New Drug Approvals





Read all about Organic Spectroscopy on ORGANIC SPECTROSCOPY INTERNATIONAL 


Blog Stats

  • 4,303,278 hits

Enter your email address to follow this blog and receive notifications of new posts by email.

Join 2,821 other subscribers

add to any


  • Molecular FormulaC12H17NO2
  • Average mass207.269 Da

2(1H)-Pyridinone, 6-cyclohexyl-1-hydroxy-4-methyl-
KS-5085, циклопирокс , سيكلوبيروكس , 环吡酮 ,  
CAS Registry Number: 29342-05-0 
CAS Name: 6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridinone 
Molecular Formula: C12H17NO2 
Molecular Weight: 207.27 
Percent Composition: C 69.54%, H 8.27%, N 6.76%, O 15.44% 
Literature References: Broad spectrum antimycotic agent with some antibacterial activity. Prepn: G. Lohaus, W. Dittmar, ZA6906039eidem,US3883545 (1970, 1975 both to Hoechst). In vitro study: eidem,Arzneim.-Forsch.23, 670 (1973). Series of articles on pharmacokinetics, pharmacology, teratology, toxicity studies: Oyo Yakuri9, 57-115 (1975), C.A.83, 53159d, 53538b, 53539c, 71844c, 90833q (1975). Series of articles on chemistry, mechanism of action, toxicology, clinical trials: Arzneim.-Forsch.31, 1309-1386 (1981). Toxicity data: H. G. Alpermann, E. Schutz, ibid. 1328. Review: S. G. Jue et al.,Drugs29, 330-341 (1985). Review of clinical experience in seborrheic dermatitis: A. Starova, R. Aly, Expert Opin. Drug Saf.4, 235-239 (2005). 
Properties: Solid, mp 144°. 
Melting point: mp 144° 

Ciclopirox olamine (Ciclopirox ethanolamine) | Fungal Inhibitor | MedChemExpress

Derivative Type: Ethanolamine salt (1:1) 
CAS Registry Number: 41621-49-2 
Additional Names: Ciclopirox olamine 
Manufacturers’ Codes: HOE-296 
Trademarks: Batrafen (HMR); Brumixol (Bruschettini); Ciclochem (Novag); Dafnegin (Poli); Loprox (HMR); Micoxolamina (Domp?; Mycoster (Fabre) 
Molecular Formula: C14H24N2O3 
Molecular Weight: 268.35 
Percent Composition: C 62.66%, H 9.01%, N 10.44%, O 17.89% 
Properties: LD50 in mice, rats (mg/kg): 2898, 3290 orally (Alpermann, Schutz). 
Toxicity data: LD50 in mice, rats (mg/kg): 2898, 3290 orally (Alpermann, Schutz)

  • EINECS:255-464-9
  • LD50:71 mg/kg (M, i.v.); 1740 mg/kg (M, p.o.);
    72 mg/kg (R, i.v.); 2350 mg/kg (R, p.o.)

Therap-Cat: Antifungal. 
Keywords: Antifungal (Synthetic).


join me on Linkedin

Anthony Melvin Crasto Ph.D – India | LinkedIn

join me on Researchgate


This image has an empty alt attribute; its file name is research.jpg

join me on Facebook

Anthony Melvin Crasto Dr. | Facebook

join me on twitter

Anthony Melvin Crasto Dr. | twitter

+919321316780 call whatsaapp

EMAIL. amcrasto@amcrasto

Ciclopirox (sometimes known by the abbreviation CPX[2]) is a synthetic antifungal agent for topical dermatologic treatment of superficial mycoses. It is most useful against Tinea versicolor. It is sold under many brand names worldwide.[1]

Medical uses

Ciclopirox is indicated for the treatment of tinea pedis and tinea corporis due to Trichophyton rubrumTrichophyton mentagrophytes and Epidermophyton floccosum, as well as seborrheic dermatitis. It is not to be used in the eyes or vagina, and nursing women should consult their doctors before use, since it is not known whether ciclopirox passes into human milk. A burning sensation may be felt when first applying ciclopirox on the skin.[3]

Nail infections

In addition to other formulations, ciclopirox is used in lacquers for topical treatment of onychomycosis (fungal infections of the nails). A meta-analysis of the six trials of nail infections available in 2009 concluded that they provided evidence that topical ciclopirox had poor cure rates and that amorolfine might be substantially more effective, but more research was required.

