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CIGLITAZONE

Product Name
CIGLITAZONE
CAS No.
74772-77-3
Chemical Name
CIGLITAZONE
Synonyms
U-63287;AD-4533;ADD 3878;CIGLITIZONE;CIGLITAZONE;CIGLITLZONE;Ciglitazona;CIGLITAZONE USP/EP/BP;Ciglitazone Solution, 100ppm;CIGLITAZONE(SUBJECTTOPATENTFREE)
CBNumber
CB5416208
Molecular Formula
C18H23NO3S
Formula Weight
333.45
MOL File
74772-77-3.mol
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CIGLITAZONE Property

Melting point:
130-131°C
Boiling point:
504.5±23.0 °C(Predicted)
Density 
1.189±0.06 g/cm3(Predicted)
storage temp. 
Store at RT
solubility 
Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml).
form 
Tan solid
pka
6.36±0.50(Predicted)
color 
Tan
Stability:
Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
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Safety

WGK Germany 
3
RTECS 
XJ5813700
HS Code 
29341000
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H361Suspected of damaging fertility or the unborn child

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P281Use personal protective equipment as required.

P308+P313IF exposed or concerned: Get medical advice/attention.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
C3974
Product name
Ciglitizone
Purity
≥98% (HPLC)
Packaging
5mg
Price
$368
Updated
2024/03/01
Sigma-Aldrich
Product number
230950
Product name
Ciglitazone
Packaging
5mg
Price
$208
Updated
2024/03/01
Alfa Aesar
Product number
J67131
Product name
Ciglitizone, 98%
Packaging
5mg
Price
$170
Updated
2021/12/16
Cayman Chemical
Product number
71730
Product name
Ciglitazone
Purity
≥98%
Packaging
1mg
Price
$23
Updated
2024/03/01
Cayman Chemical
Product number
71730
Product name
Ciglitazone
Purity
≥98%
Packaging
5mg
Price
$100
Updated
2024/03/01
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CIGLITAZONE Chemical Properties,Usage,Production

Description

Ciglitazone (74772-77-3) is a PPARγ agonist (EC50=3 μM). Stimulates adipogenesis in human mesenchymal stem cells. Ciglitazone inhibits HUVEC differentiation and angiogenesis. Cell permeable.

Chemical Properties

White Cyrstalline Solid

Originator

Ciglitazone, synthetized by Takeda and reported in 1982, was a result of screening of clofibrate analogues for hypolipidemic activity.

Uses

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

Uses

Ciglitizone has been used as a proliferator-activated receptor γ (PPARγ) agonist:

  • to study its effects on cell proliferation in human melanocytes
  • to study its effects on pigmentation and migration of human melanocytes

It also may be used to study its effects on cell cycle and apoptosis in monocytic cells.

Definition

ChEBI: 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.

General Description

A potent thiazolinedione (TDZ) type anti-hyperglycemic agent and a selective PPARγ agonist (EC50 = 3 μM).

Biological Activity

Selective agonist at PPAR γ (peroxisome proliferator-activated receptor γ ). Activates PPAR γ with an EC 50 value of 3 μ M in vitro , and is at least 33-fold selective over PPAR α and δ . Antihyperglycemic in vivo .

Biochem/physiol Actions

Ciglitizone belongs to the class of thiazolidinediones and is a peroxisome proliferator-activated receptor γ (PPARγ) agonist. It exhibits anti-diabetic activity. Ciglitizone has the potential to treat tumor necrosis factor α (TNFα)-related apoptosis-inducing ligand (TRAIL)-refractory high-grade urothelial cancers.

Pharmacology

Ciglitazone reduced plasma triglycerides, hyperglycemia and hyperinsulinemia in several insulin resistant diabetic and nondiabetic rodent models after repeated oral dosing at doses of 100 – 300 mg/kg body weight, while having little or no effect in normal rodents or those with insulin deficient diabetes. In long-term animal studies lens cataracts occurred and ciglitazone development was discontinued.

