Chemistry:Tamsulosin

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Short description: Medication
Tamsulosin
Tamsulosin.svg
Tamsulosin-from-xtal-3D-bs-17.png
Clinical data
Pronunciation/tæmˈsuːləsɪn/[1]
tam-SOO-lə-sin
Trade namesFlomax, others
AHFS/Drugs.comMonograph
MedlinePlusa698012
License data
Pregnancy
category
  • AU: B2
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability100% (by mouth)
MetabolismLiver
Elimination half-life9–13 hours
Excretion76% Kidney
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC20H28N2O5S
Molar mass408.51 g·mol−1
3D model (JSmol)
  (verify)
Tamsulosin - ARISTO Pharma - 0.4 mg prolonged-release tablets – Urologikum

Tamsulosin, sold under the brand name Flomax among others, is a medication used to treat symptomatic benign prostatic hyperplasia (BPH) and chronic prostatitis and to help with the passage of kidney stones.[5][6][7] The evidence for benefit with a kidney stone is better when the stone is larger.[7] It is taken by mouth.[5]

Common side effects include dizziness, headache, sleeplessness, nausea, blurry vision, and sexual problems.[8][5] Other side effects may include feeling lightheaded with standing due to changes in blood pressure, and angioedema.[8] Tamsulosin is an alpha blocker and works by relaxing muscles in the prostate.[9] Specifically it is an α1 adrenergic receptor blocker.[5]

Tamsulosin was approved for medical use in the United States in 1997.[5] It is available as a generic medication.[8] In 2021, it was the 24th most commonly prescribed medication in the United States, with more than 23 million prescriptions.[10][11]

Medical uses

Flomax 0.4 mg oral capsule

Tamsulosin is primarily used for benign prostatic hyperplasia (BPH) and to help with the passage of kidney stones.[12][13] Tamsulosin, however, appears to be effective only for stones over 4 mm and less than 10 mm in size.[7]

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.[14]

Tamsulosin does not decrease the overall size of the prostate in men with BPH, and is not recommended for prevention of prostate cancer.[15]

Combination therapy

The results of the CombAT (combination of dutasteride (Avodart) and tamsulosin, under the brand name 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.[16] The CombAT trial became the medication Jalyn. It was approved by the FDA on 14 June 2010.[17] This combination can be useful because it may take up to six months for symptomatic relief to be found when using 5-alpha-reductase inhibitors such as dutasteride compared to alpha-1 receptor blockers, which can provide relief in some cases within 48 hours.[18]

Adverse effects

  • Eyes: People taking tamsulosin are prone to a complication known as floppy iris syndrome during cataract surgery. Adverse outcomes 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.[19]
  • Severe hypotension.[20][21]
  • 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.[22]
  • 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.[23]

Mechanism

Main page: Chemistry:Alpha blocker

Tamsulosin is a selective α1 receptor antagonist that has preferential selectivity for the α1A receptor in the prostate versus the α1B receptor in the blood vessels.[24]

When alpha 1 receptors in the bladder neck, prostate, ureter, and urethra are blocked, a relaxation in smooth muscle tissue results.[15] This mechanism decreases resistance to urinary flow, reduces discomfort associated with BPH, and facilitates passage of kidney stones.[15]

Brand names

Tamsulosin was first marketed in 1996 under the trade name Flomax. The U.S. patent expired in October 2009.[25] The U.S. Food and Drug Administration (FDA) approved generics in March 2010.[26] In 2010, tamsulosin was available as OTC medication in UK.[27]

It is marketed by various companies under licence, including Boehringer Ingelheim and 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,[28] 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 EEA.[29] 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.[30] In Egypt,[31] 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). [citation needed] Tamsulosin hydrochloride is marketed in Bangladesh under the trade names Uromax, Prostanil MR, Tamisol MR, and Tamsin.[citation needed]

