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Details

Stereochemistry ACHIRAL
Molecular Formula C12H17NO2.C2H7NO
Molecular Weight 268.3525
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CICLOPIROX OLAMINE

SMILES

Cc1cc(C2CCCCC2)n(c(=O)c1)O.C(CO)N

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 61.0832
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C12H17NO2
Molecular Weight 207.2693
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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
LOPROX

Approved Use

Loprox Shampoo is an antifungal indicated for the topical treatment of seborrheic dermatitis of the scalp in adults.

Launch Date

4.10054394E11
Curative
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

9.4530241E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
25.02 ng/mL
5 g single, topical
dose: 5 g
route of administration: Topical
experiment type: SINGLE
co-administered:
CICLOPIROX blood
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.7 h
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
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: Page: p.11
unhealthy
n = 281
Health Status: unhealthy
Condition: Onychomycosis
Population Size: 281
Sources: Page: p.11
Disc. AE: Creatine phosphokinase increased...
AEs leading to
discontinuation/dose reduction:
Creatine phosphokinase increased (0.36%)
Sources: Page: p.11
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: Page: p.11
unhealthy
n = 281
Health Status: unhealthy
Condition: Onychomycosis
Population Size: 281
Sources: Page: p.11
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no [IC50 >500 uM]
Tox targets
PubMed

PubMed

TitleDatePubMed
Usefulness of histological examination for the diagnosis of onychomycosis.
2001
Anatomy of the primase-alpha DNA polymerase reaction accomplished by nucleoprotein complexes harboring an extrachromosomal DNA identical with avian myeloblastosis virus core-bound DNA: influencing by carbonyldiphosphonate, mimosine and butylphenyl deoxyguanosine-5'-triphosphate.
2001 Apr
Successful treatment of onychomycosis with ciclopirox nail lacquer: a case report.
2001 Aug
Role of oral antifungal agents for the treatment of superficial fungal infections in immunocompromised patients.
2001 Jul
Ciclopirox: an overview.
2001 May
Ciclopiroxolamine cream for treating seborrheic dermatitis: a double-blind parallel group comparison.
2002 Dec
[Tinea].
2002 Jul
Ciclopiroxolamine: in vitro antifungal activity against clinical yeast isolates.
2002 Nov
Ciclopirox prevents peroxynitrite toxicity in astrocytes by maintaining their mitochondrial function: a novel mechanism for cytoprotection by ciclopirox.
2002 Sep
Randomized, open-labeled, non-inferiority study between ciclopiroxolamine 1% cream and ketoconazole 2% foaming gel in mild to moderate facial seborrheic dermatitis.
2003
Onychomycosis: current treatment options.
2003 Apr
In vitro susceptibility testing of ciclopirox, terbinafine, ketoconazole and itraconazole against dermatophytes and nondermatophytes, and in vitro evaluation of combination antifungal activity.
2003 Aug
Effects of hypoxia and intracellular iron chelation on hypoxia-inducible factor-1alpha and -1beta in the rat carotid body and glomus cells.
2003 Nov
Permeation of ciclopirox across porcine hoof membrane: effect of pressure sensitive adhesives and vehicles.
2003 Nov
I've heard there's a nail polish for nail fungus. Does it work?
2003 Oct
Interdigital tinea pedis (dermatophytosis simplex and complex) and treatment with ciclopirox 0.77% gel.
2003 Sep
Evaluation of in vitro activity of ciclopirox olamine, butenafine HCl and econazole nitrate against dermatophytes, yeasts and bacteria.
2003 Sep
A randomized comparison of nail surface remanence of three nail lacquers, containing amorolfine 5%, ciclopirox 8% or tioconazole 28%, in healthy volunteers.
2004
In vitro susceptibility testing of dermatophytes: comparison of disk diffusion and reference broth dilution methods.
2004 Apr
Evaluation of the drug treatment and persistence of onychomycosis.
2004 Aug 31
Ciclopirox (Loprox) gel for superficial fungal infections.
2004 Aug-Sep
[Onychomycosis].
2004 Feb
Fungus-free versus disease-free nails.
2004 Jan
Onychomycosis: review of recurrence rates, poor prognostic factors, and strategies to prevent disease recurrence.
2004 Jul
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
Eukaryotic initiation factor 5A-1 (eIF5A-1) as a diagnostic marker for aberrant proliferation in intraepithelial neoplasia of the vulva.
2004 Jul
Ciclopirox shampoo for treating seborrheic dermatitis.
2004 Jun-Jul
The use of 40% urea cream in the treatment of moccasin tinea pedis.
2004 May
Cutaneous adiaspiromycosis: a distinct dermatologic entity associated with Chrysosporium species.
2004 Nov
[Chronic favus caused by infection with Trichophyton schönleinii].
2004 Oct
Management of onychomycosis with topicals.
2004 Oct
Ciclopirox delivery into the human nail plate.
2004 Oct
Cell cycle arrest at the initiation step of human chromosomal DNA replication causes DNA damage.
2004 Oct 1
Pharmacotherapy of onychomycosis.
2005 Apr
In vitro transungual permeation of ciclopirox from a hydroxypropyl chitosan-based, water-soluble nail lacquer.
2005 Jan
Pharmacoeconomic analysis of sequential treatment pathways in the treatment of onychomycosis.
2005 Jan
Treatment and prophylaxis of seborrheic dermatitis of the scalp with antipityrosporal 1% ciclopirox shampoo.
2005 Jan
Topical antifungal drugs for the treatment of onychomycosis: an overview of current strategies for monotherapy and combination therapy.
2005 Jan
Physicochemical studies on Ciclopirox olamine complexes with divalent metal ions.
2005 Jan 31
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
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
Ciclopirox topical solution, 8% combined with oral terbinafine to treat onychomycosis: a randomized, evaluator-blinded study.
2005 Jul-Aug
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Ciclopirox protects mitochondria from hydrogen peroxide toxicity.
2005 Jun
Copper-dependent activation of hypoxia-inducible factor (HIF)-1: implications for ceruloplasmin regulation.
2005 Jun 15
The safety and efficacy of ciclopirox olamine for the treatment of seborrheic dermatitis.
2005 Mar
Trichophyton rubrum isolated from aids and human immunodeficiency virus-infected patients in São Paulo, Brazil: antifungal susceptibility and extracellular enzyme production.
2005 Mar
Genome-wide expression profiling of the response to ciclopirox olamine in Candida albicans.
2005 May
Oxygen accessibility and iron levels are critical factors for the antifungal action of ciclopirox against Candida albicans.
2005 May
Ciclopirox nail lacquer 8% for the treatment of onychomycosis: a Canadian perspective.
2005 Sep
Patents

