5-(4-(2-(Methyl(pyridin-2-yl)amino)ethoxy)benzyl)thiazolidine-2,4-dione sodium salt CAS#: 316371-83-2

5-(4-(2-(Methyl(pyridin-2-yl)amino)ethoxy)benzyl)thiazolidine-2,4-dione sodium salt Basic information

Product Name:

5-(4-(2-(Methyl(pyridin-2-yl)amino)ethoxy)benzyl)thiazolidine-2,4-dione sodium salt

Synonyms:

rosiglitazone sodium
5-(4-(2-(methyl(pyridin-2-yl)amino)ethoxy)benzyl)thiazolidine-2,4-dione sodium salt
5-[4-[2-(N-Methyl-N-(2-pyridyl)amino)ethoxy]benzylidine]-2,4-thiazolidinedione Sodium
sodiuM 5-[(4-{2-[Methyl(pyridin-2-yl)aMino]ethoxy}phenyl)Methyl]-1,3-thiazolidine-2,4-dione
UNII:YR4MBO751R
sodium,5-[[4-[2-[methyl(pyridin-2-yl)amino]ethoxy
5-{[4-({2-[methyl(pyridin-2-yl)amino]ethyl}oxy)phenyl]methyl}-1,3-thiazolidine-2,4-dione

CAS:

316371-83-2

MF:

C18H18N3NaO3S

MW:

379.40859

Mol File:

316371-83-2.mol

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5-(4-(2-(Methyl(pyridin-2-yl)amino)ethoxy)benzyl)thiazolidine-2,4-dione sodium salt Chemical Properties

storage temp.: Sealed in dry,Room Temperature
InChI: InChI=1S/C18H19N3O3S.Na/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);/q;+1/p-1
InChIKey: XFOHHIYSRDUSCX-UHFFFAOYSA-M
SMILES: N1([Na])C(=O)C(CC2C=CC(=CC=2)OCCN(C)C2=CC=CC=N2)SC1=O

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5-(4-(2-(Methyl(pyridin-2-yl)amino)ethoxy)benzyl)thiazolidine-2,4-dione sodium salt Usage And Synthesis

Uses

Rosiglitazone sodium is a potent and selective activator of PPARγ, with EC50s of 30 nM, 100 nM and 60 nM for PPARγ1, PPARγ2, and PPARγ, respectively, and a Kd of appr 40 nM for PPARγ; Rosiglitazone sodium is also an modulator of TRP channels, inhibits TRP melastatin 2 (TRPM2), TRPM3 and activates TRP canonical 5 (TRPC5).

in vivo

Rosiglitazone (5 mg/kg, p.o.) decreases the serum glucose in diabetic rats. Rosiglitazone also decreases IL-6, TNF-α, and VCAM-1 levels in diabetic group. Rosiglitazone in combination with losartan increases glucose compared to diabetic and Los-treated groups. Rosiglitazone significantly ameliorates endothelial dysfunction indicated by a significantly lower contractile response to PE and Ang II and enhancement of ACh-provoked relaxation in aortas isolated from diabetic rats^[5].

IC 50

PPARγ1: 30 nM (EC₅₀); PPARγ2: 100 nM (EC₅₀)

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. DOI:10.1074/jbc.270.22.12953
[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. DOI:10.1021/jm950395a
[3] Thouennon E, et al. Rosiglitazone-activated PPARγ induces neurotrophic factor-α1 transcription contributing to neuroprotection. J Neurochem. 2015 Aug;134(3):463-70. DOI:10.1111/jnc.13152
[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. DOI:10.1124/mol.110.069922
[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. DOI:10.1139/cjpp-2017-0332

5-(4-(2-(Methyl(pyridin-2-yl)amino)ethoxy)benzyl)thiazolidine-2,4-dione sodium saltSupplier

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