Griseofulvin | CAS#126-07-8 | Antifungal

MedKoo Cat#: 531024 | Name: Griseofulvin

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Description:

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

Griseofulvin is an antifungal drug shown to have anti-proliferative activities. Griseofulvin reduced the potential for disease transmission in children with tinea capitis. Permeation and penetration assays revealed that Griseofulvin-loaded ethosomes have an adequate profile to be used in a topical formulation since drug retention in the stratum corneum was achieved. Cell viability tests proved this formulation presented no cytotoxicity to HaCaT cells for concentrations below 50μg/mL.

Chemical Structure

Griseofulvin

CAS#126-07-8

Theoretical Analysis

MedKoo Cat#: 531024

Name: Griseofulvin

CAS#: 126-07-8

Chemical Formula: C17H17ClO6

Exact Mass: 352.0714

Molecular Weight: 352.77

Elemental Analysis: C, 57.88; H, 4.86; Cl, 10.05; O, 27.21

Price and Availability

Size	Price	Availability	Quantity
5g	USD 250.00
25g	USD 450.00	2 Weeks

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Synonym

Griseofulvin, Griseofulvina; (+)-Griseofulvin; Amudane; Griseofulvinum; Grifulvin; Griseofulvine; Grisofulvin; Grizeofulvin; NSC 34533; NSC34533; NSC-34533

IUPAC/Chemical Name

(2S,6'R)-7-chloro-2',4,6-trimethoxy-6'-methyl-3H-spiro[benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione

InChi Key

DDUHZTYCFQRHIY-RBHXEPJQSA-N

InChi Code

InChI=1S/C17H17ClO6/c1-8-5-9(19)6-12(23-4)17(8)16(20)13-10(21-2)7-11(22-3)14(18)15(13)24-17/h6-8H,5H2,1-4H3/t8-,17+/m1/s1

SMILES Code

O=C1[C@]2(C(OC)=CC(C[C@H]2C)=O)OC3=C(Cl)C(OC)=CC(OC)=C13

Appearance

White to light pink 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:

Griseofulvin(Gris-PEG; Grifulvin) is a spirocyclic fungal natural product used in treatment of fungal dermatophytes; Antifungal drug.

In vitro activity:

Griseofulvin could inhibit the growth of K562 cells in a dose-dependent manner with a mean (SD) inhibitory concentration of 50% value of 15.38 (1.35) μg/mL compared with untreated controls. Apoptosis was induced in K562 cells (38.35% [2.73%]; P < 0.01) by griseofulvin with the observation of both an increase in phosphatidylserine level and accumulation of chromatin nucleation in griseofulvintreated cells. Reference: Curr Ther Res Clin Exp. 2010 Dec;71(6):384-97. https://pubmed.ncbi.nlm.nih.gov/24688157/

In vivo activity:

Therefore, this study evaluated the potential of griseofulvin in preventing ECM by treating WT-infected C57BL/6 mice from day 4 when the blood parasitemia was around 2%. A single dose of 2 mg/day (comparable with the dosage of humans) administered from day 4 and continued until day 8 showed the best protection. While ~80% of the control mice succumbed to ECM within day 10, >80% of the treated mice were protected from ECM. Reference: Nat Commun. 2022 Jul 12;13(1):4028. https://pubmed.ncbi.nlm.nih.gov/35821013/

	Solvent	mg/mL	mM
Solubility
	DMSO	41.7	118.11

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 352.77 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. Zhong N, Chen H, Zhao Q, Wang H, Yu X, Eaves AM, Sheng W, Miao J, Cui F, Wang J. Effects of griseofulvin on apoptosis through caspase-3- and caspase-9-dependent pathways in K562 leukemia cells: An in vitro study. Curr Ther Res Clin Exp. 2010 Dec;71(6):384-97. doi: 10.1016/S0011-393X(10)80004-9. PMID: 24688157; PMCID: PMC3969622. 2. Rathinasamy K, Jindal B, Asthana J, Singh P, Balaji PV, Panda D. Griseofulvin stabilizes microtubule dynamics, activates p53 and inhibits the proliferation of MCF-7 cells synergistically with vinblastine. BMC Cancer. 2010 May 19;10:213. doi: 10.1186/1471-2407-10-213. PMID: 20482847; PMCID: PMC2885362. 3. Chandana M, Anand A, Ghosh S, Das R, Beura S, Jena S, Suryawanshi AR, Padmanaban G, Nagaraj VA. Malaria parasite heme biosynthesis promotes and griseofulvin protects against cerebral malaria in mice. Nat Commun. 2022 Jul 12;13(1):4028. doi: 10.1038/s41467-022-31431-z. PMID: 35821013; PMCID: PMC9276668. 4. Matsumura Y, Yokota M, Yoshioka H, Shibata S, Ida S, Takiguchi Y. Acute effects of griseofulvin on the pharmacokinetics and pharmacodynamics of warfarin in rats. J Int Med Res. 1999 Jul-Aug;27(4):167-75. doi: 10.1177/030006059902700402. PMID: 10599028.

