Rosiglitazone maleate

Alias: BRL 49653; BRL49653;BRL-49653;Rosiglitazone Maleate; Avandia; Avandaryl; BRL-49653C; BRL49653C; BRL 49653C; BRL-49653-C;
Cat No.:V0824 Purity: ≥98%
Rosiglitazone maleate (TDZ01;HSDB-7555; TDZ-01;BRL-49653; trade name Avandia), the maleic acid salt form of rosiglitazone which is an approved anti-diabetic drug,is a thiazolidinedione-based antihyperglycaemic agent with antidiabetic properties and potential antineoplastic activity.
Rosiglitazone maleate Chemical Structure CAS No.: 155141-29-0
Product category: PPAR
This product is for research use only, not for human use. We do not sell to patients.
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Other Forms of Rosiglitazone maleate:

  • Rosiglitazone
  • Rosiglitazone HCl
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description

Rosiglitazone maleate (TDZ01; HSDB-7555; TDZ-01; BRL-49653; trade name Avandia), the maleic acid salt form of rosiglitazone which is an approved anti-diabetic drug, is a thiazolidinedione-based antihyperglycaemic agent with antidiabetic properties and potential antineoplastic activity.

Biological Activity I Assay Protocols (From Reference)
ln Vitro
Rosiglitazone maleate has an EC50 of 30 nM for PPARγ1 and 100 nM for PPARγ2, respectively, and a Kd of roughly 40 nM for PPARγ, making it a strong and selective PPARγ activator. The development of C3H10T1/2 stem cells into adipocytes is aided by rosiglitazone (BRL49653, 0.1, 1, 10 μM) [1]. With an EC50 of 60 nM, compound 6 (rosiglitazone) activates PPARγ[2]. As PPARγ binds to the NF-κ1 promoter, rosiglitazone (1 μM) promotes gene transcription in neurons. Furthermore, in an NF-κ1-dependent way, rosiglitazone (1 μM) increases BCL-2 expression while shielding Neuro2A cells and hippocampus neurons from oxidative stress [3]. TRPM3 is totally blocked by rosiglitazone against nifedipine- and PregS-induced activity, with IC50 values of 9.5 and 4.6 μM, respectively. However, PPARγ is not involved in this action. An IC50 of roughly 22.5 μM indicates that rosiglitazone inhibits TRPM2 at greater dosages. EC50 of ~30 μM makes rosiglitazone a potent TRPC5 channel stimulant [4].
ln Vivo
In diabetic rats, rosiglitazone (5 mg/kg, po) lowers blood glucose levels. Additionally, rosiglitazone decreased the diabetic group's levels of VCAM-1, TNF-α, and IL-6. When rosiglitazone and losartan were combined, blood glucose levels rose in comparison to the diabetes and Los treatment groups. In aortas isolated from diabetic rats, rosiglitazone markedly improves endothelial dysfunction as evidenced by significantly reduced contractile responses to PE and Ang II and increased ACh-induced relaxation [5].
Animal Protocol
Rats are intravenously injected with 38 mg/kg streptozotocin and after 48 h, diabetes is identified by urinary glucosuria and then random blood sugar is measured and this day is regarded as day 0. Animals with a serum glucose level of 220-300 mg/dL are selected to be used in this study. Rats are randomly separated into five groups for daily drug administration for 8 weeks: group 1: control nondiabetic rats given a vehicle only (0.5 mL/kg of 0.5% carboxy methyl celleluse orally), group 2: control diabetic rats given a vehicle, group 3: diabetic rats receiving Rosiglitazone (5 mg/kg orally), group 4: diabetic rats receiving losartan (2 mg/kg, orally), and group 5: diabetic rats receiving both Rosiglitazone and losartan
Rats
References
[1]. Lehmann JM, et al. An antidiabetic thiazolidinedione is a high affinity ligand for peroxisome proliferator-activated receptor gamma (PPAR gamma). J Biol Chem. 1995 Jun 2;270(22):12953-6.
[2]. Willson TM, et al. The structure-activity relationship between peroxisome proliferator-activated receptor gamma agonism and the antihyperglycemic activity of thiazolidinediones. J Med Chem. 1996 Feb 2;39(3):665-8.
[3]. Thouennon E, et al. Rosiglitazone-activated PPARγ induces neurotrophic factor-α1 transcription contributing to neuroprotection. J Neurochem. 2015 Aug;134(3):463-70.
[4]. Majeed Y, et al. Rapid and contrasting effects of rosiglitazone on transient receptor potential TRPM3 and TRPC5 channels. Mol Pharmacol. 2011 Jun;79(6):1023-30.
[5]. Ateyya H, et al. Beneficial effects of rosiglitazone and losartan combination in diabetic rats. Can J Physiol Pharmacol. 2018 Mar;96(3):215-220
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C18H19N3O3S.C4H4O4
Molecular Weight
473.5
CAS #
155141-29-0
SMILES
S1C(N([H])C(C1([H])C([H])([H])C1C([H])=C([H])C(=C([H])C=1[H])OC([H])([H])C([H])([H])N(C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=N1)=O)=O.O([H])C(/C(/[H])=C(/[H])\C(=O)O[H])=O
Synonyms
BRL 49653; BRL49653;BRL-49653;Rosiglitazone Maleate; Avandia; Avandaryl; BRL-49653C; BRL49653C; BRL 49653C; BRL-49653-C;
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: 94 mg/mL (198.5 mM)
Water:<1 mg/mL
Ethanol:<1 mg/mL
Solubility (In Vivo)