References

  1. ↑ "Tamsulosin". Merriam-Webster Dictionary. https://www.merriam-webster.com/dictionary/Tamsulosin. 
  2. ↑ "Flomaxtra XL, 400 micrograms, film-coated prolonged release tablet - Summary of Product Characteristics (SmPC)". 12 November 2019. https://www.medicines.org.uk/emc/product/97/smpc. 
  3. ↑ "Faramsil 400 microgram Prolonged-release Tablets - Summary of Product Characteristics (SmPC)". 4 November 2020. https://www.medicines.org.uk/emc/product/4948/smpc. 
  4. ↑ "Flomax- tamsulosin hydrochloride capsule". https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=6771ad8e-ac92-4aec-b484-5d8350a353f8. 
  5. ↑ 5.0 5.1 5.2 5.3 5.4 "Tamsulosin Hydrochloride Monograph for Professionals" (in en). AHFS. https://www.drugs.com/monograph/tamsulosin-hydrochloride.html. 
  6. ↑ "Prostatitis" (in en). 19 October 2017. https://www.nhs.uk/conditions/prostatitis. 
  7. ↑ 7.0 7.1 7.2 "Effect of Tamsulosin on Stone Passage for Ureteral Stones: A Systematic Review and Meta-analysis". Annals of Emergency Medicine 69 (3): 353–361.e3. March 2017. doi:10.1016/j.annemergmed.2016.06.044. PMID 27616037. 
  8. ↑ 8.0 8.1 8.2 British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 767. ISBN 9780857113382. 
  9. ↑ (in en) Fundamentals of Geriatric Pharmacotherapy: An Evidence-Based Approach. ASHP. 2010. p. 209. ISBN 9781585283057. https://books.google.com/books?id=fUtOugU_KeIC&pg=PA209. 
  10. ↑ "The Top 300 of 2021". https://clincalc.com/DrugStats/Top300Drugs.aspx. 
  11. ↑ "Tamsulosin - Drug Usage Statistics". https://clincalc.com/DrugStats/Drugs/Tamsulosin. 
  12. ↑ "Tamsulosin Aids Stone Expulsion". Renal and Urology News. 7 January 2011. https://www.renalandurologynews.com/tamsulosin-aids-stone-expulsion/article/193855/. 
  13. ↑ "Study Shows Use of Tamsulosin or Nifedipine Helps Patients to Clear Ureteral Stone Fragments Faster and Reduces Rate of Recurrence". https://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. 
  14. ↑ "Tamsulosin in the management of patients in acute urinary retention from benign prostatic hyperplasia". BJU International 95 (3): 354–357. February 2005. doi:10.1111/j.1464-410X.2005.05299.x. PMID 15679793. 
  15. ↑ 15.0 15.1 15.2 Medical-surgical nursing : assessment and management of clinical problems (Ninth ed.). St. Louis, Missouri. 5 December 2013. ISBN 978-0-323-10089-2. OCLC 228373703. 
  16. ↑ "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". The Journal of Urology 179 (2): 616–21; discussion 621. February 2008. doi:10.1016/j.juro.2007.09.084. PMID 18082216. 
  17. ↑ FDA approval letter at FDA.gov
  18. ↑ Australian Medicines Handbook [full citation needed]
  19. ↑ Medscape, Good Cataract Surgery Outcomes Possible in Intraoperative Floppy Iris Syndrome Due to Tamsulosin.
  20. ↑ "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". BMJ 347: f6320. November 2013. doi:10.1136/bmj.f6320. PMID 24192967. 
  21. ↑ "Severe hypotension associated with α blocker tamsulosin". BMJ 347: f6492. November 2013. doi:10.1136/bmj.f6492. PMID 24192968. 
  22. ↑ "Drugs That May Cause or Exacerbate Heart Failure: A Scientific Statement From the American Heart Association". Circulation 134 (6): e32–e69. August 2016. doi:10.1161/CIR.0000000000000426. PMID 27400984. 
  23. ↑ "Tamsulosin Side Effects". https://www.drugs.com/sfx/tamsulosin-side-effects.html. 
  24. ↑ Illustrated Pharmacology Memory Cards: PharMnemonics. Minireview. 2008. p. 13. ISBN 978-1-59541-101-3. 
  25. ↑ "Flomax – Big Patent Expirations of 2010". 10 February 2010. https://www.fiercepharma.com/special-reports/flomax-big-patent-expirations-2010. 
  26. ↑ "FDA Approves First Generic Tamsulosin to Treat Enlarged Prostate Gland" (Press release). U.S. Food and Drug Administration (FDA). 2 March 2010.
  27. ↑ "OTC tamsulosin for benign prostatic hyperplasia". Drug and Therapeutics Bulletin 48 (10): 113–116. October 2010. doi:10.1136/dtb.2010.10.0052. PMID 20926447. 
  28. ↑ "Pradif 0,4 Mg Capsule Rigide A Rilascio Prolungato". Torrinomedica.it. https://www.torrinomedica.it/farmaci/schedetecniche/PRADIF.asp. 
  29. ↑ "Tamsulosina Mylan 0,4 mg cápsulas duras de liberación modificada EFG". cima.aemps.es. https://cima.aemps.es/cima/pdfs/es/p/67279/67279_p.pdf. 
  30. ↑ "Drugs.com Database". https://www.drugs.com/international/harnal-d.html. 
  31. ↑ "Novartis hits Astellas with transplant drug generic". Reuters. 11 August 2009. https://www.reuters.com/article/americasRegulatoryNews/idUST34424920090811. 

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