Climbazole is a chemical compound used as an antifungal agent in cosmetic formulations and hair care products.
Chemical Industrial Synthesis Process
- Preparation of Reagents: The main reagents include imidazole derivatives and halogenated chemicals needed for the synthesis of Cimbazole.
- Synthesis of Intermediate: The synthesis of Cimbazole begins with the reaction of an imidazole derivative with a halogenating agent. This step creates a reactive intermediate necessary for subsequent synthesis steps.
- Reaction Cycle: The reactive intermediate is further processed in a series of chemical reactions that may include alkylation, acylation, and cyclization reactions. These steps gradually build the complex structure of Cimbazole.
- Purification: After synthesis, the crude product is purified to remove impurities and byproducts of the reaction. Purification techniques may include crystallization, chromatography, and vacuum distillation.
- Stabilization: Cimbazole is stabilized to ensure its stability during transportation and storage, maintaining its efficacy in product formulations.
- Quality Control: The purified Cimbazole undergoes rigorous quality testing to ensure it meets the required standards for purity, efficacy, and safety. These tests include chemical structure analysis, spectroscopy, and microbiological testing.
What it is used for and where
Climbazole is known for its effectiveness in eliminating dandruff and treating fungal infections of the scalp. It works by inhibiting the growth of pathogenic fungi and yeasts that can cause dandruff and other scalp conditions. It is a common ingredient in anti-dandruff shampoos, conditioners, and scalp treatments, providing relief and improving the overall health of the scalp. Climbazole helps maintain the balance of microbial flora, preventing the recurrence of dandruff and associated itching.
Cimbazole is an antifungal agent commonly used in cosmetic and pharmaceutical formulations to treat dandruff and other fungal infections of the skin.
Medical
- Antifungal Properties. Climbazole is effective in fighting fungi that cause skin infections such as ringworm and athlete's foot.
- Prevention of Infections. Used in cosmetic products such as creams and lotions to help prevent the reoccurrence of fungal infections, keeping skin clean and healthy.
- Scalp Treatment. Included in shampoos and scalp treatments to treat and prevent dandruff (1) and other fungal scalp conditions.
- Versatility of application. Can be incorporated into various skin and scalp care products, providing long-lasting benefits in combating fungus.
- Pharmaceuticals. Climbazole is widely used in pharmaceutical formulations to treat more severe and persistent fungal infections.
- Veterinary. Also used in veterinary products to treat fungal infections in animals (3).
Cosmetics
It is a restricted cosmetic ingredient as V/32 a Relevant Item in the Annexes of the European Cosmetics Regulation 1223/2009. Substance or ingredient reported: 1-(4-Chlorophenoxy)-1-(imidazol-1-yl)-3,3-dimethylbutan-2-one
Product Type, body parts: (a) Hair lotions (b) Face creams (c) Foot care products (d) Rinse-off shampoo
Maximum concentration in ready for use preparation: (a) 0,2 % (b) 0,2 % (c) 0,2 % (d) 0,5 %
Cosmetics - INCI Functions
- Anti-sebum. Controls and reduces emissions from the sebaceous glands, which are responsible for greasy, enlarged pores in the skin, where it occurs, particularly on the forehead, cheeks, nose and hair. Adjuvant in the treatment of acne.
- Antimicrobial agent. This ingredient is able to suppress or inhibit the growth and replication of a broad spectrum of microorganisms such as bacteria, fungi and viruses by making the stratum corneum temporarily bactericidal and fungicidal.
- Preservative. Any product containing organic, inorganic compounds, water, needs to be preserved from microbial contamination. Preservatives act against the development of harmful microorganisms and against oxidation of the product.
Molecular Formula C15H17ClN2O2
Molecular Weight 292.76 g/mol
CAS 38083-17-9
UNII 9N42CW7I54
EC Number 253-775-4
DTXSID6046555
Synonyms:
Climbazol
Baysan
Baypival
Crinipan AD
Bibliografia_____________________________________________________________________
(1) Pople JE, Moore AE, Talbot DC, Barrett KE, Jones DA, Lim FL. Climbazole increases expression of cornified envelope proteins in primary keratinocytes. Int J Cosmet Sci. 2014 Oct;36(5):419-26. doi: 10.1111/ics.12137.
