WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H524755
CAS#: 38083-17-9
Description: Climbazole is a potent inducer and inhibitor of P450-dependent drug metabolizing enzymes, which is also used as antifungal and antidandruff agent.
Hodoodo Cat#: H524755
Name: Climbazole
CAS#: 38083-17-9
Chemical Formula: C15H17ClN2O2
Exact Mass: 292.10
Molecular Weight: 292.760
Elemental Analysis: C, 61.54; H, 5.85; Cl, 12.11; N, 9.57; O, 10.93
Synonym: Climbazole; Baypival; Climbazol; Baysan.
IUPAC/Chemical Name: 1-(4-Chlorophenoxy)-1-(1H-imidazolyl)-3,3-dimethyl-2-butanone
InChi Key: YFPFGHKWUKVEFZ-UHFFFAOYSA-N
InChi Code: InChI=1S/C15H17ClN2O2/c1-15(2,3)13(19)12(14-17-8-9-18-14)20-11-6-4-10(16)5-7-11/h4-9,12H,1-3H3,(H,17,18)
SMILES Code: CC(C)(C)C(C(OC1=CC=C(Cl)C=C1)C2=NC=CN2)=O
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO, not in water
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
More Info:
| Biological target: | Climbazole (BAY-e 6975) is a potent antifungal agent that can provide anti-dandruff benefits and is also a potent inducer of rat hepatic cytochrome P450 as well as ergosterol synthesis. |
| In vitro activity: | After 24 h treatment with climbazole in the absence of S9-mix to concentrations ranging from 5 to 20 μg/mL, cytotoxicity, i.e., reduction in total cell growth, ranged from 0 to 93%. An increase of greater than 90 mutants per 106 clonable cells was observed at 15 μg/mL (mean induced mutant frequency 140) and 17.5 μg/mL (mean induced mutant frequency 135), with a no observable effect level (NOEL) of approximately 10 μg/mL. The data obtained on colony size distributions revealed an increase in the frequency of small colonies when the treated cultures were compared to the solvent control cultures. Such an effect may indicate damage to multiple loci on chromosome 11 in addition to functional loss of the tk locus. Under the conditions of the study, climbazole did not induce mutations in the mouse lymphoma assay in the absence and presence of metabolic activation after a 4 h treatment period. However, after an extended treatment period of 24 h in the absence of S9-mix, an increase mutant frequency was obtained indicative of a clastogenic or aneugenic effect. Reference: Mutat Res. 2009 Jan;672(1):27-39. https://pubmed.ncbi.nlm.nih.gov/18950734/ |
| In vivo activity: | Based on the results of the dose-range finding studies, 150 mg/kg bw was determined to be the MTD. In the mouse bone marrow micronucleus test after oral administration of climbazole, all treatment and vehicle control groups exhibited normal frequencies of micronucleated polychromatic erythrocytes, while the positive control (CPA) induced a significant increase in MNPCE frequency demonstrating the sensitivity and responsiveness the test system. It can be concluded that climbazole did not induce micronuclei in mouse bone marrow after the administration of oral doses up to the MTD (150 mg/kg). However, there was no significant reduction in the ratio of PCEs to total erythrocytes, which is indicative of cytotoxicity and hence target tissue, i.e., bone marrow, exposure. Consequently a bioavailability study was carried out using [14C]-climbazole to support the in vivo micronucleus test by demonstrating the systemic bioavailability of climbazole after oral administration to mice. Reference: Mutat Res. 2009 Jan;672(1):27-39. https://pubmed.ncbi.nlm.nih.gov/18950734/ |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 53.0 | 181.04 |
