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Troglitazone

HCID 5591
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Grundinformationen

CAS
97322-87-7
Standard-SMILES
Cc1c(C)c2c(c(C)c1O)CCC(C)(COc1ccc(CC3SC(=O)NC3=O)cc1)O2
InChIKey
GXPHKUHSUJUWKP-UHFFFAOYSA-N
Summenformel
C24H27NO5S
Durchschnittliche Molmasse
441,5 g/mol
Monoisotopische Masse
441,16099396

Überblick

Troglitazone is a member of chromanes and a thiazolidinone. It has a role as a ferroptosis inhibitor, an antioxidant, a hypoglycemic agent, an antineoplastic agent, a vasodilator agent, an anticonvulsant, an anticoagulant, a platelet aggregation inhibitor and an EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor.

Namen und Bezeichner

Bevorzugter Name
Troglitazone
IUPAC
5-[[4-[(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromen-2-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione
Englischer Name
Troglitazone
Summenformel
C24H27NO5S
Molmasse
441.54

Namen und Synonyme

troglitazone97322-87-7RezulinRomglizonePrelayCS-045RomozinNoscaltroglitazonatroglitazonumCI-991DTXSID8023719
Weitere Namen anzeigen
ci991DepotoxAKOS 91980
GR92132XGR-92132X5-(4-(6-Hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl)thiazolidine-2,4-dione5-[[4-[(3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl)methoxy]phenyl]methyl]-2,4-thiazolidinedioneCHEBI:9753I66ZZ0ZN0EDTXCID6037192,4-Thiazolidinedione, 5-((4-((3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl)methoxy)phenyl)methyl)-

Datenbank-Bezeichner

CAS
97322-87-7
PubChem CID
5591
DTXSID
DTXSID8023719
ChEMBL
CHEMBL408
ChEBI
CHEBI:9753
Nikkaji
J996.467C

Eigenschaften

Berechnete Struktureigenschaften

XLogP
5,1
Polarare Oberfläche (TPSA)
110 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
6
Frei drehbare Bindungen
5
Schwere Atome
31
Formalladung
0
Komplexität
681

Experimentelle und physikochemische Eigenschaften

Human Drugs · 2 Einträge

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Melting Point184-186 °C
Collision Cross Section193.9 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID8023719]

Physikochemische Eigenschaften

Schmelzpunkt
184 · 184-186°C
Siedepunkt
657 · 657.0±55.0 °C(Predicted)
Dichte
1.266 · 1.266±0.06 g/cm3(Predicted)
storage temp.
-20 °C · Inert atmosphere,Store in freezer, under -20°C
Löslichkeit
20 mg/mL · DMSO: 20 mg/mL
Aggregatzustand
solid
pka
6.34 · 6.34±0.50(Predicted)
Farbe
white to yellow

Sicherheit und Regulatorisches

Toxikologische Informationen

Hepatotoxicity · 1 Eintrag

Large prospective studies showed that significant elevations in serum aminotransferase levels (equal to or greater than 3 times the upper limit of the normal range [ULN]) occurred in 1.9% of patients with diabetes treated with troglitazone for 24 to 48 weeks, compared to only 0.6% in placebo recipients. These enzyme elevations were usually asymptomatic and often resolved despite continuation of therapy. Nevertheless, elevations >10 times ULN occurred in 0.5% of patients (but in no placebo recipient) and a proportion of these developed symptoms of liver injury and jaundice. Soon after the approval of troglitazone as therapy for type 2 diabetes in the United States, cases of severe acute liver injury began to be reported, and dramatic case reports as well as small case series documented that clinically significant injury was occurring in 1:1000 to 1:10,000 recipients. The latency to onset of injury was typically 1 to 6 months and the onset was marked by fatigue, weakness, dark urine and jaundice, and an acute hepatitis-like elevation in serum enzymes (hepatocellular pattern). Allergic phenomena (rash, fever, eosinophilia) were uncommon and serum autoantibodies were not usually present. Liver biopsies showed acute inflammatory changes and variable degrees of necrosis, ranging from rare spotty necrosis to bridging hepatic necrosis and submassive or massive necrosis. At least two dozen cases of acute liver failure and death or need for liver transplantation were reported to the FDA before troglitazone was withdrawn from use in 2000.

Exposure RoutesAbsorbed rapidly. Food increases the extent of absorption by 30% to 85%.
Toxicity Summary · 1 Eintrag

Troglitazone is a thiazolidinedione antidiabetic agent that lowers blood glucose by improving target cell response to insulin. It has a unique mechanism of action that is dependent on the presence of insulin for activity. Troglitazone decreases hepatic glucose output and increases insulin dependent glucose disposal in skeletal muscle. Its mechanism of action is thought to involve binding to nuclear receptors (PPAR) that regulate the transcription of a number of insulin responsive genes critical for the control of glucose and lipid metabolism. Troglitazone is a ligand to both PPAR‘± and PPAR‘_, with a highter affinity for PPAR‘_. The drug also contains an ‘±-tocopheroyl moiety, potentially giving it vitamin E-like activity. Troglitazone has been shown to reduce inflammation, and is associated with a decrase in nuclear factor kappa-B (NF-‘_B) and a concomitant increase in its inhibitor (I‘_B). NF-‘_B is an important cellular transcription regulator for the immune response. Unlike sulfonylureas, troglitazone is not an insulin secretagogue.

