3433. Doxazosin

Nomenclature

CAS number: 74191-85-8
1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-4-[(2,3-dihydro-1,4-benzodioxin-2-yl)carbonyl]piperazine; 4-amino-2-[4-(1,4-benzodioxan-2-carbonyl)piperazin-1-yl]-6,7-dimethoxyquinazoline; UK-33274.
C23H25N5O5; mol wt 451.48.
C 61.19%, H 5.58%, N 15.51%, O 17.72%.

Description and references

Selective α1-adrenergic blocker related to prazosin, q.v. Prepn: S. F. Campbell, DE 2847623; idem, US 4188390 (1979, 1980 both to Pfizer). Cardiovascular pharmacology: P. B. Timmermans et al., Arch. Int. Pharmacodyn. Ther. 245, 218 (1980). HPLC determn in plasma: M. G. Cowlishaw, J. R. Sharman, J. Chromatogr. 344, 403 (1985). Clinical pharmacokinetics: H. L. Elliott et al., Br. J. Clin. Pharmacol. 13, 699 (1982). Symposia on pharmacology and clinical efficacy in hypertension: Br. J. Clin. Pharmacol. 21, Suppl. 1, 1S-92S (1986); Am. J. Cardiol. 59, 1G-104G (1987). Review of clinical trials in benign prostatic hypertrophy: C. G. Roehrborn, R. L. Siegel, Urology 48, 406-415 (1996).

Chemical structure

Derivative

Hydrochloride.
C23H25N5O5.HCl; mol wt 487.94.
C 56.61%, H 5.37%, N 14.35%, O 16.39%, Cl 7.27%.

Properties

Crystals, mp 289-290°.

Derivative

Methanesulfonate.

Nomenclature

CAS number: 77883-43-3
Doxazosin mesylate; UK-33274-27; Alfadil (Pfizer); Alfamedin (Kade); Benur (Pfizer); Cardenalin (Pfizer); Cardular (Pfizer); Cardura (Pfizer); Carduran (Pfizer); Diblocin (AstraZeneca); Doxamax (Esparma); Zoxan (Pfizer).
C23H25N5O5.CH3SO3H; mol wt 547.58.
C 52.64%, H 5.34%, N 12.79%, O 23.37%, S 5.86%.

Therapeutic Category

Antihypertensive; in treatment of benign prostatic hypertrophy.

Keywords

α-Adrenergic Blocker; Antihypertensive; Quinazoline Derivatives; Antiprostatic Hypertrophy