Troglitazone
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MedKoo CAT#: 526511

CAS#: 97322-87-7

Description: 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. Troglitazone inhibits hepatic oval cell proliferation by inducing cell cycle arrest through Hippo/YAP pathway regulation. Troglitazone exerts metabolic and antitumor effects on T47D breast cancer cells by suppressing mitochondrial pyruvate availability. Troglitazone activates TRPV1 and causes deacetylation of PPARγ in 3T3-L1 cells.

Chemical Structure

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Troglitazone
CAS# 97322-87-7
Instruction

Theoretical Analysis

MedKoo Cat#: 526511
Name: Troglitazone
CAS#: 97322-87-7
Chemical Formula: C24H27NO5S
Exact Mass: 441.16
Molecular Weight: 441.542
Elemental Analysis: C, 65.29; H, 6.16; N, 3.17; O, 18.12; S, 7.26

Price and Availability

Size Price Availability Quantity
10mg USD 350 2 Weeks
50mg USD 950 2 Weeks
100mg USD 1650 2 Weeks
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Synonym: CI-991; CI991; CI 991; CS-045; GR 92132X; GR92132X; Prelay; Troglitazone; Rezulin, Resulin, Romozin, Noscal.

IUPAC/Chemical Name: 5-(4-((6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)methoxy)benzyl)thiazolidine-2,4-dione

InChi Key: GXPHKUHSUJUWKP-UHFFFAOYSA-N

InChi Code: InChI=1S/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)

SMILES Code: O=C(N1)SC(CC2=CC=C(OCC3(C)CCC4=C(C)C(O)=C(C)C(C)=C4O3)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

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 441.54 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.

Recalculate based on batch purity %
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:
In vitro protocol:
In vivo protocol:

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1: Tsujiya Y, Hasegawa A, Yamamori M, Okamura N. Troglitazone-Induced Autophagic Cytotoxicity in Lung Adenocarcinoma Cell Lines. Biol Pharm Bull. 2022;45(3):276-283. doi: 10.1248/bpb.b21-00785. PMID: 35228393.


2: Wei H, Li AP. Permeabilized Cryopreserved Human Hepatocytes as an Exogenous Metabolic System in a Novel Metabolism-Dependent Cytotoxicity Assay for the Evaluation of Metabolic Activation and Detoxification of Drugs Associated with Drug-Induced Liver Injuries: Results with Acetaminophen, Amiodarone, Cyclophosphamide, Ketoconazole, Nefazodone, and Troglitazone. Drug Metab Dispos. 2022 Feb;50(2):140-149. doi: 10.1124/dmd.121.000645. Epub 2021 Nov 8. PMID: 34750194.


3: Lewoniewska S, Oscilowska I, Huynh TYL, Prokop I, Baszanowska W, Bielawska K, Palka J. Troglitazone-Induced PRODH/POX-Dependent Apoptosis Occurs in the Absence of Estradiol or ERβ in ER-Negative Breast Cancer Cells. J Clin Med. 2021 Oct 10;10(20):4641. doi: 10.3390/jcm10204641. PMID: 34682765; PMCID: PMC8538344.


4: He Y, Li H, He Y, Lu C, Zhu P, Li M, Duan J, Fang Z. Troglitazone inhibits hepatic oval cell proliferation by inducing cell cycle arrest through Hippo/YAP pathway regulation. Dig Liver Dis. 2022 Jun;54(6):791-799. doi: 10.1016/j.dld.2021.08.018. Epub 2021 Sep 13. PMID: 34531129.


5: Moon JH, Hong JM, Park SY. The antidiabetic drug troglitazone protects against PrP (106‑126)‑induced neurotoxicity via the PPARγ‑autophagy pathway in neuronal cells. Mol Med Rep. 2021 Jun;23(6):430. doi: 10.3892/mmr.2021.12069. Epub 2021 Apr 13. PMID: 33846779; PMCID: PMC8047904.


6: Kores K, Konc J, Bren U. Mechanistic Insights into Side Effects of Troglitazone and Rosiglitazone Using a Novel Inverse Molecular Docking Protocol. Pharmaceutics. 2021 Feb 28;13(3):315. doi: 10.3390/pharmaceutics13030315. PMID: 33670968; PMCID: PMC7997210.


7: Dupommier D, Muller C, Comoy C, Mazerbourg S, Bordessa A, Piquard E, Pawlak M, Piquard F, Martin H, De Fays E, Grandemange S, Flament S, Boisbrun M. Corrigendum to "New desulfured troglitazone derivatives: Improved synthesis and biological evaluation" [Eur. J. Med. Chem. 187 (2020) 111939]. Eur J Med Chem. 2020 Dec 15;208:112834. doi: 10.1016/j.ejmech.2020.112834. Epub 2020 Sep 20. Erratum for: Eur J Med Chem. 2020 Feb 1;187:111939. PMID: 32966897.


8: Ito S, Kamimura H, Yamamoto Y, Chijiwa H, Okuzono T, Suemizu H, Yamazaki H. Human plasma concentration-time profiles of troglitazone and troglitazone sulfate simulated by in vivo experiments with chimeric mice with humanized livers and semi-physiological pharmacokinetic modeling. Drug Metab Pharmacokinet. 2020 Dec;35(6):505-514. doi: 10.1016/j.dmpk.2020.07.004. Epub 2020 Jul 30. PMID: 32962912.