In vitro protocol:

In vivo protocol:

1. Chandana M, Anand A, Ghosh S, Das R, Beura S, Jena S, Suryawanshi AR, Padmanaban G, Nagaraj VA. Malaria parasite heme biosynthesis promotes and griseofulvin protects against cerebral malaria in mice. Nat Commun. 2022 Jul 12;13(1):4028. doi: 10.1038/s41467-022-31431-z. PMID: 35821013; PMCID: PMC9276668. 2. Matsumura Y, Yokota M, Yoshioka H, Shibata S, Ida S, Takiguchi Y. Acute effects of griseofulvin on the pharmacokinetics and pharmacodynamics of warfarin in rats. J Int Med Res. 1999 Jul-Aug;27(4):167-75. doi: 10.1177/030006059902700402. PMID: 10599028.

1: Petersen AB, Rønnest MH, Larsen TO, Clausen MH. The chemistry of griseofulvin. Chem Rev. 2014 Dec 24;114(24):12088-107. doi: 10.1021/cr400368e. Epub 2014 Dec 5. Review. PubMed PMID: 25476923. 2: Shemer A, Grunwald MH, Gupta AK, Lyakhovitsky A, Daniel CR 3rd, Amichai B. Griseofulvin and Fluconazole Reduce Transmission of Tinea Capitis in Schoolchildren. Pediatr Dermatol. 2015 Sep-Oct;32(5):696-700. doi: 10.1111/pde.12653. Epub 2015 Jul 27. PubMed PMID: 26215468. 3: Roine J, Kaasalainen M, Peurla M, Correia A, Araújo F, Santos HA, Murtomaa M, Salonen J. Controlled Dissolution of Griseofulvin Solid Dispersions from Electrosprayed Enteric Polymer Micromatrix Particles: Physicochemical Characterization and in Vitro Evaluation. Mol Pharm. 2015 Jul 6;12(7):2254-64. doi: 10.1021/mp500787b. Epub 2015 Jun 10. PubMed PMID: 26035734. 4: Liéby-Muller F, Heudré Le Baliner Q, Grisoni S, Fournier E, Guilbaud N, Marion F. Synthesis and activities towards resistant cancer cells of sulfone and sulfoxide griseofulvin derivatives. Bioorg Med Chem Lett. 2015;25(10):2078-81. doi: 10.1016/j.bmcl.2015.03.081. Epub 2015 Apr 3. PubMed PMID: 25872984. 5: Cheng YC, Tsai MC, Huang MC. Delirium Associated With Griseofulvin and Disulfiram Coadministration. J Clin Psychopharmacol. 2015 Aug;35(4):477-8. doi: 10.1097/JCP.0000000000000334. PubMed PMID: 25938333. 6: Bhakay A, Azad M, Vizzotti E, Dave RN, Bilgili E. Enhanced recovery and dissolution of griseofulvin nanoparticles from surfactant-free nanocomposite microparticles incorporating wet-milled swellable dispersants. Drug Dev Ind Pharm. 2014 Nov;40(11):1509-22. doi: 10.3109/03639045.2013.831442. Epub 2013 Aug 28. PubMed PMID: 23981202. 7: Mahieu A, Willart JF, Dudognon E, Eddleston MD, Jones W, Danède F, Descamps M. On the polymorphism of griseofulvin: identification of two additional polymorphs. J Pharm Sci. 2013 Feb;102(2):462-8. doi: 10.1002/jps.23349. Epub 2012 Nov 6. PubMed PMID: 23132509. 8: Kahsay G, Broeckhoven K, Adams E, Desmet G, Cabooter D. Kinetic performance comparison of fully and superficially porous particles with a particle size of 5 µm: intrinsic evaluation and application to the impurity analysis of griseofulvin. Talanta. 2014 May;122:122-9. doi: 10.1016/j.talanta.2014.01.050. Epub 2014 Jan 31. PubMed PMID: 24720972. 9: Harrison AJ, Bilgili EA, Beaudoin SP, Taylor LS. Atomic force microscope infrared spectroscopy of griseofulvin nanocrystals. Anal Chem. 2013 Dec 3;85(23):11449-55. doi: 10.1021/ac4025889. Epub 2013 Nov 12. PubMed PMID: 24171582; PubMed Central PMCID: PMC3889117. 