CICLOPIROX

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 143
Iron 19 Target ID: CHEMBL2363058 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021159s020lbl.pdf	Chelating Agent 143

Conditions

Condition	Modality	Targets	Highest Phase	Product
Seborrheic dermatitis 15 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021159s020lbl.pdf	Curative		Approved 8360	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
Onychomycosis of fingernails and toenails due to Trichophyton rubrum 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21022s004lbl.pdf	Curative		Approved 8360	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

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	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

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

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 Page: p.11	unhealthy n = 281 Health Status: unhealthy Condition: Onychomycosis Population Size: 281 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21022s004lbl.pdf Page: p.11	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 Page: p.11

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 Page: p.11	unhealthy n = 281 Health Status: unhealthy Condition: Onychomycosis Population Size: 281 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21022s004lbl.pdf Page: p.11

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			binder 2 activator 13 inhibitor 1599

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
MATE1 304

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
MATE1 306	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23241029/	no [IC50 >500 uM]

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1632	activator 13 Sources: https://pubmed.ncbi.nlm.nih.gov/21158687/
hERG 1632	binder 5 Sources: https://pubmed.ncbi.nlm.nih.gov/21158687/
hERG 1632	inhibitor 1613 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
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
eMolecules	901641	https://www.emolecules.com/cgi-bin/more?vid=901641

PubMed

Title	Date	PubMed
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	11719981
Successful treatment of onychomycosis with ciclopirox nail lacquer: a case report.	2001 Aug	11665725
Six novel antimycotics.	2002	11893219
[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
[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
Extra- and intracellular free iron and the carotid body responses.	2002 Mar	12380013
Treatment of dermatophyte toenail onychomycosis in the United States. A pharmacoeconomic analysis.	2002 May	12015408
Ciclopiroxolamine: in vitro antifungal activity against clinical yeast isolates.	2002 Nov	12431873
[Therapy problems in chronic recurrent vaginal mycosis].	2002 Sep	12369153
Randomized, open-labeled, non-inferiority study between ciclopiroxolamine 1% cream and ketoconazole 2% foaming gel in mild to moderate facial seborrheic dermatitis.	2003	12673081
In vitro susceptibility testing of ciclopirox, terbinafine, ketoconazole and itraconazole against dermatophytes and nondermatophytes, and in vitro evaluation of combination antifungal activity.	2003 Aug	12932235
Ciclopirox olamine: head to foot.	2003 Jan	12852382
Onychomycosis in children: an overview.	2003 Jan	12852378
Dermatophyte infections.	2003 Jan 1	12537173
Anodic polarographic determination of ciclopirox olamine in pure and certain pharmaceutical preparations.	2003 Jun 1	12763546
Economic analysis of oral and topical therapies for onychomycosis of the toenails and fingernails.	2003 Mar	12685377
Topical treatments for onychomycosis: a historical perspective.	2003 Mar-Apr	12644521
Treatment of onychomycosis in the diabetic patient population.	2003 Mar-Apr	12614976
Permeation of ciclopirox across porcine hoof membrane: effect of pressure sensitive adhesives and vehicles.	2003 Nov	14592697
Deep mycosis caused by Trichophyton mentagrophytes in a diabetic patient.	2003 Sep	12950910
Ciclopirox gel for seborrheic dermatitis of the scalp.	2003 Sep	12895183
Evaluation of in vitro activity of ciclopirox olamine, butenafine HCl and econazole nitrate against dermatophytes, yeasts and bacteria.	2003 Sep	12895182
Ciclopirox gel: an update.	2003 Sep	12895180
Common fungal infections of the feet in patients with diabetes mellitus.	2004	14960127
In vitro susceptibility testing of dermatophytes: comparison of disk diffusion and reference broth dilution methods.	2004 Apr	15062918
[Onychomycosis].	2004 Feb	14968324
Fungus-free versus disease-free nails.	2004 Jan	14699392
Treatment of onychomycosis: pros and cons of antifungal agents.	2004 Jan-Feb	15688097
Onychomycosis in children: a brief overview with treatment strategies.	2004 Jan-Feb	14871333
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
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
Agar sublimation test for the in vitro determination of the antifungal activity of morpholine derivatives.	2004 Jun	15189181
Activation of HIF-1alpha mRNA by hypoxia and iron chelator in isolated rat carotid body.	2004 Jun 17	15182949
Ciclopirox shampoo for treating seborrheic dermatitis.	2004 Jun-Jul	15334279
Cutaneous adiaspiromycosis: a distinct dermatologic entity associated with Chrysosporium species.	2004 Nov	15577766
[Chronic favus caused by infection with Trichophyton schönleinii].	2004 Oct	16281590
Ciclopirox delivery into the human nail plate.	2004 Oct	15349963
Pharmacotherapy of onychomycosis.	2005 Apr	15934887
In vitro transungual permeation of ciclopirox from a hydroxypropyl chitosan-based, water-soluble nail lacquer.	2005 Jan	15704853
Treatment and prophylaxis of seborrheic dermatitis of the scalp with antipityrosporal 1% ciclopirox shampoo.	2005 Jan	15655141
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
Copper-dependent activation of hypoxia-inducible factor (HIF)-1: implications for ceruloplasmin regulation.	2005 Jun 15	15741220
The safety and efficacy of ciclopirox olamine for the treatment of seborrheic dermatitis.	2005 Mar	15794716
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 `Wed Jul 05 23:19:48 UTC 2023` Edited by `admin` on `Wed Jul 05 23:19:48 UTC 2023`
Record UNII	19W019ZDRJ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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

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