29342-05-0 Usage
Uses
Used in Dermatology:
Ciclopirox is used as a broad-spectrum antifungal agent for the topical dermatologic treatment of superficial mycoses, particularly Tinea versicolor. It is effective against skin filamentous bacteria, yeast fungi, and has inhibitory effects on a variety of Gram-positive and negative bacteria, chlamydia, trichomoniasis, Proteus, E. coli, Pseudomonas, and Staphylococcus bacteria.
Used in Antifungal Treatments:
Ciclopirox is used as a broad-spectrum antimycotic agent with some antibacterial activity, treating fungal skin diseases such as tinea versicolor, vulvovaginal Candida disease, and skin and finger (toe) candidiasis. It has significant effects and lower side effects.
Used in Pharmaceutical Industry:
Ciclopirox is used in the pharmaceutical industry under the brand names Loprox (Medicis) and Penlac (Sanofi Aventis) for the treatment of fungal infections.
Chemical Properties:
Ciclopirox is a solid with a melting point of 144°C. Ciclopirox Olamine is a white crystalline powder, odorless, with a bitter taste. It is soluble in methanol, ethanol, or chloroform, slightly soluble in dimethylformamide or water, and slightly soluble in ether. The melting point of Ciclopirox Olamine is 124-128°C. The acute toxicity LD50 in mice and rats is 2898 and 3290 mg/kg orally, respectively.
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 lookchem of Tian Ye.
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 ℃.
Originator
Fungirox Esmalte, UCI-Farma
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
Therapeutic Function
Antifungal
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.
Check Digit Verification of cas no
The CAS Registry Mumber 29342-05-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,9,3,4 and 2 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 29342-05:
(7*2)+(6*9)+(5*3)+(4*4)+(3*2)+(2*0)+(1*5)=110
110 % 10 = 0
So 29342-05-0 is a valid CAS Registry Number.
InChI:InChI=1/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
29342-05-0Relevant articles and documents
Visible-Light-Induced C2 Alkylation of Pyridine N-Oxides
Zhang, Wen-Man,Dai, Jian-Jun,Xu, Jun,Xu, Hua-Jian
, p. 2059 - 2066 (2017/02/26)
A photoredox catalytic method has been developed for the direct C2 alkylation of pyridine N-oxides. This reaction is compatible with a range of synthetically relevant functional groups for providing efficient synthesis of a variety of C2-alkylated pyridine N-oxides under mild conditions. Mechanistic studies are consistent with the generation of a radical intermediate along the reaction pathway.
Synthesis method of ciclopirox olamine
-
Paragraph 0031; 0033; 0039; 0040-0042, (2017/12/29)
The invention discloses a synthesis method of ciclopirox olamine. The synthesis method includes following steps: (1), preparing dimethyl methacrylate; (2), preparing cyclohexane formyl chloride; (3), preparing 5-oxo-3-methyl-5-cyclohexyl-3-methyl pentenoate; (4), preparing 1-hydroxy-4-methyl-6-cyclohexyl-2(1H)-pyridone; (5), preparing 1-hydroxy-4-methyl-6-cyclohexyl-2(1H)-pyridone-2-amino-ethylate ciclopirox olamine. The synthesis method has the advantages of high yield, high product quality, low running cost, automatic running of equipment, high stability and easiness in meeting industrial needs.
METHODS OF BLADDER CANCER TREATMENT WITH CICLOPIROX, CICLOPIROX OLAMINE, OR A CICLOPIROX PRODRUG
-
Paragraph 094, (2016/06/06)
A method of treating bladder cancer is provided. The method of treating bladder cancer can include: providing a pharmaceutical composition having ciclopirox or ciclopirox olamine or a ciclopirox-POM prodrug having a structure of one of the formulae provided herein or derivative thereof or stereoisomer thereof or pharmaceutically acceptable salt thereof; and administering the pharmaceutical composition to a subject having the bladder cancer. The ciclopirox or ciclopirox olamine or a ciclopirox-POM prodrug can be administered in a therapeutically effective amount.
