Alfuzosin

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Alfuzosin
Alfuzosin.svg
Clinical data
Pronunciation /ælˈfjuːzsɪn/ al-FEW-zoh-sin
Trade names Uroxatral, others
AHFS/Drugs.com Monograph
MedlinePlus a64002
Pregnancy
category
  • AU: B2
  • US: B (No risk in non-human studies)
Routes of
administration
By mouth (tablets)
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability 49%
Protein binding 82–90%
Metabolism Liver (CYP3A4-mediated)
Elimination half-life 10 hours
Excretion Feces (69%) and Urine (24%)
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard 100.108.671 Edit this at Wikidata
Chemical and physical data
Formula C19H27N5O4
Molar mass 389.46 g·mol−1
3D model (JSmol)
  (verify)

Alfuzosin is a medication of the α1 blocker class. It is used to treat benign prostatic hyperplasia (BPH).[1]

As an antagonist of the α1 adrenergic receptor, it works by relaxing the muscles in the prostate and bladder neck, making it easier to urinate.

Alfuzosin was approved by the U.S. FDA for treatment of BPH in June 2003. It is marketed in the United States by Sanofi Aventis under the brand name Uroxatral and elsewhere under the tradenames Xat, Xatral, Prostetrol and Alfural.

Side effects[edit]

The most common side effects are dizziness (due to postural hypotension), upper respiratory tract infection, headache, fatigue, and abdominal disturbances. Side effects include stomach pain, heartburn, and congested nose.[2] Adverse effects of alfuzosin are similar to that of tamsulosin with the exception of retrograde ejaculation.[3]

Contraindications[edit]

Alfuzosin should be used with caution in patients with severe renal insufficiency, and should not be prescribed to patients with a known history of QT prolongation who are taking medications known to prolong the QT interval.

Chemistry[edit]

Alfuzosin contains a stereocenter and is therefore chiral. There are two enantiomeric forms, (R)-alfuzosin and (S)-alfuzosin. The drug is used as a racemate, (RS)-alfuzosin, a 1: 1 mixture of the (R)- and (S)-forms.[4]

Enantiomers of alfuzosin
Strukturformel des (R)-Enantiomers
CAS number: 123739-69-5
Strukturformel des (S)-Enantiomers
CAS number.: 123739-70-8

It is provided as the hydrochloride salt.

References[edit]

  1. ^ Lepor, Herbert (2016). "Alpha-blockers for the Treatment of Benign Prostatic Hyperplasia". Urologic Clinics of North America. 43 (3): 311–23. doi:10.1016/j.ucl.2016.04.009. PMC 2213889Freely accessible. PMID 27476124. 
  2. ^ "Alfuzosin". MedlinePlus. United States National Library of Medicine. April 15, 2016. 
  3. ^ Hills, Robert K; Liu, Chenli; Zeng, Guohua; Kang, Ran; Wu, Wenqi; Li, Jiasheng; Chen, Kang; Wan, Show P. (2015). "Efficacy and Safety of Alfuzosin as Medical Expulsive Therapy for Ureteral Stones: A Systematic Review and Meta-Analysis". PLOS ONE. 10 (8): e0134589. doi:10.1371/journal.pone.0134589. ISSN 1932-6203. PMC 4526635Freely accessible. PMID 26244843.  This article incorporates text available under the CC BY 4.0 license.
  4. ^ Rote Liste Service GmbH (Hrsg.): Rote Liste 2017 - Arzneimittelverzeichnis für Deutschland (einschließlich EU-Zulassungen und bestimmter Medizinprodukte). Rote Liste Service GmbH, Frankfurt/Main, 2017, Aufl. 57, S. 159, ISBN 978-3-946057-10-9.

External links[edit]