8100. Ramatroban

Nomenclature

CAS number: 116649-85-5
(3R)-3-[[(4-Fluorophenyl)sulfonyl]amino]-1,2,3,4-tetrahydro-9H-carbazole-9-propanoic acid; (+)-(3R)-3-(p-fluorobenzenesulfonamido)-1,2,3,4-tetrahydrocarbazole-9-propionic acid; (+)-3-(4-fluorophenylsulfonamido)-9-(2-carboxyethyl)-1,2,3,4-tetrahydrocarbazole; Bay u 3405; Baynas (Bayer).
C21H21FN2O4S; mol wt 416.47.
C 60.56%, H 5.08%, F 4.56%, N 6.73%, O 15.37%, S 7.70%.

Description and references

Thromboxane A2 receptor antagonist. Prepn: H. B"oshagen et al., DE 3631824; eidem, US 4965258 (1988, 1990 both to Bayer); and absolute configuration: U. Rosentreter et al., Arzneim.-Forsch. 39, 1519 (1989). Series of articles on pharmacology: ibid. 1522-1530. Clinical evaluation in asthma: H. Aizawa et al., Chest 109, 338 (1996).

Chemical structure

Properties

Crystals from ether, mp 134-135°. [α]D +70.1° (c = 1.0 in methanol).

Therapeutic Category

Antiasthmatic; antiallergic.

Keywords

Antiallergic; Antiasthmatic (Nonbronchodilator); Thromboxane A2-Receptor Antagonist