| Revision as of 10:36, 21 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 461542868 of page Tamsulosin for the Chem/Drugbox validation project (updated: 'DrugBank'). |
Latest revision as of 23:41, 10 December 2024 edit 2601:642:c303:f370:103a:b9cd:8e09:9e6 (talk) ce |
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{{Short description|Medication}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Use dmy dates|date=October 2021}} |
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{{cs1 config |name-list-style=vanc |display-authors=6}} |
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{{Drugbox |
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{{Drugbox |
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| Watchedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 417212755 |
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| verifiedrevid = 461746753 |
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| image = Tamsulosin.svg |
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| IUPAC_name = (''R'')-5-(2-{amino}propyl)-2-methoxybenzene-1-sulfonamide |
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2D structural formula of Tamsulosin wrong: Ethyl-Group like drawn in 3D Model. |
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| image = Tamsulosin Structural Formulae.png |
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| width = 250 |
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| width = 250 |
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| alt2 = |
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| image2 = Tamsulosin-from-xtal-3D-bs-17.png |
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<!--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}} |
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<!--Clinical data--> |
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| tradename = Flomax |
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| tradename = Flomax, others |
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| Drugs.com = {{drugs.com|monograph|tamsulosin-hydrochloride}} |
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| Drugs.com = {{drugs.com|monograph|tamsulosin-hydrochloride}} |
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| MedlinePlus = a698012 |
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| MedlinePlus = a698012 |
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| licence_US = Tamsulosin |
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| DailyMedID = Tamsulosin |
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| pregnancy_AU = B2 |
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| pregnancy_AU = B2 |
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| routes_of_administration = ] |
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| pregnancy_US = B |
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| ATC_prefix = G04 |
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| ATC_suffix = CA02 |
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| legal_AU = S4 |
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| legal_AU = S4 |
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| legal_CA = Rx-only |
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| 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> |
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| legal_UK = POM |
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| legal_UK = POM |
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| 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> |
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| legal_US = Rx-only |
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| legal_US = Rx-only |
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| 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> |
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| routes_of_administration = oral |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data-->| bioavailability = 100% (by mouth) |
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| metabolism = ] |
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| bioavailability = 100% (oral) |
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| metabolism = ] |
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| elimination_half-life = 9–13 hours |
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| elimination_half-life = 9–13 hours |
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| excretion = 76% ] |
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| excretion = 76% ] |
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<!--Identifiers--> |
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<!--Identifiers-->| class = ] |
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| index2_label = as HCl |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 106133-20-4 |
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| CAS_number = 106133-20-4 |
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| ATC_prefix = G04 |
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| ATC_suffix = CA02 |
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| PubChem = 129211 |
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| PubChem = 129211 |
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| IUPHAR_ligand = 488 |
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| IUPHAR_ligand = 488 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D08560 |
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| KEGG = D08560 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| KEGG2_Ref = {{keggcite|correct|kegg}} |
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| KEGG2 = D01024 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 9398 |
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| ChEBI = 9398 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 836 |
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| ChEMBL = 836 |
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<!--Chemical data-->| IUPAC_name = (''R'')-5-(2-<nowiki/>{amino}propyl)-2-methoxybenzene-1-sulfonamide |
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<!--Chemical data--> |
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| C = 20 |
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| C=20 | H=28 | N=2 | O=5 | S=1 |
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| H = 28 |
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| molecular_weight = 408.51 |
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| N = 2 |
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| O = 5 |
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| S = 1 |
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| smiles = CCOc1ccccc1OCCN(C)Cc1ccc(OC)c(c1)S(=O)(=O)N |
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| smiles = CCOc1ccccc1OCCN(C)Cc1ccc(OC)c(c1)S(=O)(=O)N |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = DRHKJLXJIQTDTD-OAHLLOKOSA-N |
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| StdInChIKey = DRHKJLXJIQTDTD-OAHLLOKOSA-N |
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}} |
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}} |
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] |
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<!-- Definition and medical uses --> |
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'''Tamsulosin''', sold under the brand name '''Flomax''' among others, is a ] used to treat symptomatic ] (BPH) and ] and to help with the passage of ].<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/> |
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<!-- Side effects and mechanism --> |
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Common side effects include ], ], ], ], ], and ].<ref name=BNF76/><ref name=AHFS2018/> Other side effects may include ] due to changes in blood pressure, and ].<ref name=BNF76/> Tamsulosin is an ] 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 ] blocker.<ref name=AHFS2018/> |
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<!-- Society and culture --> |
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Tamsulosin was approved for medical use in the United States in 1997.<ref name=AHFS2018/> It is available as a ].<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> |
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== Medical uses == |
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] |
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Tamsulosin is primarily used for ] (BPH) and to help with the passage of ]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 mm and less than 10 mm in size.<ref name=Wang2016/> |
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Tamsulosin is also used as an add-on treatment for ]. People may void more successfully after catheter removal if they are taking tamsulosin. People taking tamsulosin also are less likely to need repeat catheterization.<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> |
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Tamsulosin does not decrease the overall size of the prostate in men with BPH and is not recommended for the prevention of ].<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> |
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=== Combination therapy === |
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The results of the CombAT (combination of ] and tamsulosin ) 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> |
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The CombAT trial became the medication ]. It was approved by the FDA on 14 June 2010.<ref> 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 ] 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> |
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== Adverse effects == |
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* Eyes: People taking tamsulosin are prone to a ] known as ] during ]. ]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, .</ref> |
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* Severe ].<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> |
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* Persons with cardiac conditions including hypotension, mechanical heart failure (valvular, pulmonary embolism, pericarditis), and congestive heart failure should be monitored carefully while taking tamsulosin. |
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* Alpha-blockers, including ], ], ], or tamsulosin, do not appear to affect all-cause mortality in ] 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> |
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*Tamsulosin can also cause ], which occurs when semen is redirected to the urinary bladder instead of being ejaculated normally. This is because tamsulosin relaxes the muscles of the ], which are normally closed during ejaculation.<ref> |
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{{Cite web|url=https://www.drugs.com/sfx/tamsulosin-side-effects.html|title=Tamsulosin Side Effects|website=Drugs.com|access-date=27 April 2011}} |
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</ref> |
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== Mechanism == |
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{{Main|Alpha blocker}} |
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Tamsulosin is a selective ] ] that has preferential selectivity for the ] in the prostate versus the ] 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> |
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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 ].<ref name=":0" /> |
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==Brand names== |
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Tamsulosin was first marketed in 1996 under the ] 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 ] (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=] (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> |
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It is marketed by various companies under licence, including ] and ]. 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 ]). Generic extended-release tablets are marketed in most countries of the ].<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 ], it is marketed as Secotex and as Harnal D in ] and ] 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 ],<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> ], ] and ], 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}} |
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== References == |
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{{Reflist}} |
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{{Drugs used in benign prostatic hypertrophy}} |
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{{Adrenergic receptor modulators}} |
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{{Portal bar | Medicine}} |
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{{Authority control}} |
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