Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Tamsulosin: Difference between pages

{{Short description|Medication}}

{{Use dmy dates|date=October 2021}}

{{cs1 config |name-list-style=vanc |display-authors=6}}

| verifiedrevid = 461746753

| image = Tamsulosin.svg

2D structural formula of Tamsulosin wrong: Ethyl-Group like drawn in 3D Model.

| alt2 =

| image2 = Tamsulosin-from-xtal-3D-bs-17.png

<!--Clinical data-->| pronounce = {{IPAc-en|t|æ|m|ˈ|s|uː|l|ə|s|ɪ|n}}{{refn|{{MerriamWebsterDictionary|Tamsulosin}}}}<br />{{respell|tam|SOO|lə|sin}}

| tradename = Flomax, others

| DailyMedID = Tamsulosin

| routes_of_administration = [[Oral administration|By mouth]]

| ATC_prefix = G04

| ATC_suffix = CA02

| legal_CA = Rx-only

| legal_CA_comment = <ref>{{cite web | title=Product monograph brand safety updates | website=Health Canada | date=February 2024 | url=https://www.canada.ca/en/health-canada/services/drugs-health-products/drug-products/drug-product-database/label-safety-assessment-update/product-monograph-brand-safety-updates.html | access-date=24 March 2024}}</ref>

| legal_UK_comment = <ref>{{cite web | title=Flomaxtra XL, 400 micrograms, film-coated prolonged release tablet – Summary of Product Characteristics (SmPC) | website=(emc) | date=12 November 2019 | url=https://www.medicines.org.uk/emc/product/97/smpc | access-date=2 December 2021}}</ref><ref>{{cite web | title=Faramsil 400 microgram Prolonged-release Tablets – Summary of Product Characteristics (SmPC) | website=(emc) | date=4 November 2020 | url=https://www.medicines.org.uk/emc/product/4948/smpc | access-date=2 December 2021}}</ref>

| legal_US_comment = <ref>{{cite web | title=Flomax– tamsulosin hydrochloride capsule | website=DailyMed | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=6771ad8e-ac92-4aec-b484-5d8350a353f8 | access-date=2 December 2021}}</ref>

<!--Pharmacokinetic data-->| bioavailability = 100% (by mouth)

| metabolism = [[Liver]]

| excretion = 76% [[Kidney]]

<!--Identifiers-->| class = [[Alpha-1 blocker|α₁ blocker]]

| index2_label = as HCl

| KEGG2_Ref = {{keggcite|correct|kegg}}

| KEGG2 = D01024

| ChEBI_Ref = {{ebicite|correct|EBI}}

<!--Chemical data-->| IUPAC_name = (''R'')-5-(2-<nowiki/>{[2-(2-Ethoxyphenoxy)ethyl]amino}propyl)-2-methoxybenzene-1-sulfonamide

| C = 20

| H = 28

| N = 2

| O = 5

| S = 1

[[File:Tamsulosin - ARISTO Pharma - 0,4 mg Retardtabletten - Urologikum.jpg|thumb|Tamsulosin – ARISTO Pharma – 0.4 mg prolonged-release tablets – Urologikum]]

<!-- Definition and medical uses -->

'''Tamsulosin''', sold under the brand name '''Flomax''' among others, is a [[medication]] used to treat symptomatic [[benign prostatic hyperplasia]] (BPH) and [[Chronic prostatitis/chronic pelvic pain syndrome|chronic prostatitis]] and to help with the passage of [[kidney stones]].<ref name=AHFS2018>{{cite web |title=Tamsulosin Hydrochloride Monograph for Professionals |url=https://www.drugs.com/monograph/tamsulosin-hydrochloride.html |website=Drugs.com |publisher=AHFS |access-date=24 December 2018 |language=en}}</ref><ref>{{cite web |title=Prostatitis |url=https://www.nhs.uk/conditions/prostatitis |website=NHS |access-date=24 December 2018 |language=en |date=19 October 2017}}</ref><ref name=Wang2016>{{cite journal | vauthors = Wang RC, Smith-Bindman R, Whitaker E, Neilson J, Allen IE, Stoller ML, Fahimi J | title = Effect of Tamsulosin on Stone Passage for Ureteral Stones: A Systematic Review and Meta-analysis | journal = Annals of Emergency Medicine | volume = 69 | issue = 3 | pages = 353–361.e3 | date = March 2017 | pmid = 27616037 | doi = 10.1016/j.annemergmed.2016.06.044 | doi-access = free }}</ref> The evidence for benefit with a kidney stone is better when the stone is larger.<ref name=Wang2016/> Tamsulosin is taken by mouth.<ref name=AHFS2018/>