METHOD OF TREATMENT WITH PRODRUGS OF 6-CYCLOHEXYL-1-HYDROXY-4-METHYLPYRIDIN IN-2-1H-ONE AND DERIVATIVES THEREOF
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Paragraph 0062, (2015/04/28)
A prodrug can have a structure of Formula 10 or derivative thereof or stereoisomer thereof or pharmaceutically acceptable salt thereof. The prodrug can be included in a pharmaceutical composition for use in treatment of fungus, cancer, dermatitis, superficial mycoses; inflammation, tinea pedis, tinea cruris, and tinea corporis, Trichophyton rubrum, Trichophyton mentagrophytes, Epidermophyton floccosum, and Microsporum canis, candidiasis (moniliasis), Candida albicans, tinea (pityriasis) vesicolor, Malassezia furfur, acute myeloid leukemia, acute lymphoid leukemia, chronic myelogenous leukemia, lymphoma or multiple myeloma.
Protective solutions for organs
-
, (2008/06/13)
Described is a protective solution for avoiding ischemic, storage or ischemia/reperfusion to organs, or to isolated cell systems, or to tissue components after perfusion, surgery, transplantation, or cryopreservation and subsequent reperfusion, which contains alkali ions, and if need be also alkaline earth ions as the electrolyte, a buffer e.g. on a histidine derivation basis, as well as a polyol and/or a saccharide, has an osmolarity of about 290 mosm/l to about 350 mosm/l, as well as a pH value of about 6.8 to about 7.4, and to which hydroxamic acid, and/or one or more hydroxamic acid derivatives are added.
Antimycotic nail varnish
-
, (2008/06/13)
A nail varnish comprising a water-insoluble film-forming substance and an antimycotic compound which is a 1-hydroxy-2-pyridone I of the general formula STR1 in which R1 is a hydrocarbon group which contains from 6 to 9 carbon atoms, but is free from olefinic and acetylenic bonds, one of the groups R2 and R4 is hydrogen and the other is hydrogen, methyl or ethyl and R3 is alkyl having up to two carbon atoms, said antimycotic ingredient being present in free form or in the form of a salt.
The chemistry of antimicrobially active 1-hydroxy-2-pyridones
Lohaus,Dittmar
, p. 1311 - 1316 (2007/10/02)
The unsaturated δ-keto esters obtained by condensation of acid chlorides with esters of di- or trialkyl-acrylic acids can be cyclized with hydroxylamine to yield 1-hydroxy-2-pyridones. However, in many cases a two-steps synthesis may be of advantage in preparative respect, the ketoesters being cyclized to 2-pyrones, which then are reacted with hydroxylamine in the presence of certain bases to give. The hydroxy-pyridones show pronounced antifungal activity in vitro as well as in experimental guinea pig dermatophytosis.
Process for the manufacture of 1-hydroxy-2-pyridones
-
, (2008/06/13)
New 1-hydroxy-2-pyridones of the general formula SPC1 In which R1 is alkyl of 1 to 17 carbon atoms, cycloalkyl of 5 to 8 carbon atoms, cyclohexylalkyl or phenalkyl both having 1 to 3 carbon atoms in the alkylene chain or α-furyl, all of which may be substituted by halogen, and R2 to R4 are hydrogen or lower alkyl, or two adjacent substituents together form a trimethylene or tetramethylene chain, and in which R1 to R4 together contain at least 2 carbon atoms, are prepared by contacting unsaturated δ-keto esters or mixtures thereof with hydroxylamine and subjecting the products to cyclization.
Process for the preparation of 1-hydroxy-pyridones
-
, (2008/06/13)
Method for making 6-substituted-1-hydroxy-2-pyridones, which may also be substituted in one or more of the 3-, 4-, and 5-positions, by reaction of the corresponding 2-pyrone with hydroxylamine or its salts in the presence of imidazole or a 2-aminopyridine which may be mono- or di-methyl substituted.