Chemical Name: 5-[[4-[2-[Methyl(pyridin-2-yl)amino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione maleate

InChi Key: SUFUKZSWUHZXAV-BTJKTKAUSA-N

InChi Code: InChI=1S/C18H19N3O3S.C4H4O4/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;5-3(6)1-2-4(7)8/h2-9,15H,10-12H2,1H3,(H,20,22,23);1-2H,(H,5,6)(H,7,8)/b;2-1-

SMILES Code: O=C(N1)SC(CC2=CC=C(OCCN(C)C3=NC=CC=C3)C=C2)C1=O.O=C(O)/C=C\C(O)=O

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.1119 mL 10.5597 mL 21.1193 mL
5 mM 0.4224 mL 2.1119 mL 4.2239 mL
10 mM 0.2112 mL 1.0560 mL 2.1119 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

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Biological Data
  • Rosiglitazone maleate


    The PPARγ agonist rosiglitazone partially reverses the effect of GCN2 deficiency on liver and serum triglycerides and lipid droplet protein expression.PLoS One. 2013; 8(10): e75917.
  • Rosiglitazone maleate


    Administration of α-GalCer induces activation of CD4+ T cells in myometrial tissues that is reduced by rosiglitazone.



    Rosiglitazone maleate


    Administration of α-GalCer induces an expansion of activated CD1d-restricted iNKT cells in decidual tissues, which is blunted by rosiglitazone.J Immunol. 2016 Feb 1; 196(3): 1044–1059.
  • Rosiglitazone maleate


    Administration of α-GalCer induces activation of innate immune cells at the maternal-fetal interface that is blunted by rosiglitazone.

    Rosiglitazone maleate


    Rosiglitazone treatment reduces the rate of α-GalCer-induced late PTB by inducing PPARγ activation at the maternal-fetal interface.J Immunol. 2016 Feb 1; 196(3): 1044–1059.
  • Rosiglitazone maleate


    Body and organ weights of animals fed for 7 wk with either nonsupplemented (gray bar) or rosiglitazone-supplemented (black bar) diet.Endocrinology.2004 Jan;145(1):401-6.
  • Rosiglitazone maleate


    DXA of total-body BMD.



    Rosiglitazone maleate


    Micro-CT representative renderings of proximal tibia from control and rosiglitazone-treated animals were generated as described in Materials and Methods.Endocrinology.2004 Jan;145(1):401-6.
  • Rosiglitazone maleate


    Representative photomicrographs of cancellous tibia.



    Rosiglitazone maleate


    Liver histological cross-sections representative for each group.Endocrinology.2004 Jan;145(1):401-6.
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