<!-- Side effects and mechanism -->

Common side effects include [[dizziness]], [[headache]], [[insomnia]], [[nausea]], [[blurry vision]], and [[Sexual dysfunction|sexual problems]].<ref name=BNF76/><ref name=AHFS2018/> Other side effects may include [[feeling lightheaded with standing]] due to changes in blood pressure, and [[angioedema]].<ref name=BNF76/> Tamsulosin is an [[alpha blocker]] and works by relaxing muscles in the prostate.<ref>{{cite book | vauthors = Hutchison LC, Sleeper RB |title=Fundamentals of Geriatric Pharmacotherapy: An Evidence-Based Approach |date=2010 |publisher=ASHP |isbn=9781585283057 |page=209 |url=https://books.google.com/books?id=fUtOugU_KeIC&pg=PA209 |language=en}}</ref> Specifically it is an [[alpha-1 adrenergic receptor|α₁-adrenergic receptor]] blocker.<ref name=AHFS2018/>

<!-- Society and culture -->

Tamsulosin was approved for medical use in the United States in 1997.<ref name=AHFS2018/> It is available as a [[generic medication]].<ref name=BNF76>{{cite book|title=British national formulary : BNF 76|date=2018|publisher=Pharmaceutical Press|isbn=9780857113382|pages=767|edition=76}}</ref> In 2022, it was the twentieth most commonly prescribed medication in the United States, with more than 25{{nbsp}}million prescriptions.<ref>{{cite web | title=The Top 300 of 2022 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=30 August 2024 | archive-date=30 August 2024 | archive-url=https://web.archive.org/web/20240830202410/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Tamsulosin Drug Usage Statistics, United States, 2013 - 2022 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Tamsulosin | access-date = 30 August 2024 }}</ref>

== Medical uses ==

[[File:000636lg Flomax 0.4 mg.jpg|left|thumb|Flomax 0.4 mg oral capsule]]

Tamsulosin is primarily used for [[benign prostatic hyperplasia]] (BPH) and to help with the passage of [[kidney stone]]s.<ref>{{cite web | url = http://www.renalandurologynews.com/tamsulosin-aids-stone-expulsion/article/193855/ | title = Tamsulosin Aids Stone Expulsion | publisher = Renal and Urology News | date = 7 January 2011 | access-date = 4 October 2012 | archive-date = 14 May 2012 | archive-url = https://web.archive.org/web/20120514032753/http://www.renalandurologynews.com/tamsulosin-aids-stone-expulsion/article/193855/ | url-status = dead }}</ref><ref>{{cite web | url = http://www.prnewswire.com/news-releases/study-shows-use-of-tamsulosin-or-nifedipine-helps-patients-to-clear-ureteral-stone-fragments-faster-and-reduces-rate-of-recurrence-54518887.html | title = Study Shows Use of Tamsulosin or Nifedipine Helps Patients to Clear Ureteral Stone Fragments Faster and Reduces Rate of Recurrence }}</ref> Tamsulosin, however, appears to be effective only for stones over 4&nbsp;mm and less than 10&nbsp;mm in size.<ref name=Wang2016/>

Tamsulosin is also used as an add-on treatment for [[acute urinary retention]]. People may void more successfully after catheter removal if they are taking tamsulosin. People taking tamsulosin also are less likely to need recatheterization.<ref>{{cite journal | vauthors = Lucas MG, Stephenson TP, Nargund V | title = Tamsulosin in the management of patients in acute urinary retention from benign prostatic hyperplasia | journal = BJU International | volume = 95 | issue = 3 | pages = 354–357 | date = February 2005 | pmid = 15679793 | doi = 10.1111/j.1464-410X.2005.05299.x | s2cid = 30254915 | doi-access = }}</ref>

Tamsulosin does not decrease the overall size of the prostate in men with BPH, and is not recommended for prevention of [[prostate cancer]].<ref name=":0">{{Cite book|title=Medical-surgical nursing : assessment and management of clinical problems| vauthors = Lewis SM, Dirksen SR, Heitkemper MM, Bucher LH |year= 2013|isbn=978-0-323-10089-2|edition=9th|location=St. Louis, Missouri|oclc=228373703}}</ref>

