Rosiglitazone | BRL49653 | CAS#122320-73-4 | PPAR

MedKoo Cat#: 319943 | Name: Rosiglitazone

Featured

Description:

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

Rosiglitazone is an antidiabetic drug in the thiazolidinedione class of drugs. It works as an insulin sensitizer, by binding to the PPAR receptors in fat cells and making the cells more responsive to insulin. Rosiglitazone is a member of the thiazolidinedione class of drugs. Thiazolidinediones act as insulin sensitizers. They reduce glucose, fatty acid, and insulin blood concentrations. They work by binding to the peroxisome proliferator-activated receptors (PPARs). PPARs are transcription factors that reside in the nucleus and become activated by ligands such as thiazolidinediones. Thiazolidinediones enter the cell, bind to the nuclear receptors, and alter the expression of genes..

Chemical Structure

Rosiglitazone

CAS#122320-73-4 (free base)

Theoretical Analysis

MedKoo Cat#: 319943

Name: Rosiglitazone

CAS#: 122320-73-4 (free base)

Chemical Formula: C18H19N3O3S

Exact Mass: 357.1147

Molecular Weight: 357.43

Elemental Analysis: C, 60.49; H, 5.36; N, 11.76; O, 13.43; S, 8.97

Price and Availability

Size	Price	Availability
500mg	USD 250.00	2 weeks
1g	USD 400.00	2 weeks
2g	USD 650.00	2 Weeks
5g	USD 1,250.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

155141-29-0 (maleate) 122320-73-4 (free base) 316371-84-3 (potassium)

Synonym

BRL49653; BRL-49653; BRL 49653; HSDB 7555; HSDB-7555; HSDB7555; TDZ 01; TDZ-01; TDZ01; Rosiglitazone. trade name Avandia.

IUPAC/Chemical Name

5-(4-(2-(methyl(pyridin-2-yl)amino)ethoxy)benzyl)thiazolidine-2,4-dione

InChi Key

YASAKCUCGLMORW-UHFFFAOYSA-N

InChi Code

InChI=1S/C18H19N3O3S/c1-21(16-4-2-3-9-19-16)10-11-24-14-7-5-13(6-8-14)12-15-17(22)20-18(23)25-15/h2-9,15H,10-12H2,1H3,(H,20,22,23)

SMILES Code

O=C(N1)SC(CC2=CC=C(OCCN(C)C3=NC=CC=C3)C=C2)C1=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, DMF, and ethanol

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:

Rosiglitazone is an orally active selective PPARγ agonist (EC50: 60 nM, Kd: 40 nM). Rosiglitazone is an TRPC5 activator (EC50: 30 μM) and TRPM3 inhibitor.

In vitro activity:

Rosiglitazone can protect granulosa cells against palmitic acid-induced cytotoxicity by inhibiting ER stress, and can recover steroidogenic capacity, indicating a potential use of rosiglitazone in the treatment of granulosa cell dysfunction. Additionally, rosiglitazone treatment rescued granulosa cells from palmitic acid-induced decrease of estrogen secretion by cAMP/PKA/CREB pathway. Reference: Reprod Biol. 2020 Sep;20(3):293-299. https://pubmed.ncbi.nlm.nih.gov/32736984/

In vivo activity:

This study provided sufficient evidence of the potential for rosiglitazone to ameliorate dexamethasone-induced depression using a mouse model. After rosiglitazone treatment, pAMPK and NGF activity increased, mTOR activity decreased, and the downstream signaling pathways pAKT, p38MAPK, and 4EBP1 were downregulated. Rosiglitazone exerts a potent inhibitory effect on the pAKT/p38MAPK/mTOR/4EBP1 pathway and causes activation of NGF in brain cells. Reference: Biomedicines. 2023 Mar 11;11(3):860. https://pubmed.ncbi.nlm.nih.gov/36979839/

	Solvent	mg/mL	mM
Solubility
	DMF	25.0	69.94
	DMSO	34.0	95.12
	Ethanol	1.0	2.80

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 357.43 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. Wan J, Liu S. Rosiglitazone ameliorates palmitic acid-induced endoplasmic reticulum stress and steroidogenic capacity in granulosa cells. Reprod Biol. 2020 Sep;20(3):293-299. doi: 10.1016/j.repbio.2020.07.004. Epub 2020 Jul 28. PMID: 32736984. 2. Fayyad AM, Khan AA, Abdallah SH, Alomran SS, Bajou K, Khattak MNK. Rosiglitazone Enhances Browning Adipocytes in Association with MAPK and PI3-K Pathways During the Differentiation of Telomerase-Transformed Mesenchymal Stromal Cells into Adipocytes. Int J Mol Sci. 2019 Apr 1;20(7):1618. doi: 10.3390/ijms20071618. PMID: 30939750; PMCID: PMC6480475. 3. Alhaddad A, Radwan A, Mohamed NA, Mehanna ET, Mostafa YM, El-Sayed NM, Fattah SA. Rosiglitazone Mitigates Dexamethasone-Induced Depression in Mice via Modulating Brain Glucose Metabolism and AMPK/mTOR Signaling Pathway. Biomedicines. 2023 Mar 11;11(3):860. doi: 10.3390/biomedicines11030860. PMID: 36979839; PMCID: PMC10046017. 4. Ma L, Ma Y, Ma BX, Ma M. Rosiglitazone ameliorates acute hepatic injury via activating the Nrf2 signaling pathway and inhibiting activation of the NLRP3 inflammasome. Exp Ther Med. 2022 Apr;23(4):300. doi: 10.3892/etm.2022.11229. Epub 2022 Feb 21. PMID: 35340872; PMCID: PMC8931635.

