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
Molecular Formula | C20H28N2O5S |
Molecular Weight | 408.512 |
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 |
---|---|---|
Human cloned alpha1A-adrenoceptor isoforms display alpha1L-adrenoceptor pharmacology in functional studies. | 1999 Apr 16 |
|
[The efficacy and safety of terazosin and tamsulosin in patients with urinary disturbance accompanying prostatic hypertrophy]. | 2001 Jan |
|
Do we know everything about alpha-blockade in the management of lower urinary tract symptoms? | 2001 Jan |
|
Antagonistic effects of selective alpha1-adrenoceptor antagonists MDL73005EF and tamsulosin and partial agonists clonidine and tizanidine in rat thoracic aorta and rabbit iliac artery. | 2001 Jan |
|
A quantitative analysis of antagonism and inverse agonism at wild-type and constitutively active hamster alpha1B-adrenoceptors. | 2001 Jan |
|
alpha-Blockade improves symptoms suggestive of bladder outlet obstruction but fails to relieve it. | 2001 Jan |
|
[Omnic (tamsulosin) in the treatment of benign prostatic hyperplasia]. | 2001 Jan-Feb |
|
Finasteride and tamsulosin used in benign prostatic hypertrophy: a review of the prescription-event monitoring data. | 2001 Jun |
|
Long-term, open-label, phase III multicenter study of tamsulosin in benign prostatic hyperplasia. | 2001 Mar |
|
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 |
|
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 |
|
[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 overview. | 2002 Apr |
|
Citalopram-induced priapism. | 2002 Apr |
|
Painful ejaculation and urinary hesitancy in association with antidepressant therapy: relief with tamsulosin. | 2002 Aug |
|
Gateways to clinical trials. | 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 |
|
Effect of fiduxosin, an antagonist selective for alpha(1A)- and alpha(1D)-adrenoceptors, on intraurethral and arterial pressure responses in conscious dogs. | 2002 Feb |
|
[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 |
|
Design of a multicenter randomized clinical trial for chronic prostatitis/chronic pelvic pain syndrome. | 2002 Jun |
|
Method for simultaneous recording of the prostatic contractile and urethral pressure responses in anesthetized rats and the effects of tamsulosin. | 2002 Nov |
|
Gateways to clinical trials. | 2002 Oct |
|
[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 |
|
Effects of intrathecal injection of tamsulosin and naftopidil, alpha-1A and 1D adrenergic receptor antagonists, on bladder activity in rats. | 2003 Apr |
|
[Generally effective for unstable bladder? Tamsulosin: application not limited to benign prostatic hyperplasia]. | 2003 Feb |
|
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 19:29:21 UTC 2022
by
admin
on
Fri Dec 16 19:29:21 UTC 2022
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Record UNII |
G3P28OML5I
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Record Status |
Validated (UNII)
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Record Version |
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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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QG04CA53
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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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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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