Ciclopirox
- CAS No.
- 29342-05-0
- Chemical Name:
- Ciclopirox
- Synonyms
- 6-Cyclohexyl-1-hydroxy-4-methylpyridin-2(1H)-one;Penlac;gopmx;geprox;Loprox;HOE296b;Mycoster;Brumixol;Dafnegin;Cidochem
- CBNumber:
- CB7673863
- Molecular Formula:
- C12H17NO2
- Molecular Weight:
- 207.27
- MDL Number:
- MFCD00599441
- MOL File:
- 29342-05-0.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| Melting point | 1440C |
|---|---|
| Boiling point | 350.0±25.0 °C(Predicted) |
| Density | 1.193±0.06 g/cm3(Predicted) |
| storage temp. | Keep in dark place,Sealed in dry,Room Temperature |
| solubility | Slightly soluble in water, freely soluble in anhydrous ethanol and in methylene chloride |
| pka | 6.25±0.58(Predicted) |
| form | Solid |
| color | Off-White |
| InChI | 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 |
| InChIKey | SCKYRAXSEDYPSA-UHFFFAOYSA-N |
| SMILES | C1(=O)N(O)C(C2CCCCC2)=CC(C)=C1 |
| CAS DataBase Reference | 29342-05-0(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | 19W019ZDRJ |
| ATC code | D01AE14,G01AX12 |
| UNSPSC Code | 41116107 |
| NACRES | NA.77 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H302+H312+H332-H319 | |||||||||
| Precautionary statements | P261-P280-P301+P312-P302+P352+P312-P304+P340+P312-P305+P351+P338 | |||||||||
| RIDADR | UN 3077 9 / PGIII | |||||||||
| WGK Germany | WGK 3 | |||||||||
| HS Code | 2933790002 | |||||||||
| Storage Class | 11 - Combustible Solids | |||||||||
| Hazard Classifications | Acute Tox. 4 Dermal Acute Tox. 4 Inhalation Acute Tox. 4 Oral Eye Irrit. 2 |
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| NFPA 704 |
|
Ciclopirox price More Price(82)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | SML2011 | Ciclopirox ≥98% (HPLC) | 29342-05-0 | 50MG | $71.5 | 2026-04-30 | Buy |
| Sigma-Aldrich | Y0000040 | Ciclopirox European Pharmacopoeia (EP) Reference Standard | 29342-05-0 | 75 mg | $167 | 2026-04-30 | Buy |
| Sigma-Aldrich | SML2011 | Ciclopirox ≥98% (HPLC) | 29342-05-0 | 100MG | $129 | 2026-04-30 | Buy |
| Sigma-Aldrich | PHR1920 | Ciclopirox Pharmaceutical Secondary Standard; Certified Reference Material | 29342-05-0 | 500mg | $263 | 2026-04-30 | Buy |
| Sigma-Aldrich | 1134018 | Ciclopirox | 29342-05-0 | 50mg | $420 | 2026-04-30 | Buy |
Ciclopirox Chemical Properties,Uses,Production
Topical antifungal
Ciclopirox is a novel broad-spectrum topical antifungal agent,it is successfully developed by pharmaceutical companies of the Federal Republic of Germany , the mechanism is by changing the integrity of the fungal cell membrane, causing intracellular material outflow, and blocking intake of protein precursors, resulting in fungal cell death, it has a strong bactericidal effect against dermatophytes, yeasts, molds, etc. And it has strong permeability . At higher concentrations,it can also have a certain extent inhibiting effect on a variety of actinomycetes, Gram-positive and Gram-negative bacteria and mycoplasma, chlamydia, trichomonas, Trichomonas vaginalis and Pseudomonas aeruginosa.
Compared with imidazole antifungal, ciclopirox has strong penetration ability in cuticle where skin fungus survive, so it has a significant inhibition effect on the cuticle deep fungi, such as onychomycosis.
Mainly it is used in clinical for superficial skin fungal infections, such as ringworm, athlete's foot, jock itch, tinea manus and pedis(especially keratosis thickening), tinea versicolor, skin candidiasis, Candida albicans and onychomycosis treatment.
The above information is edited by the chemicalbook of Tian Ye.
Chemical Properties
Solid, m.p. 144 ℃.
Ciclopirox Olamine: [41621-49-2]. White crystalline powder, odorless, bitter taste. Soluble in methanol, ethanol or chloroform, slightly soluble in dimethylformamide or water, slightly soluble in ether. Melting point 124-128 ℃. Acute toxicity LD50 in mice, rats (mg/kg): 2898,3290 orally.