In vitro protocol:

In vivo protocol:

1. Alhaddad A, Radwan A, Mohamed NA, Mehanna ET, Mostafa YM, El-Sayed NM, Fattah SA. Rosiglitazone Mitigates Dexamethasone-Induced Depression in Mice via Modulating Brain Glucose Metabolism and AMPK/mTOR Signaling Pathway. Biomedicines. 2023 Mar 11;11(3):860. doi: 10.3390/biomedicines11030860. PMID: 36979839; PMCID: PMC10046017. 2. Ma L, Ma Y, Ma BX, Ma M. Rosiglitazone ameliorates acute hepatic injury via activating the Nrf2 signaling pathway and inhibiting activation of the NLRP3 inflammasome. Exp Ther Med. 2022 Apr;23(4):300. doi: 10.3892/etm.2022.11229. Epub 2022 Feb 21. PMID: 35340872; PMCID: PMC8931635.

1: Choi S, Dalloul RSD, Vemulapalli PB, Yousef S, Goswami N, Schmidt F. Comprehensive Proteomic Profiling of Converted Adipocyte-like Cells from Normal Human Dermal Fibroblasts Using Data-Independent Acquisition Mass Spectrometry. ACS Omega. 2024 Sep 9;9(38):40034-40050. doi: 10.1021/acsomega.4c05852. PMID: 39346858; PMCID: PMC11425921. 2: Bauzá-Thorbrügge M, Amengual-Cladera E, Galmés-Pascual BM, Morán-Costoya A, Gianotti M, Valle A, Proenza AM, Lladó I. Impact of Sex on the Therapeutic Efficacy of Rosiglitazone in Modulating White Adipose Tissue Function and Insulin Sensitivity. Nutrients. 2024 Sep 11;16(18):3063. doi: 10.3390/nu16183063. PMID: 39339665; PMCID: PMC11434741. 3: Yu H, Zhang Y, Zhang Y, Chen S, Li Z, Pi W, Zeng W, Hu G. Effects of Exogenous Regulation of PPARγ on Ovine Oocyte Maturation and Embryonic Development In Vitro. Vet Sci. 2024 Aug 28;11(9):397. doi: 10.3390/vetsci11090397. PMID: 39330776; PMCID: PMC11435492. 4: Yang Y, Huang S, Ma Q, Li N, Li R, Wang Y, Liu H. Combined therapeutic strategy based on blocking the deleterious effects of AGEs for accelerating diabetic wound healing. Regen Biomater. 2024 Jun 5;11:rbae062. doi: 10.1093/rb/rbae062. PMID: 39323743; PMCID: PMC11424028. 5: Li H, Xie JZ, Fan RX, Yang L, Zhou QY, Zhou NN. [Effect of Sijunzi Decoction on intestinal barrier of type 2 diabetic mice]. Zhongguo Zhong Yao Za Zhi. 2024 Aug;49(16):4510-4520. Chinese. doi: 10.19540/j.cnki.cjcmm.20240429.401. PMID: 39307787. 6: Wu Q, Jiao Y, Li J, Ma Y, Wang J, Luo M, Wang Y, Fan X, Liu C. Flavokawain B is an effective natural peroxisome proliferator-activated receptor γ-selective agonist with a strong glucose-lowering effect. Biochem Pharmacol. 2024 Sep 18;229:116548. doi: 10.1016/j.bcp.2024.116548. Epub ahead of print. PMID: 39304103. 7: Sun Y, Lian Y, Mei X, Xia J, Feng L, Gao J, Xu H, Zhang X, Yang H, Hao X, Feng Y. Cinobufagin inhibits M2‑like tumor‑associated macrophage polarization to attenuate the invasion and migration of lung cancer cells. Int J Oncol. 2024 Nov;65(5):102. doi: 10.3892/ijo.2024.5690. Epub 2024 Sep 20. PMID: 39301639; PMCID: PMC11419410. 8: Cuzzocrea S, Pisano B, Dugo L, Ianaro A, Maffia P, Patel NSA, Di Paola R, Ialenti A, Genovese T, Chatterjee PK, Di Rosa M, Caputi AP, Thiemermann C. Retraction notice to "Rosiglitazone, a ligand of the peroxisome proliferator- activated receptor-gamma, reduces acute inflammation" [Eur. J. Pharmacol 483 (1) (2024) 79-93]. Eur J Pharmacol. 2024 Sep 18:177006. doi: 10.1016/j.ejphar.2024.177006. Epub ahead of print. PMID: 39299820. 9: Li H, Liao X, Lan M, He J, Gao J, Fan Z, Huang J, Wu X, Chen J, Sun G. Arctigenin Modulates Adipogenic-Osteogenic Balance in the Bone Marrow Microenvironment of Ovariectomized Rats via the MEK1/PPARγ/Wnt/β-Catenin Pathway. Chem Biol Drug Des. 2024 Sep;104(3):e14625. doi: 10.1111/cbdd.14625. PMID: 39289148. 