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

A - Alimentary tract and metabolism

QA - Alimentary tract and metabolism

Protein Binding> 99% (primarily to serum albumin)
Pharmacodynamics · 1 Eintrag

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.

Mechanism of Action · 1 Eintrag

Troglitazone is a thiazolidinedione antidiabetic agent that lowers blood glucose by improving target cell response to insulin. It has a unique mechanism of action that is dependent on the presence of insulin for activity. Troglitazone decreases hepatic glucose output and increases insulin dependent glucose disposal in skeletal muscle. Its mechanism of action is thought to involve binding to nuclear receptors (PPAR) that regulate the transcription of a number of insulin responsive genes critical for the control of glucose and lipid metabolism. Troglitazone is a ligand to both PPARα and PPARγ, with a highter affinity for PPARγ. The drug also contains an α-tocopheroyl moiety, potentially giving it vitamin E-like activity. Troglitazone has been shown to reduce inflammation, and is associated with a decrase in nuclear factor kappa-B (NF-κB) and a concomitant increase in its inhibitor (IκB). Unlike sulfonylureas, troglitazone is not an insulin secretagogue.

Biological Half-Life16-34 hours
Metabolism/Metabolites · 3 Einträge

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.

Zugehörige Reaktionen

20
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 128899
HRID 128899als Eduktuspto-grants-1995_11
Reaktionsgleichung von HRID 174949
HRID 174949als EduktTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
Reaktionsgleichung von HRID 199828
HRID 199828als ProduktTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
Reaktionsgleichung von HRID 306425
HRID 306425als EduktTraining data from https://doi.org/10.1039/C8SC04228D (8/10)
Reaktionsgleichung von HRID 1030369
HRID 1030369als Produktuspto-grants-1992_04
Reaktionsgleichung von HRID 1030371
HRID 1030371als Eduktuspto-grants-1992_04
Reaktionsgleichung von HRID 1030373
HRID 1030373als Produktuspto-grants-1992_04
Reaktionsgleichung von HRID 1030382
HRID 1030382als Eduktuspto-grants-1992_04
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Stabilität
1 year · 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.
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
SMILES
S1C(CC2=CC=C(OCC3(C)OC4=C(C)C(C)=C(O)C(C)=C4CC3)C=C2)C(=O)NC1=O
CAS Datenbank
97322 · 97322-87-7(CAS DataBase Reference)
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 6 Einträge

Drug Induced Liver Injury Rank (DILIrank 2.0)

Troglitazone

vMost-DILI-concern

8

Withdrawn

DOI:10.1016/j.drudis.2016.02.015

Sicherheitsdaten

wgk
2
hs_code
29145090
RTECS-Nr.
XJ5813130
safety_code
22-24/25
Speicherklasse
11 - Combustible Solids

Troglitazone has known human metabolites that include (2S,3S,4S,5R)-6-[[2-[[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]methyl]-2,5,7,8-tetramethyl-3,4-dihydrochromen-6-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid.

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. Half Life: 16-34 hours

MeSH Pharmacological ClassificationSubstances which lower blood glucose levels.
Absorption, Distribution and ExcretionAbsorbed rapidly. Food increases the extent of absorption by 30% to 85%.

Verwendung und Herstellung

UsesFor 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.
Anwendungen · 3 Einträge

BeschreibungRezulin was launched in Japan, the UK (subseqently withdrawn) and the US for treatment of type Ⅱ diabetes. Two approaches, four steps and six steps, converge on 6-acetoxy-2-(4-aminophenoxymethyl)-2,5,7,8-tetramethylchroman which can be elaborated in two steps to Rezulin. It is the first of a new class of thiazolidenediones for NIDDM that reduces glucose concentrations without effecting insulin secretion. It binds to peroxisome proliferator-activated receptor gamma (PPARγ) thus activating this nuclear receptor which then influences carbohydrate metabolism. This is accomplished by increasing insulin sensitivity by upregulating glucose transporter (Glut1 and/or Glut4) expression without affecting the number or affinity of insulin receptors. There is also an increase in hepatic glycogen synthase activity which enhances glucose utilization and a reduction in hepatic gluconeogenesis by inhibiting fructose-1 ,&bisphosphatase. Pancreatic islet cell destruction is prevented. It reduces serum triglycerides because PPARγ causes fibroblasts to differentiate into adipocytes and does not activate RARα. It has a half-life of 9 h and is metabolized into three compounds having no activity.

HistoryTroglitazone (Sankyo) was firstly approved 1995 in Japan and 1997 in USA and UK. It was launched in these countries in 1997. The recommended starting dose was 400 mg/d and the highest dose 600 mg. After being marketed, the daily practice revealed adverse events in the liver with cases of fatal liver failure. This lead to withdrawal of troglitazone from the market in the UK already after two months, in USA and Japan in the year 2000.

VerwendenTroglitazone is an an oral hypoglycemic agent which improves insulin sensitivity and decreases hepatic glucose production. Antidiabetic.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Formyl chlorideTrifluormethansulfonsaeureanhydrid2-Methylpentan4-HydroxybenzaldehydAnhydrous pyridineDilute hydrochloric acidThioharnstoffEssigsureHydrogenchlorid

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