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Wikipedia - Troglitazone

Troglitazone
Systematic (IUPAC) name
(RS)-5-(4-[(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)methoxy]benzyl)thiazolidine-2,4-dione
Identifiers
CAS number 97322-87-7
ATC code A10BG01
PubChem CID 5591
DrugBank APRD00488
Chemical data
Formula C24H27NO5S 
Mol. mass 441.541 g/mol
Pharmacokinetic data
Half-life 16-34 hours
Therapeutic considerations
Pregnancy cat.  ?
Legal status

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it in January 1997.[2] Subsequently, once the prevalence of adverse liver effects became known, troglitazone was withdrawn from the United Kingdom market in December 1997, from the USA market in 2000, and from the Japan market soon afterwards.

Contents

[edit] Mode of action

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

Troglitazone is a ligand to both PPARa and - more strongly - PPAR?. Troglitazone also contains an a-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-?B) and a concomitant increase in its inhibitor (I?B). NF?B is an important cellular transcription regulator for the immune response.

[edit] Chemistry

Troglitazone Rx.png

Yoshioka, Takao; Fujita, Takashi; Kanai, Tsutomu; Aizawa, Yuichi; Kurumada, Tomoyuki; Hasegawa, Kazuo; Horikoshi, Hiroyoshi (1989). "Studies on hindered phenols and analogs. 1. Hypolipidemic and hypoglycemic agents with ability to inhibit lipid peroxidation". Journal of Medicinal Chemistry 32: 421. doi:10.1021/jm00122a022. 

[edit] 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. 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. 

[edit] External links

v • d • e
Oral anti-diabetic drugs and Insulin analogs (A10)
Insulin
Pioglitazone · Rivoglitazone† · Rosiglitazone · Troglitazone‡
Meglitinides/"glinides"
Analogs/other insulins
Other
Amylin analog
SGLT2 inhibitor
Other
Retrieved from "http://en.wikipedia.org/wiki/Troglitazone"

This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Troglitazone".

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