The following data is based on the product molecular weight 292.76 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | 1. Pérez-Rivera AA, Hu T, Aardema MJ, Nash JF. Evaluation of the genotoxicity of the imidazole antifungal climbazole: comparison to published results for other azole compounds. Mutat Res. 2009 Jan;672(1):27-39. doi: 10.1016/j.mrgentox.2008.09.011. Epub 2008 Oct 2. PMID: 18950734. 2. Kobayashi Y, Suzuki M, Ohshiro N, Sunagawa T, Sasaki T, Tokuyama S, Yamamoto T, Yoshida T. Climbazole is a new potent inducer of rat hepatic cytochrome P450. J Toxicol Sci. 2001 Aug;26(3):141-50. doi: 10.2131/jts.26.141. PMID: 11552297. |
| In vitro protocol: | 1. Pérez-Rivera AA, Hu T, Aardema MJ, Nash JF. Evaluation of the genotoxicity of the imidazole antifungal climbazole: comparison to published results for other azole compounds. Mutat Res. 2009 Jan;672(1):27-39. doi: 10.1016/j.mrgentox.2008.09.011. Epub 2008 Oct 2. PMID: 18950734. 2. Kobayashi Y, Suzuki M, Ohshiro N, Sunagawa T, Sasaki T, Tokuyama S, Yamamoto T, Yoshida T. Climbazole is a new potent inducer of rat hepatic cytochrome P450. J Toxicol Sci. 2001 Aug;26(3):141-50. doi: 10.2131/jts.26.141. PMID: 11552297. |
| In vivo protocol: | 1. Pérez-Rivera AA, Hu T, Aardema MJ, Nash JF. Evaluation of the genotoxicity of the imidazole antifungal climbazole: comparison to published results for other azole compounds. Mutat Res. 2009 Jan;672(1):27-39. doi: 10.1016/j.mrgentox.2008.09.011. Epub 2008 Oct 2. PMID: 18950734. |
1: Petit JY, Cavana P, Thoumire S, Guillot J, Perrot S. Use of a modified hair strand test to assess the antifungal activity kinetics of dog hair after a 2% climbazole shampoo application. Vet Dermatol. 2016 Jun;27(3):148-e38. doi: 10.1111/vde.12304. Epub 2016 Apr 12. PubMed PMID: 27072515.
2: 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. 2016 Jan 25. pii: 1098612X15626197. [Epub ahead of print] PubMed PMID: 26809882.
3: Cavana P, Petit JY, Perrot S, Guechi R, Marignac G, Reynaud K, Guillot J. Efficacy of a 2% climbazole shampoo for reducing Malassezia population sizes on the skin of naturally infected dogs. J Mycol Med. 2015 Dec;25(4):268-73. doi: 10.1016/j.mycmed.2015.10.004. Epub 2015 Nov 18. PubMed PMID: 26603053.
4: Castro G, Casado J, Rodríguez I, Ramil M, Ferradás A, Cela R. Time-of-flight mass spectrometry assessment of fluconazole and climbazole UV and UV/H2O2 degradability: Kinetics study and transformation products elucidation. Water Res. 2016 Jan 1;88:681-90. doi: 10.1016/j.watres.2015.10.053. Epub 2015 Nov 2. PubMed PMID: 26575477.
5: Chen G, Miao M, Hoptroff M, Fei X, Collins LZ, Jones A, Janssen HG. Sensitive and simultaneous quantification of zinc pyrithione and climbazole deposition from anti-dandruff shampoos onto human scalp. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Oct 15;1003:22-6. doi: 10.1016/j.jchromb.2015.09.009. Epub 2015 Sep 11. PubMed PMID: 26397749.
6: Cavana P, Peano A, Petit JY, Tizzani P, Perrot S, Bensignor E, Guillot J. A pilot study of the efficacy of wipes containing chlorhexidine 0.3%, climbazole 0.5% and Tris-EDTA to reduce Malassezia pachydermatis populations on canine skin. Vet Dermatol. 2015 Aug;26(4):278-e61. doi: 10.1111/vde.12220. Epub 2015 Jun 16. PubMed PMID: 26083147; PubMed Central PMCID: PMC4660877.
7: Zhang QQ, Ying GG, Chen ZF, Liu YS, Liu WR, Zhao JL. Multimedia fate modeling and risk assessment of a commonly used azole fungicide climbazole at the river basin scale in China. Sci Total Environ. 2015 Jul 1;520:39-48. doi: 10.1016/j.scitotenv.2015.03.038. Epub 2015 Mar 17. PubMed PMID: 25794970.
8: 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. Epub 2014 Jul 25. PubMed PMID: 24811958.
