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MedKoo Cat#: 464341 | Name: Griseofulvin-d3
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Description:

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

Griseofulvin-d3 is intended for use as an internal standard for the quantification of griseofulvin by GC- or LC-MS. Griseofulvin is a fungal metabolite that has been found in Penicillium and has diverse biological activities. It is active against clinical isolates of the dermatophytes T. rubrum, T. tonsurans, and M. canis (MICs = 0.0078-0.0156, 1-4, and 0.5-2 µg/ml, respectively). Griseofulvin binds to tubulin (Kd = 300 µM) and reduces the growth rate and shortening rate of isolated bovine brain microtubulin, indicating stabilization of microtubule dynamics, when used at concentrations ranging from 0.5 to 20 µM. It induces abnormal microtubule polymerization and cell cycle arrest at the G2/M phase in HT-29 cells when used at a concentration of 20 µM. Griseofulvin (30 mg/kg), alone or in combination with nocodazole, reduces tumor growth in a COLO 205 mouse xenograft model. Formulations containing griseofulvin have been used in the treatment of fungal infections.

Chemical Structure

Griseofulvin-d3
Griseofulvin-d3
CAS#1279033-22-5

Theoretical Analysis

MedKoo Cat#: 464341

Name: Griseofulvin-d3

CAS#: 1279033-22-5

Chemical Formula: C17H14D3ClO6

Exact Mass: 355.0902

Molecular Weight: 355.79

Elemental Analysis: C, 57.39; H, 5.66; Cl, 9.96; O, 26.98

Price and Availability

Size Price Availability Quantity
1mg USD 450.00 2 Weeks
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Synonym
Griseofulvin-d3; Griseofulvin d3;
IUPAC/Chemical Name
(2S,6'R)-7-chloro-4,6-dimethoxy-2'-(methoxy-d3)-6'-methyl-3H-spiro[benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione
InChi Key
DDUHZTYCFQRHIY-BCBJJHLGSA-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/i4D3
SMILES Code
C[C@@H]([C@](OC1=C(Cl)C(OC)=C2)(C(OC([2H])([2H])[2H])=C3)C(C1=C2OC)=O)CC3=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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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-d3 is the deuterium labeled Griseofulvin. Griseofulvin (Gris-PEG) 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/

