Troglitazone

Modify Date: 2024-01-02 04:22:18

Troglitazone structure	Common Name	Troglitazone
	CAS Number	97322-87-7	Molecular Weight	441.540
	Density	1.3±0.1 g/cm3	Boiling Point	657.0±55.0 °C at 760 mmHg
	Molecular Formula	C₂₄H₂₇NO₅S	Melting Point	184-186°C
	MSDS	USA	Flash Point	351.2±31.5 °C

Use of Troglitazone

Troglitazone is a PPARγ agonist, with EC50s of 550 nM and 780 nM for human and murine PPARγ receptor, respectively.

Name	troglitazone
Synonym	More Synonyms

Description	Troglitazone is a PPARγ agonist, with EC50s of 550 nM and 780 nM for human and murine PPARγ receptor, respectively.
Related Catalog	Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Cell Cycle/DNA Damage >> PPAR Research Areas >> Cancer
Target	PPARγ:550 nM (EC50, Human PPARγ)
In Vitro	Troglitazone is a PPARγ agonist, with EC50s of 550 nM and 780 nM for human and murine PPARγ receptor, respectively[1]. Troglitazone (2-200 μM) is cytotoxic to the pancreatic cancer cell lines (MIA Paca2 and PANC-1 cells), with IC50s of 49.9 ± 1.2 and 51.3 ± 5.3 μM, respectively. Troglitazone (50 μM) increases chromatin condensation in MIA Paca2 and PANC-1 cells, enhances the activity of caspase-3 and decreases Bcl-2 expression[2]. Troglitazone (0, 1, 2, and 4 μM) sensitizes TRAIL-mediated apoptosis in human lung adenocarcinoma cells. Troglitazone enhancement of TRAIL-induced apoptosis is blocked by inhibition of autophagy, via activation of autophagy flux. In addition, the effects of troglitazone are induced by PPARγ activation in A549 cells[3].
In Vivo	Troglitazone (200 mg/kg, p.o.) shows inhibitory effects on the growth of tumor in the MIA Paca2 xenograft model[2].
Cell Assay	Briefly, cells are seeded into 96-well plates at a density of 1 × 105 cells/well and incubated for 24 h. The cells are treated with Troglitazone in the presence or absence of other chemicals for a further 24 h using FBS-free medium. The assay utilizes the conversion of alamar blue reagent to fluorescent resorufin by metabolically active cells. The resorufin signal is measured at an excitation wavelength of 530 nm and an emission wavelength of 580 nm. The 50% growth inhibitory concentrations (IC50) are calculated according to the sigmoid inhibitory effect model E = IC50 γ/(IC50 γ + Cγ), where E represents the surviving fraction (% of control), C represents the drug concentration in the medium, and γ represents the Hill coefficient. For co-exposure studies, the Troglitazone dosage is set to approximately the IC50 value for each cell line[2].
Animal Admin	Balb/c male mice (4 weeks old) are subcutaneously inoculated in the back with MIA Paca2 cells (5 × 106 cells/100 μL in PBS) 14 days prior to starting Troglitazone administration. Mice are then orally administered 200 mg/kg Troglitazone in 0.5% methylcellulose solution or vehicle daily for 5 weeks. Tumor size is measured bi-dimensionally and the volume is calculated using the formula (length × width2) × 0.5. Body weights of mice are also monitored throughout the experiment[2].
References	[1]. Willson TM, et al. The PPARs: from orphan receptors to drug discovery. J Med Chem. 2000 Feb 24;43(4):527-50. [2]. Fujita M, et al. In vitro and in vivo cytotoxicity of troglitazone in pancreatic cancer. J Exp Clin Cancer Res. 2017 Jul 3;36(1):91. [3]. Nazim UM, et al. PPARγ activation by troglitazone enhances human lung cancer cells to TRAIL-induced apoptosis via autophagy flux. Oncotarget. 2017 Apr 18;8(16):26819-26831.

Density	1.3±0.1 g/cm3
Boiling Point	657.0±55.0 °C at 760 mmHg
Melting Point	184-186°C
Molecular Formula	C₂₄H₂₇NO₅S
Molecular Weight	441.540
Flash Point	351.2±31.5 °C
Exact Mass	441.160980
PSA	110.16000
LogP	4.99
Vapour Pressure	0.0±2.1 mmHg at 25°C
Index of Refraction	1.608
Storage condition	Store at -20°C
Water Solubility	DMSO: 20 mg/mL

CHEMICAL IDENTIFICATION

RTECS NUMBER :: XJ5813130

CHEMICAL NAME :: 2,4-Thiazolidinedione, 5-((4-((3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H- 1-benzopyran-2-yl)met hoxy)phenyl)methyl)-

CAS REGISTRY NUMBER :: 97322-87-7

LAST UPDATED :: 199806

DATA ITEMS CITED :: 7

MOLECULAR FORMULA :: C24-H27-N-O5-S

MOLECULAR WEIGHT :: 441.58

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 26,953,1995

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >4 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 26,953,1995

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >300 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: EPXXDW European Patent Application. (U.S. Patent and Trademark Office, Foreign Patents, Washington, DC 20231) Volume(issue)/page/year: #439321

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 26,953,1995 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 4550 mg/kg/13W-I

TOXIC EFFECTS :: Liver - other changes Liver - changes in liver weight

REFERENCE :: TOXID9 Toxicologist. (Soc. of Toxicology, Inc., 475 Wolf Ledge Parkway, Akron, OH 44311) V.1- 1981- Volume(issue)/page/year: 36(1,pt2),273,1997

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 36400 mg/kg/13W-I

TOXIC EFFECTS :: Cardiac - changes in heart weight Blood - changes in bone marrow (not otherwise specified) Related to Chronic Data - changes in testicular weight

REFERENCE :: TOXID9 Toxicologist. (Soc. of Toxicology, Inc., 475 Wolf Ledge Parkway, Akron, OH 44311) V.1- 1981- Volume(issue)/page/year: 36(1,pt2),273,1997

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: 109 gm/kg/52W-I

TOXIC EFFECTS :: Liver - changes in liver weight Blood - normocytic anemia Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol)

REFERENCE :: TOXID9 Toxicologist. (Soc. of Toxicology, Inc., 475 Wolf Ledge Parkway, Akron, OH 44311) V.1- 1981- Volume(issue)/page/year: 36(1,pt2),273,1997

Safety Phrases	S22-S24/25
WGK Germany	2
RTECS	XJ5813130

Precursor 5
CAS#:109-86-4 2-methoxyethanol CAS#:79907-49-6 2-HYDROXYMETHYL... CAS#:107188-58-9 6-Hydroxy-2,5,7... CAS#:118070-84-1 6-(Methoxymetho...
CAS#:107187-56-4 (+/-)-5-[4-(6-h...
DownStream 0

Romglizone

5-{4-[(6-Hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl)methoxy]benzyl}-1,3-thiazolidine-2,4-dione

Rezulin (TN)

Rezulin

5-[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl-methoxy)-benzyl]thiazolidine-2,4-dione

MFCD00878416

5-[(4-{[(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl)methyl]oxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione

5-[4-[(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)methoxy]-benzyl]-2,4-thiazolidinedione

CS-045

3-phenyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine

Noscal

Prelay

[14C]-Troglitazone

2,4-Thiazolidinedione, 5-[[4-[(3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl)methoxy]phenyl]methyl]-

5-[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]-2,4-dioxothiazolidine

5-[[4-[(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromen-2-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione

Romozin

Troglitazone

[3H]-Troglitazone

Resulin

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