Alfuzosin

Structural formula
Simplified structural formula without stereochemistry
General
Non-proprietary name	Alfuzosin
other names	( RS ) -Tetrahydro-2-furancarboxylic acid 3 - [(4-amino-6,7-dimethoxy-2-quinazolinyl) -methyl-amino] propylamide ( RS ) - N - [3 - [(4-Amino-6,7-dimethoxyquinazolin-2-yl) (methyl) amino] tetrahydrofuran-2-carboxamide
Molecular formula	C 19 H 27 N 5 O 4 C 19 H 27 N 5 O 4
External identifiers / databases
CAS number 81403-80-7 81403-68-1 ( hydrochloride ) 123739-69-5 ( R ) -Alfuzosin 123739-70-8 ( S ) -Alfuzosin EC number 617-230-8 ECHA InfoCard 100.108.671 PubChem 2092 ChemSpider 2008 DrugBank DB00346 Wikidata Q2736873
Drug information
ATC code	G04 CA01
Drug class	Alpha blockers
Mechanism of action	α 1 adrenergic receptor antagonist
properties
Molar mass	389.45 g · mol -1 (alfuzosin) 425.9 g · mol -1 (alfuzosin · HCl)
Physical state	firmly
Melting point	225 ° C ( hydrochloride )
pK s value	8.13
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed GHS labeling of hazardous substances Caution H and P phrases H: 302 P: no P-phrases
Toxicological data	146 mg kg −1 ( LD 50 ,  rat ,  intravenous , hydrochloride) 235 mg kg −1 ( LD 50 ,  mouse ,  intravenous , hydrochloride)
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Alfuzosin is a drug from the group of α ₁ -adrenoreceptor antagonists ( alpha blockers ), which is used in the treatment of benign prostatic hyperplasia (BPH). The chiral compound is derived from quinazoline . It was patented by Synthélabo (now Sanofi ) as an antihypertensive agent in 1979 and 1982 .

Clinical information

application areas

The drug is used to treat the symptoms of benign prostatic hyperplasia. It has no influence on the size of the prostate .

Contraindications (contraindications)

In the presence of severe hepatic insufficiency or orthostatic hypotension (low blood pressure), administration is contraindicated, as is treatment with other alpha blockers.

Adverse effects (side effects)

Possible side effects include fatigue, dizziness, headache, flu symptoms, and hypotonic dysregulation.

Pharmacological properties

As an antagonist, alfuzosin binds selectively to postsynaptic α ₁ -adrenoreceptors and thus relaxes the smooth muscles of the prostate and urethra. This increases the flow of urine and facilitates urination . The bioavailability is 64% and the plasma half-life is 4 to 6 hours. The maximum plasma concentration is reached after 90 minutes.

Stereochemistry

Alfuzosin contains a stereocenter and is therefore chiral . There are two enantiomeric forms, ( R ) -form and ( S ) -form. However, only the racemate [( RS ) -Alfuzosin], a 1: 1 mixture of the ( R ) -enantiomer and the ( S ) -enantiomer, has practical significance :

Alfuzosin enantiomers
( R ) -Alfuzosin	( S ) -Alfuzosin

Trade names

Alfunar (D), Fuzocim (CH), Urion (D), UroXatral (D), Xatral (CH)

Individual evidence

1. ↑ ^{a b c} Entry on alfuzosin. In: Römpp Online . Georg Thieme Verlag, accessed on September 9, 2014.
2. ↑ ^{a b c d} Datasheet Alfuzosin hydrochloride from Sigma-Aldrich , accessed on September 9, 2014 ( PDF ).
3. ↑ ^{a b c} Michael C. Truß, Christian G. Stief, Stefan Machtens, Till Wagner, Udo Jonas: Pharmacotherapy in urology. 2nd, completely revised edition. Springer, Heidelberg 2005, ISBN 3-540-23449-7 , p. 302 ff.
4. ↑ Rote Liste Service GmbH (Ed.): Rote Liste 2017 - drug directory for Germany (including EU approvals and certain medical devices) . Rote Liste Service GmbH, Frankfurt / Main, 2017, edition 57, p. 159, ISBN 978-3-946057-10-9 .
5. ↑ ROTE LISTE 2017, Verlag Rote Liste Service GmbH, Frankfurt am Main, ISBN 978-3-946057-10-9 , p. 159.

This article is about a health issue. It is not used for self-diagnosis and does not replace a diagnosis by a doctor. Please note the information on health issues !