Preparing Stock Solutions

The following data is based on the product molecular weight 355.79 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. 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:
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.
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: Dahiya R, Rampersad S, Ramnanansingh TG, Kaur K, Kaur R, Mourya R, Chennupati SV, Fairman R, Jalsa NK, Sharma A, Fuloria S, Fuloria NK. Synthesis and Bioactivity of a Cyclopolypeptide from Caribbean Marine Sponge. Iran J Pharm Res. 2020 Summer;19(3):156-170. doi: 10.22037/ijpr.2020.15405.13075. PMID: 33680019; PMCID: PMC7757994. 2: Shehabeldine A, El-Hamshary H, Hasanin M, El-Faham A, Al-Sahly M. Enhancing the Antifungal Activity of Griseofulvin by Incorporation a Green Biopolymer- Based Nanocomposite. Polymers (Basel). 2021 Feb 12;13(4):542. doi: 10.3390/polym13040542. PMID: 33673135; PMCID: PMC7918479. 3: Meng F, Paul SK, Borde S, Chauhan H. Investigating crystallization tendency, miscibility, and molecular interactions of drug-polymer systems for the development of amorphous solid dispersions. Drug Dev Ind Pharm. 2021 Mar 2:1-30. doi: 10.1080/03639045.2021.1892747. Epub ahead of print. PMID: 33651659. 4: Messina F, Walker L, Romero MLM, Arechavala AI, Negroni R, Depardo R, Marin E, Santiso GM. Tinea capitis: aspectos clínicos y alternativas terapéuticas [Tinea capitis: clinical features and therapeutic alternatives]. Rev Argent Microbiol. 2021 Feb 19:S0325-7541(21)00011-0. Spanish. doi: 10.1016/j.ram.2021.01.004. Epub ahead of print. PMID: 33618899. 5: Sleziona D, Mattusch A, Schaldach G, Ely DR, Sadowski G, Thommes M. Determination of Inherent Dissolution Performance of Drug Substances. Pharmaceutics. 2021 Jan 22;13(2):146. doi: 10.3390/pharmaceutics13020146. PMID: 33499428; PMCID: PMC7911123. 6: Yang Z, Chen W, Wan Z, Song Y, Li R. Tinea Capitis by Microsporum canis in an Elderly Female with Extensive Dermatophyte Infection. Mycopathologia. 2021 Jan 26. doi: 10.1007/s11046-020-00519-9. Epub ahead of print. PMID: 33496917. 7: Kenechukwu FC, Dias ML, Ricci-Júnior E. Biodegradable nanoparticles from prosopisylated cellulose as a platform for enhanced oral bioavailability of poorly water-soluble drugs. Carbohydr Polym. 2021 Mar 15;256:117492. doi: 10.1016/j.carbpol.2020.117492. Epub 2020 Dec 19. PMID: 33483021. 8: Cano EJ, Yetmar ZA, Razonable RR. Cryptococcus Species Other Than Cryptococcus neoformans and Cryptococcus gattii: Are They Clinically Significant? Open Forum Infect Dis. 2020 Oct 29;7(12):ofaa527. doi: 10.1093/ofid/ofaa527. PMID: 33324722; PMCID: PMC7717158. 9: Zareshahrabadi Z, Totonchi A, Rezaei-Matehkolaei A, Ilkit M, Ghahartars M, Arastehfar A, Motamedi M, Nouraei H, Sharifi Lari M, Mohammadi T, Zomorodian K. Molecular identification and antifungal susceptibility among clinical isolates of dermatophytes in Shiraz, Iran (2017-2019). Mycoses. 2021 Apr;64(4):385-393. doi: 10.1111/myc.13226. Epub 2020 Dec 20. PMID: 33295089. 10: da Igreja P, Erve A, Thommes M. Melt milling as manufacturing method for solid crystalline suspensions. Eur J Pharm Biopharm. 2021 Jan;158:245-253. doi: 10.1016/j.ejpb.2020.11.020. Epub 2020 Nov 27. PMID: 33253891. 11: Lima PG, Souza PFN, Freitas CDT, Bezerra LP, Neto NAS, Silva AFB, Oliveira JTA, Sousa DOB. Synthetic peptides against Trichophyton mentagrophytes and T. rubrum: Mechanisms of action and efficiency compared to griseofulvin and itraconazole. Life Sci. 2021 Jan 15;265:118803. doi: 10.1016/j.lfs.2020.118803. Epub 2020 Nov 23. PMID: 33238167. 12: Brinkmann J, Exner L, Luebbert C, Sadowski G. In-Silico Screening of Lipid- Based Drug Delivery Systems. Pharm Res. 2020 Nov 23;37(12):249. doi: 10.1007/s11095-020-02955-0. PMID: 33230602; PMCID: PMC7683453. 13: Ansari S, Ahmadi B, Hedayati MT, Nouripour-Sisakht S, Taghizadeh-Armaki M, Fathi M, Deravi N, Shokoohi GR, Rezaei-Matehkolaei A. Investigation of in vitro antifungal susceptibility testing and genetic diversity of clinical isolates of Trichophyton benhamiae and Trichophyton eriotrephon in Iran. Mycoses. 2021 Mar;64(3):316-323. doi: 10.1111/myc.13210. Epub 2020 Nov 25. PMID: 33190353. 14: Genedy RM, Sorour OA, Elokazy MAW. Trichoscopic signs of tinea capitis: a guide for selection of appropriate antifungal. Int J Dermatol. 2021 Apr;60(4):471-481. doi: 10.1111/ijd.15289. Epub 2020 Nov 3. PMID: 33141453. 15: Elele E, Shen Y, Boppana R, Afolabi A, Bilgili E, Khusid B. Electro- Hydrodynamic Drop-on-Demand Printing of Aqueous Suspensions of Drug Nanoparticles. Pharmaceutics. 2020 Oct 29;12(11):1034. doi: 10.3390/pharmaceutics12111034. PMID: 33138033; PMCID: PMC7693662. 16: Happi GM, Mouthe Kemayou GP, Stammler HG, Neumann B, Ismail M, Kouam SF, Wansi JD, Tchouankeu JC, Frese M, Lenta BN, Sewald N. Three phragmalin-type limonoids orthoesters and the structure of odoratone isolated from the bark of Entandrophragma candollei (Meliaceae). Phytochemistry. 2021 Jan;181:112537. doi: 10.1016/j.phytochem.2020.112537. Epub 2020 Oct 21. PMID: 33099226. 17: de Oliveira JC, de Vasconcelos Pinto Â, de Medeiros CAC, Ponte HAS, Pereira FO. The Sensitivity Modifying Activity of Nerolidol and α-Bisabolol Against Trichophyton spp. Indian J Microbiol. 2020 Dec;60(4):505-510. doi: 10.1007/s12088-020-00895-2. Epub 2020 Jun 13. PMID: 33088000; PMCID: PMC7539253. 18: Gorkem Buyukgoz G, Soffer D, Defendre J, Pizzano GM, Davé RN. Exploring tablet design options for tailoring drug release and dose via fused deposition modeling (FDM) 3D printing. Int J Pharm. 2020 Dec 15;591:119987. doi: 10.1016/j.ijpharm.2020.119987. Epub 2020 Oct 16. PMID: 33069894. 19: Aleohin N, Bar J, Bar-Ilan E, Samuelov L, Sprecher E, Mashiah J. Laboratory monitoring during antifungal treatment of paediatric tinea capitis. Mycoses. 2021 Feb;64(2):157-161. doi: 10.1111/myc.13197. Epub 2020 Oct 27. PMID: 33064847. 20: Paudel V. Surgery of Kerion, a Nightmare for Nondermatologists. Case Rep Dermatol Med. 2020 Sep 15;2020:8825912. doi: 10.1155/2020/8825912. PMID: 33014477; PMCID: PMC7512080.