10: Marto J, Vitor C, Guerreiro A, Severino C, Eleutério C, Ascenso A, Simões S. Ethosomes for enhanced skin delivery of griseofulvin. Colloids Surf B Biointerfaces. 2016 Oct 1;146:616-23. doi: 10.1016/j.colsurfb.2016.07.021. Epub 2016 Jul 9. PubMed PMID: 27429295. 11: Reitz E, Vervaet C, Neubert RH, Thommes M. Solid crystal suspensions containing griseofulvin--preparation and bioavailability testing. Eur J Pharm Biopharm. 2013 Feb;83(2):193-202. doi: 10.1016/j.ejpb.2012.09.012. Epub 2012 Oct 26. PubMed PMID: 23108185. 12: Jadeja D, Jaiswal CS, Panchasra A, Tripathi CB. Griseofulvin and/or Terbinafine Induced Toxic Epidermal Necrolysis in an Adult Female Patient - A Case Report. Curr Drug Saf. 2016;11(2):192-4. PubMed PMID: 26695069. 13: Gupta AK, Drummond-Main C. Meta-analysis of randomized, controlled trials comparing particular doses of griseofulvin and terbinafine for the treatment of tinea capitis. Pediatr Dermatol. 2013 Jan-Feb;30(1):1-6. doi: 10.1111/j.1525-1470.2012.01866.x. Epub 2012 Sep 20. Review. PubMed PMID: 22994156. 14: Marcos X, Pérez-Casas S, Llovo J, Concheiro A, Alvarez-Lorenzo C. Poloxamer-hydroxyethyl cellulose-α-cyclodextrin supramolecular gels for sustained release of griseofulvin. Int J Pharm. 2016 Mar 16;500(1-2):11-9. doi: 10.1016/j.ijpharm.2016.01.015. Epub 2016 Jan 12. PubMed PMID: 26795192. 15: Tarbin JA, Fussell RJ. Metabolite profiling using liquid chromatography/quadrupole time-of-flight mass spectrometry for the identification of a suitable marker and target matrix of griseofulvin use in bovines. Rapid Commun Mass Spectrom. 2013 Jun 30;27(12):1287-93. doi: 10.1002/rcm.6574. PubMed PMID: 23681805. 16: Rønnest MH, Raab MS, Anderhub S, Boesen S, Krämer A, Larsen TO, Clausen MH. Disparate SAR data of griseofulvin analogues for the dermatophytes Trichophyton mentagrophytes, T. rubrum, and MDA-MB-231 cancer cells. J Med Chem. 2012 Jan 26;55(2):652-60. doi: 10.1021/jm200835c. Epub 2012 Jan 17. PubMed PMID: 22191585. 17: Petersen AB, Konotop G, Hanafiah NHM, Hammershøj P, Raab MS, Krämer A, Clausen MH. Strategies for improving the solubility and metabolic stability of griseofulvin analogues. Eur J Med Chem. 2016 Jun 30;116:210-215. doi: 10.1016/j.ejmech.2016.03.071. Epub 2016 Mar 28. PubMed PMID: 27061984. 18: Aggarwal N, Goindi S. Preparation and in vivo evaluation of solid lipid nanoparticles of griseofulvin for dermal use. J Biomed Nanotechnol. 2013 Apr;9(4):564-76. PubMed PMID: 23621015. 19: Aggarwal N, Goindi S, Khurana R. Formulation, characterization and evaluation of an optimized microemulsion formulation of griseofulvin for topical application. Colloids Surf B Biointerfaces. 2013 May 1;105:158-66. doi: 10.1016/j.colsurfb.2013.01.004. Epub 2013 Jan 7. PubMed PMID: 23357739. 20: Rydberg HA, Yanez Arteta M, Berg S, Lindfors L, Sigfridsson K. Probing adsorption of DSPE-PEG2000 and DSPE-PEG5000 to the surface of felodipine and griseofulvin nanocrystals. Int J Pharm. 2016 Aug 20;510(1):232-9. doi: 10.1016/j.ijpharm.2016.06.046. Epub 2016 Jun 18. PubMed PMID: 27329674.