Chemistry:Alfuzosin
 | |
| Clinical data | |
|---|---|
| Pronunciation | /ælˈfjuːzoʊsɪn/ 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 | |
| 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 | |
| Chemical and physical data | |
| Formula | C19H27N5O4 |
| Molar mass | 389.456 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
| (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 | |
|---|---|
-Alfuzosin_Structural_Formula_V2.svg) CAS number: 123739-69-5 |
-Alfuzosin_Structural_Formula_V2.svg) 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
- ↑ "Alpha-blockers for the Treatment of Benign Prostatic Hyperplasia". The Urologic Clinics of North America 43 (3): 311–23. August 2016. doi:10.1016/j.ucl.2016.04.009. PMID 27476124.
- ↑ Analogue-based Drug Discovery. John Wiley & Sons. 2006. p. 455. ISBN 9783527607495. https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA455.
- ↑ "The Top 300 of 2020". https://clincalc.com/DrugStats/Top300Drugs.aspx.
- ↑ "Alfuzosin - Drug Usage Statistics". https://clincalc.com/DrugStats/Drugs/Alfuzosin.
- ↑ "Alfuzosin". MedlinePlus. 15 April 2016. https://medlineplus.gov/druginfo/meds/a604002.html#side-effects.
- ↑ "Efficacy and Safety of Alfuzosin as Medical Expulsive Therapy for Ureteral Stones: A Systematic Review and Meta-Analysis". PLOS ONE 10 (8): e0134589. 2015. doi:10.1371/journal.pone.0134589. PMID 26244843. Bibcode: 2015PLoSO..1034589L.
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". https://www.mayoclinic.org/drugs-supplements/alfuzosin-oral-route/description/drg-20061611.
- ↑ "Prostetrol 10mg 30 tablet" (in en). https://royalph.com/en/prostetrol-10mg-30tab.html.
- ↑ "Γαληνός - Φάρμακο - ALFURAL" (in el). https://www.galinos.gr/web/drugs/main/drugs/alfural.
{{Navbox
| name = Drugs used in benign prostatic hypertrophy | title = Drugs used in [[Medicine:Benign prostatic hyperpbenign prostatic hyperplasia (G04C) | state = collapsed | listclass = hlist
| group1 = 5α-Reductase inhibitors | list1 =
| group2 = Alpha-1 blockers | list2 =
| group3 = Steroidal antiandrogens | list3 =
| group4 = Herbal products | list4 =
| group5 = Others | list5 =
}}
 |  |
