Myclobutanil
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 540304

CAS#: 88671-89-0

Description: Myclobutanil is a 14-α demethylase inhibitor that inhibits ergosterol synthesis and fungal cell wall formation. It also weakly inhibits testosterone production.

Chemical Structure

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Myclobutanil
CAS# 88671-89-0
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 540304
Name: Myclobutanil
CAS#: 88671-89-0
Chemical Formula: C15H17ClN4
Exact Mass: 288.11
Molecular Weight: 288.779
Elemental Analysis: C, 62.39; H, 5.93; Cl, 12.28; N, 19.40

Price and Availability

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100mg USD 215
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Synonym: Myclobutanil; HOE 39304F; HOE39304F; HOE-39304F; HSDB 6708; HSDB6708; HSDB-6708; Systhane

IUPAC/Chemical Name: 2-((1H-1,2,4-triazol-1-yl)methyl)-2-(4-chlorophenyl)hexanenitrile

InChi Key: HZJKXKUJVSEEFU-UHFFFAOYSA-N

InChi Code: InChI=1S/C15H17ClN4/c1-2-3-8-15(9-17,10-20-12-18-11-19-20)13-4-6-14(16)7-5-13/h4-7,11-12H,2-3,8,10H2,1H3

SMILES Code: N#CC(C1=CC=C(Cl)C=C1)(CCCC)CN2N=CN=C2

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

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:

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: Myclobutanil is a conazole class fungicide widely used as an agrichemical.
In vitro activity: This study investigated myclobutanil's effects on the human liver cell line HepG2. This study found that myclobutanil increases the amount of fatty acids in these hepatic cells, as evaluated with Oil Red O staining, and progressively reduces cell viability from 1ppm to 500ppm. Analysis of biomarkers such as Bcl-xL/Bak and Mcl-1/Bak confirmed activation of cell death pathways at low doses. Reference: Toxicol Lett. 2016 Nov 16;262:100-104. https://pubmed.ncbi.nlm.nih.gov/27693777/
In vivo activity: In a diet-induced NAFLD study, low-fat diet (LFD) fed mice administered myclobutanil displayed decreased FXR activity in the liver and ileum, while high-fat-high-sugar-diet (HFHSD) fed mice showed an increase in hepatic FXR activity and an induction of target genes regulated by constitutive androstane receptor and/or pregnane X receptor. Reference: Toxicol Sci. 2023 Feb 17;191(2):387-399. https://pubmed.ncbi.nlm.nih.gov/36511616/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 79.0 273.57

Preparing Stock Solutions

The following data is based on the product molecular weight 288.78 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.

Recalculate based on batch purity %
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. Terpou A, Dimopoulou M, Belka A, Kallithraka S, Nychas GE, Papanikolaou S. Effect of Myclobutanil Pesticide on the Physiological Behavior of Two Newly Isolated Saccharomyces cerevisiae Strains during Very-High-Gravity Alcoholic Fermentation. Microorganisms. 2019 Dec 9;7(12):666. doi: 10.3390/microorganisms7120666. PMID: 31835377; PMCID: PMC6956295. 2. Stellavato A, Lamberti M, Pirozzi AVA, de Novellis F, Schiraldi C. Myclobutanil worsens nonalcoholic fatty liver disease: An in vitro study of toxicity and apoptosis on HepG2 cells. Toxicol Lett. 2016 Nov 16;262:100-104. doi: 10.1016/j.toxlet.2016.09.013. Epub 2016 Sep 28. PMID: 27693777. 3. Taylor R, Armstrong L, Bhattacharya A, Henry Z, Brinker A, Buckley B, Kong B, Guo G. Myclobutanil-mediated alteration of liver-gut FXR signaling in mice. Toxicol Sci. 2023 Feb 17;191(2):387-399. doi: 10.1093/toxsci/kfac129. PMID: 36511616; PMCID: PMC9936201.
In vitro protocol: 1. Terpou A, Dimopoulou M, Belka A, Kallithraka S, Nychas GE, Papanikolaou S. Effect of Myclobutanil Pesticide on the Physiological Behavior of Two Newly Isolated Saccharomyces cerevisiae Strains during Very-High-Gravity Alcoholic Fermentation. Microorganisms. 2019 Dec 9;7(12):666. doi: 10.3390/microorganisms7120666. PMID: 31835377; PMCID: PMC6956295. 2. Stellavato A, Lamberti M, Pirozzi AVA, de Novellis F, Schiraldi C. Myclobutanil worsens nonalcoholic fatty liver disease: An in vitro study of toxicity and apoptosis on HepG2 cells. Toxicol Lett. 2016 Nov 16;262:100-104. doi: 10.1016/j.toxlet.2016.09.013. Epub 2016 Sep 28. PMID: 27693777.
In vivo protocol: 1. Taylor R, Armstrong L, Bhattacharya A, Henry Z, Brinker A, Buckley B, Kong B, Guo G. Myclobutanil-mediated alteration of liver-gut FXR signaling in mice. Toxicol Sci. 2023 Feb 17;191(2):387-399. doi: 10.1093/toxsci/kfac129. PMID: 36511616; PMCID: PMC9936201.

