74772-77-3

74772-77-3 structure

Name: Ciglitazone
Chemical Name: ciglitazone
CAS Number: 74772-77-3
Molecular Formula: C₁₈H₂₃NO₃S
Molecular Weight: 333.445
Catalog: Signaling Pathways Cell Cycle/DNA Damage PPAR
Create Date: 2018-04-01 08:00:00
Modify Date: 2024-01-10 17:44:45
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].

Name	ciglitazone
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

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.

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

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

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

1158522-08-7	940364-43-2
134104-43-1	131615-57-1
6906-52-1	930439-75-1
2227846-68-4	1018584-77-4
1375289-11-4	849349-65-1