Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H28N2O5S |
Molecular Weight | 408.512 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCOC1=C(OCCN[C@H](C)CC2=CC(=C(OC)C=C2)S(N)(=O)=O)C=CC=C1
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 |
---|---|---|
Initial choices and final outcomes in lower urinary tract symptoms. | 2001 |
|
Our experience with the treatment of benign prostatic hyperplasia (BPH) with tamsulosin. | 2001 |
|
[The efficacy and safety of terazosin and tamsulosin in patients with urinary disturbance accompanying prostatic hypertrophy]. | 2001 Jan |
|
Tamsulosin in men with confirmed bladder outlet obstruction: a clinical and urodynamic analysis from a single centre in New Zealand. | 2001 Jan |
|
[Omnic (tamsulosin) in the treatment of benign prostatic hyperplasia]. | 2001 Jan-Feb |
|
A 6-month large-scale study into the safety of tamsulosin. | 2001 Jun |
|
Worldwide experience with alfuzosin and tamsulosin. | 2001 Oct |
|
Stimulatory effect of phenylephrine on the secretion of beta-endorphin from rat adrenal medulla in vitro. | 2001 Oct 8 |
|
Terazosin for benign prostatic hyperplasia. | 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 |
|
Citalopram-induced priapism. | 2002 Apr |
|
[Alpha 1-adrenoceptor antagonists for treatment of prostatic hyperplsia]. | 2002 Dec |
|
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 |
|
[Transition zone index in predicting therapeutic efficacy of benign prostatic hyperplasia]. | 2002 Jan |
|
[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 |
|
Biochemical and functional characterization of alpha-adrenergic receptors in the rabbit vagina. | 2002 Nov 1 |
|
Gateways to clinical trials. | 2002 Oct |
|
Identification of binding sites of prazosin, tamsulosin and KMD-3213 with alpha(1)-adrenergic receptor subtypes by molecular modeling. | 2002 Oct 11 |
|
[alpha 1-receptor blockade in therapy of benign prostatic hyperplasia syndrome. Correct dosing for optimal effectiveness]. | 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 |
|
[Correction of urination disorders caused by benign prostatic hyperplasia in cardiac surgery]. | 2003 |
|
A randomized, double-blind crossover study of tamsulosin and controlled-release doxazosin in patients with benign prostatic hyperplasia. | 2003 Jan |
|
Combination treatment with an alpha-blocker plus an anticholinergic for bladder outlet obstruction: a prospective, randomized, controlled study. | 2003 Jun |
|
Drug treatment of benign prostatic hyperplasia and hospital admission for BPH-related surgery. | 2003 May |
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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QG04CA52
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G04CA52
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N0000175553
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NBK548017
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NCI_THESAURUS |
C29713
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QG04CA02
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N0000000099
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WHO-VATC |
QG04CA53
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WHO-ATC |
G04CA53
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WHO-ATC |
G04CA02
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106133-20-4
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TAMSULOSIN
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9398
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77492
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M10451
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DTXSID3023631
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G3P28OML5I
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DB00706
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2562
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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
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