1132641-22-5

1132641-22-5 structure

Name: Rosiglitazone-d3
Chemical Name: 5-(4-{2-[(2H3)Methyl(2-pyridinyl)amino]ethoxy}benzyl)-1,3-thiazolidine-2,4-dione
CAS Number: 1132641-22-5
Molecular Formula: C₁₈H₁₆D₃N₃O₃S
Molecular Weight: 360.44500
Catalog: Signaling Pathways Apoptosis Ferroptosis
Create Date: 2016-04-10 03:13:05
Modify Date: 2024-01-20 13:12:45
Rosiglitazone-d3 (BRL 49653-d3) is the deuterium labeled Rosiglitazone. Rosiglitazone (BRL 49653) is a selective, orally active PPARγ agonist with EC50s of 30 nM, 100 nM and 60 nM for PPARγ1, PPARγ2, and PPARγ, respectively. Rosiglitazone binds to PPARγ with a Kd of approximately 40 nM. Rosiglitazone is also an activator of TRPC5 (EC50=~30 μM) and an inhibitor of TRPM3[1][2][3][4].

Name	5-(4-{2-[(2H3)Methyl(2-pyridinyl)amino]ethoxy}benzyl)-1,3-thiazolidine-2,4-dione
Synonyms	5-(4-{2-[(H)Methyl(2-pyridinyl)amino]ethoxy}benzyl)-1,3-thiazolidine-2,4-dione 2,4-Thiazolidinedione, 5-[[4-[2-(methyl-d-2-pyridinylamino)ethoxy]phenyl]methyl]-

Description	Rosiglitazone-d3 (BRL 49653-d3) is the deuterium labeled Rosiglitazone. Rosiglitazone (BRL 49653) is a selective, orally active PPARγ agonist with EC50s of 30 nM, 100 nM and 60 nM for PPARγ1, PPARγ2, and PPARγ, respectively. Rosiglitazone binds to PPARγ with a Kd of approximately 40 nM. Rosiglitazone is also an activator of TRPC5 (EC50=~30 μM) and an inhibitor of TRPM3[1][2][3][4].
Related Catalog	Signaling Pathways >> Membrane Transporter/Ion Channel >> TRP Channel Research Areas >> Cancer Signaling Pathways >> Apoptosis >> Ferroptosis Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Cell Cycle/DNA Damage >> PPAR Research Areas >> Inflammation/Immunology Research Areas >> Metabolic Disease Research Areas >> Neurological Disease
In Vitro	Stable heavy isotopes of hydrogen, carbon, and other elements have been incorporated into drug molecules, largely as tracers for quantitation during the drug development process. Deuteration has gained attention because of its potential to affect the pharmacokinetic and metabolic profiles of drugs[1].
References	[1]. Russak EM, et al. Impact of Deuterium Substitution on the Pharmacokinetics of Pharmaceuticals. Ann Pharmacother. 2019;53(2):211-216. [2]. 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. [3]. 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. [4]. Thouennon E, et al. Rosiglitazone-activated PPARγ induces neurotrophic factor-α1 transcription contributing to neuroprotection. J Neurochem. 2015 Aug;134(3):463-70. [5]. 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. [6]. Ateyya H, et al. Beneficial effects of rosiglitazone and losartan combination in diabetic rats. Can J Physiol Pharmacol. 2018 Mar;96(3):215-220.

Density	1.3±0.0 g/cm3
Boiling Point	585.0±0.0 °C at 760 mmHg
Molecular Formula	C₁₈H₁₆D₃N₃O₃S
Molecular Weight	360.44500
Flash Point	307.6±0.0 °C
Exact Mass	360.13400
PSA	96.83000
LogP	3.02
Vapour Pressure	0.0±0.0 mmHg at 25°C
Index of Refraction	1.642

1132641-22-5	1185245-57-1
122320-73-4	397263-60-4
1019201-23-0	288853-63-4
155141-29-0	920338-48-3
302543-62-0	1215168-64-1