Tamsulosin
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| Systematic (IUPAC) name | |
| (R)-5-(2-{[2-(2-ethoxyphenoxy)ethyl]amino}propyl)-2-methoxybenzene-1-sulfonamide | |
| Clinical data | |
| Trade names | Flomax |
| AHFS/Drugs.com | monograph |
| MedlinePlus | a698012 |
| Licence data | US FDA:link |
| Pregnancy cat. | B2(AU) B(US) |
| Legal status | Prescription Only (S4) (AU) POM (UK) ℞-only (US) |
| Routes | oral |
| Pharmacokinetic data | |
| Bioavailability | 100% (oral) |
| Metabolism | hepatic |
| Half-life | 9–13 hours |
| Excretion | 76% renal |
| Identifiers | |
| CAS number | 106133-20-4  |
| ATC code | G04CA02 |
| PubChem | CID 129211 |
| IUPHAR ligand | 488 |
| DrugBank | APRD00036 |
| ChemSpider | 114457 |
| UNII | G3P28OML5I |
| KEGG | D08560 |
| ChEBI | CHEBI:9398 |
| ChEMBL | CHEMBL836 |
| Chemical data | |
| Formula | C20H28N2O5S |
| Mol. mass | 408.51 |
| SMILES | eMolecules & PubChem |
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Tamsulosin (rINN) (
/tæmˈsuːlɵsɨn/ or /tæmsʉˈloʊsɨn/) is an α1a-selective alpha blocker used in the symptomatic treatment of benign prostatic hyperplasia (BPH). Tamsulosin was developed by Yamanouchi Pharmaceuticals (now part of Astellas Pharma) and was first marketed under the trade name Flomax. It is now marketed by various companies under licence, including Boehringer-Ingelheim and CSL.
Tamsulosin hydrochloride extended-release capsules are marketed under the trade names Flomax, Flomaxtra, Contiflo XL and Urimax, although generic, non-modified-release capsules are still approved and marketed in many countries (such as Canada). In Mexico it is marketed as Secotex and as Harnal D in Japan and Indonesia.[1] In Egypt[2], Italy and Iceland, it is marketed under the trade name Omnic by Astellas Pharma Europe.
The U.S. patent for Flomax expired in October 2009.[3] The U.S. Food and Drug Administration (FDA) approved generic Flomax in March 2010.[4]
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[edit] Mechanism
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.[5]
[edit] Clinical uses
Tamsulosin is primarily used for benign prostatic hyperplasia, but is sometimes used for the passage of kidney stones by the same mechanism of smooth muscle relaxation via alpha antagonism.[citation needed]
[edit] Adverse effects
Two ADRs (Adverse Drug Reactions) have been reported:
- Immunologic: It contains a sulfa moiety, thus causing typical reactions to sulfa drugs.[citation needed]
- Ophthalmologic: Patients 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 patient's history with this drug, and thus having the option of alternative techniques.[6]
Tamsulosin has also affected the sexual function in men. Tamsulosin can cause males to experience retrograde ejaculation.[7] In males, retrograde ejaculation occurs when the fluid to be ejaculated, which would normally exit the body via the urethra, is redirected to the urinary bladder. Normally, the sphincter of the bladder contracts and the ejaculate goes to the urethra, the area of least pressure. In retrograde ejaculation, this sphincter does not function properly.
Occasionally, tamsulosin can cause a drop in blood pressure, rarely resulting in dizziness or fainting.[citation needed] Other reported side effects include headache, dizziness, nasal congestion, and palpitations.[citation needed]
[edit] Clinical comparison
Although prostate specific, it does not have the prostate apoptotic effects of other alpha-blockers such as doxazosin and terazosin.[citation needed]
[edit] Use in combination therapy
The results of the CombAT (Combination of Avodart and Tamsulosin) trial in 2008 demonstrated that treatment with the combination of dutasteride (Avodart) and tamsulosin provides greater symptom benefits compared to monotherapy with either agent alone for treatment of benign prostatic hyperplasia. [8]
[edit] References
- Notes
- ^ "Drugs.com Database". http://www.drugs.com/international/harnal-d.html.
- ^ "Novartis hits Astellas with transplant drug generic". Reuters. 11 August 2009. http://www.reuters.com/article/americasRegulatoryNews/idUST34424920090811. Retrieved 11 August 2009.
- ^ "Flomax - Big Patent Expirations of 2010". February 10, 2010. http://www.fiercepharma.com/special-reports/flomax-big-patent-expirations-2010. Retrieved 14 January 2012.
- ^ "FDA Approves First Generic Tamsulosin to Treat Enlarged Prostate Gland" (Press release). U.S. Food and Drug Administration (FDA). March 2, 2010. http://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm202728.htm.
- ^ Shen, Howard (2008). Illustrated Pharmacology Memory Cards: PharMnemonics. Minireview. p. 13. ISBN 1-59541-101-1.
- ^ Medscape, Good Cataract Surgery Outcomes Possible in Intraoperative Floppy Iris Syndrome Due to Tamsulosin.
- ^ "Tamsulosin Side Effects". Drugs.com. http://www.drugs.com/sfx/tamsulosin-side-effects.html. Retrieved 2011-04-27
- ^ Roehrborn CG, Siami P, Barkin J, et al. (February 2008). "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". J. Urol. 179 (2): 616–21; discussion 621. doi:10.1016/j.juro.2007.09.084. PMID 18082216.
[edit] External links
- Tamsulosin – information from USP DI Advice for the Patient
- Flomax (drugs.com) – U.S. product information
- Product label U.S. Food and Drug Administration (FDA)
- Flomax (Official Site) – Official Site
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