Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H28N2O5S |
Molecular Weight | 408.5136 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCOc1ccccc1OCCN[C@]([H])(C)Cc2ccc(c(c2)S(=O)(=O)N)OC
InChI
InChIKey=DRHKJLXJIQTDTD-OAHLLOKOSA-N
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
Molecular Formula | C20H28N2O5S |
Molecular Weight | 408.5136 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment:: Description was created based on several sources, including https://www.drugbank.ca/drugs/DB00706
Curator's Comment:: Description was created based on several sources, including https://www.drugbank.ca/drugs/DB00706
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. Tamsulosin is sold under the trade name Flomax.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22500249
Curator's Comment:: Tamsulosin can across the blood-brain barrier.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2094251 |
0.19 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | FLOMAX Approved UseFlomax® (tamsulosin hydrochloride) capsules are indicated for the treatment of the signs and symptoms of benign prostatic hyperplasia (BPH) Launch Date8.6106243E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10.1 ng/mL |
0.4 mg 1 times / day multiple, oral dose: 0.4 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TAMSULOSIN HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: LOW-FAT |
|
17.1 ng/mL |
0.4 mg 1 times / day multiple, oral dose: 0.4 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TAMSULOSIN HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
29.8 ng/mL |
0.8 mg 1 times / day multiple, oral dose: 0.8 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TAMSULOSIN HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: LOW-FAT |
|
29.1 ng/mL |
0.8 mg 1 times / day multiple, oral dose: 0.8 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TAMSULOSIN HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: HIGH-FAT |
|
41.6 ng/mL |
0.8 mg 1 times / day multiple, oral dose: 0.8 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TAMSULOSIN HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
8.8694 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01149733 |
0.4 mg single, oral dose: 0.4 mg route of administration: oral experiment type: single co-administered: |
TAMSULOSIN plasma | Homo sapiens population: healthy age: sex: food status: Fed |
|
9.015 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01149733 |
0.4 mg single, oral dose: 0.4 mg route of administration: oral experiment type: single co-administered: |
TAMSULOSIN plasma | Homo sapiens population: healthy age: sex: food status: Fed |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
151 ng × h/mL |
0.4 mg 1 times / day multiple, oral dose: 0.4 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TAMSULOSIN HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: LOW-FAT |
|
199 ng × h/mL |
0.4 mg 1 times / day multiple, oral dose: 0.4 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TAMSULOSIN HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
440 ng × h/mL |
0.8 mg 1 times / day multiple, oral dose: 0.8 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TAMSULOSIN HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: LOW-FAT |
|
449 ng × h/mL |
0.8 mg 1 times / day multiple, oral dose: 0.8 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TAMSULOSIN HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: HIGH-FAT |
|
557 ng × h/mL |
0.8 mg 1 times / day multiple, oral dose: 0.8 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TAMSULOSIN HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
137.0248 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01149733 |
0.4 mg single, oral dose: 0.4 mg route of administration: oral experiment type: single co-administered: |
TAMSULOSIN plasma | Homo sapiens population: healthy age: sex: food status: Fed |
|
148.9023 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01149733 |
0.4 mg single, oral dose: 0.4 mg route of administration: oral experiment type: single co-administered: |
TAMSULOSIN plasma | Homo sapiens population: healthy age: sex: food status: Fed |
|
143.274899999999 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01149733 |
0.4 mg single, oral dose: 0.4 mg route of administration: oral experiment type: single co-administered: |
TAMSULOSIN plasma | Homo sapiens population: healthy age: sex: food status: Fed |
|
157.945499999999 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01149733 |
0.4 mg single, oral dose: 0.4 mg route of administration: oral experiment type: single co-administered: |
TAMSULOSIN plasma | Homo sapiens population: healthy age: sex: food status: Fed |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
14.9 h |
0.8 mg 1 times / day multiple, oral dose: 0.8 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TAMSULOSIN HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6% |
0.4 mg 1 times / day multiple, oral dose: 0.4 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TAMSULOSIN HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: LOW-FAT |
Doses
Dose | Population | Adverse events |
---|---|---|
0.4 mg 1 times / day multiple, oral Recommended Dose: 0.4 mg, 1 times / day Route: oral Route: multiple Dose: 0.4 mg, 1 times / day Sources: |
