Ciclopirox olamine is a chemical compound derived from hydroxypyridone, the olamine salt form of cyclopirox, a synthetically produced antifungal agent.

What it is used for and where

Medical

Topical antifungal agent licensed by the FDA in 2004, used in formulations for the treatment of cutaneous fungal infections and included in gels, creams and shampoos. It is involved in protecting against ferritin degradation and ferroptosis (1) and can also inhibit intracellular iron-dependent enzymes such as ribonucleotide reductase and components of hypoxia signalling (2). In addition, it has been shown that its olamine salt can reach the urinary tract and influence fluid secretion by inhibiting the progression of renal cell cysts (3).

Primary applications of Ciclopirox olamine include the topical formulation of nail varnish for the treatment of onychomycosis. 

It is effective against clinically relevant yeasts and moulds, including some azole-resistant Candida species, such as Candida krusei, Candida glabrata, against many gram-negative (Proteus spp. and Pseudomonas aeruginosa) and gram-positive (Streptococci, Micrococci, Staphylococcus spp.) bacteria.

It has activity against Gardnerella vaginalis and Trichomonas vaginalis for multiple vaginal infections and also against symptomatic intertriginous fungal diseases secondarily infected by bacteria.

Use (4):

• for dermatophyte and yeast infections 1%
• for seborrhoeic dermatitis 1% - 1.5%.
• for seborrhoeic dermatitis 8%

Ciclopirox olamine has also been shown to have some anti-inflammatory activity.

For further information on the subject:

Ciclopirox olamine studies

Appearance	Powder
Boiling Point	350ºC at 760 mmHg
Melting Point	144ºC
Flash Point	165.5°C
PSA	88.48000
LogP	2.07940
Safety

• Molecular Formula  C₁₄H₂₄N₂O₃        C₁₂H₁₇NO₂ · C₂H₇NO
• Molecular Weight     268.35
• Exact Mass    268.178680
• CAS  41621-49-2
• UNII    50MD4SB4AP
• EC Number   255-464-9
• DSSTox Substance ID  DTXSID6045583
• IUPAC  2-aminoethanol;6-cyclohexyl-1-hydroxy-4-methylpyridin-2-one
• 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
• InChl Key   MBRHNTMUYWQHMR-UHFFFAOYSA-N
• SMILES   CC1=CC(=O)N(C(=C1)C2CCCCC2)O.C(CO)N
• MDL number  MFCD00078997
• PubChem Substance ID    RXCUI
• RXCUI   52172 
• NSC   756694    336278
• RTECS   UU7785500
• NACRES  NA.24 
• NCI   C65327

Synonyms

• 2-aminoethanol;6-cyclohexyl-1-hydroxy-4-methylpyridin-2-one
• Ciclopiroxolamine
• Ciclopirox ethanolamine
• 6-Cyclohexyl-1-hydroxy-4-methylpyridin-2(1H)-one compound with 2-aminoethanol
• 6-Cyclohexyl-1-hydroxy-4-methylpyridin-2(1H)-one compound with 2-aminoethanol
• 6-Cyclohexyl-1-hydroxy-4-methylpyridin-2(1H)-on--2-aminoethanol(1:1)
• 2(1H)-Pyridinone, 6-cyclohexyl-1-hydroxy-4-methyl-, compd. with 2-aminoethanol (1:1)

References________________________________________________________________________

(1) Hayano M, Yang WS, Corn CK, Pagano NC, Stockwell BR. Loss of cysteinyl-tRNA synthetase (CARS) induces the transsulfuration pathway and inhibits ferroptosis induced by cystine deprivation. Cell Death Differ. 2016 Feb;23(2):270-8. doi: 10.1038/cdd.2015.93.

(2) Song S, Christova T, Perusini S, Alizadeh S, Bao RY, Miller BW, Hurren R, Jitkova Y, Gronda M, Isaac M, Joseph B, Subramaniam R, Aman A, Chau A, Hogge DE, Weir SJ, Kasper J, Schimmer AD, Al-awar R, Wrana JL, Attisano L. Wnt inhibitor screen reveals iron dependence of β-catenin signaling in cancers. Cancer Res. 2011 Dec 15;71(24):7628-39. doi: 10.1158/0008-5472.CAN-11-2745.

(3) Radadiya PS, Thornton MM, Puri RV, Yerrathota S, Dinh-Phan J, Magenheimer B, Subramaniam D, Tran PV, Zhu H, Bolisetty S, Calvet JP, Wallace DP, Sharma M. Ciclopirox olamine induces ferritinophagy and reduces cyst burden in polycystic kidney disease. JCI Insight. 2021 Mar 30;6(8):e141299. doi: 10.1172/jci.insight.141299.