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MedKoo Cat#: 317524 | Name: Ciclopirox
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Description:

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

Ciclopirox is a broad spectrum antimycotic agent with some antibacterial activity. Ciclopirox is a synthetic antifungal agent for topical dermatologic treatment of superficial mycoses. It is most useful against Tinea versicolor.

Chemical Structure

Ciclopirox
Ciclopirox
CAS#29342-05-0 (free)

Theoretical Analysis

MedKoo Cat#: 317524

Name: Ciclopirox

CAS#: 29342-05-0 (free)

Chemical Formula: C12H17NO2

Exact Mass: 207.1259

Molecular Weight: 207.27

Elemental Analysis: C, 69.54; H, 8.27; N, 6.76; O, 15.44

Price and Availability

Size Price Availability Quantity
1g USD 250.00 2 weeks
5g USD 550.00 2 weeks
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Related CAS #
29342-05-0 (free) 41621-49-2 (olamine)
Synonym
Ciclopirox; Loprox; Penlac; Batrafen; Ciclopiroxum; HOE 296b; HOE-296b; HOE296b;
IUPAC/Chemical Name
6-cyclohexyl-1-hydroxy-4-methylpyridin-2-one
InChi Key
SCKYRAXSEDYPSA-UHFFFAOYSA-N
InChi Code
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
SMILES Code
CC1=CC(=O)N(C(=C1)C2CCCCC2)O
Appearance
White to off-white solid powder.
Purity
>95% (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, not in water
Shelf Life
>2 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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 207.27 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.

