Alfuzosin

Alfuzosin
Clinical data
Pronunciation /ælˈfjuːzoʊsɪn/ 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

    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

    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

    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

    CAS number: 123739-69-5
    CAS number.: 123739-70-8

    It is provided as the hydrochloride salt.

    References

    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 2213889. 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 4526635. 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.
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