5-({4-[(1-methylcyclohexyl)methoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione

• ChemBase ID: 133657
• Molecular Formular: C18H23NO3S
• Molecular Mass: 333.44512
• Monoisotopic Mass: 333.1398646
• SMILES: CC1(CCCCC1)COc1ccc(cc1)CC1C(=O)NC(=O)S1
• Canonical SMILES: O=C1NC(=O)C(S1)Cc1ccc(cc1)OCC1(C)CCCCC1
• InChI: InChI=1S/C18H23NO3S/c1-18(9-3-2-4-10-18)12-22-14-7-5-13(6-8-14)11-15-16(20)19-17(21)23-15/h5-8,15H,2-4,9-12H2,1H3,(H,19,20,21)
• InChIKey: YZFWTZACSRHJQD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-({4-[(1-methylcyclohexyl)methoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione
• IUPAC Traditional name: ciglitazone
• Synonyms: (±)-5-[4-(1-Methylcyclohexylmethoxy)benzyl]thiazolidine-2,4-dione; Ciglitazone; Ciglitizone; (+/-)-5-[4-(1-methylcyclohexylmethoxy)benzyl]thiazolidine-2,4-dione; ADD-3878; Ciglitazone; 2-amino-5-[[4-[(1-methylcyclohexyl)methoxy]phenyl]methyl]-4(5H)-thiazolone; rac 2-Imino-5-[4-(1-methylcyclohexylmethoxyl)benzyl]thiazolidine-4one

Database IDs

• CAS Number: 85010-66-8; 74772-77-3
• MDL Number: MFCD00865499
• PubChem SID: 24892661; 162227934
• PubChem CID: 2750

CALCULATED PROPERTIES

• Acid pKa: 6.6135864
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.25011
• LogD (pH = 7.4): 3.459027
• Log P: 4.281939
• Molar Refractivity: 91.2588 cm^3
• Polarizability: 36.03663 Å^3
• Polar Surface Area: 55.4 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Ethanol
• Apperance: White Powder; White Solid
• Melting Point: 130-131°C; 264°C

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: XJ5813700
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)

Pharmacology Properties

• Gene Information: human ... PPARG(5468)mouse ... Pparg(19016)

Product Information

• Purity: ≥99% (TLC)

DETAILS

Sigma Aldrich - C3974

Biochem/physiol Actions
Selective peroxisome proliferator-activated receptor-γ (PPARγ) agonist (EC50 = 3 μM) and antihyperglycemic agent displaying activity in genetically obese C57 B1/6 ob/ob mice.

Toronto Research Chemicals - C441000

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

Toronto Research Chemicals - I423750

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

REFERENCES

• Clark, D.A., et al.: J. Med. Chem., 34, 319-325 (1991)
• Sohda, T., et al.: Chem. Pharm. Bull., 30(1991)
• 3580-3600, (1982)
• Clark, D.A., et al.: J. Med. Chem., 34, 319-325 (1991)
• Sohda, T., et al.: Chem. Pharm. Bull., 30(1991)
• 3580-3600, (1982)