U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of CICLOPIROX

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
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

1982
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

1999
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
Evaluation of in vitro resistance in patients with onychomycosis who fail antifungal therapy.
2003
Successful treatment of dandruff with 1.5% ciclopirox olamine shampoo in Korea.
2003 Dec
Action mechanisms of modern antifungal agents and resulting problems in the management of onychomycosis.
2003 Dec
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
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
Managing simple chronic paronychia and onycholysis with ciclopirox 0.77% and an irritant-avoidance regimen.
2004 Jan
Dermacase. Pityriasis rosea.
2004 Jan
Fungus-free versus disease-free nails.
2004 Jan
Treatment of onychomycosis: pros and cons of antifungal agents.
2004 Jan-Feb
Onychomycosis in children: a brief overview with treatment strategies.
2004 Jan-Feb
Onychomycosis: review of recurrence rates, poor prognostic factors, and strategies to prevent disease recurrence.
2004 Jul
Management of onychomycosis: examining the role of monotherapy and dual, triple, or quadruple therapies.
2004 Jul
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
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
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
Ciclopirox: a broad-spectrum antifungal with antibacterial and anti-inflammatory properties.
2004 Jul
Eukaryotic initiation factor 5A-1 (eIF5A-1) as a diagnostic marker for aberrant proliferation in intraepithelial neoplasia of the vulva.
2004 Jul
Tinea capitis favosa in Poland.
2004 Jun
Agar sublimation test for the in vitro determination of the antifungal activity of morpholine derivatives.
2004 Jun
Activation of HIF-1alpha mRNA by hypoxia and iron chelator in isolated rat carotid body.
2004 Jun 17
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
In vitro susceptibility of 15 strains of zygomycetes to nine antifungal agents as determined by the NCCLS M38-A microdilution method.
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 Dec 15 15:51:28 GMT 2023
Edited
by admin
on Fri Dec 15 15:51:28 GMT 2023
Record UNII
19W019ZDRJ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CICLOPIROX
EP   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
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
LOPROX
Brand 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
Created by admin on Fri Dec 15 15:51:28 GMT 2023 , Edited by admin on Fri Dec 15 15:51:28 GMT 2023
WHO-VATC QG01AX12
Created by admin on Fri Dec 15 15:51:28 GMT 2023 , Edited by admin on Fri Dec 15 15:51:28 GMT 2023
WHO-VATC QD01AE14
Created by admin on Fri Dec 15 15:51:28 GMT 2023 , Edited by admin on Fri Dec 15 15:51:28 GMT 2023
WHO-ATC G01AX12
Created by admin on Fri Dec 15 15:51:28 GMT 2023 , Edited by admin on Fri Dec 15 15:51:28 GMT 2023
NDF-RT N0000008841
Created by admin on Fri Dec 15 15:51:28 GMT 2023 , Edited by admin on Fri Dec 15 15:51:28 GMT 2023
NDF-RT N0000008853
Created by admin on Fri Dec 15 15:51:28 GMT 2023 , Edited by admin on Fri Dec 15 15:51:28 GMT 2023
NDF-RT N0000000150
Created by admin on Fri Dec 15 15:51:28 GMT 2023 , Edited by admin on Fri Dec 15 15:51:28 GMT 2023
