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Substance Name: Troglitazone [USAN:INN:BAN]
RN: 97322-87-7
UNII: I66ZZ0ZN0E
InChIKey: GXPHKUHSUJUWKP-UHFFFAOYSA-N

Note

  • PPAR agonist formerly used for type II diabetes.

Molecular Formula

  • C24-H27-N-O5-S

Molecular Weight

  • 441.545
 

Classification Codes

  • Antidiabetic
  • Cytochrome P-450 CYP3A Inducers
  • Drug / Therapeutic Agent
  • Human Data
  • Hypoglycemic Agents
  • Metabolic Side Effects of Drugs and Substances
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Names and Synonyms

Name of Substance

  • Troglitazone
  • Troglitazone [USAN:INN:BAN]

Synonyms

  • (+-)-all-rac-5-(p-((6-Hydroxy-2,5,7,8-tetramethyl-2-chromanyl)methoxy)benzyl)-2,4-thiazolidinedione
  • 2,4-Thiazolidinedione, 5-((4-((3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl)methoxy)phenyl)methyl)-
  • 5-(4-(6-Hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl)thiazolidine-2,4-dione
  • BRN 4338399
  • CCRIS 8969
  • CI 991
  • CI-991
  • CS 045
  • CS-045
  • GR 92132X
  • GR92132X
  • Prelay
  • Rezulin
  • Romglizone
  • Troglitazone
  • UNII-I66ZZ0ZN0E

Systematic Name

  • 2,4-Thiazolidinedione, 5-((4-((3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl)methoxy)phenyl)methyl)-

Registry Numbers

CAS Registry Number

  • 97322-87-7

FDA UNII

  • I66ZZ0ZN0E

System Generated Number

  • 0097322877

Structure Descriptors

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

c12c(CC[C@@](O1)(COc1ccc(C[C@@H]3C(NC(S3)=O)=O)cc1)C)c(c(O)c(c2C)C)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
monkey LD50 oral > 2gm/kg (2000mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 38, Pg. 1121, 1996.
mouse LD oral > 300mg/kg (300mg/kg)   European Patent Application. Vol. #439321,
mouse LD50 intraperitoneal > 5gm/kg (5000mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 953, 1995.
mouse LD50 intravenous 42mg/kg (42mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 9, Pg. 759, 1967.
rat LD50 intraperitoneal > 4gm/kg (4000mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 953, 1995.
rat LD50 oral > 5gm/kg (5000mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 953, 1995.
women TDLo oral 840mg/kg/15W- (840mg/kg) LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"

LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE"

BRAIN AND COVERINGS: ENCEPHALITIS
Annals of Internal Medicine. Vol. 129, Pg. 98, 1998.