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1: Wang Y, Qiu J, Zhu W, Wang X, Zhang P, Wang D, Zhou Z. Enantioselective Metabolism and Interference on Tryptophan Metabolism of Myclobutanil in Rat Hepatocytes. Chirality. 2015 Sep;27(9):643-9. doi: 10.1002/chir.22479. Epub 2015 Jun 26. PubMed PMID: 26115377.

2: Li Y, Dong F, Liu X, Xu J, Han Y, Zheng Y. Enantioselectivity in tebuconazole and myclobutanil non-target toxicity and degradation in soils. Chemosphere. 2015 Mar;122:145-153. doi: 10.1016/j.chemosphere.2014.11.031. Epub 2014 Dec 2. PubMed PMID: 25475972.

3: Yan J, Zhang P, Wang X, Wang Y, Zhou Z, Zhu W. Stereoselective degradation of chiral fungicide myclobutanil in rat liver microsomes. Chirality. 2014 Jan;26(1):51-5. doi: 10.1002/chir.22265. Epub 2013 Nov 19. PubMed PMID: 24249205.

4: Cheng C, Huang L, Diao J, Zhou Z. Enantioselective toxic effects and degradation of myclobutanil enantiomers in Scenedesmus obliquus. Chirality. 2013 Dec;25(12):858-64. doi: 10.1002/chir.22226. Epub 2013 Aug 13. PubMed PMID: 23939881.

5: Liu Y, Sun H, Liu F, Wang S. Dissipation and residue of myclobutanil in lychee. Bull Environ Contam Toxicol. 2012 Jun;88(6):902-5. doi: 10.1007/s00128-012-0610-2. Epub 2012 Apr 17. PubMed PMID: 22526985.

6: Lv X, Liu C, Li Y, Gao Y, Guo B, Wang H, Li J. Bioaccumulation and excretion of enantiomers of myclobutanil in Tenebrio molitor larvae through dietary exposure. Chirality. 2013 Dec;25(12):890-6. doi: 10.1002/chir.22230. Epub 2013 Sep 7. PubMed PMID: 24014248.

7: Sun M, Liu D, Qiu X, Zhou Q, Shen Z, Wang P, Zhou Z. Acute toxicity, bioactivity, and enantioselective behavior with tissue distribution in rabbits of myclobutanil enantiomers. Chirality. 2014 Dec;26(12):784-9. doi: 10.1002/chir.22353. Epub 2014 Jul 21. PubMed PMID: 25043148.

8: Gao WH, Liu B, Li XF, Han JH, Jia YM. [Study on the choice of functional monomer before preparation of myclobutanil molecularly imprinted polymer]. Guang Pu Xue Yu Guang Pu Fen Xi. 2014 Mar;34(3):791-4. Chinese. PubMed PMID: 25208414.

9: Wang Y, Wang CW, Gao J, Cui LL, Xu YC. [Determination of myclobutanil 25% WG degradation dynamics in ginseng root, stem, leaf and soil by HPLC-MS/MS]. Zhongguo Zhong Yao Za Zhi. 2014 Jul;39(13):2464-8. Chinese. PubMed PMID: 25276964.

