Ciglitazone

Modify Date: 2024-01-10 17:44:45

Ciglitazone Structure
Ciglitazone structure
Common Name Ciglitazone
CAS Number 74772-77-3 Molecular Weight 333.445
Density 1.2±0.1 g/cm3 Boiling Point 504.5±23.0 °C at 760 mmHg
Molecular Formula C18H23NO3S Melting Point 130-131ºC
MSDS Chinese USA Flash Point 258.9±22.6 °C

 Use of Ciglitazone


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].

 Names

Name ciglitazone
Synonym More Synonyms

 Ciglitazone 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
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

 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

 Articles32

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 Synonyms

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