=== Combination therapy ===

The results of the CombAT (combination of [[dutasteride]] [Avodart] and tamsulosin [Duodart]) trial in 2008 demonstrated that treatment with the combination of dutasteride and tamsulosin provides greater symptom benefits compared to monotherapy with either agent alone for treatment of benign prostatic hyperplasia.<ref name="Roehrborn2008">{{cite journal | vauthors = Roehrborn CG, Siami P, Barkin J, Damião R, Major-Walker K, Morrill B, Montorsi F | title = The effects of dutasteride, tamsulosin and combination therapy on lower urinary tract symptoms in men with benign prostatic hyperplasia and prostatic enlargement: 2-year results from the CombAT study | journal = The Journal of Urology | volume = 179 | issue = 2 | pages = 616–621; discussion 621 | date = February 2008 | pmid = 18082216 | doi = 10.1016/j.juro.2007.09.084 }}</ref>

The CombAT trial became the medication [[Dutasteride/tamsulosin|Jalyn]]. It was approved by the FDA on 14 June 2010.<ref>[http://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022460Orig1s000Approv.pdf FDA approval letter] at FDA.gov</ref> This combination can be useful because it may take up to six months for symptomatic relief to be found when using [[5α-Reductase inhibitor|5α-Reductase inhibitors]] such as dutasteride compared to alpha-1 receptor blockers, which can provide relief in some cases within 48 hours.<ref>Australian Medicines Handbook {{full citation needed|date=September 2016}}</ref>

== Adverse effects ==

* Eyes: People taking tamsulosin are prone to a [[complication (medicine)|complication]] known as [[intraoperative floppy iris syndrome|floppy iris syndrome]] during [[cataract surgery]]. [[Adverse outcome]]s of the surgery are greatly reduced by the surgeon's prior knowledge of the person's history with this drug, and thus having the option of alternative techniques.<ref>Medscape, [http://www.medscape.com/viewarticle/547937 Good Cataract Surgery Outcomes Possible in Intraoperative Floppy Iris Syndrome Due to Tamsulosin].</ref>

* Severe [[hypotension]].<ref name="BirdDelaney2013">{{cite journal | vauthors = Bird ST, Delaney JA, Brophy JM, Etminan M, Skeldon SC, Hartzema AG | title = Tamsulosin treatment for benign prostatic hyperplasia and risk of severe hypotension in men aged 40-85 years in the United States: risk window analyses using between and within patient methodology | journal = BMJ | volume = 347 | pages = f6320 | date = November 2013 | pmid = 24192967 | pmc = 3817852 | doi = 10.1136/bmj.f6320 }}</ref><ref>{{cite journal | vauthors = Ramirez J | title = Severe hypotension associated with α blocker tamsulosin | journal = BMJ | volume = 347 | pages = f6492 | date = November 2013 | pmid = 24192968 | doi = 10.1136/bmj.f6492 | hdl-access = free | s2cid = 24324483 | hdl = 10906/78488 }}</ref>

* Persons with cardiac conditions including hypotension, mechanical heart failure (valvular, pulmonary embolism, pericarditis), and congestive heart failure should be monitored carefully while taking tamsulosin.

* Alpha blockers, including [[prazosin]], [[terazosin]], [[doxazosin]], or tamsulosin, do not appear to affect all-cause mortality in [[heart failure]] rehospitalization in those also receiving β-blockers.<ref>{{cite journal | vauthors = Page RL, O'Bryant CL, Cheng D, Dow TJ, Ky B, Stein CM, Spencer AP, Trupp RJ, Lindenfeld J | display-authors = 6 | title = Drugs That May Cause or Exacerbate Heart Failure: A Scientific Statement From the American Heart Association | journal = Circulation | volume = 134 | issue = 6 | pages = e32–e69 | date = August 2016 | pmid = 27400984 | doi = 10.1161/CIR.0000000000000426 | doi-access = free }}</ref>

*Tamsulosin can also cause [[retrograde ejaculation]], which occurs when semen is redirected to the urinary bladder instead of being ejaculated normally. This is because tamsulosin relaxes the muscles of the [[urethral sphincters]], which are normally closed during ejaculation.<ref>

{{Cite web|url=https://www.drugs.com/sfx/tamsulosin-side-effects.html|title=Tamsulosin Side Effects|website=Drugs.com|access-date=27 April 2011}}

</ref>

== Mechanism ==

{{Main|Alpha blocker}}

Tamsulosin is a selective [[alpha 1 receptor|α₁ receptor]] [[receptor antagonist|antagonist]] that has preferential selectivity for the [[Alpha-1A adrenergic receptor|α_1A receptor]] in the prostate versus the [[Alpha-1B adrenergic receptor|α_1B receptor]] in the blood vessels.<ref name=pharmnemonics>{{Cite book | vauthors = Shen H | title=Illustrated Pharmacology Memory Cards: PharMnemonics | year=2008 | publisher=Minireview | isbn=978-1-59541-101-3 | page=13}}</ref>

