Griseofulvic Acid | CAS#469-54-5 | Griseofulvin metabolite

MedKoo Cat#: 464060 | Name: Griseofulvic Acid

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Description:

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

Griseofulvic acid is a metabolite of the antifungal griseofulvin. It induces protein aggregation and tubulin polymerization in cell-free assays.

Chemical Structure

Griseofulvic Acid

CAS#469-54-5

Theoretical Analysis

MedKoo Cat#: 464060

Name: Griseofulvic Acid

CAS#: 469-54-5

Chemical Formula: C16H15ClO6

Exact Mass: 338.0557

Molecular Weight: 338.74

Elemental Analysis: C, 56.73; H, 4.46; Cl, 10.47; O, 28.34

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 900.00	Back order

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Synonym

Griseofulvic Acid; (±)-Griseofulvic Acid; Griseofulvate; Griseofulvicacid

IUPAC/Chemical Name

(2S,2'R)-7-chloro-4,6-dimethoxy-2'-methyl-3H-spiro[benzofuran-2,1'-cyclohexane]-3,4',6'-trione

InChi Key

YIQRSAKVWZVLDN-QZTNRIJFSA-N

InChi Code

InChI=1S/C16H15ClO6/c1-7-4-8(18)5-11(19)16(7)15(20)12-9(21-2)6-10(22-3)13(17)14(12)23-16/h6-7H,4-5H2,1-3H3/t7-,16+/m1/s1

SMILES Code

O=C1CC(C[C@@H](C)[C@@]1(OC2=C(Cl)C(OC)=C3)C(C2=C3OC)=O)=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

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
	Soluble in DMSO	0.0	100.00

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 338.74 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: Leśniewska B, Jebors S, Coleman AW, Suwińska K. Transformations of griseofulvin in strong acidic conditions--crystal structures of 2'-demethylgriseofulvin and dimerized griseofulvin. Nat Prod Commun. 2012 Mar;7(3):327-32. PMID: 22545405. 2: Zia H, Proveaux WJ, O'Donnell JP, Ma JK. Chromatographic analysis of griseofulvin and metabolites in biological fluids. J Chromatogr. 1980 Jan 11;181(1):77-84. doi: 10.1016/s0378-4347(00)81271-2. PMID: 7364918. 3: Zia H, O'Donnell JP, Ma JK. Identification of griseofulvic acid as a urine metabolite of griseofulvin in humans. J Pharm Sci. 1979 Oct;68(10):1335-6. doi: 10.1002/jps.2600681042. PMID: 512877.