unhealthy, 54 years n = 1 Health Status: unhealthy Condition: benign prostatic hyperplasia Age Group: 54 years Sex: M Population Size: 1 Sources: |
Disc. AE: Drug eruption... AEs leading to discontinuation/dose reduction: Drug eruption (1 patient) Sources: |
0.8 mg 1 times / day steady, oral Recommended Dose: 0.8 mg, 1 times / day Route: oral Route: steady Dose: 0.8 mg, 1 times / day Sources: |
unhealthy n = 492 Health Status: unhealthy Population Size: 492 Sources: |
Disc. AE: Abnormal ejaculation... AEs leading to discontinuation/dose reduction: Abnormal ejaculation (1.6%) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Drug eruption | 1 patient Disc. AE |
0.4 mg 1 times / day multiple, oral Recommended Dose: 0.4 mg, 1 times / day Route: oral Route: multiple Dose: 0.4 mg, 1 times / day Sources: |
unhealthy, 54 years n = 1 Health Status: unhealthy Condition: benign prostatic hyperplasia Age Group: 54 years Sex: M Population Size: 1 Sources: |
Abnormal ejaculation | 1.6% Disc. AE |
0.8 mg 1 times / day steady, oral Recommended Dose: 0.8 mg, 1 times / day Route: oral Route: steady Dose: 0.8 mg, 1 times / day Sources: |
unhealthy n = 492 Health Status: unhealthy Population Size: 492 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Lower urinary tract symptoms: what are the implications for the patients? | 2001 |
|
Efficacy and tolerability of drugs for treatment of benign prostatic hyperplasia. | 2001 |
|
Results of treatment with tamsulosin in men with acute urinary retention. | 2001 Dec |
|
Tamsulosin: current clinical experience. | 2001 Dec |
|
Tamsulosin as an effective treatment for reboxetine-associated urinary hesitancy. | 2001 Nov |
|
Worldwide experience with alfuzosin and tamsulosin. | 2001 Oct |
|
Long-term use of tamsulosin to treat lower urinary tract symptoms/benign prostatic hyperplasia. | 2001 Oct |
|
Stimulatory effect of phenylephrine on the secretion of beta-endorphin from rat adrenal medulla in vitro. | 2001 Oct 8 |
|
Classical vs reverse pharmacology in drug discovery. | 2001 Sep |
|
Speedy elimination of ureterolithiasis in lower part of ureters with the alpha 1-blocker--Tamsulosin. | 2002 |
|
Terazosin for benign prostatic hyperplasia. | 2002 |
|
[The clinical efficacy of Naftopidil tablet in the treatment of benign prostatic hyperplasia]. | 2002 |
|
[Tamsulosin for the treatment of chronic abacterial prostatitis]. | 2002 |
|
Clinical characteristics of alpha-blocker responders in men with benign prostatic hyperplasia. | 2002 |
|
Tamsulosin: an overview. | 2002 Apr |
|
Successful treatment of reboxetine-induced urinary hesitancy with tamsulosin. | 2002 Apr |
|
Painful ejaculation and urinary hesitancy in association with antidepressant therapy: relief with tamsulosin. | 2002 Aug |
|
Effects of intrathecal injection of tamsulosin and naftopidil, alpha-1A and -1D adrenergic receptor antagonists, on bladder activity in rats. | 2002 Aug 2 |
|
Gateways to clinical trials. | 2002 Dec |
|
[Alpha 1-adrenoceptor antagonists for treatment of prostatic hyperplsia]. | 2002 Dec |
|
Effects of the concomitant administration of tamsulosin (0.8 mg) on the pharmacokinetic and safety profile of intravenous digoxin (Lanoxin) in normal healthy subjects: a placebo-controlled evaluation. | 2002 Feb |
|
The use of alpha-adrenoceptor antagonists in lower urinary tract disease. | 2002 Feb |
|
Managing reboxetine-associated urinary hesitancy in a patient with major depressive disorder: a case study. | 2002 Feb |
|
Effect of fiduxosin, an antagonist selective for alpha(1A)- and alpha(1D)-adrenoceptors, on intraurethral and arterial pressure responses in conscious dogs. | 2002 Feb |
|
Quantitation of tamsulosin in human plasma by liquid chromatography-electrospray ionization mass spectrometry. | 2002 Feb 5 |
|
[A comparative study assessing clinical effects of naftopidil and tamsulosin hydrochloride on benign prostatic hyperplasia]. | 2002 Jan |
|
[Transition zone index in predicting therapeutic efficacy of benign prostatic hyperplasia]. | 2002 Jan |
|
Spinal substance P immunoreactivity is enhanced by acute chemical stimulation of the rat prostate. | 2002 Jan |
|
Tamsulosin for treating lower urinary tract symptoms compatible with benign prostatic obstruction: a systematic review of efficacy and adverse effects. | 2002 Jan |
|
Quinazoline-derived alpha1-adrenoceptor antagonists induce prostate cancer cell apoptosis via an alpha1-adrenoceptor-independent action. | 2002 Jan 15 |
|
alpha-Adrenoceptor antagonists in the treatment of benign prostate hyperplasia. | 2002 Jul |
|
Managing benign prostatic hyperplasia. | 2002 Jul 1 |
|
[Tamsulosin with or without Serenoa repens in benign prostatic hyperplasia: the OCOS trial]. | 2002 Jun |
|
Decrease of ultrasound estimated bladder weight during tamsulosin treatment in patients with benign prostatic enlargement. | 2002 Jun |
|
Design of a multicenter randomized clinical trial for chronic prostatitis/chronic pelvic pain syndrome. | 2002 Jun |
|
[Clinical evaluation of the effect of tamsulosin hydrochloride and cernitin pollen extract on urinary disturbance associated with benign prostatic hyperplasia in a multicentered study]. | 2002 May |
|
Comparison of a phytotherapeutic agent (Permixon) with an alpha-blocker (Tamsulosin) in the treatment of benign prostatic hyperplasia: a 1-year randomized international study. | 2002 May |
|