9: Saito M, Fujita Y, Kuribayashi N, Uchida D, Komiyama Y, Fukumoto C, Hasegawa T, Kawamata H. Troglitazone, a Selective Ligand for PPARγ, Induces Cell-cycle Arrest in Human Oral SCC Cells. Anticancer Res. 2020 Mar;40(3):1247-1254. doi: 10.21873/anticanres.14066. PMID: 32132021.


10: Tao K, Bai X, Zhang D, Liu M, Zhang Y, Han F, Yang X, Han J, Hu D. Encapsulation of troglitazone and AVE0991 by gelation microspheres promotes epithelial transformation of adipose-derived stem cells. Mol Cell Probes. 2020 Jun;51:101543. doi: 10.1016/j.mcp.2020.101543. Epub 2020 Feb 24. PMID: 32105703.


11: Jung KH, Lee JH, Park JW, Moon SH, Cho YS, Lee KH. Troglitazone exerts metabolic and antitumor effects on T47D breast cancer cells by suppressing mitochondrial pyruvate availability. Oncol Rep. 2020 Feb;43(2):711-717. doi: 10.3892/or.2019.7436. Epub 2019 Dec 16. PMID: 31894283.


12: Dupommier D, Muller C, Comoy C, Mazerbourg S, Bordessa A, Piquard E, Pawlak M, Piquard F, Martin H, De Fays E, Grandemange S, Flament S, Boisbrun M. New desulfured troglitazone derivatives: Improved synthesis and biological evaluation. Eur J Med Chem. 2020 Feb 1;187:111939. doi: 10.1016/j.ejmech.2019.111939. Epub 2019 Dec 4. Erratum in: Eur J Med Chem. 2020 Dec 15;208:112834. PMID: 31838327.


13: Yu L, Li H, Zhang C, Zhang Q, Guo J, Li J, Yuan H, Li L, Carmichael P, Peng S. Integrating in vitro testing and physiologically-based pharmacokinetic (PBPK) modelling for chemical liver toxicity assessment-A case study of troglitazone. Environ Toxicol Pharmacol. 2020 Feb;74:103296. doi: 10.1016/j.etap.2019.103296. Epub 2019 Nov 5. PMID: 31783317.


14: Sato T, Segawa M, Sekine S, Ito K. Mild depolarization is involved in troglitazone-induced liver mitochondrial membrane permeability transition via mitochondrial iPLA2 activation. J Toxicol Sci. 2019;44(11):811-820. doi: 10.2131/jts.44.811. PMID: 31708537.


15: Chang JH, Sangaraju D, Liu N, Jaochico A, Plise E. Comprehensive Evaluation of Bile Acid Homeostasis in Human Hepatocyte Co-Culture in the Presence of Troglitazone, Pioglitazone, and Acetylsalicylic Acid. Mol Pharm. 2019 Oct 7;16(10):4230-4240. doi: 10.1021/acs.molpharmaceut.9b00562. Epub 2019 Sep 26. PMID: 31509422.


16: Jia R, Oda S, Tsuneyama K, Urano Y, Yokoi T. Establishment of a mouse model of troglitazone-induced liver injury and analysis of its hepatotoxic mechanism. J Appl Toxicol. 2019 Nov;39(11):1541-1556. doi: 10.1002/jat.3838. Epub 2019 Jul 11. PMID: 31294483.


17: Fukano K, Tsukuda S, Oshima M, Suzuki R, Aizaki H, Ohki M, Park SY, Muramatsu M, Wakita T, Sureau C, Ogasawara Y, Watashi K. Troglitazone Impedes the Oligomerization of Sodium Taurocholate Cotransporting Polypeptide and Entry of Hepatitis B Virus Into Hepatocytes. Front Microbiol. 2019 Jan 8;9:3257. doi: 10.3389/fmicb.2018.03257. PMID: 30671048; PMCID: PMC6331526.


18: Krishnan V, Baskaran P, Thyagarajan B. Troglitazone activates TRPV1 and causes deacetylation of PPARγ in 3T3-L1 cells. Biochim Biophys Acta Mol Basis Dis. 2019 Feb 1;1865(2):445-453. doi: 10.1016/j.bbadis.2018.11.004. Epub 2018 Nov 26. PMID: 30496795; PMCID: PMC6364553.


19: Chang SN, Lee JM, Oh H, Kim U, Ryu B, Park JH. Troglitazone inhibits the migration and invasion of PC-3 human prostate cancer cells by upregulating E-cadherin and glutathione peroxidase 3. Oncol Lett. 2018 Oct;16(4):5482-5488. doi: 10.3892/ol.2018.9278. Epub 2018 Aug 8. PMID: 30250621; PMCID: PMC6144768.


20: Zhong WB, Tsai YC, Chin LH, Tseng JH, Tang LW, Horng S, Fan YC, Hsu SP. A Synergistic Anti-Cancer Effect of Troglitazone and Lovastatin in a Human Anaplastic Thyroid Cancer Cell Line and in a Mouse Xenograft Model. Int J Mol Sci. 2018 Jun 22;19(7):1834. doi: 10.3390/ijms19071834. PMID: 29932104; PMCID: PMC6073567.