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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.

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
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
Ciclopirox: an overview.
2001 May
Randomized, placebo-controlled, double-blind study on clinical efficacy of ciclopiroxolamine 1% cream in facial seborrhoeic dermatitis.
2001 May
[Mode of action of ciclopiroxolamine on Candida albicans].
2002
Six novel antimycotics.
2002
[Batrafen in the treatment of fungal diseases of the skin and nails].
2002 Aug
Ciclopiroxolamine: in vitro antifungal activity against clinical yeast isolates.
2002 Nov
Randomized prospective comparative study: short-term treatment with ciclopiroxolamine (cream and solution) versus boric acid in the treatment of otomycosis.
2002 Oct
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
Seborrheic dermatitis today, gone tomorrow? The link between the biocene and treatment.
2003
The possible mechanism of action of ciclopirox olamine in the yeast Saccharomyces cerevisiae.
2003 Feb 28
The use of topical therapies to treat onychomycosis.
2003 Jul
Economic analysis of oral and topical therapies for onychomycosis of the toenails and fingernails.
2003 Mar
Deep mycosis caused by Trichophyton mentagrophytes in a diabetic patient.
2003 Sep
Assessing treatment outcomes in toenail onychomycosis clinical trials.
2004
In vitro susceptibility testing of dermatophytes: comparison of disk diffusion and reference broth dilution methods.
2004 Apr
Managing simple chronic paronychia and onycholysis with ciclopirox 0.77% and an irritant-avoidance regimen.
2004 Jan
Fungus-free versus disease-free nails.
2004 Jan
Onychomycosis: review of recurrence rates, poor prognostic factors, and strategies to prevent disease recurrence.
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
Activation of HIF-1alpha mRNA by hypoxia and iron chelator in isolated rat carotid body.
2004 Jun 17
Management of onychomycosis with topicals.
2004 Oct
Cell cycle arrest at the initiation step of human chromosomal DNA replication causes DNA damage.
2004 Oct 1
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
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Copper-dependent activation of hypoxia-inducible factor (HIF)-1: implications for ceruloplasmin regulation.
2005 Jun 15
Genome-wide expression profiling of the response to ciclopirox olamine in 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 15:15:51 GMT 2023
Edited
by admin
on Fri Dec 15 15:15:51 GMT 2023
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
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
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 [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
BATRAFEN
Brand Name English
MYCOSTER
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C514
Created by admin on Fri Dec 15 15:15:51 GMT 2023 , Edited by admin on Fri Dec 15 15:15:51 GMT 2023
Code System Code Type Description
CAS
41621-49-2
Created by admin on Fri Dec 15 15:15:51 GMT 2023 , Edited by admin on Fri Dec 15 15:15:51 GMT 2023
PRIMARY
ECHA (EC/EINECS)
255-464-9
Created by admin on Fri Dec 15 15:15:51 GMT 2023 , Edited by admin on Fri Dec 15 15:15:51 GMT 2023
PRIMARY
SMS_ID
100000084827
Created by admin on Fri Dec 15 15:15:51 GMT 2023 , Edited by admin on Fri Dec 15 15:15:51 GMT 2023
PRIMARY
DAILYMED
50MD4SB4AP
Created by admin on Fri Dec 15 15:15:51 GMT 2023 , Edited by admin on Fri Dec 15 15:15:51 GMT 2023
PRIMARY
NCI_THESAURUS
C65327
Created by admin on Fri Dec 15 15:15:51 GMT 2023 , Edited by admin on Fri Dec 15 15:15:51 GMT 2023
PRIMARY
EPA CompTox
DTXSID6045583
Created by admin on Fri Dec 15 15:15:51 GMT 2023 , Edited by admin on Fri Dec 15 15:15:51 GMT 2023
PRIMARY
DRUG BANK
DBSALT001147
Created by admin on Fri Dec 15 15:15:51 GMT 2023 , Edited by admin on Fri Dec 15 15:15:51 GMT 2023
PRIMARY
MERCK INDEX
m3539
Created by admin on Fri Dec 15 15:15:51 GMT 2023 , Edited by admin on Fri Dec 15 15:15:51 GMT 2023
PRIMARY Merck Index
ChEMBL
CHEMBL1413
Created by admin on Fri Dec 15 15:15:51 GMT 2023 , Edited by admin on Fri Dec 15 15:15:51 GMT 2023
PRIMARY
RS_ITEM_NUM
1134030
Created by admin on Fri Dec 15 15:15:51 GMT 2023 , Edited by admin on Fri Dec 15 15:15:51 GMT 2023
PRIMARY
FDA UNII
50MD4SB4AP
Created by admin on Fri Dec 15 15:15:51 GMT 2023 , Edited by admin on Fri Dec 15 15:15:51 GMT 2023
PRIMARY
RXCUI
52172
Created by admin on Fri Dec 15 15:15:51 GMT 2023 , Edited by admin on Fri Dec 15 15:15:51 GMT 2023
PRIMARY RxNorm
EVMPD
SUB01294MIG
Created by admin on Fri Dec 15 15:15:51 GMT 2023 , Edited by admin on Fri Dec 15 15:15:51 GMT 2023
PRIMARY
PUBCHEM
38911
Created by admin on Fri Dec 15 15:15:51 GMT 2023 , Edited by admin on Fri Dec 15 15:15:51 GMT 2023
PRIMARY
NSC
336278
Created by admin on Fri Dec 15 15:15:51 GMT 2023 , Edited by admin on Fri Dec 15 15:15:51 GMT 2023
PRIMARY
Related Record Type Details
CONSTITUENT ALWAYS PRESENT -> PARENT
ASSAY (TITRATION)
EP
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
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PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
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at 220 nm
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