Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H28N2O5S.ClH |
| Molecular Weight | 444.973 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CCOC1=CC=CC=C1OCCN[C@H](C)CC2=CC=C(OC)C(=C2)S(N)(=O)=O
InChI
InChIKey=ZZIZZTHXZRDOFM-XFULWGLBSA-N
InChI=1S/C20H28N2O5S.ClH/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);1H/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 |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 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 Date1997 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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 |
|
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 |
|
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 |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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 |
|
157.9455 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 |
|
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 |
|
143.2749 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 |
|
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 |
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 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Priapism following ingestion of tamsulosin. | 2003-06 |
|
| Combination treatment with an alpha-blocker plus an anticholinergic for bladder outlet obstruction: a prospective, randomized, controlled study. | 2003-06 |
|
| Quinazoline-based alpha 1-adrenoceptor antagonists induce prostate cancer cell apoptosis via TGF-beta signalling and I kappa B alpha induction. | 2003-05-19 |
|
| Drug treatment of benign prostatic hyperplasia and hospital admission for BPH-related surgery. | 2003-05 |
|
| Nocturia and benign prostatic hyperplasia. | 2003-04 |
|
| Effects of intrathecal injection of tamsulosin and naftopidil, alpha-1A and 1D adrenergic receptor antagonists, on bladder activity in rats. | 2003-04 |
|
| Doxazosin and terazosin suppress prostate growth by inducing apoptosis: clinical significance. | 2003-04 |
|
| A placebo-controlled pharmacodynamic and pharmacokinetic interaction study between tamsulosin and acenocoumarol. | 2003-03 |
|
| Anoikis induction by quinazoline based alpha 1-adrenoceptor antagonists in prostate cancer cells: antagonistic effect of bcl-2. | 2003-03 |
|
| [Generally effective for unstable bladder? Tamsulosin: application not limited to benign prostatic hyperplasia]. | 2003-02 |
|
| Comparison of tamsulosin and finasteride for lower urinary tract symptoms associated with benign prostatic hyperplasia in Korean patients. | 2003-01-16 |
|
| [Comparative evaluation of the efficacy of using terazosin and tamsulosin in patients with benign prostatic hyperplasia]. | 2003-01-10 |
|
| A randomized, double-blind crossover study of tamsulosin and controlled-release doxazosin in patients with benign prostatic hyperplasia. | 2003-01 |
|
| [Correction of urination disorders caused by benign prostatic hyperplasia in cardiac surgery]. | 2003 |
|
| Tamsulosin for benign prostatic hyperplasia. | 2003 |
|
| Gateways to clinical trials. | 2002-12 |
|
| [Alpha 1-adrenoceptor antagonists for treatment of prostatic hyperplsia]. | 2002-12 |
|
| Biochemical and functional characterization of alpha-adrenergic receptors in the rabbit vagina. | 2002-11-01 |
|
| Method for simultaneous recording of the prostatic contractile and urethral pressure responses in anesthetized rats and the effects of tamsulosin. | 2002-11 |
|
| [Experience in long term use of tamsulosin (Omnik) in patients with chronic prostatitis]. | 2002-10-31 |
|
| Identification of binding sites of prazosin, tamsulosin and KMD-3213 with alpha(1)-adrenergic receptor subtypes by molecular modeling. | 2002-10-11 |
|
| Gateways to clinical trials. | 2002-10 |
|
| Effects of KMD-3213, a uroselective alpha 1A-adrenoceptor antagonist, on the tilt-induced blood pressure response in normotensive rats. | 2002-10 |
|
| Prophylactic versus therapeutic alpha-blockers after permanent prostate brachytherapy. | 2002-10 |
|
| Gateways to Clinical Trials. | 2002-09 |
|
| [alpha 1-receptor blockade in therapy of benign prostatic hyperplasia syndrome. Correct dosing for optimal effectiveness]. | 2002-09 |
|
| [Drug therapy of benign prostatic hyperplasia syndrome with alpha 1-receptor blockers. Basic principles and clinical results]. | 2002-09 |
|
| [Comparison of prazosin, terazosin and tramsulosin: functional and binding studies in isolated prostatic and vascular human tissues]. | 2002-09 |
|
| Effects of intrathecal injection of tamsulosin and naftopidil, alpha-1A and -1D adrenergic receptor antagonists, on bladder activity in rats. | 2002-08-02 |
|
| Painful ejaculation and urinary hesitancy in association with antidepressant therapy: relief with tamsulosin. | 2002-08 |
|
| Managing benign prostatic hyperplasia. | 2002-07-01 |
|
| alpha-Adrenoceptor antagonists in the treatment of benign prostate hyperplasia. | 2002-07 |
|
| [Tamsulosin with or without Serenoa repens in benign prostatic hyperplasia: the OCOS trial]. | 2002-06 |
|
| [Comparison of a phytotherapeutic agent (Permixon) with an alpha-blocker (Tamsulosin) in the treatment of benign prostatic hyperplasia: a 1-year randomized international study]. | 2002-06 |
|
| Decrease of ultrasound estimated bladder weight during tamsulosin treatment in patients with benign prostatic enlargement. | 2002-06 |
|
| Design of a multicenter randomized clinical trial for chronic prostatitis/chronic pelvic pain syndrome. | 2002-06 |
|
| [Clinical evaluation of the effect of tamsulosin hydrochloride and cernitin pollen extract on urinary disturbance associated with benign prostatic hyperplasia in a multicentered study]. | 2002-05 |
|
| Comparison of a phytotherapeutic agent (Permixon) with an alpha-blocker (Tamsulosin) in the treatment of benign prostatic hyperplasia: a 1-year randomized international study. | 2002-05 |
|
| Tamsulosin: effect on quality of life in 2740 patients with lower urinary tract symptoms managed in real-life practice in Spain. | 2002-04-18 |
|
| Tamsulosin: an overview. | 2002-04 |
|
| Citalopram-induced priapism. | 2002-04 |
|
| Long-term risk of re-treatment of patients using alpha-blockers for lower urinary tract symptoms. | 2002-04 |
|
| Successful treatment of reboxetine-induced urinary hesitancy with tamsulosin. | 2002-04 |
|
| Effects of the concomitant administration of tamsulosin (0.8 mg/day) on the pharmacokinetic and safety profile of theophylline (5 mg/kg): a placebo-controlled evaluation. | 2002-03-30 |
|
| 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: a review of its pharmacology and therapeutic efficacy in the management of lower urinary tract symptoms. | 2002 |
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
| Substance Class |
Chemical
Created
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on
Edited
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| Record UNII |
11SV1951MR
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| Record Status |
Validated (UNII)
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C29713
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