When alpha 1 receptors in the bladder neck, prostate, ureter, and urethra are blocked, a relaxation in smooth muscle tissue results.<ref name=":0" /> This mechanism decreases resistance to urinary flow, reduces discomfort associated with BPH, and facilitates passage of [[kidney stone disease|kidney stones]].<ref name=":0" />

==Brand names==

Tamsulosin was first marketed in 1996 under the [[trade name]] Flomax. The U.S. patent expired in October 2009.<ref>{{cite web|title=Flomax – Big Patent Expirations of 2010|url=http://www.fiercepharma.com/special-reports/flomax-big-patent-expirations-2010|date=10 February 2010|access-date=14 January 2012|archive-date=22 April 2012|archive-url=https://web.archive.org/web/20120422163615/http://www.fiercepharma.com/special-reports/flomax-big-patent-expirations-2010|url-status=dead}}</ref> The [[Food and Drug Administration (United States)|U.S. Food and Drug Administration]] (FDA) approved generics in March 2010.<ref>{{cite press release| url = https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm202728.htm| title = FDA Approves First Generic Tamsulosin to Treat Enlarged Prostate Gland| date = 2 March 2010| publisher=[[Food and Drug Administration (United States)|U.S. Food and Drug Administration]] (FDA)}}</ref> In 2010, tamsulosin was available as OTC medication in UK.<ref>{{cite journal | vauthors = | title = OTC tamsulosin for benign prostatic hyperplasia | journal = Drug and Therapeutics Bulletin | volume = 48 | issue = 10 | pages = 113–116 | date = October 2010 | pmid = 20926447 | doi = 10.1136/dtb.2010.10.0052 | s2cid = 32141889 }}</ref>

It is marketed by various companies under licence, including [[Boehringer Ingelheim]] and [[CSL Limited|CSL]]. Tamsulosin hydrochloride extended-release capsules are marketed under the trade names Urimax 0.4 (India),Tamlocept 0.4 (India), Flomax, Flomaxtra, Contiflo XL, bestflo, Mecir LP (France), Urimax, Pamsvax, and Pradif,<ref>{{cite web|title=Pradif 0,4 Mg Capsule Rigide A Rilascio Prolungato |url=http://www.torrinomedica.it/farmaci/schedetecniche/PRADIF.asp |work=Torrinomedica.it|access-date=15 November 2012 | vauthors = Magnanelli S, Vetere AM }}</ref> although generic, unmodified-release capsules are still approved and marketed in many countries (such as [[Canada]]). Generic extended-release tablets are marketed in most countries of the [[European Economic Area|EEA]].<ref>{{cite web|title=Tamsulosina Mylan 0,4 mg cápsulas duras de liberación modificada EFG|url=http://cima.aemps.es/cima/pdfs/es/p/67279/67279_p.pdf|work=cima.aemps.es|access-date=29 October 2018 }}</ref> In [[Mexico]], it is marketed as Secotex and as Harnal D in [[Japan]] and [[Indonesia]] and as Harnal OCAS (oral controlled absorption system) in Thailand.<ref>{{cite web | title = Drugs.com Database | url= https://www.drugs.com/international/harnal-d.html}}</ref> In [[Egypt]],<ref>{{cite news |title= Novartis hits Astellas with transplant drug generic|url=https://www.reuters.com/article/americasRegulatoryNews/idUST34424920090811 |publisher= Reuters|date= 11 August 2009|access-date=11 August 2009}}</ref> [[Italy]], [[Russia]] and [[Iceland]], it is marketed under the trade name Omnic by Astellas Pharma Europe. The largest manufacturer of tamsulosin is Synthon BV (the Netherlands).{{Cn|date=September 2023}} Tamsulosin hydrochloride is marketed in Bangladesh under the trade names Uromax, Prostanil MR, Tamisol MR, and Tamsin.{{citation needed|date=August 2017}}

<div style="clear:both"></div>

== References ==

{{Reflist}}

{{Drugs used in benign prostatic hypertrophy}}

{{Adrenergic receptor modulators}}

{{Portal bar | Medicine}}

{{Authority control}}

[[Category:Alpha-1 blockers]]

[[Category:Astellas Pharma]]

[[Category:Phenethylamines]]

[[Category:Phenol ethers]]

[[Category:Prostate disorders]]

[[Category:Substituted amphetamines]]

[[Category:Sulfonamides]]

[[Category:Wikipedia medicine articles ready to translate]]