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Ciglitazone

Ciglitazone structure

CAS No:
74772-77-3
Formula:
C18H23NO3S
Chemical Name:
Ciglitazone
Synonyms:
2,4-Thiazolidinedione,5-[[4-[(1-methylcyclohexyl)methoxy]phenyl]methyl]-;5-[[4-[(1-Methylcyclohexyl)methoxy]phenyl]methyl]-2,4-thiazolidinedione;ADD 3878;Ciglitazone;U 63287
Categories:
Flavors and Fragrances > Natural Spices

Description

White Cyrstalline Solid

Ciglitazone is an aromatic ether that consists of 1,3-thiazolidine-2,4-dione with position 5 substituted by a 4-[(1-methylcyclohexyl)methoxy]benzyl group. A selective PPARgamma agonist. It has a role as an insulin-sensitizing drug and an antineoplastic agent. It is a thiazolidinone and an aromatic ether.|Developed by Takeda Pharmaceuticals in the early 1980s, it is considered the prototypical compound for the thiazolidinedione class. Ciglitazone was never used as a medication, but it sparked interest in the effects of thiazolidinediones. Several analogues were later developed, some of which—such as pioglitazone and troglitazone—made it to the market. Ciglitazone significantly decreases VEGF production by human granulosa cells in an in vitro study, and may potentially be used in ovarian hyperstimulation syndrome. Ciglitazone is a potent and selective PPARγ ligand with an EC50 of 3.0 µM. It is also an anti-hyperglycemic agent in the ob/ob murine model in vivo. Ciglitazone increases adipogenesis, decreases differentiation and angiogenesis in human umbilical vein endothelial cell (HUVEC), and osteoblastogenesis in human mesenchymal stem cells.

Ciglitazone Basic Attributes

Molecular Weight：

333.45

Exact Mass：

333.45

DSSTox ID：

DTXSID0040757

HScode：

29341000

Characteristics

PSA：

80.7

XLogP3：

4.69

Appearance：

white cyrstalline solid

Density：

1.2±0.1 g/cm3

Melting Point：

130-131 °C @ Solvent: Ethanol

Boiling Point：

504.5±23.0 °C at 760 mmHg

Flash Point：

258.9±22.6 °C

Refractive Index：

1.568

Storage Conditions：

Store at RT

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

RTECS Number：

XJ5813700

Precautionary statement(s)：

P201, P202, P281, P308+P313, P405, P501

Hazard Statements：

H361

GHS Classification：

|Warning|H361 (100%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]|P201, P202, P281, P308+P313, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Drug Information

MeSH：

Substances which lower blood glucose levels. (See all compounds classified as Hypoglycemic Agents.)

MeSH Entry Terms：

5-(4-(1-methylcyclohexylmethoxy)benzyl)thiazolidine-2,4-dione

Ciglitazone Use and Manufacturing

Displays antihyperglycemic activity in genetically obese mice. It is a selective PPARg agonist

Computed Properties

Molecular Weight:333.4
XLogP3:4.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:5
Exact Mass:333.13986477
Monoisotopic Mass:333.13986477
Topological Polar Surface Area:80.7
Heavy Atom Count:23
Complexity:440
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes