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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
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
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
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
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
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:
unhealthy
Disc. AE: Creatine phosphokinase increased...
AEs leading to
discontinuation/dose reduction:
Creatine phosphokinase increased (0.36%)
Sources:
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:
unhealthy
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
Role of oral antifungal agents for the treatment of superficial fungal infections in immunocompromised patients.
2001 Jul
[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
The antifungal drug ciclopirox inhibits deoxyhypusine and proline hydroxylation, endothelial cell growth and angiogenesis in vitro.
2002 Aug 1
Homologous recombination induced by replication inhibition, is stimulated by expression of mutant p53.
2002 Jan 17
[Tinea].
2002 Jul
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
Treatment of dermatophyte toenail onychomycosis in the United States. A pharmacoeconomic analysis.
2002 May
Ciclopirox prevents peroxynitrite toxicity in astrocytes by maintaining their mitochondrial function: a novel mechanism for cytoprotection by ciclopirox.
2002 Sep
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
Polarographic determination of ciclopirox olamine in pure substance and in different pharmaceutical preparations.
2003 Dec
Effects of hypoxia and intracellular iron chelation on hypoxia-inducible factor-1alpha and -1beta in the rat carotid body and glomus cells.
2003 Nov
Ciclopirox gel in the treatment of patients with interdigital tinea pedis.
2003 Sep
[Onychomycosis].
2004 Feb
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
Ciclopirox: a broad-spectrum antifungal with antibacterial and anti-inflammatory properties.
2004 Jul
Activation of HIF-1alpha mRNA by hypoxia and iron chelator in isolated rat carotid body.
2004 Jun 17
The use of 40% urea cream in the treatment of moccasin tinea pedis.
2004 May
[Chronic favus caused by infection with Trichophyton schönleinii].
2004 Oct
Pharmacotherapy of onychomycosis.
2005 Apr
Treatment and prophylaxis of seborrheic dermatitis of the scalp with antipityrosporal 1% ciclopirox shampoo.
2005 Jan
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
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Trichophyton rubrum isolated from aids and human immunodeficiency virus-infected patients in São Paulo, Brazil: antifungal susceptibility and extracellular enzyme production.
2005 Mar
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 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
Related Record Type Details
CONSTITUENT ALWAYS PRESENT -> PARENT
ASSAY (TITRATION)
EP
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
USP
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
IMPURITY -> PARENT
at 220 nm
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY