5-(4-[(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)methoxy]benzyl)thiazolidine-2,4-dione
Troglitazone
CAS: 97322-87-7
Molecular Formula: C24H27NO5S
5-(4-[(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)methoxy]benzyl)thiazolidine-2,4-dione - Names and Identifiers
| Name | Troglitazone |
| Synonyms | Troglitazone TroglitazoneMesylate Troglitazone for research 2,4-thiazolidinedione,5-((4-((3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2h-1-b 5-(4-[(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)methoxy]benzyl)thiazolidine-2,4-dione CS-045, (±)-5-[4-[(6-Hydroxy-2,5,7,8-tetramethylchroman-2-yl)methoxy]benzyl]-2,4-thiazolidinedione 5-[[4-[(3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl)methoxy]-phenyl]methyl]-2,4-thiazolidinedione, Romglizone, CS-045, CI-991,Noscal, |
| CAS | 97322-87-7 |
| InChI | InChI=1/C24H27NO5S/c1-13-14(2)21-18(15(3)20(13)26)9-10-24(4,30-21)12-29-17-7-5-16(6-8-17)11-19-22(27)25-23(28)31-19/h5-8,19,26H,9-12H2,1-4H3,(H,25,27,28) |
| InChIKey | GXPHKUHSUJUWKP-UHFFFAOYSA-N |
5-(4-[(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)methoxy]benzyl)thiazolidine-2,4-dione - Physico-chemical Properties
| Molecular Formula | C24H27NO5S |
| Molar Mass | 441.54 |
| Density | 1.266±0.06 g/cm3(Predicted) |
| Melting Point | 184-186°C |
| Boling Point | 657.0±55.0 °C(Predicted) |
| Solubility | DMSO : 80 mg/mL mother liquor preservation: sub-package and freeze storage to avoid repeated freezing and thawing;-20 ℃,1 month;-80 ℃,6 months (after dilution, the solution temperature is low and storage may precipitate, try to use it now) Cell experiment: Dissolve with DMSO first: dilute with culture medium then, and the dilution process is recommended to be carried out in stages to avoid too fast concentration change leading to compound precipitation. If the compound is precipitated during the dilution process, it can be redissolved by ultrasound. During dilution, ensure that the final concentration of DMSO in the working fluid should be below 0.1% as far as possible, and the maximum should not exceed 0.5%, and set up a DMSO control group with corresponding concentration. Animal experiment: Dissolve with DMSO first: dilute with water or normal saline, etc. The dilution process is recommended to be carried out in sections to avoid excessive concentration changes leading to compound p |
| Appearance | solid |
| Color | white to yellow |
| pKa | 6.34±0.50(Predicted) |
| Storage Condition | Inert atmosphere,Store in freezer, under -20°C |
| Stability | Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months. |
| Physical and Chemical Properties | Crystallized from benzene-acetone, melting point 184-186 ℃. |
| Use | Troglitazone, also known as CI991, is a potent PPAR agonist. Troglitazone is an antidiabetic and anti-inflammatory drug, and a member of the drug class of the thiazolidinediones. It was prescribed for patients with diabetes mellitus type 2 in Japan Troglitazone, like the other thiazolidinediones (pioglitazone and rosiglitazone), works by activating peroxisome proliferator-activated receptors (PPARs). Troglitazone is a ligand to both PPARα and - more strongly - PPARγ. |
| Target | PPARγ |
| In vitro study | Troglitazone significantly inhibits cell growth by arresting the cell cycle and causing apoptotic cell death. In FTC-133 cells, the surface expression of CD97 (a novel dedifferentiation marker) was down-regulated; In TPC-1 and FTC-133 cells, the sodium iodide transporter NIS mRNA was up-regulated. As a PPARγ agonist, Troglitazone induces antiproliferative and redifferentiation effects in thyroid cancer cells. In human prostate cancer cells, Troglitazone induces Erk phosphorylation independent of the PPARγ signaling pathway. TGZ(Troglitazone) upregulates NOS, induces p53 pathway, inhibits cholesterol synthesis, induces p21 cyclin-dependent kinase inhibitor, has antioxidant function, and activates ERK in a mechanism independent of PPARγ. TGZ can also induce the expression of Egr-1 through transcriptional and post-transcriptional regulation, and enhance the binding affinity and transactivation activity of promoters containing Egr-1 consensus sequences, thus inducing the production of other antitumor proteins. |
| In vivo study | Troglitazone is an effective anti-diabetic drug that works by a completely new mechanism. However, within a few years of its widespread use, it was found to cause liver damage and liver failure in some individuals. TGZ significantly inhibited tumor growth in immunodeficient mice harboring HCT-116, MCF-7, PC-3 cancer cells. In an experimental model of chronic pancreatitis, Troglitazone reduces pancreatic injury and inflammation. |
5-(4-[(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)methoxy]benzyl)thiazolidine-2,4-dione - Risk and Safety
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 2 |
| RTECS | XJ5813130 |
| HS Code | 29145090 |
5-(4-[(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)methoxy]benzyl)thiazolidine-2,4-dione - Reference
| Reference Show more | 1: Ikeda T. Drug-induced idiosyncratic hepatotoxicity: prevention strategy developed after the troglitazone case. Drug Metab Pharmacokinet. 2011;26(1):60-70. Epub 2010 Dec 17. Review. PubMed PMID: 21178300. 2: Sangraula H, Paudel KR, Sharma M. Metformin and troglitazone in the treatment of female infertility associated with polycystic ovarian syndrome. JNMA J Nepal Med Assoc. 2009 Oct-Dec;48(176):335-9. Review. PubMed PMID: 21105563. 3: Yokoi T. Troglitazone. Handb Exp Pharmacol. 2010;(196):419-35. doi: 10.1007/978-3-642-00663-0_14. Review. PubMed PMID: 20020270. 4: Masubuchi Y. Metabolic and non-metabolic factors determining troglitazone hepatotoxicity: a review. Drug Metab Pharmacokinet. 2006 Oct;21(5):347-56. Review. PubMed PMID: 17072088. 5: Chojkier M. Troglitazone and liver injury: in search of answers. Hepatology. 2005 Feb;41(2):237-46. Review. PubMed PMID: 15657914. 6: Hug H, Dannecker R, Schindler R, Bagatto D, Stephan A, Wess RA, Gut J. Ontology-based knowledge management of troglitazone-induced hepatotoxicity. Drug Discov Today. 2004 Nov 15;9(22):948-54. Review. PubMed PMID: 15539136. 7: Lord JM, Flight IH, Norman RJ. Insulin-sensitising drugs (metformin, troglitazone, rosiglitazone, pioglitazone, D-chiro-inositol) for polycystic ovary syndrome. Cochrane Database Syst Rev. 2003;(3):CD003053. Review. Update in: Cochrane Database Syst Rev. 2009;(3):CD003053. PubMed PMID: 12917943. 8: Smith MT. Mechanisms of troglitazone hepatotoxicity. Chem Res Toxicol. 2003 Jun;16(6):6 |
5-(4-[(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)methoxy]benzyl)thiazolidine-2,4-dione - Preparation solution concentration reference
| 1mg | 5mg | 10mg | |
|---|---|---|---|
| 1 mM | 2.265 ml | 11.324 ml | 22.648 ml |
| 5 mM | 0.453 ml | 2.265 ml | 4.53 ml |
| 10 mM | 0.226 ml | 1.132 ml | 2.265 ml |
| 5 mM | 0.045 ml | 0.226 ml | 0.453 ml |
Last Update：2024-01-02 23:10:35
5-(4-[(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)methoxy]benzyl)thiazolidine-2,4-dione - Cell Experiment
Troglitazone is made at 100 mM concentration in DMSO and added to the culture medium at the final concentration of less than 0.1%. The effect of PPARγ ligands on cell proliferation of RCC cells is determined using MTT assay. Briefly, cells of 0.5×l04 cells/well are inoculated into a 96-well plate, treated with pioglitazone or troglitazone at various concentrations. After an incubation for 24 h, 20 µL/well 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT, 5 g/L) is added to each well, the medium is then removed, and 200 µL of 0.04mol/LHCl in isopropanol is added to dissolve the reduced formazan product. The plate is read in a microplate reader at 590 nm. Cell lines: Thyroid cancer cell lines TPC-1, FTC-133, FTC-236, FTC-238, XTC-1 and ARO82-1 cell lines
Last Update：2023-08-16 21:32:38
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View History
5-(4-[(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)methoxy]benzyl)thiazolidine-2,4-dione
2-Chloro-8-isopropoxyquinazoline
1037082-11-3
1-(2-fluoro-5-methylphenyl)-2-methylbutan-1-ol
405140-31-0
1000576-85-1
61319-99-1
(1R-TRANS)-Α-ACETATE 1-HYDROXY-4-(1-METHYLETHENYL)-2-CYCLOHEXENE-1-METHANOL
2-{[1-(3-iodophenyl)-1H-imidazol-2-yl]sulfanyl}acetic acid
Vamorolone Impurity 58
2-Chloro-8-isopropoxyquinazoline
1037082-11-3
1-(2-fluoro-5-methylphenyl)-2-methylbutan-1-ol
405140-31-0
1000576-85-1
61319-99-1
(1R-TRANS)-Α-ACETATE 1-HYDROXY-4-(1-METHYLETHENYL)-2-CYCLOHEXENE-1-METHANOL
2-{[1-(3-iodophenyl)-1H-imidazol-2-yl]sulfanyl}acetic acid
Vamorolone Impurity 58