9154. Terazosin

Nomenclature

CAS number: 63590-64-7
1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-4-[(tetrahydro-2-furanyl)carbonyl]piperazine; 2-[(4-tetrahydro-2-furoyl)-1-piperazinyl]-4-amino-6,7-dimethoxyquinazoline.
C19H25N5O4; mol wt 387.43.
C 58.90%, H 6.50%, N 18.08%, O 16.52%.

Description and references

α1-Adrenergic blocker related to prazosin, q.v. Prepn: M. Winn et al., DE 2646186; eidem, US 4026894 (both 1977 to Abbott); of the hydrochloride dihydrate: R. Roteman, DE 2831112; idem, US 4251532 (1979, 1981 both to Abbott). HPLC determn in biological fluids: S. E. Patterson, J. Chromatogr. 311, 206 (1984). Toxicity in rats: F. L. Fort et al., Drug Chem. Toxicol. 7, 435 (1984). Clinical study in essential hypertension: P. A. Abraham et al., Pharmacotherapy 5, 285 (1985); in treatment of benign prostatic hyperplasia: H. Lepor et al., J. Urol. 148, 1467 (1992). Symposium on pharmacology, pharmacokinetics, and clinical efficacy in hypertension: Am. J. Med. 80, Suppl. 5B, 1-105 (1986). Comprehensive description: Z. L. Chang, J. F. Bauer, Anal. Profiles Drug Subs. 20, 693-727 (1991). Review of pharmacology and therapeutic efficacy: R. Achari, A. Laddu, J. Clin. Pharmacol. 32, 520-523 (1992).

Chemical structure

Properties

Fine, white, odorless crystals, mp 272.6-274°. Soly at 25°C (mg/ml): methanol 33.7; water 29.7; 95% ethanol 4.1; 0.1N HCl 3.8; chloroform 1.2; acetone 0.01. Practically insol in hexane. uv max (0.005% in water): 212, 245, 330 nm (a 65.7, 127.5, 24.0). pKa (0.1N NaOH): 7.1.

Derivative

Hydrochloride.
C19H25N5O4.HCl; mol wt 423.89.
C 53.84%, H 6.18%, N 16.52%, O 15.10%, Cl 8.36%.

Properties

Hygroscopic crystals from isopropyl alc, mp 278-279°. Soly in water: 761.2 mg/ml. LD50 in mice (mg/kg): 259.3 i.v. (Winn).

Derivative

Hydrochloride dihydrate.

Nomenclature

CAS number: 70024-40-7
Abbott 45975; Heitrin (Abbott); Hytracin (Dainabot-Dainippon); Hytrin (Abbott); Hytrinex (Abbott); Itrin (Abbott); Urodie (Abbott); Vasocard (Abbott); Vasomet (Sanko-Nikken); Vicard (Abbott).
C19H25N5O4.HCl.2H2O; mol wt 459.92.
C 49.62%, H 6.57%, N 15.23%, O 20.87%, Cl 7.71%.

Properties

mp 271-274°. Soly in water: 24.2 mg/ml. LD50 in male, female rats (mg/kg): 277, 293 i.v. (Fort).

Therapeutic Category

Antihypertensive. In treatment of benign prostatic hyperplasia.

Keywords

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