10: Marín-Benito JM, Herrero-Hernández E, Andrades MS, Sánchez-Martín MJ, Rodríguez-Cruz MS. Effect of different organic amendments on the dissipation of linuron, diazinon and myclobutanil in an agricultural soil incubated for different time periods. Sci Total Environ. 2014 Apr 1;476-477:611-21. doi: 10.1016/j.scitotenv.2014.01.052. Epub 2014 Feb 3. PubMed PMID: 24496034.

11: Wang X, Li Y, Xu G, Sun H, Xu J, Zheng X, Wang F. Dissipation and residues of myclobutanil in tobacco and soil under field conditions. Bull Environ Contam Toxicol. 2012 May;88(5):759-63. doi: 10.1007/s00128-012-0596-9. Epub 2012 Mar 14. PubMed PMID: 22415649.

12: Stellavato A, Lamberti M, Pirozzi AVA, de Novellis F, Schiraldi C. Myclobutanil worsens nonalcoholic fatty liver disease: An in vitro study of toxicity and apoptosis on HepG2 cells. Toxicol Lett. 2016 Nov 16;262:100-104. doi: 10.1016/j.toxlet.2016.09.013. Epub 2016 Sep 28. PubMed PMID: 27693777.

13: Cho EM, Singh DK, Ganbold EO, Dembereldorj U, Jang SW, Kim D, Choo J, Kim S, Lee CM, Yang SI, Joo SW. Interactions between the antifungal drug myclobutanil and gold and silver nanoparticles in Penicillium digitatum investigated by surface-enhanced Raman scattering. Appl Spectrosc. 2014;68(3):307-14. doi: 10.1366/13-07084. PubMed PMID: 24666947.

14: Dong F, Cheng L, Liu X, Xu J, Li J, Li Y, Kong Z, Jian Q, Zheng Y. Enantioselective analysis of triazole fungicide myclobutanil in cucumber and soil under different application modes by chiral liquid chromatography/tandem mass spectrometry. J Agric Food Chem. 2012 Feb 29;60(8):1929-36. doi: 10.1021/jf204762t. Epub 2012 Feb 15. PubMed PMID: 22288843.

15: Nagel DA, Hill EJ, O'Neil J, Mireur A, Coleman MD. The effects of the fungicides fenhexamid and myclobutanil on SH-SY5Y and U-251 MG human cell lines. Environ Toxicol Pharmacol. 2014 Nov;38(3):968-76. doi: 10.1016/j.etap.2014.09.005. Epub 2014 Sep 16. PubMed PMID: 25461557.

16: Lin CH, Chou PH, Chen PJ. Two azole fungicides (carcinogenic triadimefon and non-carcinogenic myclobutanil) exhibit different hepatic cytochrome P450 activities in medaka fish. J Hazard Mater. 2014 Jul 30;277:150-8. doi: 10.1016/j.jhazmat.2014.05.083. Epub 2014 Jun 6. PubMed PMID: 24962053.

17: Ju C, Xu J, Wu X, Dong F, Liu X, Zheng Y. Effects of myclobutanil on soil microbial biomass, respiration, and soil nitrogen transformations. Environ Pollut. 2016 Jan;208(Pt B):811-20. doi: 10.1016/j.envpol.2015.11.003. Epub 2015 Nov 15. PubMed PMID: 26590854.

18: Huang AG, Tu X, Liu L, Wang GX, Ling F. The oxidative stress response of myclobutanil and cyproconazole on Tetrahymena thermophila. Environ Toxicol Pharmacol. 2016 Jan;41:211-8. doi: 10.1016/j.etap.2015.12.008. Epub 2015 Dec 17. PubMed PMID: 26724607.

19: Kemmitt GM, DeBoer G, Ouimette D, Iamauti M. Systemic properties of myclobutanil in soybean plants, affecting control of Asian soybean rust (Phakopsora pachyrhizi). Pest Manag Sci. 2008 Dec;64(12):1285-93. doi: 10.1002/ps.1630. PubMed PMID: 18683908.

20: Zhang H, Wang X, Qian M, Wang X, Xu H, Xu M, Wang Q. Residue analysis and degradation studies of fenbuconazole and myclobutanil in strawberry by chiral high-performance liquid chromatography-tandem mass spectrometry. J Agric Food Chem. 2011 Nov 23;59(22):12012-7. doi: 10.1021/jf202975x. Epub 2011 Oct 19. PubMed PMID: 21967215.