NCI_THESAURUS C514
Created by admin on Fri Dec 15 15:51:28 GMT 2023 , Edited by admin on Fri Dec 15 15:51:28 GMT 2023
WHO-ATC D01AE14
Created by admin on Fri Dec 15 15:51:28 GMT 2023 , Edited by admin on Fri Dec 15 15:51:28 GMT 2023
NDF-RT N0000008577
Created by admin on Fri Dec 15 15:51:28 GMT 2023 , Edited by admin on Fri Dec 15 15:51:28 GMT 2023
NDF-RT N0000008841
Created by admin on Fri Dec 15 15:51:28 GMT 2023 , Edited by admin on Fri Dec 15 15:51:28 GMT 2023
EU-Orphan Drug EU/3/17/1960
Created by admin on Fri Dec 15 15:51:28 GMT 2023 , Edited by admin on Fri Dec 15 15:51:28 GMT 2023
Code System Code Type Description
INN
3101
Created by admin on Fri Dec 15 15:51:28 GMT 2023 , Edited by admin on Fri Dec 15 15:51:28 GMT 2023
PRIMARY
PUBCHEM
2749
Created by admin on Fri Dec 15 15:51:28 GMT 2023 , Edited by admin on Fri Dec 15 15:51:28 GMT 2023
PRIMARY
FDA UNII
19W019ZDRJ
Created by admin on Fri Dec 15 15:51:28 GMT 2023 , Edited by admin on Fri Dec 15 15:51:28 GMT 2023
PRIMARY
DRUG CENTRAL
636
Created by admin on Fri Dec 15 15:51:28 GMT 2023 , Edited by admin on Fri Dec 15 15:51:28 GMT 2023
PRIMARY
RXCUI
21090
Created by admin on Fri Dec 15 15:51:28 GMT 2023 , Edited by admin on Fri Dec 15 15:51:28 GMT 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
249-577-2
Created by admin on Fri Dec 15 15:51:28 GMT 2023 , Edited by admin on Fri Dec 15 15:51:28 GMT 2023
PRIMARY
CAS
29342-05-0
Created by admin on Fri Dec 15 15:51:28 GMT 2023 , Edited by admin on Fri Dec 15 15:51:28 GMT 2023
PRIMARY
ChEMBL
CHEMBL1413
Created by admin on Fri Dec 15 15:51:28 GMT 2023 , Edited by admin on Fri Dec 15 15:51:28 GMT 2023
PRIMARY
DAILYMED
19W019ZDRJ
Created by admin on Fri Dec 15 15:51:28 GMT 2023 , Edited by admin on Fri Dec 15 15:51:28 GMT 2023
PRIMARY
MERCK INDEX
m3539
Created by admin on Fri Dec 15 15:51:28 GMT 2023 , Edited by admin on Fri Dec 15 15:51:28 GMT 2023
PRIMARY Merck Index
WIKIPEDIA
CICLOPIROX
Created by admin on Fri Dec 15 15:51:28 GMT 2023 , Edited by admin on Fri Dec 15 15:51:28 GMT 2023
PRIMARY
CHEBI
453011
Created by admin on Fri Dec 15 15:51:28 GMT 2023 , Edited by admin on Fri Dec 15 15:51:28 GMT 2023
PRIMARY
EPA CompTox
DTXSID9048564
Created by admin on Fri Dec 15 15:51:28 GMT 2023 , Edited by admin on Fri Dec 15 15:51:28 GMT 2023
PRIMARY
MESH
C011585
Created by admin on Fri Dec 15 15:51:28 GMT 2023 , Edited by admin on Fri Dec 15 15:51:28 GMT 2023
PRIMARY
NCI_THESAURUS
C61677
Created by admin on Fri Dec 15 15:51:28 GMT 2023 , Edited by admin on Fri Dec 15 15:51:28 GMT 2023
PRIMARY
USAN
EE-51
Created by admin on Fri Dec 15 15:51:28 GMT 2023 , Edited by admin on Fri Dec 15 15:51:28 GMT 2023
PRIMARY
LACTMED
Ciclopirox
Created by admin on Fri Dec 15 15:51:28 GMT 2023 , Edited by admin on Fri Dec 15 15:51:28 GMT 2023
PRIMARY
SMS_ID
100000081889
Created by admin on Fri Dec 15 15:51:28 GMT 2023 , Edited by admin on Fri Dec 15 15:51:28 GMT 2023
PRIMARY
RS_ITEM_NUM
1134018
Created by admin on Fri Dec 15 15:51:28 GMT 2023 , Edited by admin on Fri Dec 15 15:51:28 GMT 2023
PRIMARY
EVMPD
SUB06245MIG
Created by admin on Fri Dec 15 15:51:28 GMT 2023 , Edited by admin on Fri Dec 15 15:51:28 GMT 2023
PRIMARY
DRUG BANK
DB01188
Created by admin on Fri Dec 15 15:51:28 GMT 2023 , Edited by admin on Fri Dec 15 15:51:28 GMT 2023
PRIMARY
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