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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/ælˈfjuːzsɪn/ al-FEW-zoh-sin
Trade namesUroxatral, 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
  • (RS)-N-[3-[(4-Amino-6,7-dimethoxy-quinazolin-2-yl)- methyl-amino]propyl] tetrahydrofuran- 2-carboxamide
CAS Number
  • 81403-80-7 Y
PubChem CID
  • 2092
IUPHAR/BPS
  • 7109
DrugBank
  • DB00346 Y
ChemSpider
  • 2008 Y
UNII
  • 90347YTW5F
KEGG
  • D07124 Y
ChEBI
  • CHEBI:51141 Y
ChEMBL
  • ChEMBL709 Y
CompTox Dashboard (EPA)
  • DTXSID6048549
ECHA InfoCard100.108.671
Chemical and physical data
FormulaC19H27N5O4
Molar mass389.456 g·mol−1
3D model (JSmol)
  • Interactive image
  • O=C(NCCCN(c2nc1cc(OC)c(OC)cc1c(n2)N)C)C3OCCC3
  • 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 urination easier.

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 2020, it was the 336th-most commonly prescribed medication in the United States, with more than 700 thousand prescriptions.[3][4]

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.[5] Adverse effects of alfuzosin are similar to that of tamsulosin but with 70% lower rate of retrograde ejaculation.[6]

Chemistry edit

Alfuzosin contains a stereocenter, so is chiral, with two enantiomeric forms, (R)- 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 edit

Brand names edit

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

References edit

  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 2020". ClinCalc. Retrieved 7 October 2022.
  4. ^ "Alfuzosin - Drug Usage Statistics". ClinCalc. Retrieved 7 October 2022.
  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, sold, under, brand, name, uroxatral, among, others, medication, blocker, class, used, treat, benign, prostatic, hyperplasia, clinical, datapronunciation, juː, sintrade, namesuroxatral, othersahfs, drugs, commonographmedlineplusa64002license, dataus,. Alfuzosin sold under the brand name Uroxatral among others is a medication of the a1 blocker class It is used to treat benign prostatic hyperplasia BPH 1 AlfuzosinClinical dataPronunciation ae l ˈ f juː z oʊ s ɪ n al FEW zoh sinTrade namesUroxatral othersAHFS Drugs comMonographMedlinePlusa64002License dataUS DailyMed AlfuzosinPregnancycategoryAU B2Routes ofadministrationBy mouthATC codeG04CA01 WHO Legal statusLegal statusUK POM Prescription only US onlyPharmacokinetic dataBioavailability49 Protein binding82 90 MetabolismLiver CYP3A4 mediated Elimination half life10 hoursExcretionFeces 69 and Urine 24 IdentifiersIUPAC name RS N 3 4 Amino 6 7 dimethoxy quinazolin 2 yl methyl amino propyl tetrahydrofuran 2 carboxamideCAS Number81403 80 7 YPubChem CID2092IUPHAR BPS7109DrugBankDB00346 YChemSpider2008 YUNII90347YTW5FKEGGD07124 YChEBICHEBI 51141 YChEMBLChEMBL709 YCompTox Dashboard EPA DTXSID6048549ECHA InfoCard100 108 671Chemical and physical dataFormulaC 19H 27N 5O 4Molar mass389 456 g mol 13D model JSmol Interactive imageSMILES O C NCCCN c2nc1cc OC c OC cc1c n2 N C C3OCCC3InChI 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 YKey WNMJYKCGWZFFKR UHFFFAOYSA N Y verify As an antagonist of the a1 adrenergic receptor it works by relaxing the muscles in the prostate and bladder neck making urination easier 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 2020 it was the 336th most commonly prescribed medication in the United States with more than 700 thousand prescriptions 3 4 Contents 1 Side effects 2 Chemistry 3 Society and culture 3 1 Brand names 4 ReferencesSide effects editThe 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 but with 70 lower rate of retrograde ejaculation 6 Chemistry editAlfuzosin contains a stereocenter so is chiral with two enantiomeric forms R 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 nbsp CAS number 123739 69 5 nbsp CAS number 123739 70 8It is provided as the hydrochloride salt Society and culture editBrand names edit It is sold under the brand names Alfosoft Uroxatral 8 Xatral Prostetrol 9 and Alfural 10 unreliable source References edit 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 Fischer J Ganellin CR 2006 Analogue based Drug Discovery John Wiley amp Sons p 455 ISBN 9783527607495 The Top 300 of 2020 ClinCalc Retrieved 7 October 2022 Alfuzosin Drug Usage Statistics ClinCalc Retrieved 7 October 2022 Alfuzosin MedlinePlus United States National Library of Medicine 15 April 2016 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 nbsp This article incorporates text available under the CC BY 4 0 license Rote Liste Service GmbH Hrsg Rote Liste 2017 Arzneimittelverzeichnis fur Deutschland einschliesslich EU Zulassungen und bestimmter Medizinprodukte Rote Liste Service GmbH Frankfurt Main 2017 Aufl 57 S 159 ISBN 978 3 946057 10 9 Alfuzosin Oral Route Description and Brand Names Mayo Clinic www mayoclinic org Retrieved 21 September 2022 Prostetrol 10mg 30 tablet royalph com Retrieved 21 September 2022 Galhnos Farmako ALFURAL www galinos gr in Greek Retrieved 21 September 2022 Portals nbsp Medicine nbsp Viruses Retrieved from https en wikipedia org w index php title Alfuzosin amp oldid 1149847943, wikipedia, wiki, book, books, library,

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