CICLOPIROX OLAMINE

PRODUCT IDENTIFICATION

CAS NO. 41621-49-2
29342-05-0 (free form)
CICLOPIROX OLAMINE
EINECS NO. 255-464-9
FORMULA C12H17NO2·C2H7NO
MOL WT. 268.35

TOXICITY

Oral Rat LD50: 2350mg/kg

H.S. CODE

2933.39.9100
SYNONYMS Ciclopirox olamine; Ciclopiroxolamin; Ciclopiroxolamine;
Micoxolamina; 6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridone 2-aminoethanol salt; 6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridone ethanolamine salt; Batrafen; Brumixol; Ciclopirox ethanolamine salt; Loprox; 6-Cyclohexyl-1-hydroxy-4-methylpyridin-2(1H)-one  compound with 2-aminoethanol;
SMILES c1(C2CCCCC2)n(O)c(cc(c1)C)=O.NCCO

CLASSIFICATION

Antifungal, Anti-Infective, 2-Pyridone

EXTRA NOTES

 

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE white to yellowish crystalline powder
MELTING POINT

143 C

BOILING POINT

 

SPECIFIC GRAVITY  
SOLUBILITY IN WATER Slightly soluble
SOLVENT SOLUBILITY Soluble in alcohol, Methylene chloride. Practically insoluble in Cyclohexane

pH

8.0 - 9.0

REFRACTIVE INDEX

 

NFPA RATINGS

Health hazard: 2, Fire: 0, Reactivity Hazard: 0

AUTOIGNITION

 

FLASH POINT

 

STABILITY Stable under normal conditions.

EXTERNAL LINKS & GENERAL DESCRIPTION

Wikipedia Linking

Google Scholar Search

Drug Information Portal (U.S. National Library of Medicine) - Ciclopirox olamine

PubChem Compound Summary - Ciclopirox olamine

Drug Bank -  Ciclopirox olamine

KEGG (Kyoto Encyclopedia of Genes and Genomes) -  Ciclopirox olamine

http://www.ebi.ac.uk/chebi/ -  Ciclopirox olamine

http://www.ncbi.nlm.nih.gov/ -  Ciclopirox

http://aac.asm.org/
The hydroxypyridone ciclopirox olamine belongs to the antimycotic drugs used for the treatment of superficial mycoses. In contrast to the azoles and other antimycotic drugs, its specific mode of action is only poorly understood. To investigate the mode of action of ciclopirox olamine on fungal viability, pathogenicity, and drug resistance, we examined the expression patterns of 47
Candida albicans genes in cells grown in the presence of a subinhibitory concentration (0.6 μg/ml) of ciclopirox olamine by reverse transcription-PCR. In addition, we used suppression-subtractive hybridization to further identify genes that are up-regulated in the presence of ciclopirox olamine. The expression of essential genes such as ACT1 was not significantly modified in cells exposed to ciclopirox olamine. Most putative and known virulence genes such as genes encoding secreted proteinases or lipases had no or only moderately reduced expression levels. In contrast, exposure of cells to ciclopirox olamine led to a distinct up- or down-regulation of genes encoding iron permeases or transporters (FTR1, FTR2, FTH1), a copper permease (CCC2), an iron reductase (CFL1), and a siderophore transporter (SIT1); these effects resembled those found under iron-limited conditions.

http://www.globalrph.com/
Ciclopirox is a broad-spectrum, antifungal agent that inhibits the growth of pathogenic dermatophytes, yeasts, and Malassezia furfur. Ciclopirox exhibits fungicidal activity in vitro against isolates of Trichophyton rubrum, Trichophyton mentagrophytes, Epidermophyton floccosum, Microsporum canis, and Candida albicans. Pharmacokinetic studies in men with tagged ciclopirox solution in polyethylene glycol 400 showed an average of 1.3% absorption of the dose when it was applied topically to 750 cm2 on the back followed by occlusion for 6 hours. The biological half-life was 1.7 hours and excretion occurred via the kidney. Two days after application only 0.01% of the dose applied could be found in the urine. Fecal excretion was negligible. Penetration studies in human cadaverous skin from the back, with ciclopirox cream 0.77% with tagged ciclopirox showed the presence of 0.8 to 1.6% of the dose in the stratum corneum 1.5 to 6 hours after application. The levels in the dermis were still 10 to 15 times above the minimum inhibitory concentrations.

SALES SPECIFICATION

APPEARANCE

white to yellowish crystalline powder

ASSAY

98.0% - 102.0%

LOSS ON DRYING

1.5%

RESIDUE ON IGNITION

0.1%

TRANSPORTATION
PACKING
 
HAZARD CLASS  
UN NO. Not regulated
SAFETY INFORMATION

HAZARD OVERVIEW

Irritant

GHS

 

SIGNAL WORD

Warning

PICTOGRAMS

HAZARD STATEMENTS

H303 May be harmful if swallowed.
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.

PRECAUTIONARY STATEMENTS

P261 Avoid breathing dust/fume/gas/mist/vapours/spray.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

EC DIRECTIVES

 

HAZARD CODES

Xi Irritant

RISK PHRASES

 36/37/38 Irritating to eyes, respiratory system and skin

SAFETY PHRASES

26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice

PRICE INFORMATION