro resistance in patients with onychomycosis who fail antifungal therapy.
2003
Patents

Patents

JP2006347989A
3
JP2011001365A
2

Sample Use Guides

In Vivo Use Guide
Curator's Comment: http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21022s004lbl.pdf
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
Sources: www.ncbi.nlm.nih.gov/pubmed/25049036
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
  • Download
Name Type Language
CICLOPIROX OLAMINE
EP   INCI   JAN   MART.   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INCI   EP  
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
Created by admin on Mon Mar 31 17:52:04 GMT 2025 , Edited by admin on Mon Mar 31 17:52:04 GMT 2025
Code System Code Type Description
CAS
41621-49-2
Created by admin on Mon Mar 31 17:52:04 GMT 2025 , Edited by admin on Mon Mar 31 17:52:04 GMT 2025
PRIMARY
ECHA (EC/EINECS)
255-464-9
Created by admin on Mon Mar 31 17:52:04 GMT 2025 , Edited by admin on Mon Mar 31 17:52:04 GMT 2025
PRIMARY
SMS_ID
100000084827
Created by admin on Mon Mar 31 17:52:04 GMT 2025 , Edited by admin on Mon Mar 31 17:52:04 GMT 2025
PRIMARY
DAILYMED
50MD4SB4AP
Created by admin on Mon Mar 31 17:52:04 GMT 2025 , Edited by admin on Mon Mar 31 17:52:04 GMT 2025
PRIMARY
NCI_THESAURUS
C65327
Created by admin on Mon Mar 31 17:52:04 GMT 2025 , Edited by admin on Mon Mar 31 17:52:04 GMT 2025
PRIMARY
EPA CompTox
DTXSID6045583
Created by admin on Mon Mar 31 17:52:04 GMT 2025 , Edited by admin on Mon Mar 31 17:52:04 GMT 2025
PRIMARY
DRUG BANK
DBSALT001147
Created by admin on Mon Mar 31 17:52:04 GMT 2025 , Edited by admin on Mon Mar 31 17:52:04 GMT 2025
PRIMARY
MERCK INDEX
m3539
Created by admin on Mon Mar 31 17:52:04 GMT 2025 , Edited by admin on Mon Mar 31 17:52:04 GMT 2025
PRIMARY Merck Index
ChEMBL
CHEMBL1413
Created by admin on Mon Mar 31 17:52:04 GMT 2025 , Edited by admin on Mon Mar 31 17:52:04 GMT 2025
PRIMARY
RS_ITEM_NUM
1134030
Created by admin on Mon Mar 31 17:52:04 GMT 2025 , Edited by admin on Mon Mar 31 17:52:04 GMT 2025
PRIMARY
FDA UNII
50MD4SB4AP
Created by admin on Mon Mar 31 17:52:04 GMT 2025 , Edited by admin on Mon Mar 31 17:52:04 GMT 2025
PRIMARY
RXCUI
52172
Created by admin on Mon Mar 31 17:52:04 GMT 2025 , Edited by admin on Mon Mar 31 17:52:04 GMT 2025
PRIMARY RxNorm
EVMPD
SUB01294MIG
Created by admin on Mon Mar 31 17:52:04 GMT 2025 , Edited by admin on Mon Mar 31 17:52:04 GMT 2025
PRIMARY
PUBCHEM
38911
Created by admin on Mon Mar 31 17:52:04 GMT 2025 , Edited by admin on Mon Mar 31 17:52:04 GMT 2025
PRIMARY
NSC
336278
Created by admin on Mon Mar 31 17:52:04 GMT 2025 , Edited by admin on Mon Mar 31 17:52:04 GMT 2025
PRIMARY
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Structure of CICLOPIROX OLAMINE
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ACTIVE MOIETY
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NCATS
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