Piroctone olamine | CAS#68890-66-4 | fungicide

MedKoo Cat#: 558578 | Name: Piroctone olamine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Piroctone olamine is an ethanolamine salt of the hydroxamic acid derivative piroctone used to treat fungal infections.

Chemical Structure

Piroctone olamine

CAS#68890-66-4 (olamine)

Theoretical Analysis

MedKoo Cat#: 558578

Name: Piroctone olamine

CAS#: 68890-66-4 (olamine)

Chemical Formula: C16H30N2O3

Exact Mass: 0.0000

Molecular Weight: 298.22

Elemental Analysis: C, 64.40; H, 10.13; N, 9.39; O, 16.08

Price and Availability

Size	Price	Availability
500mg	USD 150.00	Ready to ship
1g	USD 250.00	2 weeks
5g	USD 550.00	2 weeks
10g	USD 950.00	2 weeks

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Related CAS #

50650-76-5 (free base) 68890-66-4 (olamine)

Synonym

Piroctone olamine; Piroctone ethanolamine salt; Octopirox; Kopirox;

IUPAC/Chemical Name

(R)-1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)pyridin-2(1H)-one compound with 2-aminoethan-1-ol (1:1)

InChi Key

BTSZTGGZJQFALU-MERQFXBCSA-N

InChi Code

InChI=1S/C14H23NO2.C2H7NO/c1-10-6-12(15(17)13(16)8-10)7-11(2)9-14(3,4)5;3-1-2-4/h6,8,11,17H,7,9H2,1-5H3;4H,1-3H2/t11-;/m0./s1

SMILES Code

C(C[C@@H](C)Cc1n(c(cc(c1)C)=O)O)(C)(C)C.NCCO

Appearance

Solid powder

Purity

>97% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot# T8C10I09

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Antifungal.

In vitro activity:

With increasing piroctone olamine (PO) concentrations, the inhibition rates of collagen matrix degradation and the mineral loss were increased. Moreover, there was a positive statistical correlation between mineral loss and collagen matrix degradation, demonstrating that preservation of the collagen matrix would contribute to inhibiting acid demineralization. While the spectroscopic measurements indicated that PO possessed binding to these substances, PO exerted its inhibitory action primarily on the collagenolytic activity. Reference: Am J Dent. 2009 Apr;22(2):115-21. https://pubmed.ncbi.nlm.nih.gov/19626976/

In vivo activity:

The antifungal activity of piroctone olamine in the treatment of intra-abdominal candidiasis was evaluated in an experimental model using Swiss mice. The mice (n = 6) were infected by intraperitoneal injection of 0.2 ml of C. albicans (107cells/ml in saline). The animals were observed daily for clinical signs and mortality for 14 days. The treatment with piroctone olamine (0.5 mg/kg) was performed 72 h after infection by intraperitoneal administration. The mycological diagnosis was made by collecting the liver, spleen and kidneys. Data regarding the fungal growth and mortality were analyzed statistically by Student’s t test and analysis of variance (ANOVA), with level of significance set at P < 0.05. The difference in fungal growth scoring between the control group and the treatment group (piroctone olamine) was statistically significant (P < 0.05). Reference: Springerplus. 2016 Apr 16;5:468. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4833761/

	Solvent	mg/mL	mM
Solubility
	Water	50.0	167.66
	DMSO	11.1	37.25

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 298.22 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Fukuda Y, Nakashima S, Ujiie T. The in vitro effect of a collagenolytic enzyme inhibitor on lesion development in root dentin. Am J Dent. 2009 Apr;22(2):115-21. PMID: 19626976. 2. do Couto FM, do Nascimento SC, Júnior SF, da Silva VK, Leal AF, Neves RP. Antifungal activity of the piroctone olamine in experimental intra-abdominal candidiasis. Springerplus. 2016 Apr 16;5:468. doi: 10.1186/s40064-016-2130-8. PMID: 27119072; PMCID: PMC4833761.

In vitro protocol:

1. Fukuda Y, Nakashima S, Ujiie T. The in vitro effect of a collagenolytic enzyme inhibitor on lesion development in root dentin. Am J Dent. 2009 Apr;22(2):115-21. PMID: 19626976.

In vivo protocol:

1. do Couto FM, do Nascimento SC, Júnior SF, da Silva VK, Leal AF, Neves RP. Antifungal activity of the piroctone olamine in experimental intra-abdominal candidiasis. Springerplus. 2016 Apr 16;5:468. doi: 10.1186/s40064-016-2130-8. PMID: 27119072; PMCID: PMC4833761.