10: Engin AB, Engin ED, Engin A. Targeted Nano-Based Systems for the Anti- Obesity Agent's Delivery. Adv Exp Med Biol. 2024;1460:657-676. doi: 10.1007/978-3-031-63657-8_22. PMID: 39287868. 11: Engin A. Endothelial Dysfunction in Obesity and Therapeutic Targets. Adv Exp Med Biol. 2024;1460:489-538. doi: 10.1007/978-3-031-63657-8_17. PMID: 39287863. 12: Zhao J, Qian H, An Y, Chu L, Tan D, Qin C, Sun Q, Wang Y, Qi W. PPARγ and C/EBPα enable adipocyte differentiation upon inhibition of histone methyltransferase PRC2 in malignant tumors. J Biol Chem. 2024 Sep 12:107765. doi: 10.1016/j.jbc.2024.107765. Epub ahead of print. PMID: 39276936. 13: Ben-Yishay R, Globus O, Balint-Lahat N, Arbili-Yarhi S, Bar-Hai N, Bar V, Aharon S, Kosenko A, Zundelevich A, Berger R, Ishay-Ronen D. Class Effect Unveiled: PPARγ Agonists and MEK Inhibitors in Cancer Cell Differentiation. Cells. 2024 Sep 9;13(17):1506. doi: 10.3390/cells13171506. PMID: 39273076; PMCID: PMC11394433. 14: Lam IH, Chan CI, Han M, Li L, Yu HH. ACSL4 mediates inflammatory bowel disease and contributes to LPS-induced intestinal epithelial cell dysfunction by activating ferroptosis and inflammation. Open Med (Wars). 2024 Sep 3;19(1):20240993. doi: 10.1515/med-2024-0993. PMID: 39247444; PMCID: PMC11377980. 15: Liu PP, Yang ZJ, Song WJ, Ding SJ, Li HX, Li CB. Optimization of differentiation conditions for porcine adipose-derived mesenchymal stem cells and analysis of fatty acids in cultured fat. Food Res Int. 2024 Oct;194:114853. doi: 10.1016/j.foodres.2024.114853. Epub 2024 Jul 29. PMID: 39232503. 16: Cao S, Wei Y, Yue Y, Chen Y, Qian J, Wang D, Xiong A, Liu P, Zeng H. Rosiglitazone retards the progression of iron overload-induced osteoarthritis by impeding chondrocyte ferroptosis. iScience. 2024 Jul 31;27(9):110526. doi: 10.1016/j.isci.2024.110526. PMID: 39224514; PMCID: PMC11366908. 17: Qi S, Zhang T, Zhang C, Jiang B, Huang C, Yong Q, Jin Y. Sucrose-derived porous carbon catalyzed lignin depolymerization to obtain a product with application in type 2 diabetes mellitus. Int J Biol Macromol. 2024 Aug 29;279(Pt 2):135170. doi: 10.1016/j.ijbiomac.2024.135170. Epub ahead of print. PMID: 39214225. 18: Desai A, Yang Loureiro Z, DeSouza T, Yang Q, Solivan-Rivera J, Corvera S. PPARγ activation by lipolysis-generated ligands is required for cAMP dependent UCP1 induction in human thermogenic adipocytes. bioRxiv [Preprint]. 2024 Aug 11:2024.08.10.607465. doi: 10.1101/2024.08.10.607465. PMID: 39211160; PMCID: PMC11360943. 19: Fadaly WAA, Elshewy A, Nemr MTM, Abdou K, Sayed AM, Kahk NM. Discovery of novel thiazole derivatives containing pyrazole scaffold as PPAR-γ Agonists, α-Glucosidase, α-Amylase and COX-2 inhibitors; Design, synthesis and in silico study. Bioorg Chem. 2024 Nov;152:107760. doi: 10.1016/j.bioorg.2024.107760. Epub 2024 Aug 25. PMID: 39197383. 20: Ozhava D, Lee K, Bektas C, Jackson A, Patel K, Mao Y. Optimized Adipogenic Differentiation and Delivery of Bovine Umbilical Cord Stem Cells for Cultivated Meat. Gels. 2024 Jul 24;10(8):488. doi: 10.3390/gels10080488. PMID: 39195017; PMCID: PMC11354103.

View History

Description:

Chemical Structure

Theoretical Analysis

Price and Availability

Preparing Stock Solutions

View History

SAR103168

Avanafil dibesylate

Naphthonone

NSC-36398

Propargyl-PEG5-Br

Luteolin monohydrate

Error message: