From Wikipedia, the free encyclopedia
Chemical compound alfa1-blocker
Alfuzosin
Pronunciation
al-FEW -zoh-sin
Trade names Uroxatral, others
AHFS /
Drugs.com
Monograph
MedlinePlus
a64002
License data
Pregnancy category
Routes of administration
By mouth
ATC code
Legal status
Bioavailability 49%
Protein binding 82–90%
Metabolism
Liver (
CYP3A4 -mediated)
Elimination half-life 10 hours
Excretion
Feces (69%) and
Urine (24%)
(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 InfoCard
100.108.671
Formula C 19 H 27 N 5 O 4
Molar mass 389.456 g·mol−1 3D model (
JSmol )
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)
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]
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
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
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
Brand names
It is sold under the brand names Alfosoft, Uroxatral,
[8] Xatral, Prostetrol,
[9] and Alfural.
[10] .[
unreliable source? ]
References
^ 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 & 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 .
This article incorporates
text available under the
CC BY 4.0 license.
^ 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 .
^
"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 .
^
"Γαληνός - Φάρμακο - ALFURAL" . www.galinos.gr (in Greek). Retrieved 21 September 2022 .
α1
Agonists Antagonists
Abanoquil
Ajmalicine
Alfuzosin
Anisodamine
Anisodine
Atiprosin
Atypical antipsychotics (e.g.,
brexpiprazole ,
clozapine ,
olanzapine ,
quetiapine ,
risperidone )
Benoxathian
Beta blockers (e.g.,
adimolol ,
amosulalol ,
arotinolol ,
carvedilol ,
eugenodilol ,
labetalol )
Buflomedil
Bunazosin
Corynanthine
Dapiprazole
Domesticine
Doxazosin
Ergolines (e.g.,
acetergamine ,
ergotamine ,
dihydroergotamine ,
lisuride ,
nicergoline ,
terguride )
Etoperidone
Fenspiride
Hydroxyzine
Indoramin
Ketanserin
L-765,314
mCPP
Mepiprazole
Metazosin
Monatepil
Moxisylyte
Naftopidil
Nantenine
Neldazosin
Niaprazine
Niguldipine
Pardoprunox
Pelanserin
Perlapine
Phendioxan
Phenoxybenzamine
Phentolamine
Phenylpiperazine
antidepressants (e.g.,
hydroxynefazodone ,
nefazodone ,
trazodone ,
triazoledione )
Piperoxan
Prazosin
Quinazosin
Quinidine
Silodosin
Spegatrine
Spiperone
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Tamsulosin
Terazosin
Tiodazosin
Tolazoline
Tetracyclic antidepressants (e.g.,
amoxapine ,
maprotiline ,
mianserin )
Tricyclic antidepressants (e.g.,
amitriptyline ,
clomipramine ,
doxepin ,
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trimipramine )
Trimazosin
Typical antipsychotics (e.g.,
chlorpromazine ,
fluphenazine ,
loxapine ,
thioridazine )
Urapidil
WB-4101
Zolertine
α2
Agonists Antagonists
1-PP
Adimolol
Amesergide
Aptazapine
Atipamezole
Atypical antipsychotics (e.g.,
asenapine ,
brexpiprazole ,
clozapine ,
lurasidone ,
olanzapine ,
paliperidone ,
quetiapine ,
risperidone ,
zotepine )
Azapirones (e.g.,
buspirone ,
gepirone ,
ipsapirone ,
tandospirone )
BRL-44408
Buflomedil
Cirazoline
Efaroxan
Esmirtazapine
Fenmetozole
Fluparoxan
Idazoxan
Ketanserin
Lisuride
mCPP
Mianserin
Mirtazapine
NAN-190
Pardoprunox
Phentolamine
Phenoxybenzamine
Piperoxan
Piribedil
Rauwolscine
Rotigotine
Setiptiline
Spegatrine
Spiroxatrine
Sunepitron
Terguride
Tolazoline
Typical antipsychotics (e.g.,
chlorpromazine ,
fluphenazine ,
loxapine ,
thioridazine )
Yohimbine
β