Glibornuride
Glibornuride Basic information
- Product Name:
- Glibornuride
- Synonyms:
-
- 1-[p-Tolylsulfonyl]-3-[2-endo-hydroxy-3-endo-D-bornyl] urea
- N-((3-hydroxy-4,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)carbamoyl)-4-methylbenzenesulfonamide
- Glibornuride (Mixture of Diastereomers)
- Glibornuride
- Glitrim
- N-[[[(1S,2S,3R,4R)-2-Hydroxyborn-3-yl]amino]carbonyl]-4-methylbenzenesulfonamide
- Ro-6-4563
- 1-(3-hydroxy-4,7,7-trimethyl-norbornan-2-yl)-3-(4-methylphenyl)sulfonyl-urea
- CAS:
- 26944-48-9
- MF:
- C18H26N2O4S
- MW:
- 366.47504
- EINECS:
- 2481246
- Product Categories:
-
- Amines, Aromatics, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals, Sulfur & Selenium Compounds
- Mol File:
- 26944-48-9.mol
Glibornuride Chemical Properties
- Melting point:
- 192-195° (ethanol-water); also reported as 195-198°
- alpha
- D +63.8° (ethanol)
- Density
- 1.1793 (rough estimate)
- refractive index
- 1.6930 (estimate)
- storage temp.
- Store at -20°C
- solubility
- DMSO : 250 mg/mL (682.17 mM; Need ultrasonic)
- form
- Solid
- pka
- 5.20±0.10(Predicted)
- color
- White to off-white
Glibornuride Usage And Synthesis
Originator
Glutril,Roche,W. Germany,1972
Uses
Glibornuride has been shown to antagonize the relaxant response to the K+ channel opener cromakalim and produce airway smooth muscle relaxation. Glibornuride is associated with lactic acidosis and hypoglycemia in patients with type 2 diabetes melitus.
Definition
ChEBI: Glibornuride is a monoterpenoid.
Manufacturing Process
2.1 grams of 3-endo-aminoborneol hydrochloride and 2.4 grams of O-methylN-p-toluene-sulfonyl-urea are heated at 125°C for 3 hours with 2 ml of dimethylformamide. After cooling, the reaction mixture is stirred with 100 ml of water for 10 minutes, while a pH of 3.5 is maintained by the addition of a few drops of dilute hydrochloric acid. The precipitate is removed by filtration, washed with water and suspended in 100 ml of water. The suspension is dissolved by the addition of 20 ml of 1 N caustic soda. The alkaline solution is extracted with ether, acidified with dilute hydrochloric acid and filtered. The precipitate is washed with water and recrystallized from alcohol/water to yield 1-(p-toluene-sulfonyl)-3-(2-endo-hydroxy-3-endo-bornyl)-urea having a melting point of 193° to 195°C.
brand name
Glutril (Hoffmann-LaRoche).
Therapeutic Function
Oral hypoglycemic
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