storage

Room temperature

Mode of action

Ciglitizone is a thiazolidine-2,4-dione derivative. The mechanism of blood glucose lowering activity by thiazolidinedione derivatives has not been fully elucidated yet. Only minor or no effects are observed in normal animals or insulin sensitive diabetes models. In obese or hyperinsulinemic insulin resistant rodents thiazolidinediones lower insulin and triglyceride levels after treatment for 2 to 8 d. If hyperglycemia occurs, also the blood glucose concentration is reduced. Mechanistic in vitro studies with adipocytes have shown that the thiazolidinediones are ligands of the peroxisome proliferator activated receptor. Peroxisome proliferator activated receptors (PPARs) belong to the nuclear receptor superfamily of ligand-activated transcription factors. So far, three receptor subtypes have been identified: PPAR , PPAR , and PPAR . The PPARs are believed to play a physiological role in the regulation of lipid metabolism. The in vivo antihyperglycemic activity of thiazolidinediones strongly correlates with their potency as PPAR agonists in vitro.

References

1) Cantello et al. (1994) [[omega-(Heterocyclylamino)alkoxy]benzyl]-2,4-thiazolidinediones as potent antihyperglycemic agents; J. Med. Chem. 37 3977 2) Xin et al. (1999) Peroxisome proliferator-activated receptor gamma ligands are potent inhibitors of angiogenesis in vitro and in vivo; J. Biol. Chem. 274 9116

CIGLITAZONE Preparation Products And Raw materials

Raw materials

Preparation Products

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CIGLITAZONE Suppliers

Shanghai Boyle Chemical Co., Ltd.
Tel
Fax
86-21-57758967
Email
sales@boylechem.com
Country
China
ProdList
2922
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55
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
94657
Advantage
76
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15839
Advantage
69
Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
32321
Advantage
50
Jiangsu Aikon Biopharmaceutical R&D co.,Ltd.
Tel
025-66099280 17798518460
Fax
(1)02557626880
Email
cfzhang@aikonchem.com
Country
China
ProdList
19915
Advantage
55
Sigma-Aldrich
Tel
021-61415566 800-8193336
Email
orderCN@merckgroup.com
Country
China
ProdList
51456
Advantage
80
Alta Scientific Co., Ltd.
Tel
022-6537-8550 15522853686
Fax
022-2532-9655
Email
sales@altasci.com.cn
Country
China
ProdList
4511
Advantage
55
Shanghai Synchem Pharma Co., ltd
Tel
21-619849051-1 18521059765
Email
synchempharma@aliyun.com
Country
China
ProdList
6463
Advantage
55
EMMX Biotechnology LLC
Tel
888-539-0666
Fax
888-539-0666
Email
info@emmx.com
Country
United States
ProdList
8447
Advantage
60
Shanghai EFE Biological Technology Co., Ltd.
Tel
021-65675885 18964387627
Fax
021-65675885
Email
info@efebio.com
Country
China
ProdList
9806
Advantage
58

74772-77-3, CIGLITAZONERelated Search:


  • Ciglitazone - CAS 74772-77-3 - Calbiochem
  • 5-((4-((1-methylcyclohexyl)methoxy)phenyl)methyl)-4-thiazolidinedione
  • U-63287
  • (+/-)-5-[4-(1-METHYLCYCLOHEXYLMETHOXY)BENZYL]-THIAZOLIDINE-2,4-DIONE
  • 5-[[4-[(1-METHYLCYCLOHEXYL)METHOXY]PHENYL]METHYL]-2,4-THIAZOLIDINEDIONE
  • ADD 3878
  • CIGLITAZONE
  • CIGLITIZONE
  • CIGLITAZONE(SUBJECTTOPATENTFREE)
  • CIGLITLZONE
  • 5-[p-[2,2-(Pentane-1,5-diyl)propyloxy]benzyl]thiazolidine-2,4-dione
  • AD-4533
  • Ciglitazone Solution, 100ppm
  • 2,4-Thiazolidinedione, 5-[[4-[(1-methylcyclohexyl)methoxy]phenyl]methyl]-
  • Ciglitazone Solution in Acetonitrile, 100μg/mL
  • CIGLITAZONE USP/EP/BP
  • Ciglitazona
  • 74772-77-3
  • C18H23NO3S
  • BioChemical
  • Cell Signaling and Neuroscience
  • Cell Biology
  • PPAR and RXR Regulators
  • Gene Regulation and Expression
  • Active Pharmaceutical Ingredients
  • Metal Isotopes
  • Sulfur & Selenium Compounds
  • API's
  • Intracellular receptor