9: Richter E, Wick A, Ternes TA, Coors A. Ecotoxicity of climbazole, a fungicide contained in antidandruff shampoo. Environ Toxicol Chem. 2013 Dec;32(12):2816-25. doi: 10.1002/etc.2367. PubMed PMID: 23982925.
10: Chen G, Hoptroff M, Fei X, Su Y, Janssen HG. Ultra-high-performance liquid chromatography-tandem mass spectrometry measurement of climbazole deposition from hair care products onto artificial skin and human scalp. J Chromatogr A. 2013 Nov 22;1317:155-8. doi: 10.1016/j.chroma.2013.08.032. Epub 2013 Aug 13. PubMed PMID: 23958691.
11: Schwartz JR, Bacon RA, Shah R, Mizoguchi H, Tosti A. Therapeutic efficacy of anti-dandruff shampoos: a randomized clinical trial comparing products based on potentiated zinc pyrithione and zinc pyrithione/climbazole. Int J Cosmet Sci. 2013 Aug;35(4):381-7. doi: 10.1111/ics.12055. Epub 2013 May 24. PubMed PMID: 23614401.
12: Chen ZF, Ying GG, Ma YB, Lai HJ, Chen F, Pan CG. Occurrence and dissipation of three azole biocides climbazole, clotrimazole and miconazole in biosolid-amended soils. Sci Total Environ. 2013 May 1;452-453:377-83. doi: 10.1016/j.scitotenv.2013.03.004. Epub 2013 Mar 26. PubMed PMID: 23542433.
13: Turner GA, Matheson JR, Li GZ, Fei XQ, Zhu D, Baines FL. Enhanced efficacy and sensory properties of an anti-dandruff shampoo containing zinc pyrithione and climbazole. Int J Cosmet Sci. 2013 Feb;35(1):78-83. doi: 10.1111/ics.12007. Epub 2012 Oct 8. PubMed PMID: 22970742.
14: Pérez-Rivera AA, Hu T, Aardema MJ, Nash JF. Evaluation of the genotoxicity of the imidazole antifungal climbazole: comparison to published results for other azole compounds. Mutat Res. 2009 Jan;672(1):27-39. doi: 10.1016/j.mrgentox.2008.09.011. Epub 2008 Oct 2. PubMed PMID: 18950734.
15: Abu-Jdayil B, Mohameed HA. Rheology of Dead Sea shampoo containing the antidandruff climbazole. Int J Cosmet Sci. 2004 Dec;26(6):281-9. doi: 10.1111/j.1467-2494.2004.00240.x. PubMed PMID: 18492152.
16: Yang YW, Zhu Y, Su XQ. [Determination of antidangdruff agent salicylic acid, zinc pyrithione, octopirox, climbazole and ketoconazole in shampoo by high performance liquid chromatography]. Wei Sheng Yan Jiu. 2005 Sep;34(5):626-8. Chinese. PubMed PMID: 16329615.
17: Kobayashi Y, Suzuki M, Ohshiro N, Sunagawa T, Sasaki T, Oguro T, Tokuyama S, Yamamoto T, Yoshida T. Induction and inhibition of cytochrome P450 and drug-metabolizing enzymes by climbazole. Biol Pharm Bull. 2002 Jan;25(1):53-7. PubMed PMID: 11824557.
18: Kobayashi Y, Suzuki M, Ohshiro N, Sunagawa T, Sasaki T, Tokuyama S, Yamamoto T, Yoshida T. Climbazole is a new potent inducer of rat hepatic cytochrome P450. J Toxicol Sci. 2001 Aug;26(3):141-50. PubMed PMID: 11552297.
19: Wigger-Alberti W, Kluge K, Elsner P. [Clinical effectiveness and tolerance of climbazole containing dandruff shampoo in patients with seborrheic scalp eczema]. Praxis (Bern 1994). 2001 Aug 16;90(33):1346-9. German. PubMed PMID: 11534318.
20: Coiffard C, Coiffard L, de Roeck-Holtzhauer Y. [Comparison of the thermostability of natural (sulfoprolamine and sodium usnate) and synthetic (climbazole and piroctone olamine) antidandruff agents]. Ann Pharm Fr. 1999 Sep;57(5):392-6. French. PubMed PMID: 10520510.
