Alfuzosin

Alfuzosin, sold under the brand name Alfosoft, 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 namesAlfosoft, Uroxatral, others
AHFS/Drugs.comMonograph
MedlinePlusa64002
License data
Pregnancy
category
  • AU: B2
Routes of
administration		By mouth
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
IUPAC name
  • (RS)-N-[3-[(4-Amino-6,7-dimethoxy-quinazolin-2-yl)- methyl-amino]propyl] tetrahydrofuran- 2-carboxamide
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)
SMILES
  • O=C(NCCCN(c2nc1cc(OC)c(OC)cc1c(n2)N)C)C3OCCC3
InChI
  • InChI=1S/C19H27N5O4/c1-24(8-5-7-21-18(25)14-6-4-9-28-14)19-22-13-11-16(27-3)15(26-2)10-12(13)17(20)23-19/h10-11,14H,4-9H2,1-3H3,(H,21,25)(H2,20,22,23) Y
  • Key:WNMJYKCGWZFFKR-UHFFFAOYSA-N Y
  (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 benign prostatic hyperplasia in 2003. In 2019, it was the 327th most commonly prescribed medication in the United States, with more than 1 million prescriptions.[3][4]

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.[5] Adverse effects of alfuzosin are similar to that of tamsulosin with the exception of retrograde ejaculation.[6]

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.[7]

Enantiomers of alfuzosin

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

It is provided as the hydrochloride salt.

Society and culture

Brand names

It is sold under the brand names Alfosoft, Uroxatral,[8] Xatral, Prostetrol,[9] and Alfural[10].

References
  1. Lepor H (August 2016). "Alpha-blockers for the Treatment of Benign Prostatic Hyperplasia". The Urologic Clinics of North America. 43 (3): 311–23. doi:10.1016/j.ucl.2016.04.009. PMC 2213889. PMID 27476124.
  2. Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 455. ISBN 9783527607495.
  3. "The Top 300 of 2019". ClinCalc. Retrieved 16 October 2021.
  4. "Alfuzosin - Drug Usage Statistics". ClinCalc. Retrieved 16 October 2021.
  5. "Alfuzosin". MedlinePlus. United States National Library of Medicine. 15 April 2016.
  6. Liu C, Zeng G, Kang R, Wu W, Li J, Chen K, Wan SP (2015). "Efficacy and Safety of Alfuzosin as Medical Expulsive Therapy for Ureteral Stones: A Systematic Review and Meta-Analysis". PLOS ONE. 10 (8): e0134589. Bibcode:2015PLoSO..1034589L. doi:10.1371/journal.pone.0134589. PMC 4526635. PMID 26244843. This article incorporates text available under the CC BY 4.0 license.
  7. 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.
  8. "Alfuzosin (Oral Route) Description and Brand Names - Mayo Clinic". www.mayoclinic.org. Retrieved 21 September 2022.
  9. "Prostetrol 10mg 30 tablet". royalph.com. Retrieved 21 September 2022.
  10. "Γαληνός - Φάρμακο - ALFURAL". www.galinos.gr (in Greek). Retrieved 21 September 2022.
  • "Alfuzosin". Drug Information Portal. U.S. National Library of Medicine.
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