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QuickView for Tamsulosin (compound)


PubChem
Name: tamsulosin
PubChem Compound ID: 129211
Molecular formula: C20H28N2O5S
Molecular weight: 408.513 g/mol
Synonyms:
Tamsulosin; 106133-20-4; Tamsulosina [INN-Spanish]; Tamsulosine [INN-French]; Benzenesulfonamide, 5-(2-((2-(2-ethoxyphenoxy)ethyl)amino)propyl)-2-methoxy-, (R)-; C07124; 66-23-9; (R)-5-(2-((2-(2-Ethoxyphenoxy)ethyl)amino)propyl)-2-methoxybenzenesulfonamide; Tamsulosinum [INN-Latin]
DrugBank
Identification
Name: tamsulosin
Name (isomeric): DB00706
Drug Type: small molecule
Synonyms:
YM-617
Brand: Tamsulosine [INN-French], Pradif, Omnic, Tamsulosina [INN-Spanish], Harnal, Tamsolusin, Flomax, Tamsulosinum [INN-Latin]
Category: Antineoplastic Agents, Adrenergic alpha-Antagonists
CAS number: 106133-20-4
Pharmacology
Indication: Used in the treatment of signs and symptoms of benign prostatic hyperplasia (reduction in urinary obstruction and relief of associated manifestations such as hesitancy, terminal dribbling of urine, interrupted or weak stream...etc.)
Pharmacology:
Tamsulosin, a sulfamoylphenethylamine-derivative alpha-adrenoceptor blocker with enhanced specificity for the alpha-adrenoceptors of the prostate, is commonly used to treat benign prostatic hyperplasia (BPH). The drug is commercially available in a racemic mixture of 2 isomers, and is pharmacologically related to doxazocin, prazosin, and terazosin....
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Mechanism of Action:
Tamsulosin is a selective antagonist at alpha-1A and alpha-1B-adrenoceptors in the prostate, prostatic capsule, prostatic urethra, and bladder neck. At least three discrete alpha1-adrenoceptor subtypes have been identified: alpha-1A, alpha-1B and alpha-1D; their distribution differs between human organs and tissue. Approximately 70% of the alpha1-r...
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Absorption: Absorption of tamsulosin HCI from capsules 0.4 mg is essentially complete (>90%) following oral administration under fasting conditions.
Protein binding: 94%-99%
Biotransformation: Tamsulosin HCI is extensively metabolized by cytochrome P450 enzymes in the liver, however, the pharmacokinetic profile of the metabolites in humans has not been established.
Route of elimination: Tamsulosin hydrochloride is extensively metabolized by cytochrome P450 enzymes in the liver and less than 10% of the dose is excreted in urine unchanged. The metabolites of tamsulosin hydrochloride undergo extensive conjugation to glucuronide or sulfate prior to renal excretion. On administration of the radiolabeled dose of tamsulosin hydrochloride to four healthy volunteers, 97% of the administered radioactivity was recovered, with urine (76%) representing the primary route of excretion compared to feces (21%) over 168 hours.
Half Life: 5-7 hours
Clearance: 2.88 L/h
Toxicity: LD50 = 650 mg/kg (in rats)
Affected organisms: Humans and other mammals
Interactions
Food interaction:
Take 30 minutes after a meal (always after the same meal). Taking the drug with food minimizes plasma levels variations.
Drug interaction:
MethadoneMethadone, a CYP2D6 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP2D6 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Methadone is initiated, discontinued, or dose changed.
NefazodoneNefazodone, a CYP3A4 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Nefazodone is initiated, discontinued, or dose changed.
PyrimethaminePyrimethamine, a CYP2D6 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP2D6 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Pyrimethamine is initiated, discontinued, or dose changed.
PosaconazolePosaconazole, a CYP3A4 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Posaconazole is initiated, discontinued, or dose changed.
RanolazineRanolazine, a CYP3A4/2D6 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4/2D6 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Ranolazine is initiated, discontinued, or dose changed.
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