Structure via PubChem · Public domain (PubChem)
(RS)-troglitazone
Sign in to saveAlso known as 5-[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione
Troglitazone is an antidiabetic and anti-inflammatory drug, and a member of the drug class of the thiazolidinediones. It was prescribed for people with diabetes mellitus type 2.
Chemical data
- Formula
- C24H27NO5S
- Molecular weight
- 441.5 g/mol
- IUPAC name
- 5-[[4-[(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromen-2-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione
- SMILES
- CC1=C(C2=C(CCC(O2)(C)COC3=CC=C(C=C3)CC4C(=O)NC(=O)S4)C(=C1O)C)C
- InChIKey
- GXPHKUHSUJUWKP-UHFFFAOYSA-N
- XLogP
- 5.1
- Polar surface area
- 110 Ų
- H-bond donors
- 2
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
Withdrawn- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1997
- Admin. routes
- oral
- Indications
- diabetes mellitus, sarcoma
via ChEMBL · EBI
Research
11 papers- Mechanistic Insights into Side Effects of Troglitazone and Rosiglitazone Using a Novel Inverse Molecular Docking Protocol.Pharmaceutics · 2021
- Differential effects among thiazolidinediones on the transcription of thromboxane receptor and angiotensin II type 1 receptor genes.Hypertension research : official journal of the Japanese Society of Hypertension · 2001
- Physical property of troglitazone, an equal mixture of four stereoisomers.International journal of pharmaceutics · 2002
- Activation of PPARG inhibits dominant follicle development in cattle.Theriogenology · 2020
- Solid-state variation of troglitazone drug substance by using a different recrystallization method.Drug development and industrial pharmacy · 2003
via PubMed
Wikidata facts
- Subclass of
- glitazone
- Mass
- 441.160994
- Has use
- medication
Show 6 more facts
- chemical formula
- C₂₄H₂₇NO₅S
- canonical SMILES
- CC1=C(C(=C2CCC(OC2=C1C)(C)COC3=CC=C(C=C3)CC4C(=O)NC(=O)S4)C)O
- Commons category
- Troglitazone
- defined daily dose
- 0.4
- approved by
- United States Food and Drug Administration
- has effect
- liver failure
via Wikidata · CC0
~8 min read
Encyclopedic overview
6 sectionsContents
- Mechanism of action
- History
- Mechanisms of hepatotoxicity
- Lawsuits
- References
- External links
Troglitazone is an antidiabetic and anti-inflammatory drug, and a member of the drug class of the thiazolidinediones. It was prescribed for people with diabetes mellitus type 2.
It was patented in 1983 and approved for medical use in 1997. It was subsequently withdrawn.
Excerpted from Wikipedia’s “(RS)-troglitazone” article, available under the CC BY-SA 4.0 licence.
Gallery (3)
Available in 12 languages
via Wikidata sitelinks · CC0