Alfuzosin

Title: Alfuzosin
CAS Registry Number: 81403-80-7
CAS Name: N-[3-[(4-Amino-6,7-dimethoxy-2-quinazolinyl)methylamino]propyl]tetrahydro-2-furancarboxamide
Additional Names: N1-(4-amino-6,7-dimethoxyquinazol-2-yl)-N1-methyl-N2-(tetrahydrofuroyl-2)-propylenediamine
Manufacturers' Codes: SL-77.499
Molecular Formula: C19H27N5O4
Molecular Weight: 389.45
Percent Composition: C 58.60%, H 6.99%, N 17.98%, O 16.43%
Literature References: a1-Adrenoceptor antagonist structurally similar to prazosin, q.v. Prepn: P. M. J. Manoury, DE 2904445; idem, US 4315007 (1979, 1982 both to Synthelabo); and antihypertensive activity in rats: P. M. Manoury et al., J. Med. Chem. 29, 19 (1986). Pharmacology: A. G. Ramage, Eur. J. Pharmacol. 129, 307 (1986). HPLC determn in biological fluids: P. Guinebault et al., J. Chromatogr. 353, 361 (1986). Pharmacology in humans: A. H. Deering, Br. J. Clin. Pharmacol. 25, 417 (1988). Clinical evaluation in essential hypertension: S. Leto Di Priolo et al., Eur. J. Clin. Pharmacol. 35, 25 (1988); A. K. Ghosh, S. Ghosh, Ger. Cardiovasc. Med. 1, 81 (1988). Clinical trial in benign prostatic hyperplasia (BPH): C. G. Roehrborn et al., BJU Int. 92, 257 (2003). Review of clinical experience in BPH: D. M. Weiner, F. C. Lowe, Expert Opin. Pharmacother. 4, 2057-2063 (2003).
Derivative Type: Hydrochloride
CAS Registry Number: 81403-68-1
Manufacturers' Codes: SL-77.499-10
Trademarks: Mittoval (Schering AG); Urion (Zambon); UroXatral (Sanofi-Synthelabo); Xatral (Sanofi-Synthelabo)
Molecular Formula: C19H27N5O4.HCl
Molecular Weight: 425.91
Percent Composition: C 53.58%, H 6.63%, N 16.44%, O 15.03%, Cl 8.32%
Properties: Crystals from ethanol + ether, mp 225° (Manoury, 1986), also reported earlier as mp 235° (dec) (Manoury, 1982). pKa 8.13.
Melting point: mp 225° (Manoury, 1986); mp 235° (dec) (Manoury, 1982)
pKa: pKa 8.13
Therap-Cat: Antihypertensive. In treatment of benign prostatic hypertrophy.
Keywords: Antihypertensive; Quinazoline Derivatives; Antiprostatic Hypertrophy; a-Adrenergic Blocker.
Algestone Algestone Acetophenide Algin Alginic Acid Alibendol

Alfuzosin
Alfuzosin.svg
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Systematic (IUPAC) name
N-[3-[(4-amino-6,7-dimethoxy-quinazolin-2-yl)- methyl-amino]propyl] tetrahydrofuran- 2-carboxamide
Clinical data
Trade names Uroxatral
AHFS/Drugs.com monograph
MedlinePlus a604002
Pregnancy cat. B2 (AU) B (US)
Legal status POM (UK) -only (US)
Routes Oral
Pharmacokinetic data
Bioavailability 49%
Protein binding 82%-90%
Metabolism Hepatic (CYP3A4-mediated)
Half-life 10 hours
Excretion Fecal (69%) and renal (24%)
Identifiers
CAS number 81403-80-7 YesY
ATC code G04CA01
PubChem CID 2092
DrugBank DB00346
ChemSpider 2008 YesY
UNII 90347YTW5F YesY
KEGG D07124 YesY
ChEBI CHEBI:51141 YesY
ChEMBL CHEMBL709 YesY
Chemical data
Formula C19H27N5O4 
Mol. mass 389.449 g/mol
 YesY (what is this?)  (verify)

Alfuzosin (INN, provided as the hydrochloride salt) is an α1 receptor antagonist used to treat benign prostatic hyperplasia (BPH). It works by relaxing the muscles in the prostate and bladder neck, making it easier to urinate.

Alfuzosin is marketed in the United States by Sanofi Aventis under the brand name Uroxatral and elsewhere under the tradename Xatral, and in Egypt under name of Prostetrol. Alfuzosin was approved by the FDA for treatment of BPH in June 2003.