Recalculate based on batch purity %
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
1: Täuber A, Müller-Goymann CC. In vitro model of infected stratum corneum for the efficacy evaluation of poloxamer 407-based formulations of ciclopirox olamine against Trichophyton rubrum as well as differential scanning calorimetry and stability studies. Int J Pharm. 2015 Oct 15;494(1):304-11. doi: 10.1016/j.ijpharm.2015.08.023. Epub 2015 Aug 11. PubMed PMID: 26276254. 2: Täuber A, Müller-Goymann CC. In vitro permeation and penetration of ciclopirox olamine from poloxamer 407-based formulations--comparison of isolated human stratum corneum, bovine hoof plates and keratin films. Int J Pharm. 2015 Jul 15;489(1-2):73-82. doi: 10.1016/j.ijpharm.2015.04.043. Epub 2015 Apr 17. PubMed PMID: 25895717. 3: Gómez-Moyano E, Hiraldo Gamero A, Vera Casaño Á, Crespo Erchiga V, González Enseñat MA, Vicente Villa MA, Zsolt Fradera I, Moreno Giménez JC. [Phase III study of the efficacy and safety of ciclopirox olamine cream in small children with dermatomycosis]. Rev Iberoam Micol. 2015 Jul-Sep;32(3):164-9. doi: 10.1016/j.riam.2014.04.002. Epub 2014 Oct 27. Spanish. PubMed PMID: 25728876. 4: Kim KS, Kim T, Pan JG. In vitro evaluation of ciclopirox as an adjuvant for polymyxin B against gram-negative bacteria. J Antibiot (Tokyo). 2015 Jun;68(6):395-8. doi: 10.1038/ja.2014.164. Epub 2015 Jan 14. PubMed PMID: 25586022. 5: Pinheiro VA, Serikaku D, Baby AR, Velasco MV, Kaneko TM, Consiglieri VO. Development of ciclopirox olamine topical formulations: evaluation of drug release, penetration and cutaneous retention. Pharm Dev Technol. 2015 Mar;20(2):197-203. doi: 10.3109/10837450.2013.860544. Epub 2013 Nov 29. PubMed PMID: 24286179. 6: Tabara K, Szewczyk AE, Bienias W, Wojciechowska A, Pastuszka M, Oszukowska M, Kaszuba A. Amorolfine vs. ciclopirox - lacquers for the treatment of onychomycosis. Postepy Dermatol Alergol. 2015 Feb;32(1):40-5. doi: 10.5114/pdia.2014.40968. Epub 2015 Feb 3. Review. PubMed PMID: 25821426; PubMed Central PMCID: PMC4360009. 7: Zhou H, Shen T, Shang C, Luo Y, Liu L, Yan J, Li Y, Huang S. Ciclopirox induces autophagy through reactive oxygen species-mediated activation of JNK signaling pathway. Oncotarget. 2014 Oct 30;5(20):10140-50. PubMed PMID: 25294812; PubMed Central PMCID: PMC4259411. 8: Täuber A, Müller-Goymann CC. Comparison of the antifungal efficacy of terbinafine hydrochloride and ciclopirox olamine containing formulations against the dermatophyte Trichophyton rubrum in an infected nail plate model. Mol Pharm. 2014 Jul 7;11(7):1991-6. doi: 10.1021/mp400711q. Epub 2014 Feb 12. PubMed PMID: 24490976. 9: Hafeez F, Hui X, Selner M, Rosenthal B, Maibach H. Ciclopirox delivery into the human nail plate using novel lipid diffusion enhancers. Drug Dev Ind Pharm. 2014 Jun;40(6):838-44. doi: 10.3109/03639045.2013.788016. Epub 2013 Apr 19. PubMed PMID: 23600655. 10: Minden MD, Hogge DE, Weir SJ, Kasper J, Webster DA, Patton L, Jitkova Y, Hurren R, Gronda M, Goard CA, Rajewski LG, Haslam JL, Heppert KE, Schorno K, Chang H, Brandwein JM, Gupta V, Schuh AC, Trudel S, Yee KW, Reed GA, Schimmer AD. Oral ciclopirox olamine displays biological activity in a phase I study in patients with advanced hematologic malignancies. Am J Hematol. 2014 Apr;89(4):363-8. doi: 10.1002/ajh.23640. Epub 2014 Mar 3. PubMed PMID: 24273151. 11: Monti D, Tampucci S, Chetoni P, Burgalassi S, Mailland F. Ciclopirox vs amorolfine: in vitro penetration into and permeation through human healthy nails of commercial nail lacquers. J Drugs Dermatol. 2014 Feb;13(2):143-7. PubMed PMID: 24509963. 12: Lim SH, Kim C, Aref AR, Kamm RD, Raghunath M. Complementary effects of ciclopirox olamine, a prolyl hydroxylase inhibitor and sphingosine 1-phosphate on fibroblasts and endothelial cells in driving capillary sprouting. Integr Biol (Camb). 2013 Dec;5(12):1474-84. doi: 10.1039/c3ib40082d. PubMed PMID: 24190477. 13: Nair AB, Singh K, Al-Dhubiab BE, Attimarad M, Harsha S, Alhaider IA. Skin uptake and clearance of ciclopirox following topical application. Biopharm Drug Dispos. 2013 Dec;34(9):540-9. doi: 10.1002/bdd.1866. PubMed PMID: 24123146. 14: [Ciclopirox (Mycosten), topically]. J Pharm Belg. 2013 Sep;(3):47-8. French. PubMed PMID: 24804412. 15: Sen S, Hassane DC, Corbett C, Becker MW, Jordan CT, Guzman ML. Novel mTOR inhibitory activity of ciclopirox enhances parthenolide antileukemia activity. Exp Hematol. 2013 Sep;41(9):799-807.e4. doi: 10.1016/j.exphem.2013.04.012. Epub 2013 May 6. PubMed PMID: 23660068; PubMed Central PMCID: PMC3809917. 16: Carlson-Banning KM, Chou A, Liu Z, Hamill RJ, Song Y, Zechiedrich L. Toward repurposing ciclopirox as an antibiotic against drug-resistant Acinetobacter baumannii, Escherichia coli, and Klebsiella pneumoniae. PLoS One. 2013 Jul 23;8(7):e69646. doi: 10.1371/journal.pone.0069646. Print 2013. PubMed PMID: 23936064; PubMed Central PMCID: PMC3720592. 17: Nogueiras-Nieto L, Begoña Delgado-Charro M, Otero-Espinar FJ. Thermogelling hydrogels of cyclodextrin/poloxamer polypseudorotaxanes as aqueous-based nail lacquers: application to the delivery of triamcinolone acetonide and ciclopirox olamine. Eur J Pharm Biopharm. 2013 Apr;83(3):370-7. doi: 10.1016/j.ejpb.2012.11.004. Epub 2012 Nov 29. PubMed PMID: 23201053. 18: Cursi ÍB, Silva RT, Succi IB, Bernardes-Engemann AR, Orofino-Costa R. Onychomycosis due to Neoscytalidium treated with oral terbinafine, ciclopirox nail lacquer and nail abrasion: a pilot study of 25 patients. Mycopathologia. 2013 Feb;175(1-2):75-82. doi: 10.1007/s11046-012-9580-5. Epub 2012 Sep 14. PubMed PMID: 22976905. 19: Monti D, Herranz U, Dal Bo L, Subissi A. Nail penetration and predicted mycological efficacy of an innovative hydrosoluble ciclopirox nail lacquer vs. a standard amorolfine lacquer in healthy subjects. J Eur Acad Dermatol Venereol. 2013 Feb;27(2):e153-8. doi: 10.1111/j.1468-3083.2012.04529.x. Epub 2012 Mar 26. PubMed PMID: 22449201. 20: Morales-Molina JA, Pérez-Moyano R, Fayet-Pérez A, Urquízar-Rodríguez O, Gíménez-López MJ. Interaction between ciclopirox and acenocoumarol. Eur J Clin Pharmacol. 2013 Mar;69(3):727-8. doi: 10.1007/s00228-012-1347-x. Epub 2012 Jul 12. PubMed PMID: 22791274.