Tamsulosin

CAS No:
106133-20-4 Category:
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Product Details:

  • CAS No: 106133-20-4
  • AHFC code: 32:00.0
  • Synonyms: YM-617
  • ATC Code: G04CA02
  • Chemical Formula: C20H28N2O5S
  • Molecular Weight: 408.512
  • Assay/Purity: Typically NLT 98%
  • DrugBank: DB00706 (APRD00036)
  • SMILES: CCOC1=CC=CC=C1OCCN[C,H](C)CC1=CC(=C(OC)C=C1)S(N)(=O)=O
  • InChl: DRHKJLXJIQTDTD-OAHLLOKOSA-N
  • PubChem: 129211
  • IUPAC: 5-[(2R)-2-{[2-(2-ethoxyphenoxy)ethyl]amino}propyl]-2-methoxybenzene-1-sulfonamide

Additional Details

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.)
Pharmacodynamics:
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. However, unlike these drugs, tamsulosin has a higher affinity for the alpha-1A- adrenergic receptors, which are located in vascular smooth muscle. Studies show that tamsulosin has about 12 times greater affinity for alpha-1 adrenergic receptors in the prostate than those in the aorta, which may result in a reduced incidence of adverse cardiovascular effects.
Mode 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-receptors in human prostate are of the alpha-1A subtype. Blockage of these receptors causes relaxation of smooth muscles in the bladder neck and prostate, and thus decreases urinary outflow resistance in men.
Metabolism:
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.
Toxicity:
LD50 = 650 mg/kg (in rats)
General Reference:
Dunn CJ, Matheson A, Faulds DM: Tamsulosin: a review of its pharmacology and therapeutic efficacy in the management of lower urinary tract symptoms. Drugs Aging. 2002;19(2):135-61. Pubmed Lyseng-Williamson KA, Jarvis B, Wagstaff AJ: Tamsulosin: an update of its role in the management of lower urinary tract symptoms. Drugs. 2002;62(1):135-67. Pubmed Wilt TJ, Mac Donald R, Rutks I: Tamsulosin for benign prostatic hyperplasia. Cochrane Database Syst Rev. 2003;(1):CD002081. Pubmed
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