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 Fri Jun 25 20:55:39 UTC 2021
Edited
by admin
on Fri Jun 25 20:55:39 UTC 2021
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  
Official Name English
CICLOPIROX OLAMINE [USP-RS]
Common Name English
CICLOPIROX OLAMINE [JAN]
Common Name English
CICLOPIROX OLAMINE [EP]
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
CICLOPIROX OLAMINE [WHO-DD]
Common Name English
CICLOPIROX OLAMINE [INCI]
Common Name English
BRUMIXOL
Brand Name English
CICLOPIROX OLAMINE [VANDF]
Common Name English
CICLOPIROX ETHANOLAMINE SALT (1:1) [MI]
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
BATRAFEN
Brand Name English
MYCOSTER
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C514
Created by admin on Fri Jun 25 20:55:39 UTC 2021 , Edited by admin on Fri Jun 25 20:55:39 UTC 2021
Code System Code Type Description
CAS
41621-49-2
Created by admin on Fri Jun 25 20:55:39 UTC 2021 , Edited by admin on Fri Jun 25 20:55:39 UTC 2021
PRIMARY
ECHA (EC/EINECS)
255-464-9
Created by admin on Fri Jun 25 20:55:39 UTC 2021 , Edited by admin on Fri Jun 25 20:55:39 UTC 2021
PRIMARY
NCI_THESAURUS
C65327
Created by admin on Fri Jun 25 20:55:39 UTC 2021 , Edited by admin on Fri Jun 25 20:55:39 UTC 2021
PRIMARY
EPA CompTox
41621-49-2
Created by admin on Fri Jun 25 20:55:39 UTC 2021 , Edited by admin on Fri Jun 25 20:55:39 UTC 2021
PRIMARY
DRUG BANK
DBSALT001147
Created by admin on Fri Jun 25 20:55:39 UTC 2021 , Edited by admin on Fri Jun 25 20:55:39 UTC 2021
PRIMARY
MERCK INDEX
M3539
Created by admin on Fri Jun 25 20:55:39 UTC 2021 , Edited by admin on Fri Jun 25 20:55:39 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL1413
Created by admin on Fri Jun 25 20:55:39 UTC 2021 , Edited by admin on Fri Jun 25 20:55:39 UTC 2021
PRIMARY
FDA UNII
50MD4SB4AP
Created by admin on Fri Jun 25 20:55:39 UTC 2021 , Edited by admin on Fri Jun 25 20:55:39 UTC 2021
PRIMARY
RXCUI
52172
Created by admin on Fri Jun 25 20:55:39 UTC 2021 , Edited by admin on Fri Jun 25 20:55:39 UTC 2021
PRIMARY RxNorm
EVMPD
SUB01294MIG
Created by admin on Fri Jun 25 20:55:39 UTC 2021 , Edited by admin on Fri Jun 25 20:55:39 UTC 2021
PRIMARY
PUBCHEM
38911
Created by admin on Fri Jun 25 20:55:39 UTC 2021 , Edited by admin on Fri Jun 25 20:55:39 UTC 2021
PRIMARY
USP_CATALOG
1134030
Created by admin on Fri Jun 25 20:55:39 UTC 2021 , Edited by admin on Fri Jun 25 20:55:39 UTC 2021
PRIMARY USP-RS
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CONSTITUENT ALWAYS PRESENT -> PARENT
ASSAY (TITRATION)
EP
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
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PARENT -> SALT/SOLVATE
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IMPURITY -> PARENT
at 220 nm
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