Climbazole

• CAS: 38083-17-9
• Catalog Number: ACM38083179
• Category: Main Products
• Molecular Weight: 292.76
• Molecular Formula: C15H17ClN2O2
• Description: Climbazole is a topical antifungal agent commonly used in the treatment of human fungal skin infections such as dandruff and eczema. Climbazole has shown a high in vitro and in vivo efficacy against Pityrosporum ovale that appears to play an important role in the pathogenesis of dandruff. Its chemical structure and properties are similar to other fungicides such as ketoconazole and miconazole.
• Synonyms: Crinipan AD;1-(4-chlorophenoxy)-3,3-dimethyl-1-(imidazol-1-yl)-butan-2-one;CLIMBAZOL;1-(4-chloro-phenoxy)-1-imidazol-1-yl-3,3-dimethyl-butan-2-one;1-(4-Chlorophenoxy)-1-(imidazol-1-yl)-3,3-dimethyl-2-butanone
• Melting Point: 96-100ºC
• Flash Point: 224.4ºC
• Density: 1.17 g/cmH3
• Appearance: Off-white to pale yellow crystalline powder
• Hazard Codes: Xn
• HS Code: 2933290012
• LogP: 3.72930
• PSA: 44.12
• Refractive Index: 1.56
• RIDADR: UN 3077

Case Study

Climbazole Induces Oxidative Stress and Apoptosis in Fish Gut via CYP450-Mediated Pathways

Lu Z-J, et al. Science of The Total Environment, 2024, 923, 171475.

Climbazole (CBZ) has been identified as a potent inducer of oxidative stress, inflammation, and apoptosis in aquatic organisms. Experimental exposure of grass carp (Ctenopharyngodon idella) to CBZ (0.2-20 μg/L) for 42 days revealed significant intestinal toxicity, characterized by excessive reactive oxygen species (ROS) generation due to CYP450 imbalance. CBZ exposure suppressed the antioxidant defense system by inhibiting Nrf2 and Keap1 pathways, leading to increased oxidative stress. Concurrently, activation of NF-κB signaling elevated pro-inflammatory cytokine levels (TNF-α, IL-1β/6/8), exacerbating inflammation. Apoptotic markers, including caspase-3, FADD, and BAD1, were upregulated, while anti-apoptotic genes (BCL-2, BCL-XL) were downregulated, confirming CBZ-induced programmed cell death. Molecular docking studies further demonstrated CBZ's stable binding to CYP1A, implicating its direct role in CYP450-mediated oxidative stress. These findings provide critical insights into CBZ's environmental impact and mechanistic toxicity, underscoring the need for its risk assessment in aquatic ecosystems.

Climbazole as a Tool for Investigating Androgenic Pathway Disruption in Mammalian Cells

Ndiaye D, et al. Toxicology in Vitro, 2024, 99, 105854.

Climbazole (CBZ) has emerged as a valuable experimental tool for studying endocrine disruption, particularly its effects on steroidogenesis and androgenic pathways in mammalian cells. Utilizing OECD test guidelines, researchers have demonstrated that CBZ effectively inhibits testosterone and estradiol production in H295R cells at concentrations as low as 0.3 μM. This suppression is associated with decreased levels of 17α-hydroxypregnenolone and 17α-hydroxyprogesterone, implicating the inhibition of cytochrome P450 17α-hydroxylase/17,20-lyase (Cyp17A1) activity. Additionally, CBZ functions as an androgen receptor (AR) antagonist in AR-EcoScreen cells and exerts estrogen receptor α (ERα) antagonism in HeLa9903 cells. These properties position CBZ as a useful compound for probing the molecular mechanisms of endocrine disruption, facilitating the study of steroidogenic enzyme regulation and receptor-mediated hormonal pathways in toxicological and pharmacological research.

Climbazole as an Antimycotic Agent: Human Urinary Excretion Kinetics and Biomonitoring

Schönrath I, et al. Toxicology Letters, 2024, 399, 25-33.

Climbazole, a widely used antimycotic agent in anti-dandruff formulations and cosmetic preservatives, undergoes metabolic biotransformation in the human body, yielding (OH)₂-climbazole and cx-OH-climbazole as key biomarkers of exposure. A pharmacokinetic study revealed that, following oral administration, approximately 24% of the dose was excreted in urine within 48 hours, demonstrating its systemic metabolism and elimination profile. Notably, the diastereomeric ratios of (OH)₂-climbazole shifted during excretion, suggesting metabolic selectivity. Dermal application through rinse-off shampoos and leave-on tonics exhibited delayed urinary excretion peaks, highlighting the influence of exposure duration and formulation on systemic absorption. The estimated systemic intake via dermal exposure was 18.5 µg/kg bw/day for hair tonic and 6.6 µg/kg bw/day for anti-dandruff shampoo, underscoring the relevance of biomonitoring in assessing human exposure. These findings provide a robust basis for reverse dosimetry approaches, ensuring safer regulatory thresholds for climbazole usage in personal care products.

Custom Q&A

What is the molecular formula of Climbazole?

The molecular formula of Climbazole is C15H17ClN2O2.

What is the molecular weight of Climbazole?

The molecular weight of Climbazole is 292.76 g/mol.

What is the IUPAC Name of Climbazole?

The IUPAC Name of Climbazole is 1-(4-chlorophenoxy)-1-imidazol-1-yl-3,3-dimethylbutan-2-one.

What is the Canonical SMILES representation of Climbazole?

The Canonical SMILES representation of Climbazole is CC(C)(C)C(=O)C(N1C=CN=C1)OC2=CC=C(C=C2)Cl.

What is the InChIKey of Climbazole?

The InChIKey of Climbazole is OWEGWHBOCFMBLP-UHFFFAOYSA-N.

How many hydrogen bond donor counts does Climbazole have?

Climbazole has 0 hydrogen bond donor counts.

How many hydrogen bond acceptor counts does Climbazole have?

Climbazole has 3 hydrogen bond acceptor counts.

What is the exact mass of Climbazole?

The exact mass of Climbazole is 292.0978555 g/mol.

What is the topological polar surface area of Climbazole?

The topological polar surface area of Climbazole is 44.1 2.

How many rotatable bond counts does Climbazole have?

Climbazole has 5 rotatable bond counts.