“Combining data from 2 trials of ciclopiroxolamine versus placebo found treatments failure rates of 61% and 64% for ciclopiroxolamine. These outcomes followed long treatment times (48 weeks) and this makes ciclopiroxolamine a poor choice for nail infections. Better results were observed with the use of amorolfine lacquer; 6% treatment failure rates were found after 1 month of treatment but these data were collected on a very small sample of people and these high rates of success might be unreliable.”[4]



In contrast to the azoles and other antimycotic drugs, the mechanism of action of ciclopirox is poorly understood.[5] However, loss of function of certain catalase and peroxidase enzymes has been implicated as the mechanism of action, as well as various other components of cellular metabolism. In a study conducted to further elucidate ciclopirox’s mechanism, several Saccharomyces cerevisiae mutants were screened and tested. Results from interpretation of the effects of both the drug treatment and mutation suggested that ciclopirox may exert its effect by disrupting DNA repair, cell division signals and structures (mitotic spindles) as well as some elements of intracellular transport.[6]

It is currently being investigated as an alternative treatment to ketoconazole for seborrhoeic dermatitis as it suppresses growth of the yeast Malassezia furfur. Initial results show similar efficacy to ketoconazole with a relative increase in subjective symptom relief due to its inherent anti-inflammatory properties.[7]


Ciclopirox is a considered a hydroxypyrimidine (sic) antifungal agent.[citation needed] Structurally, ciclopirox is the N-oxide of a 2-hydroxypyridine derivative and therefore ought to be termed a hydroxypyridine antifungal agent. Additionally, the structure as drawn above is the lactam tautomer and indicates the molecule being an N-Hydroxy-2-pyridone. Hence the classification of ciclopirox as a 2-pyridone antifungal agent.

Ciclopirox is used clinically as ciclopirox olamine, the olamine salt of ciclopirox.

Lohaus; Dittmar Arzneimittel-Forschung/Drug Research, 1981 , vol. 31, # 8 a p. 1311 – 1316

Hoechst Aktiengesellschaft Patent: US3972888 A1, 1976 ;




W. Dittmar, E. Druckrey andBroad spectrum antimycotic agent with some antibacterial activity. Prepn: G. Lohaus, W. Dittmar, ZA 6906039; eidem, US 3883545 (1970, 1975 both to Hoechst). In vitro study: eidem, Arzneim.-Forsch. 23, 670 (1973).

H. Urbach, J. Med. Chem., 17, 753 (1974); W. Dittmar and G. Lohaus,

German Patent 2,214,608 (1973); Chem. Abstr., 79: 146419w (1973).

File:Ciclopirox synthesis.svg


ethanolamine (CAS NO.: ), with other names as 6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridinone 2-aminoethanol, could be produced through the following synthetic routes.

Preparation of Ciclopirox ethanolamine

Compound can be prepared in two different ways: 1) The reaction of methyl 5-oxo-5-cyclohexyl-3-methylpentenoate (I) with NH2OH gives the corresponding oxime (II), which is then cyclized to 6-cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridone (III). Finally, this compound is salified with ethanolamine (IV). 2) Compound (III) can also be obtained by reaction of 6-cyclohexyl-4-methyl-2-pyron (V) with hydroxylamine hydrochloride in hot 2-aminopyridine.


CAS-RNFormulaChemical NameCAS Index Name
14818-35-0C12H16O26-cyclohexyl-4-methyl-2-pyrone2H-Pyran-2-one, 6-cyclohexyl-4-methyl-
141-43-5C2H7NOethanolamineEthanol, 2-amino-


The molecule 6-cyclohexyl-1-hydroxy-4-methylpyridin-2(1H)-one, also known as Ciclopirox, is a commercially available antifungal agent as an olamine salt. Ciclopirox olamine has been used to treat superficial mycoses and Tinea versicolor following topical application to the skin. Following enteral administration, ciclopirox undergoes significant first-pass effect resulting in low oral bioavailability. The oral route of administration is also associated with gastrointestinal toxicities observed in animals and humans limiting its benefit in animal and human health applications. Ciclopirox olamine has poor solubility, limiting opportunities to deliver the antifungal agent via parenteral administration of suitably potent solutions and suspensions. As such, it would be beneficial to configure ciclopirox for improved water solubility in order to deliver the drug by parenteral routes of administration.