Method for simultaneous recording of the prostatic contractile and urethral pressure responses in anesthetized rats and the effects of tamsulosin. | 2002 Nov |
|
Biochemical and functional characterization of alpha-adrenergic receptors in the rabbit vagina. | 2002 Nov 1 |
|
Comparison of tamsulosin and finasteride for lower urinary tract symptoms associated with benign prostatic hyperplasia in Korean patients. | 2002 Nov-Dec |
|
Gateways to clinical trials. | 2002 Oct |
|
Gateways to Clinical Trials. | 2002 Sep |
|
[alpha 1-receptor blockade in therapy of benign prostatic hyperplasia syndrome. Correct dosing for optimal effectiveness]. | 2002 Sep |
|
[Drug therapy of benign prostatic hyperplasia syndrome with alpha 1-receptor blockers. Basic principles and clinical results]. | 2002 Sep |
|
[Comparative evaluation of the efficacy of using terazosin and tamsulosin in patients with benign prostatic hyperplasia]. | 2002 Sep-Oct |
|
[Correction of urination disorders caused by benign prostatic hyperplasia in cardiac surgery]. | 2003 |
|
Tamsulosin for benign prostatic hyperplasia. | 2003 |
|
A randomized, double-blind crossover study of tamsulosin and controlled-release doxazosin in patients with benign prostatic hyperplasia. | 2003 Jan |
|
Priapism following ingestion of tamsulosin. | 2003 Jun |
|
Quinazoline-based alpha 1-adrenoceptor antagonists induce prostate cancer cell apoptosis via TGF-beta signalling and I kappa B alpha induction. | 2003 May 19 |
Sample Use Guides
FLOMAX (tamsulosin HCl) capsules 0.4 mg once daily is recommended as the dose for the
treatment of the signs and symptoms of BPH. It should be administered approximately onehalf
hour following the same meal each day.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28068846
Tamsulosin at concentrations of 0.1 and 1 uM directly inhibited MCh-induced contractility of pregnant rat ureters.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 14:01:31 UTC 2021
by
admin
on
Sat Jun 26 14:01:31 UTC 2021
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Record UNII |
G3P28OML5I
|
Record Status |
Validated (UNII)
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Record Version |
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-
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WHO-VATC |
QG04CA52
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WHO-ATC |
G04CA52
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N0000175553
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LIVERTOX |
922
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NCI_THESAURUS |
C29713
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WHO-VATC |
QG04CA02
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NDF-RT |
N0000000099
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WHO-VATC |
QG04CA53
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WHO-ATC |
G04CA53
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WHO-ATC |
G04CA02
Created by
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106133-20-4
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TAMSULOSIN
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77492
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M10451
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106133-20-4
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DB00706
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2562
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G3P28OML5I
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129211
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488
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6750
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C088482
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SUB10827MIG
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CHEMBL836
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C75055
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7744
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Related Record | Type | Details | ||
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TARGET -> INHIBITOR |
Ki
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METABOLIC ENZYME -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT | |||
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BINDER->LIGAND |
BINDING
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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TARGET -> INHIBITOR |
Ki
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Related Record | Type | Details | ||
---|---|---|---|---|
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METABOLITE -> PARENT |
PLASMA
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METABOLITE -> PARENT |
PLASMA; URINE
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METABOLITE -> PARENT |
PLASMA
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
PLASMA; URINE
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METABOLITE -> PARENT |
PLASMA
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METABOLITE -> PARENT |
PLASMA
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
PLASMA
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Tmax | PHARMACOKINETIC |
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ORAL ADMINISTRATION |
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Biological Half-life | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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