Alfuzosin

Alfuzosin, sold under the brand name Uroxatral among others, is a medication of the α1 blocker class. It is used to treat benign prostatic hyperplasia (BPH).[1]

Alfuzosin
Clinical data
Pronunciation/ælˈfjuːzoʊsɪn/ al-FEW-zoh-sin
Trade namesUroxatral, others
AHFS/Drugs.comMonograph
MedlinePlusa64002
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
    Bioavailability49%
    Protein binding82–90%
    MetabolismLiver (CYP3A4-mediated)
    Elimination half-life10 hours
    ExcretionFeces (69%) and Urine (24%)
    Identifiers
    CAS Number
    PubChem CID
    IUPHAR/BPS
    DrugBank
    ChemSpider
    UNII
    KEGG
    ChEBI
    ChEMBL
    CompTox Dashboard (EPA)
    ECHA InfoCard100.108.671
    Chemical and physical data
    FormulaC19H27N5O4
    Molar mass389.456 g·mol−1
    3D model (JSmol)
      (verify)

    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 patented in 1978 and approved for medical use in 1988.[2] It was approved in the US for BPH in 2003.

    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.[3] Adverse effects of alfuzosin are similar to that of tamsulosin with the exception of retrograde ejaculation.[4]

    Contraindications

    Alfuzosin should be used with caution in patients with severe chronic kidney disease, and should not be prescribed to patients with a known history of QT prolongation or those 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.[5]

    Enantiomers of alfuzosin

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

    It is provided as the hydrochloride salt.

    Brand names

    It is marketed under the brand name Uroxatral and elsewhere under the tradenames Xat, Xatral, Prostetrol and Alfural.

    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. Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 455. ISBN 9783527607495.
    3. "Alfuzosin". MedlinePlus. United States National Library of Medicine. April 15, 2016.
    4. 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.
    5. 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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