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
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 |
|
Potential mechanisms of action of superselective alpha(1)-adrenoceptor antagonists. | 2001 |
|
Efficacy and tolerability of drugs for treatment of benign prostatic hyperplasia. | 2001 |
|
Effect of tamsulosin hydrochloride on sympathetic hyperactivity in amyotrophic lateral sclerosis. | 2001 Apr 12 |
|
Molecular cloning and functional expression of the guinea pig alpha(1a)-adrenoceptor. | 2001 Aug 31 |
|
Stimulatory effect of isoferulic acid on alpha1A-adrenoceptor to increase glucose uptake into cultured myoblast C2C12 cell of mice. | 2001 May 14 |
|
Review of orthostatic tests on the safety of tamsulosin, a selective alpha1A-adrenergic receptor antagonist, shows lack of orthostatic hypotensive effects. | 2001 May-Jun |
|
[A case of heparin-induced thrombocytopenia after transurethral resection of prostate during anticoagulant therapy]. | 2001 Nov |
|
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 |
|
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 |
|
Tamsulosin: a review of its pharmacology and therapeutic efficacy in the management of lower urinary tract symptoms. | 2002 |
|
Tamsulosin: an update of its role in the management of lower urinary tract symptoms. | 2002 |
|
Tamsulosin: an overview. | 2002 Apr |
|
Citalopram-induced priapism. | 2002 Apr |
|
Long-term risk of re-treatment of patients using alpha-blockers for lower urinary tract symptoms. | 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 |
|
Gateways to clinical trials. | 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 |
|
Digoxin-drug interactions: study design and generalizability. | 2002 Feb |
|
[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 |
|
Tamsulosin for treating lower urinary tract symptoms compatible with benign prostatic obstruction: a systematic review of efficacy and adverse effects. | 2002 Jan |
|
Managing benign prostatic hyperplasia. | 2002 Jul 1 |
|
[Tamsulosin with or without Serenoa repens in benign prostatic hyperplasia: the OCOS trial]. | 2002 Jun |
|
[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 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 |
|
Method for simultaneous recording of the prostatic contractile and urethral pressure responses in anesthetized rats and the effects of tamsulosin. | 2002 Nov |
|
Comparison of tamsulosin and finasteride for lower urinary tract symptoms associated with benign prostatic hyperplasia in Korean patients. | 2002 Nov-Dec |
|
Prophylactic versus therapeutic alpha-blockers after permanent prostate brachytherapy. | 2002 Oct |
|
Identification of binding sites of prazosin, tamsulosin and KMD-3213 with alpha(1)-adrenergic receptor subtypes by molecular modeling. | 2002 Oct 11 |
|
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 |
|
[Comparison of prazosin, terazosin and tramsulosin: functional and binding studies in isolated prostatic and vascular human tissues]. | 2002 Sep |
|
[Comparative evaluation of the efficacy of using terazosin and tamsulosin in patients with benign prostatic hyperplasia]. | 2002 Sep-Oct |
|
[Experience in long term use of tamsulosin (Omnik) in patients with chronic prostatitis]. | 2002 Sep-Oct |
|
Tamsulosin for benign prostatic hyperplasia. | 2003 |
|
Effects of intrathecal injection of tamsulosin and naftopidil, alpha-1A and 1D adrenergic receptor antagonists, on bladder activity in rats. | 2003 Apr |
|
Doxazosin and terazosin suppress prostate growth by inducing apoptosis: clinical significance. | 2003 Apr |
|
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 |
|
Combination treatment with an alpha-blocker plus an anticholinergic for bladder outlet obstruction: a prospective, randomized, controlled study. | 2003 Jun |
|
Anoikis induction by quinazoline based alpha 1-adrenoceptor antagonists in prostate cancer cells: antagonistic effect of bcl-2. | 2003 Mar |
|
Drug treatment of benign prostatic hyperplasia and hospital admission for BPH-related surgery. | 2003 May |
|
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.
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QG04CA52
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WHO-ATC |
G04CA52
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NDF-RT |
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
admin on Sat Jun 26 14:01:33 UTC 2021 , Edited by admin on Sat Jun 26 14:01:33 UTC 2021
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Code System | Code | Type | Description | ||
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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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ACTIVE MOIETY
METABOLITE (PARENT)
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SALT/SOLVATE (PARENT)