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106133-20-4 molecular structure
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5-[(2R)-2-{[2-(2-ethoxyphenoxy)ethyl]amino}propyl]-2-methoxybenzene-1-sulfonamide

ChemBase ID: 587
Molecular Formular: C20H28N2O5S
Molecular Mass: 408.51172
Monoisotopic Mass: 408.17189301
SMILES and InChIs

SMILES:
S(=O)(=O)(N)c1cc(C[C@H](NCCOc2c(OCC)cccc2)C)ccc1OC
Canonical SMILES:
CCOc1ccccc1OCCN[C@@H](Cc1ccc(c(c1)S(=O)(=O)N)OC)C
InChI:
InChI=1S/C20H28N2O5S/c1-4-26-17-7-5-6-8-18(17)27-12-11-22-15(2)13-16-9-10-19(25-3)20(14-16)28(21,23)24/h5-10,14-15,22H,4,11-13H2,1-3H3,(H2,21,23,24)/t15-/m1/s1
InChIKey:
DRHKJLXJIQTDTD-OAHLLOKOSA-N

Cite this record

CBID:587 http://www.chembase.cn/molecule-587.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
5-[(2R)-2-{[2-(2-ethoxyphenoxy)ethyl]amino}propyl]-2-methoxybenzene-1-sulfonamide
IUPAC Traditional name
tamsulosin
Brand Name
Flomax
Harnal
Omnic
Pradif
Tamsolusin
Tamsulosina [INN-Spanish]
Tamsulosine [INN-French]
Tamsulosinum [INN-Latin]
Synonyms
tamsulosin
YM-617
Tamsulosin
(R)-5-(2-((2-(2-Ethoxyphenoxy)ethyl)aMino)propyl)-2-MethoxybenzenesulfonaMide
CAS Number
106133-20-4
PubChem SID
46507763
160964050
PubChem CID
129211

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
A&J Pharmtech
AJA-O6211 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 9.932656  H Acceptors
H Donor LogD (pH = 5.5) -0.6416307 
LogD (pH = 7.4) 0.46680295  Log P 2.038114 
Molar Refractivity 108.8649 cm3 Polarizability 43.42021 Å3
Polar Surface Area 99.88 Å2 Rotatable Bonds 11 
Lipinski's Rule of Five true 
Log P 3.05  LOG S -4.79 
Solubility (Water) 6.55e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Product Information Bioassay(PubChem)
Solubility
Sparingly soluble in water expand Show data source
Hydrophobicity(logP)
2.3 expand Show data source
Purity
97% expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00706 external link
Item Information
Drug Groups approved; investigational
Description 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.
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. 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.
Toxicity LD50 = 650 mg/kg (in rats)
Affected Organisms
Humans and other mammals
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.
Absorption Absorption of tamsulosin HCI from capsules 0.4 mg is essentially complete (>90%) following oral administration under fasting conditions.
Half Life 5-7 hours
Protein Binding 94%-99%
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.
Distribution * 16 L [intravenous administration to ten healthy male adults]
Clearance * 2.88 L/h
References
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]
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

REFERENCES

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  • • 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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PATENTS

PATENTS

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