Troglitazone

Troglitazone
Troglitazone
Systematic (IUPAC) name
(RS)-5-(4-[(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)methoxy]benzyl)thiazolidine-2,4-dione
Clinical data
Pregnancy cat.  ?
Legal status  ?
Pharmacokinetic data
Half-life 16-34 hours
Identifiers
CAS number 97322-87-7 N
ATC code A10BG01
PubChem CID 5591
DrugBank APRD00488
ChemSpider 5389 YesY
UNII I66ZZ0ZN0E YesY
KEGG D00395 YesY
ChEBI CHEBI:9753 YesY
ChEMBL CHEMBL408 YesY
Chemical data
Formula C24H27NO5S 
Mol. mass 441.541 g/mol
SMILES eMolecules & PubChem
 N(what is this?)  (verify)

Troglitazone (Rezulin, Resulin or Romozin) is an anti-diabetic and antiinflammatory drug, and a member of the drug class of the thiazolidinediones. It was developed by Daiichi Sankyo Co.(Japan). In the United States, it was introduced and manufactured by Parke-Davis in the late 1990s, but turned out to be associated with an idiosyncratic reaction leading to drug-induced hepatitis. One FDA medical officer evaluating troglitazone, John Gueriguian, did not recommend its approval due to potential high liver toxicity,[1] but a full panel of experts approved it in January 1997.[2] Once the prevalence of adverse liver effects became known, troglitazone was withdrawn from the British market in December 1997, from the United States market in 2000, and from the Japan market soon afterwards.

Mode of action

Troglitazone, like the other thiazolidinediones (pioglitazone and rosiglitazone), works by activating peroxisome proliferator-activated receptors (PPARs).

Troglitazone is a ligand to both PPARα and – more strongly – PPARγ. Troglitazone also contains an α-tocopheroyl moiety, potentially giving it vitamin E-like activity in addition to its PPAR activation. It has been shown to reduce inflammation:[3] troglitazone use was associated with a decrease of nuclear factor kappa-B (NF-κB) and a concomitant increase in its inhibitor (IκB). NFκB is an important cellular transcription regulator for the immune response.

References

  1. ^ Retired Drugs: Failed Blockbusters, Homicidal Tampering, Fatal Oversights, wired.com
  2. ^ Cohen, J. S. (2006). "Risks of troglitazone apparent before approval in USA". Diabetologia 49 (6): 1454–5. doi:10.1007/s00125-006-0245-0. PMID 16601971. 
  3. ^ Aljada A, Garg R, Ghanim H, et al. (2001). "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. 86 (7): 3250–6. doi:10.1210/jc.86.7.3250. PMID 11443197. 

External links

v · d · eOral anti-diabetic drugs and Insulin analogs (A10)
Insulin
Metformin# • Buformin‡ • Phenformin‡
Pioglitazone • Rivoglitazone† • Rosiglitazone • Troglitazone‡
K+ ATP
Meglitinides/"glinides"
GLP-1 analogs
Exenatide • Liraglutide • Taspoglutide† • Albiglutide† • Lixisenatide
Analogs/other insulins
fast-acting (Insulin lispro • Insulin aspart • Insulin glulisine) • short-acting (Regular insulin) • long-acting (Insulin glargine • Insulin detemir • NPH insulin) • ultra-long-acting (Insulin degludec†) • inhalable Exubera‡
Other
Amylin analog
SGLT2 inhibitors
Canagliflozin† • Dapagliflozin† • Remogliflozin§ • Sergliflozin§
Other

M: END

anat/phys/devp/horm

noco(d)/cong/tumr, sysi/epon

proc, drug (A10/H1/H2/H3/H5)

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