  1. Jump up to:a b International brand names for ciclopirox Page accessed January 201, 2016
  2. ^ Ciclopirox
  3. ^ “Ciclopirox Olamine Antifungal Shampoo”Okdermo. Retrieved 2019-08-06.
  4. ^ Crawford F (2007). “Topical treatments for fungal infections of the skin and nails of the foot”The Cochrane Database of Systematic Reviews2007 (3): CD001434. doi:10.1002/14651858.CD001434.pub2PMC 7073424PMID 17636672.
  5. ^ Niewerth M, Kunze D, Seibold M, Schaller M, Korting HC, Hube B (June 2003). “Ciclopirox Olamine Treatment Affects the Expression Pattern of Candida albicans Genes Encoding Virulence Factors, Iron Metabolism Proteins, and Drug Resistance Factors”Antimicrobial Agents and Chemotherapy47 (6): 1805–1817. doi:10.1128/AAC.47.6.1805-1817.2003PMC 155814PMID 12760852.
  6. ^ Leem SH, Park JE, Kim IS, Chae JY, Sugino A, Sunwoo Y (2003). “The possible mechanism of action of ciclopirox olamine in the yeast Saccharomyces cerevisiae”Mol. Cells15 (1): 55–61. PMID 12661761.
  7. ^ Ratnavel RC, Squire RA, Boorman GC (2007). “Clinical efficacies of shampoos containing ciclopirox olamine (1.5%) and ketoconazole (2.0%) in the treatment of seborrhoeic dermatitis”. J Dermatolog Treat18 (2): 88–96. doi:10.1080/16537150601092944PMID 17520465S2CID 34852507.
Clinical data
Trade namesMany brand names worldwide[1]
AHFS/Drugs.comMicromedex Detailed Consumer Information
Routes of
Topical (applied as a nail lacquer, skin cream or shampoo)
ATC codeD01AE14 (WHOG01AX12 (WHO)
Legal status
Legal statusUS: ℞-onlyRx-only (CA)
Pharmacokinetic data
Bioavailability<5% with prolonged use
Protein binding94 to 97%
Elimination half-life1.7 hours
showIUPAC name
CAS Number29342-05-0 
PubChem CID2749
CompTox Dashboard (EPA)DTXSID9048564 
ECHA InfoCard100.045.056 
Chemical and physical data
Molar mass207.269 g·mol−1
3D model (JSmol)Interactive image






Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

This site uses Akismet to reduce spam. Learn how your comment data is processed.


Follow New Drug Approvals on

Enter your email address to follow this blog and receive notifications of new posts by email.

Join 2,821 other subscribers


DR ANTHONY MELVIN CRASTO, Born in Mumbai in 1964 and graduated from Mumbai University, Completed his Ph.D from ICT, 1991,Matunga, Mumbai, India, in Organic Chemistry, The thesis topic was Synthesis of Novel Pyrethroid Analogues, Currently he is working with AFRICURE PHARMA, ROW2TECH, NIPER-G, Department of Pharmaceuticals, Ministry of Chemicals and Fertilizers, Govt. of India as ADVISOR, earlier assignment was with GLENMARK LIFE SCIENCES LTD, as CONSUlTANT, Retired from GLENMARK in Jan2022 Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 32 plus yrs, Prior to joining Glenmark, he has worked with major multinationals like Hoechst Marion Roussel, now Sanofi, Searle India Ltd, now RPG lifesciences, etc. He has worked with notable scientists like Dr K Nagarajan, Dr Ralph Stapel, Prof S Seshadri, etc, He did custom synthesis for major multinationals in his career like BASF, Novartis, Sanofi, etc., He has worked in Discovery, Natural products, Bulk drugs, Generics, Intermediates, Fine chemicals, Neutraceuticals, GMP, Scaleups, etc, he is now helping millions, has 9 million plus hits on Google on all Organic chemistry websites. His friends call him Open superstar worlddrugtracker. His New Drug Approvals, Green Chemistry International, All about drugs, Eurekamoments, Organic spectroscopy international, etc in organic chemistry are some most read blogs He has hands on experience in initiation and developing novel routes for drug molecules and implementation them on commercial scale over a 32 PLUS year tenure till date Feb 2023, Around 35 plus products in his career. He has good knowledge of IPM, GMP, Regulatory aspects, he has several International patents published worldwide . He has good proficiency in Technology transfer, Spectroscopy, Stereochemistry, Synthesis, Polymorphism etc., He suffered a paralytic stroke/ Acute Transverse mylitis in Dec 2007 and is 90 %Paralysed, He is bound to a wheelchair, this seems to have injected feul in him to help chemists all around the world, he is more active than before and is pushing boundaries, He has 100 million plus hits on Google, 2.5 lakh plus connections on all networking sites, 100 Lakh plus views on dozen plus blogs, 227 countries, 7 continents, He makes himself available to all, contact him on +91 9323115463, email, Twitter, @amcrasto , He lives and will die for his family, 90% paralysis cannot kill his soul., Notably he has 38 lakh plus views on New Drug Approvals Blog in 227 countries...... , He appreciates the help he gets from one and all, Friends, Family, Glenmark, Readers, Wellwishers, Doctors, Drug authorities, His Contacts, Physiotherapist, etc He has total of 32 International and Indian awards

Personal Links

View Full Profile →


Follow my blog with Bloglovin The title of your home page You could put your verification ID in a comment Or, in its own meta tag Or, as one of your keywords Your content is here. The verification ID will NOT be detected if you put it here.
%d bloggers like this: