Ciglitazone

Names

[ Name ]:
Ciglitazone

[Synonym ]:
Ciglitazone
UNII:U8QXS1WU8G
ciglitazonum
2,4-Thiazolidinedione, 5-[[4-[(1-methylcyclohexyl)methoxy]phenyl]methyl]-
CIGLITIZONE
CIGLITLZONE
MFCD00865499
5-[4-(1-methylcyclohexylmethoxy) benzyl]-thiazolidine-2,4-dione
Flurofamide
AD-4533
ciglitazona
ADD 3878
5-{4-[(1-Methylcyclohexyl)methoxy]benzyl}-1,3-thiazolidine-2,4-dione
Ciglitazone,5-[[4-[(1-Methylcyclohexyl)methoxy]phenyl]methyl]-2,4-thiazolidinedione

Biological Activity

[Description]:

Ciglitazone is a potent and selective PPARγ agonist (EC50=3 μM). Ciglitazone inhibits proliferation and differentiation of th17 cells. Ciglitazone is a hypoglycemic agent orally active in the obese-hyperglycemic animal models. Ciglitazone induces apoptosis accompanied by activation of p38 MAPK and nuclear translocation of apoptosis inducing factor (AIF) in opossum kidney (OK) renal epithelial cells[1][2][3][4].

[Related Catalog]:

Research Areas >> Cancer

Research Areas >> Cardiovascular Disease

Signaling Pathways >> Cell Cycle/DNA Damage >> PPAR

[In Vitro]

Ciglitazone (0-20 μM; 24 hours) induces apoptosis through PPAR-independent mechanism. Ciglitazone causes generation of ROS and an increase in intracellular Ca2+[4].

[In Vivo]

In C57BL/6J-ob/ob mice, Ciglitazone (100 mg/kg/day; 2 days) elicits a drastic fall in blood glucose. Regranulation of islet beta-cells and increased pancreatic insulin content are observed in ob/ob mice treated for 41-44 days with 100 mg/kg/day Ciglitazone[3].

[References]

[1]. 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;39(3):665-668.

[2]. Kim DH, et al. Ciglitazone, a peroxisome proliferator-activated receptor gamma ligand, inhibits proliferation and differentiation of th17 cells. Biomol Ther (Seoul). 2015;23(1):71-76.

[3]. Chang AY, et al. Ciglitazone, a new hypoglycemic agent. I. Studies in ob/ob and db/db mice, diabetic Chinese hamsters, and normal and streptozotocin-diabetic rats. Diabetes. 1983;32(9):830-838.

[4]. Kwon CH, et al. Ciglitazone induces apoptosis via activation of p38 MAPK and AIF nuclear translocation mediated by reactive oxygen species and Ca(2+) in opossum kidney cells. Toxicology. 2009;257(1-2):1-9.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
504.5±23.0 °C at 760 mmHg

[ Melting Point ]:
130-131ºC

[ Molecular Formula ]:
C₁₈H₂₃NO₃S

[ Molecular Weight ]:
333.445

[ Flash Point ]:
258.9±22.6 °C

[ Exact Mass ]:
333.139862

[ PSA ]:
80.70000

[ LogP ]:
4.69

[ Vapour Pressure ]:
0.0±1.3 mmHg at 25°C

[ Index of Refraction ]:
1.568

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: XJ5813700

CHEMICAL NAME :: 2,4-Thiazolidinedione, 5-((4-((1-methylcyclohexyl)methoxy)phenyl)methyl)-

CAS REGISTRY NUMBER :: 74772-77-3

LAST UPDATED :: 198910

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C18-H23-N-O3-S

MOLECULAR WEIGHT :: 333.48

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 950 mg/kg

SEX/DURATION :: female 1-19 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)

REFERENCE :: SEIJBO Senten Ijo. Congenital Anomalies. (Nippon Senten Ijo Gakkai, c/o Kinki Daigaku Igakubu Kaibagaku Kyoshitsu, 380 Nishiyama, Sayama-cho, Mirami-Kawachi-gun, Osaka-fu, Japan) V.1-26, 1960-86. For publisher information, see CGANE7. Volume(issue)/page/year: 26,169,1986

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;half-mask respirator (US);multi-purpose combination respirator cartridge (US)

[ Hazard Codes ]:
Xn

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
XJ5813700

Articles

Developmental regulation and induction of cytochrome P450 2W1, an enzyme expressed in colon tumors.

PLoS ONE 10(4) , e0122820, (2015)

Cytochrome P450 2W1 (CYP2W1) is expressed predominantly in colorectal and also in hepatic tumors, whereas the levels are insignificant in the corresponding normal human adult tissues. CYP2W1 has been ...

Autonomous inhibition of apoptosis correlates with responsiveness of colon carcinoma cell lines to ciglitazone.

PLoS ONE 9(12) , e114158, (2014)

Colorectal cancer is a leading cause of mortality worldwide. Resistance to therapy is common and often results in patients succumbing to the disease. The mechanisms of resistance are poorly understood...

Thiazolidinedione insulin sensitizers alter lipid bilayer properties and voltage-dependent sodium channel function: implications for drug discovery.

J. Gen. Physiol. 138(2) , 249-70, (2011)

The thiazolidinediones (TZDs) are used in the treatment of diabetes mellitus type 2. Their canonical effects are mediated by activation of the peroxisome proliferator-activated receptor γ (PPARγ) tran...