Uses
Pyridine ketones broad-spectrum antifungal agents, have inhibiting effects on a variety of skin fungi . They can prevent the substances necessary for Candida albicans cells survival such as amino acids, potassium ions, phosphate,going through the cell membrane ,which can cause by certain important matrix or intracellular ions failure,and then inhibit or kill fungal cells. There are a wide range of anti-fungal effects, they can have a killing effect on the skin filamentous bacteria, yeast fungi , they have inhibition effects on a variety of Gram positive and negative bacteria, chlamydia, trichomoniasis, Proteus, E. coli, Pseudomonas and Staphylococcus bacteria. They are used to treat fungal skin disease, tinea versicolor, vulvovaginal Candida disease, skin and fingers (toe) candidiasis ,they have significant effects , and lower side effects.
production method
4-methyl-3-penten-2-one by oxidation of sodium hypochlorite (56% yield), is esterified to produce methyl-2-butenoate (the I), 67% yield, b.p. 135~139 ℃.
Cyclohexane carboxylic acid and thionyl chloride react to obtain cyclohexane carboxylic acid chloride. In the role of aluminum chloride,it reacts with methyl-2-butenoate (I) in a methylene chloride solvent, and the reaction is stirred for 4h, after post-treatment, vacuum collect 140-145 ℃ (0.4kPa) the distillate, 3-methyl-5-oxo-5-cyclohexyl-3-pentenoate (ciclopirox, II) is generated in 75% yield. And then it is stirred at room temperature for 20h together with hydroxylamine hydrochloride, sodium acetate, methanol and water , then it is added 50% sodium hydroxide , then it is stirred for 1h. After cooling with benzene extraction, the aqueous phase is acidified to Ph = 6. The precipitated crystals are recrystallized from ethanol, to give ciclopirox, m.p. 140~142 ℃, yield 48.3%. Finally,it is salified with the hydroxyl amine in methylene chloride to give almost quantitative ciclopirox, melting point 97~99 ℃.
Chemical Properties
White or Light-Yellow Powder
Originator
Fungirox Esmalte, UCI-Farma
Uses
Broad spectrum antimycotic agent with some antibacterial activity.
Uses
Ciclopirox (Penlac) is a synthetic antifungal agent. Ciclopirox (Penlac) is used for topical dermatologic treatment of superficial mycoses. Ciclopirox (Penlac) is most useful against Tinea versicolor. [1] In a study conducted to further elucidate ciclopir
Definition
ChEBI: A cyclic hydroxamic acid that is 1-hydroxypyridin-2(1H)-one in which the hydrogens at positions 4 and 6 are substituted by methyl and cyclohexyl groups, repectively. A broad spectrum antigfungal agent, it also exhibits antibacterial acti ity against many Gram-positive and Gram-negative bacteria, and has anti-inflammatory properties. It is used a a topical treatment of fungal skin and nail infections.
Indications
Ciclopirox penetrates rapidly into and through the skin and nail keratin. After dermal application ofa1% cream formulation, about 1.3 % of the dose is absorbed. Serum levels range around 10 μg/L after application of a dose of 37 mg of ciclopirox. After vaginal administration, 15 – 20 % of the dose is absorbed. Ciclopirox penetrates well into the skin and nail matrix. Absorbed ciclopirox is mainly eliminated by the kidneys; 1.1 – 1.7 % of the topical dose is eliminated in the urine within four days. Only a fraction thereof is unaltered ciclopirox. Approximately 96% of the absorbed drug is bound to human serum proteins.
Manufacturing Process
A mixture of 5-oxo-3-methyl-5-cyclohexylpentene-2 acid 1-methyl ester and
5-oxo-3-methyl-5-cyclohexylpentene-3 acid 1-methyl ester was obtained by
condensation of hexahydrobenzoyl chloride with β,β-dimethylacrylic acid
methyl ester. 11.2 g of this mixture and a solution of 4.6 g of sodium acetate
and 4 g of hydroxylamine hydrochloride were shaken for 20 hours at 25°C
with a mixture of 8 ml of water and 15 ml methanol. Subsequently, a solution
of 4 g of sodium hydroxide in 8 ml of water was then added, while cooling,
shaken for 1 hour at room temperature. The mixture was extracted by means
of benzene and the aqueous phase was acidified to reach a pH of 6. 3.5 g of
1-hydroxy-4-methyl-6-cyclohexyl-2-pyridone were obtained; melting point
144°C.
For preparation of cyclopirox from 1-hydroxy-4-methyl-6-cyclohexyl-2-
pyridone was added 2-aminoethanol (1:1).Merck Index, Monograph number: 2325, Twelfth edition, 1996, Editor: S.
Budavari; Merck and Co., Inc.
Greene L.A.; US Patent No. 5,846,984; Dec. 8, 1998; Assigned to The
Trustees of Columbia University in the City of New York (New York, NY)
Lohaus G. et al.; US Patent No. 3,883,545; May 13, 1975; Assigned to
Hoechst Aktiengesellschaft, Frankfurt am Main, Germany
brand name
Loprox(Medicis); Penlac (Sanofi Aventis).
Therapeutic Function
Antifungal
Antimicrobial activity
Ciclopirox has a broad in vitro antifungal activity spectrum, including dermatophytes, yeasts, and moulds. The most important fungi within the activity spectrum of ciclopirox. Ciclopirox is primarily fungistatic, but if the contact time is long enough and the concentration exceeds 20 μg/mL, it exerts a fungicidal effect on yeasts and dermatophytes. In vitro, the effect is limited to proliferating fungi and is greatly dependent on the nutrient medium.
