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97322-87-7 molecular structure
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5-({4-[(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl)methoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione

ChemBase ID: 82
Molecular Formular: C24H27NO5S
Molecular Mass: 441.53988
Monoisotopic Mass: 441.16099397
SMILES and InChIs

SMILES:
S1C(Cc2ccc(OCC3(Oc4c(CC3)c(c(O)c(c4C)C)C)C)cc2)C(=O)NC1=O
Canonical SMILES:
O=C1NC(=O)C(S1)Cc1ccc(cc1)OCC1(C)CCc2c(O1)c(C)c(c(c2C)O)C
InChI:
InChI=1S/C24H27NO5S/c1-13-14(2)21-18(15(3)20(13)26)9-10-24(4,30-21)12-29-17-7-5-16(6-8-17)11-19-22(27)25-23(28)31-19/h5-8,19,26H,9-12H2,1-4H3,(H,25,27,28)
InChIKey:
GXPHKUHSUJUWKP-UHFFFAOYSA-N

Cite this record

CBID:82 http://www.chembase.cn/molecule-82.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
5-({4-[(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl)methoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione
IUPAC Traditional name
troglitazone
Brand Name
Noscal
Prelay
Rezulin
Romglizone
Resulin
Romozin
Synonyms
(±)-5-[4-[(6-Hydroxy-2,5,7,8-tetramethylchroman-2-yl)methoxy]benzyl]-2,4-thiazolidinedione
5-[[4-[(3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl)methoxy]phenyl]methyl]-2,4-thiazolidinedione
CI 991
CS 045
Depotox
GR 92132X
Noscal
Rezulin
Romglizone
CS-045
Troglitazone
Troglitazone
CAS Number
97322-87-7
MDL Number
MFCD00878416
PubChem SID
24724629
46504655
160963545
PubChem CID
5591

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 6.613558  H Acceptors
H Donor LogD (pH = 5.5) 5.463373 
LogD (pH = 7.4) 4.6721177  Log P 5.4952044 
Molar Refractivity 120.9914 cm3 Polarizability 46.61733 Å3
Polar Surface Area 84.86 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P 4.16  LOG S -5.56 
Solubility (Water) 1.21e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
DMSO: soluble20 mg/mL expand Show data source
Methanol expand Show data source
Apperance
White Solid expand Show data source
white to yellow solid expand Show data source
Melting Point
184-186°C expand Show data source
Hydrophobicity(logP)
3.6 expand Show data source
Storage Condition
-20°C Freezer expand Show data source
RTECS
XJ5813130 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Gene Information
human ... PPARA(5465), PPARG(5468) expand Show data source
Purity
≥98% (HPLC) expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C24H27NO5S expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00197 external link
Item Information
Drug Groups withdrawn
Description Troglitazone was withdrawn in 2000 due to risk of hepatotoxicity. It was superseded by pioglitazone and rosiglitazone.
Indication For the treatment of Type II diabetes mellitus. It is used alone or in combination with a sulfonylurea, metformin, or insulin as an adjunct to diet and exercise.
Pharmacology Troglitazone is an oral antihyperglycemic agent which acts primarily by decreasing insulin resistance. Troglitazone is used in the management of type II diabetes (noninsulin-dependent diabetes mellitus (NIDDM) also known as adult-onset diabetes). It improves sensitivity to insulin in muscle and adipose tissue and inhibits hepatic gluconeogenesis. Troglitazone is not chemically or functionally related to either the sulfonylureas, the biguanides, or the g-glucosidase inhibitors. Troglitazone may be used concomitantly with a sulfonylurea or insulin to improve glycemic control.
Affected Organisms
Humans and other mammals
Biotransformation A sulfate conjugate metabolite (Metabolite 1) and a quinone metabolite (Metabolite 3) have been detected in the plasma of healthy males. A glucuronide conjugate (Metabolite 2) has been detected in the urine and also in negligible amounts in the plasma. In healthy volunteers and in patients with type 2 diabetes, the steady-state concentration of Metabolite 1 is six to seven times that of troglitazone and Metabolite 3. In in vivo drug interaction studies, troglitazone has been shown to induce cytochrome P450 CYP3A4 at clinically relevant doses.
Absorption Absorbed rapidly. Food increases the extent of absorption by 30% to 85%.
Half Life 16-34 hours
Protein Binding > 99% (primarily to serum albumin)
References
Aljada A, Garg R, Ghanim H, Mohanty P, Hamouda W, Assian E, Dandona P: Nuclear factor-kappaB suppressive and inhibitor-kappaB stimulatory effects of troglitazone in obese patients with type 2 diabetes: evidence of an antiinflammatory action? J Clin Endocrinol Metab. 2001 Jul;86(7):3250-6. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Sigma Aldrich - T2573 external link
Biochem/physiol Actions
PPARγ agonist; anti-diabetic thiazolidinedione (TZD) with anti-inflammatory and anti-tumor activity; induces apoptosis via a p53 pathway.
Toronto Research Chemicals - T892500 external link
Troglitazone is an an oral hypoglycemic agent which improves insulin sensitivity and decreases hepatic glucose production. Antidiabetic.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Aljada A, Garg R, Ghanim H, Mohanty P, Hamouda W, Assian E, Dandona P: Nuclear factor-kappaB suppressive and inhibitor-kappaB stimulatory effects of troglitazone in obese patients with type 2 diabetes: evidence of an antiinflammatory action? J Clin Endocrinol Metab. 2001 Jul;86(7):3250-6. Pubmed
  • • Ciaraldi, T.P., et al.: Metabolism, 39, 1056 (1990)
  • • Kuzuya, T., et al.: Diabetes Res. Clin. Pract., 11, 147 (1990)
  • • Kellerer, M., et al.: Diabetes, 43, 447 (1990)
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PATENTS

PATENTS

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INTERNET

INTERNET

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