(2) Filatov, V. A., Kulyak, O. Y., & Kalenikova, E. I. (2023). Chemical composition and antimicrobial potential of a plant-based substance for the treatment of seborrheic dermatitis. Pharmaceuticals, 16(3), 328.
Abstract. Seborrheic dermatitis (SD) is the most prevalent dermatological disease, occurring in up to 50% of newborns, children, and adults around the world. The antibacterial and antifungal resistance contributed to the search for new natural substances and the development of a novel substance based on Melaleuca alternifolia (M. alternifolia) leaf oil (TTO), 1,8-cineole (eucalyptol), and α-(-)-bisabolol. Thus, this work aimed to determine the chemical composition of the novel plant-based substance and to evaluate its antimicrobial activity against standard microorganisms involved in the pathogenesis of SD. Moreover, the chemical composition of the substance was analyzed by gas chromatography coupled with mass spectrometry (GC/MS). Staphylococcus epidermidis (S. epidermidis), Staphylococcus aureus (S. aureus), Micrococcus luteus (M. luteus), and Candida albicans (C. albicans) were used for antimicrobial and antifungal assays by means of the broth microdilution method to determine the minimal inhibitory concentration (MIC). Finally, the substance’s ability to inhibit Malassezia furfur (M. furfur) was evaluated. Eighteen compounds from different chemical groups were identified by GC/MS. The major biologically active compounds of the substance were terpinen-4-ol (20.88%), 1,8-cineole (22.28%), (-)-α-bisabolol (25.73%), and o-cymene (8.16%). The results showed that the substance has a synergistic antimicrobial and antifungal activity, while S. epidermidis and C. albicans strains were the most susceptible. Furthermore, the substance inhibited M. furfur, which is a main pathogen involved in the pathogenesis of SD and clinical manifestations. It can be concluded that the novel plant-based substance has a promising potential against M. furfur and scalp commensal bacteria and may be helpful for the development of new drugs for treatment of dandruff and SD.
(3) Moriello KA. In vitro efficacy of shampoos containing miconazole, ketoconazole, climbazole or accelerated hydrogen peroxide against Microsporum canis and Trichophyton species. J Feline Med Surg. 2017 Apr;19(4):370-374. doi: 10.1177/1098612X15626197.
Abstract. Objectives The objective was to evaluate the antifungal efficacy of shampoo formulations of ketoconazole, miconazole or climbazole and accelerated hydrogen peroxide wash/rinse against Microsporum canis and Trichophyton species spores. Methods Lime sulfur (1:16)-treated control, enilconazole (1:100)-treated control, accelerated hydrogen peroxide (AHP 7%) 1:20 and a 1:10 dilution of shampoo formulations of miconazole 2%, miconazole 2%/chlorhexidine gluconate 2-2.3%, ketoconazole 1%/chlorhexidine 2%, climbazole 0.5%/chlorhexidine 3% and sterile water-untreated control were tested in three experiments. In the first, a suspension of infective spores and hair/scale fragments was incubated with a 1:10, 1:5 and 1:1 dilution of spores to test solutions for 10 mins. In the second, toothbrushes containing infected cat hair in the bristles were soaked and agitated in test solutions for 10 mins, rinsed, dried and then fungal cultured (n = 12×). In the third, a 3 min contact time combined with an AHP rinse was tested (n = 10×). Good efficacy was defined as no growth. Results Water controls grew >300 colony-forming units/plate and all toothbrushes were culture-positive prior to testing. For the suspension tests, all test products showed good efficacy. Miconazole 2%, ketoconazole 1% and AHP showed good efficacy after a 10 min contact time. Good efficacy was achieved with a shorter contact time (3 mins) only if combined with an AHP rinse. Conclusions and relevance Lime sulfur and enilconazole continued to show good efficacy. In countries or situations where these products cannot be used, shampoos containing ketoconazole, miconazole or climbazole are alternative haircoat disinfectants, with a 10 min contact time or 3 mins if combined with an AHP rinse.
Climbazole 
Imidazole