1: do Couto FM, do Nascimento SC, Júnior SF, da Silva VK, Leal AF, Neves RP. Antifungal activity of the piroctone olamine in experimental intra-abdominal candidiasis. Springerplus. 2016 Apr 16;5:468. doi: 10.1186/s40064-016-2130-8. eCollection 2016. PubMed PMID: 27119072; PubMed Central PMCID: PMC4833761. 2: Shakibaie M, Haghiri M, Jafari M, Amirpour-Rostami S, Ameri A, Forootanfar H, Mehrabani M. Preparation and evaluation of the effect of Fe3 O4 @piroctone olamine magnetic nanoparticles on matrix metalloproteinase-2: a preliminary in vitro study. Biotechnol Appl Biochem. 2014 Nov-Dec;61(6):676-82. doi: 10.1002/bab.1231. PubMed PMID: 24716879. 3: Schmidt-Rose T, Braren S, Fölster H, Hillemann T, Oltrogge B, Philipp P, Weets G, Fey S. Efficacy of a piroctone olamine/climbazol shampoo in comparison with a zinc pyrithione shampoo in subjects with moderate to severe dandruff. Int J Cosmet Sci. 2011 Jun;33(3):276-82. doi: 10.1111/j.1468-2494.2010.00623.x. Epub 2011 Jan 27. PubMed PMID: 21272039. 4: Kim Y, Alpmann P, Blaum-Feder S, Krämer S, Endo T, Lu D, Carson D, Schmidt-Wolf IG. Increased in vivo efficacy of lenalidomide by addition of piroctone olamine. In Vivo. 2011 Jan-Feb;25(1):99-103. PubMed PMID: 21282741. 5: Allgood GS, Miller JM, Schardein JL. The effect of piroctone olamine on reproduction of male and female rats. Fundam Appl Toxicol. 1991 Jan;16(1):31-40. PubMed PMID: 2019350. 6: Coiffard C, Coiffard L, de Roeck-Holtzhauer Y. [Comparison of the thermostability of natural (sulfoprolamine and sodium usnate) and synthetic (climbazole and piroctone olamine) antidandruff agents]. Ann Pharm Fr. 1999 Sep;57(5):392-6. French. PubMed PMID: 10520510. 7: Dubini F, Bellotti MG, Frangi A, Monti D, Saccomani L. In vitro antimycotic activity and nail permeation models of a piroctone olamine (octopirox) containing transungual water soluble technology. Arzneimittelforschung. 2005;55(8):478-83. PubMed PMID: 16149717. 8: Youn HJ, Kim SY, Park M, Jung WH, Lee YW, Choe YB, Ahn KJ. Efficacy and Safety of Cream Containing Climbazole/Piroctone Olamine for Facial Seborrheic Dermatitis: A Single-Center, Open-Label Split-Face Clinical Study. Ann Dermatol. 2016 Dec;28(6):733-739. Epub 2016 Nov 23. PubMed PMID: 27904273; PubMed Central PMCID: PMC5125955. 9: Nolen GA, Baines D, Poynter JI, Weaver JE, Slough CL. The effects of dietary iron supplementation on the toxicity of piroctone olamine in the growing rat. Drug Chem Toxicol. 1989 Jun;12(2):111-21. PubMed PMID: 2598828. 10: Piérard-Franchimont C, Goffin V, Henry F, Uhoda I, Braham C, Piérard GE. Nudging hair shedding by antidandruff shampoos. A comparison of 1% ketoconazole, 1% piroctone olamine and 1% zinc pyrithione formulations. Int J Cosmet Sci. 2002 Oct;24(5):249-56. doi: 10.1046/j.1467-2494.2002.00145.x. PubMed PMID: 18498517. 11: Lodén M, Wessman C. The antidandruff efficacy of a shampoo containing piroctone olamine and salicylic acid in comparison to that of a zinc pyrithione shampoo. Int J Cosmet Sci. 2000 Aug;22(4):285-9. doi: 10.1046/j.1467-2494.2000.00024.x. PubMed PMID: 18503415. 12: Reygagne P, Piérard GE, Loussouarn G, Le Nôtre N, Ziane S. [How I treat … dandruff using a shampoo with a sulfate-free tensio-active]. Rev Med Liege. 2016 Sep;71(9):365-370. French. PubMed PMID: 28383830. 13: Bartalini P, Bilenchi R, Dina F. [Anti-pityriasis activity of a line of products containing piroctone olamine]. G Ital Dermatol Venereol. 1987 Mar;122(3):XI-XIX. Italian. PubMed PMID: 3596640. 14: Wall I, Schmidt-Wolf IG. Effect of Wnt inhibitors in pancreatic cancer. Anticancer Res. 2014 Oct;34(10):5375-80. PubMed PMID: 25275031. 15: VON Schulz-Hausmann SA, Schmeel LC, Schmeel FC, Schmidt-Wolf IG. Targeting the Wnt/beta-catenin pathway in renal cell carcinoma. Anticancer Res. 2014 Aug;34(8):4101-8. PubMed PMID: 25075035. 16: Koller CM, Kim Y, Schmidt-Wolf IG. Targeting renal cancer with a combination of WNT inhibitors and a bi-functional peptide. Anticancer Res. 2013 Jun;33(6):2435-40. PubMed PMID: 23749892. 17: Piérard-Franchimont C, Uhoda E, Loussouarn G, Saint-Léger D, Piérard GE. Effect of residence time on the efficacy of antidandruff shampoos. Int J Cosmet Sci. 2003 Dec;25(6):267-71. doi: 10.1111/j.1467-2494.2003.00195.x. PubMed PMID: 18494909. 18: Foti C, Bonamonte D, Cassano N, Conserva A, Vena GA. Allergic contact dermatitis to propyl gallate and pentylene glycol in an emollient cream. Australas J Dermatol. 2010 May;51(2):147-8. doi: 10.1111/j.1440-0960.2009.00618.x. PubMed PMID: 20546226. 19: Sigle HC, Schäfer-Korting M, Korting HC, Hube B, Niewerth M. In vitro investigations on the mode of action of the hydroxypyridone antimycotics rilopirox and piroctone on Candida albicans. Mycoses. 2006 May;49(3):159-68. PubMed PMID: 16681805. 20: Gianni C. Treatment and prevention of paronychia using a new combination of topicals: report of 30 cases. G Ital Dermatol Venereol. 2015 Aug;150(4):357-62. Epub 2015 Apr 9. PubMed PMID: 25854670.