1631. Cadralazine

Nomenclature

CAS number: 64241-34-5
2-[6-[Ethyl(2-hydroxypropyl)amino]-3-pyridazinyl]hydrazinecarboxylic acid ethyl ester; ethyl 6-[ethyl(2-hydroxypropyl)amino]-3-pyridazinecarbazate; 3-(2-carbethoxyhydrazino)-6-[N-(2-hydroxypropyl)ethylamino]pyridazine; DC-826; ISF-2469; Cadral (Novartis); Cadraten (ISF); Cadrilan (Novartis); Presmode (Sankyo).
C12H21N5O3; mol wt 283.33.
C 50.87%, H 7.47%, N 24.72%, O 16.94%.

Description and references

Peripheral vasodilator similar to hydralazine, q.v. Prepn: C. Carpi et al., BE 811847; eidem, US 3925381; US 4002753 (1974, 1975, 1977 all to ISF); F. Parravicini et al., Farmaco Ed. Sci. 34, 299 (1979). Analytical profile: L. Citerio et al., Boll. Chim. Farm. 120, 222 (1981). Pharmacology: C. Semeraro et al., J. Cardiovasc. Pharmacol. 3, 455 (1981). HPLC determn in plasma and urine: T. Crolla et al., J. Chromatogr. 310, 139 (1984). Hemodynamic effects in dogs: L. Dorigotti et al., Arzneim.-Forsch. 34, 984 (1984); in humans: B. Persson et al., Eur. J. Clin. Pharmacol. 31, 513 (1987). Pharmacokinetics and metabolism in humans: H. Schütz et al., Eur. J. Drug Metab. Pharmacokinet. 10, 147 (1985); S. A. Hauffe et al., ibid. 217. Preliminary clinical evaluations: R. Buoninconti, M. Motolese, Int. J. Clin. Pharmacol. Ther. Toxicol. 23, 613 (1985); A. Salvadeo et al., Arzneim.-Forsch. 35, 623 (1985).

Chemical structure

Properties

Crystals from acetone, mp 160-162°. pKa 6.0. uv max: 248, 340 nm (ε 22100, 2250). Soly (mg/ml): water 1.3; HCl 235.0; DMSO 323.0; methanol 21.0; dioxane 18.6; chloroform 8.5; diethyl ether, benzene, cyclohexane <0.1. LD50 in rats, dogs (mg/kg): 269, approx 400 i.v.; 2060, >2000 orally (Semeraro); in mice (mg/kg): 700 i.p. (Parravicini).

Therapeutic Category

Antihypertensive.

Keywords

Antihypertensive; Hydrazines/Phthalazines