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

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	MOL RATIO 1 MOL RATIO (average)

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

Description

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	Chelating Agent 142
Iron 18	Chelating Agent 142

Conditions

Condition	Modality	Targets	Highest Phase	Product
Seborrheic dermatitis 15	Curative		Approved 8,429	LOPROX
Onychomycosis of fingernails and toenails due to Trichophyton rubrum 2	Curative		Approved 8,429	PENALC

C_max

Value	Dose	Co-administered	Analyte	Population
25.02 ng/mL	5 g single, topical		CICLOPIROX blood	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.7 h	9 mg single, topical		CICLOPIROX unknown	Homo sapiens

Doses

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Dose	Population	Adverse events
8 % 1 times / day multiple, topical Recommended	unhealthy n = 281	Disc. AE: Creatine phosphokinase increased...

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AEs

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AE	Significance	Dose	Population
Creatine phosphokinase increased	0.36% Disc. AE	8 % 1 times / day multiple, topical Recommended	unhealthy n = 281

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			binder 2 activator 14 inhibitor 1,612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
MATE1 306

Drug as perpetrator

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Target	Modality	Activity	Metabolite	Clinical evidence
MATE1 308	inhibitor 3,277	no [IC50 >500 uM]

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1,647	activator 14
hERG 1,647	binder 5
hERG 1,647	inhibitor 1,626

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Sourcing

Sourcing

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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

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PubMed

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Title	Date	PubMed
A method to measure the amount of drug penetrated across the nail plate.	2001 Oct	11697474
Homologous recombination induced by replication inhibition, is stimulated by expression of mutant p53.	2002 Jan 17	11821962
Evaluation of in vitro resistance in patients with onychomycosis who fail antifungal therapy.	2003	14657630
A randomized comparison of nail surface remanence of three nail lacquers, containing amorolfine 5%, ciclopirox 8% or tioconazole 28%, in healthy volunteers.	2004	15573688
Onychomycosis: review of recurrence rates, poor prognostic factors, and strategies to prevent disease recurrence.	2004 Jul	15287395

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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.