Systematic (IUPAC) name | |
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(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 is 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, though generic non-modified release capsules are still approved and marketed in many countries, such as Canada. In Colombia (South America) it is marketed under Uripur from Laboratorios Bussié, beside it is marketed under Harnal D in some places.[1] The U.S. patent for Flomax expired in October 2009. The U.S. Food and Drug Administration (FDA) approved generic Flomax in March 2010.[2]
In Egypt[3] Italy and Iceland it is marketed under the trade Omnic by Astellas Pharma Europe.
Contents |
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.[4]
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.
Two ADRs (Adverse Drug Reactions) have been reported:
Tamsulosin has also affected the sexual function in men. Tamsulosin can cause males to experience retrograde ejaculation.[6] 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. Other reported side effects include headache, dizziness, nasal congestion, and palpitations.
Although prostate specific, it does not have the prostate apoptotic effects of other alpha-blockers such as doxazosin and terazosin.
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. [7]
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