3416. Domitroban

Nomenclature

CAS number: 112966-96-8
(5Z)-7-[(1R,2S,3S,4S)-3-[(Phenylsulfonyl)amino]bicyclo[2.2.1]hept-2-yl]-5-heptenoic acid; (+)-(5Z)-7-[3-endo-[(phenylsulfonyl)amino]bicyclo[2.2.1]hept-2-exo-yl]-5-heptenoic acid; (+)-S-145.
C20H27NO4S; mol wt 377.50.
C 63.63%, H 7.21%, N 3.71%, O 16.95%, S 8.49%.

Description and references

Thromboxane A2-receptor antagonist. Prepn of (±)-form: F. Watanabe et al., EP 226346; eidem, US 4861913 (1987, 1989 both to Shionogi); and isomers: M. Narisada et al., J. Med. Chem. 31, 1847 (1988). Prepn of (+)-form: M. J. Martinelli, J. Org. Chem. 55, 5065 (1990); M. Ohtani et al., ibid. 56, 2122 (1991). Pharmacology: A. Arimura et al., Int. Arch. Allergy Immunol. 98, 239 (1992). GC determn in plasma: J. Okamoto et al., J. Chromatogr. 583, 45 (1992); in urine: eidem, ibid. 53. Clinical pharmacokinetics: A. Fujimura et al., J. Clin. Pharmacol. 36, 409 (1996). Clinical evaluation in asthma: M. Fujimura et al., Pulm. Pharmacol. 8, 251 (1995).

Chemical structure

Properties

Colorless crystals from toluene + hexane, mp 60-62°. uv max (ethanol): 225 nm (ε 5270). [α]589 +28.7° (c = 1.00 in methanol).

Derivative

Calcium salt.

Nomenclature

CAS number: 132747-47-8
S-1452; Anboxan (Shionogi).
C40H52CaN2O8S2; mol wt 793.06.
C 60.58%, H 6.61%, Ca 5.05%, N 3.53%, O 16.14%, S 8.09%.

Properties

Prepd as the dihydrate. Colorless pillars, mp >300° (dec). [α]D26 +19.0 ±0.6° (c = 1.010 in methanol).

Derivative

(±)-Form.

Nomenclature

CAS number: 115266-92-7
S-145.

Properties

Colorless plates from ether + n-hexane, mp 85-86°.

Therapeutic Category

Antiasthmatic.

Keywords

Antiasthmatic (Nonbronchodilator); Thromboxane A2-Receptor Antagonist