Biological Activity
Ciclopirox is a chemical compound belonging to the class of hydroxypyridones. It is found active against dermatophytes, yeasts, molds, some bacterias and also azole-resistant Candida species. Unlike other antifungal agents th at act for ergosterol inhibition, ciclopirox has a different action. It targets metal-dependent enzymes, which degrades fungal cell peroxides. This unique action of ciclopirox provides less chance for resistance in pathogenic fungi. This compound is used in topical formulations specifically for nails and skin.', 'Ciclopirox is an antifungal and cell-permeable iron-chelating agent. It has been found to inhibit multiple enzymes and signaling pathways including prolyl hydroxylase 2 (PHD2), eukaryotic translation initiation factor 5A (eIF5A), Wnt/β-catenin, hypoxia-inducible factor-1α (HIF-1 α)/vascular endothelial growth factor (VEGF), vascular endothelial growth factor receptor 3 (VEGFR-3), mammalian target of rapamycin (mTOR), and cyclin dependent kinases (CDKs). Ciclopirox has been shown to have anti-viral and anticancer activity in addition to its antifungal activity. Ciclopirox has also been shown to counteract glucotoxicity in diabetic mice in a p21-dependent manner.
Mechanism of action
Ciclopirox is a substituted pyridione derivative. Experiments show that the mechanism of action involves a disruption of transport mechanisms into the cell plasma, especially the uptake of leucine. Further, the uptake of other amino acids such as phenylalanine and lysine, as well as the uptake of potassium and phosphate ions is impaired. This all probably involves a change in membrane permeability, as reported for some other antimycotics, although ciclopirox does not show lytic activity. Consecutively, the substance significantly reduces fungal growth rates.
Mechanism of action
Ciclopirox has a unique mechanism of action through chelation of polyvalent cations, such as Fe3+, which causes inhibition of a number of metal-dependent enzymes within the fungal cell.
Clinical Use
Ciclopirox is a hydroxylated pyridinone that is employed for superficial dermatophytic infections, principally onychomycosis.
Side effects
Topically applied, ciclopirox is well tolerated. The incidence of local irritations such as itching and burning sensations range between 1 and 4 % and are often due to the galenic formulation.
storage
Store at +4°C
References
[1] Patent: US2015/111858, 2015, A1. Location in patent: Paragraph 0062
[2] Patent: WO2016/77346, 2016, A1. Location in patent: Paragraph 094
Ciclopirox Preparation Products And Raw materials
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Sichuan Hainuowei Technology Co. Ltd. | 13708085536 13708085536 | hanovichem@163.com | China | 3268 | 56 |
| Hubei wei shi reagent group ltd., company | 027-59102966 18717199209 | 2853877583@QQ.com | China | 7306 | 58 |
| J & K SCIENTIFIC LTD. | 18210857532 18210857532 | jkinfo@jkchemical.com | China | 96815 | 76 |
| INTATRADE GmbH | +49 3493/605464 | sales@intatrade.de | Germany | 3563 | 66 |
| TAIYUAN RHF CO.,LTD. | +86 351 7031519 | sales@RHFChem.com | China | 2334 | 56 |
| Beijing HwrkChemical Technology Co., Ltd | 89508211 18501085097 | sales.bj@hwrkchemical.com | China | 9407 | 55 |
| Shijiazhuang Sdyano Fine Chemical Co., Ltd. | 0311-89250318 13582355795 | master@sjzsdyn.com | China | 2776 | 65 |
| Beijing Ouhe Technology Co., Ltd | 13552068683 13522913783 | 2355560935@qq.com | China | 11777 | 60 |
| Jia Xing Isenchem Co.,Ltd | 0573-85285100 18627885956 | isenchem@163.com | China | 9389 | 66 |
| Pure Chemistry Scientific Inc. | 001-857-928-2050 or 1-888-588-9418 | sales@chemreagents.com | United States | 10174 | 62 |
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- Mar 31,2022
View Lastest Price from Ciclopirox manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2026-09-12 | Ciclopirox
29342-05-0
|
0.99 | RongNa Biotechnology Co.,Ltd | ||||
 |
2026-09-11 | Ciclopirox
29342-05-0
|
1KG | 98%min | 30tons/month | WUHAN FORTUNA CHEMICAL CO., LTD | ||
 |
2026-08-20 | Ciclopirox USP/EP/BP
29342-05-0
|
$1.10 | 1g | 99.9% | 100 Tons Min | Dideu Industries Group Limited |
-
- Ciclopirox
29342-05-0
- 0.99
- RongNa Biotechnology Co.,Ltd
-
- Ciclopirox
29342-05-0
- $0.00
- 98%min
- WUHAN FORTUNA CHEMICAL CO., LTD
-
- Ciclopirox USP/EP/BP
29342-05-0
- $1.10
- 99.9%
- Dideu Industries Group Limited
