U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of TAMSULOSIN

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

HIDE SMILES / InChI

Description
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

Curator's Comment:: Tamsulosin can across the blood-brain barrier.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
FLOMAX

Approved Use

Flomax® (tamsulosin hydrochloride) capsules are indicated for the treatment of the signs and symptoms of benign prostatic hyperplasia (BPH)

Launch Date

8.6106243E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
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
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
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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

AEs

AESignificanceDosePopulation
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

PubMed

TitleDatePubMed
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
Patents

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
Tamsulosin at concentrations of 0.1 and 1 uM directly inhibited MCh-induced contractility of pregnant rat ureters.
Name Type Language
TAMSULOSIN
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
TAMSULON
Brand Name English
HIP1402
Code English
TAMSULOSIN [INN]
Common Name English
TAMSULOSIN [HSDB]
Common Name English
HIP-1402
Code English
TAMSULOSIN [VANDF]
Common Name English
TAMSULOSIN [MI]
Common Name English
TAMSULOSIN [WHO-DD]
Common Name English
BENZENESULFONAMIDE, 5-(2-((2-(2-ETHOXYPHENOXY)ETHYL)AMINO)PROPYL)-2-METHOXY-, (R)-
Common Name English
HGP-0412
Code English
(-)-(R)-5-(2-((2-(O-ETHOXYPHENOXY)ETHYL)AMINO)PROPYL)-2-METHOXYBENZENESULFONAMIDE
Common Name English
Classification Tree Code System Code
WHO-VATC QG04CA52
Created by admin on Sat Jun 26 14:01:33 UTC 2021 , Edited by admin on Sat Jun 26 14:01:33 UTC 2021
WHO-ATC G04CA52
Created by admin on Sat Jun 26 14:01:33 UTC 2021 , Edited by admin on Sat Jun 26 14:01:33 UTC 2021
NDF-RT N0000175553
Created by admin on Sat Jun 26 14:01:33 UTC 2021 , Edited by admin on Sat Jun 26 14:01:33 UTC 2021
LIVERTOX 922
Created by admin on Sat Jun 26 14:01:33 UTC 2021 , Edited by admin on Sat Jun 26 14:01:33 UTC 2021
NCI_THESAURUS C29713
Created by admin on Sat Jun 26 14:01:33 UTC 2021 , Edited by admin on Sat Jun 26 14:01:33 UTC 2021
WHO-VATC QG04CA02
Created by admin on Sat Jun 26 14:01:33 UTC 2021 , Edited by admin on Sat Jun 26 14:01:33 UTC 2021
NDF-RT N0000000099
Created by admin on Sat Jun 26 14:01:33 UTC 2021 , Edited by admin on Sat Jun 26 14:01:33 UTC 2021
WHO-VATC QG04CA53
Created by admin on Sat Jun 26 14:01:33 UTC 2021 , Edited by admin on Sat Jun 26 14:01:33 UTC 2021
WHO-ATC G04CA53
Created by admin on Sat Jun 26 14:01:33 UTC 2021 , Edited by admin on Sat Jun 26 14:01:33 UTC 2021
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
Code System Code Type Description
CAS
106133-20-4
Created by admin on Sat Jun 26 14:01:33 UTC 2021 , Edited by admin on Sat Jun 26 14:01:33 UTC 2021
PRIMARY
WIKIPEDIA
TAMSULOSIN
Created by admin on Sat Jun 26 14:01:33 UTC 2021 , Edited by admin on Sat Jun 26 14:01:33 UTC 2021
PRIMARY
RXCUI
77492
Created by admin on Sat Jun 26 14:01:33 UTC 2021 , Edited by admin on Sat Jun 26 14:01:33 UTC 2021
PRIMARY RxNorm
MERCK INDEX
M10451
Created by admin on Sat Jun 26 14:01:33 UTC 2021 , Edited by admin on Sat Jun 26 14:01:33 UTC 2021
PRIMARY Merck Index
EPA CompTox
106133-20-4
Created by admin on Sat Jun 26 14:01:33 UTC 2021 , Edited by admin on Sat Jun 26 14:01:33 UTC 2021
PRIMARY
DRUG BANK
DB00706
Created by admin on Sat Jun 26 14:01:33 UTC 2021 , Edited by admin on Sat Jun 26 14:01:33 UTC 2021
PRIMARY
DRUG CENTRAL
2562
Created by admin on Sat Jun 26 14:01:33 UTC 2021 , Edited by admin on Sat Jun 26 14:01:33 UTC 2021
PRIMARY
FDA UNII
G3P28OML5I
Created by admin on Sat Jun 26 14:01:33 UTC 2021 , Edited by admin on Sat Jun 26 14:01:33 UTC 2021
PRIMARY
PUBCHEM
129211
Created by admin on Sat Jun 26 14:01:33 UTC 2021 , Edited by admin on Sat Jun 26 14:01:33 UTC 2021
PRIMARY
IUPHAR
488
Created by admin on Sat Jun 26 14:01:33 UTC 2021 , Edited by admin on Sat Jun 26 14:01:33 UTC 2021
PRIMARY
INN
6750
Created by admin on Sat Jun 26 14:01:33 UTC 2021 , Edited by admin on Sat Jun 26 14:01:33 UTC 2021
PRIMARY
MESH
C088482
Created by admin on Sat Jun 26 14:01:33 UTC 2021 , Edited by admin on Sat Jun 26 14:01:33 UTC 2021
PRIMARY
EVMPD
SUB10827MIG
Created by admin on Sat Jun 26 14:01:33 UTC 2021 , Edited by admin on Sat Jun 26 14:01:33 UTC 2021
PRIMARY
ChEMBL
CHEMBL836
Created by admin on Sat Jun 26 14:01:33 UTC 2021 , Edited by admin on Sat Jun 26 14:01:33 UTC 2021
PRIMARY
NCI_THESAURUS
C75055
Created by admin on Sat Jun 26 14:01:33 UTC 2021 , Edited by admin on Sat Jun 26 14:01:33 UTC 2021
PRIMARY
HSDB
7744
Created by admin on Sat Jun 26 14:01:33 UTC 2021 , Edited by admin on Sat Jun 26 14:01:33 UTC 2021
PRIMARY