TAMSULOSIN

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 Search

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
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020579s016lbl.pdf
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adrenergic receptor alpha-1 161 Target ID: CHEMBL2094251 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020579s016lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/11026539	Antagonist 2575		0.19 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Benign prostatic hyperplasia 28 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020579s016lbl.pdf	Primary		Approved 8043	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

C_max

Value	Dose	Analyte	Population
10.1 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020579s033lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020579s033lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020579s033lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020579s033lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020579s033lbl.pdf	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	Analyte	Population
151 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020579s033lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020579s033lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020579s033lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020579s033lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020579s033lbl.pdf	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
14.9 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020579s033lbl.pdf	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
6% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020579s033lbl.pdf	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: https://pubmed.ncbi.nlm.nih.gov/31541583	unhealthy, 54 years n = 1 Health Status: unhealthy Condition: benign prostatic hyperplasia Age Group: 54 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/31541583	Disc. AE: Drug eruption... AEs leading to discontinuation/dose reduction: Drug eruption (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/31541583
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020579s033lbl.pdf	unhealthy n = 492 Health Status: unhealthy Population Size: 492 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020579s033lbl.pdf	Disc. AE: Abnormal ejaculation... AEs leading to discontinuation/dose reduction: Abnormal ejaculation (1.6%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020579s033lbl.pdf

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: https://pubmed.ncbi.nlm.nih.gov/31541583	unhealthy, 54 years n = 1 Health Status: unhealthy Condition: benign prostatic hyperplasia Age Group: 54 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/31541583
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020579s033lbl.pdf	unhealthy n = 492 Health Status: unhealthy Population Size: 492 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020579s033lbl.pdf

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:9398	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9398
ChemicalBook	CB22675761	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB22675761
ChemicalBook	CB3128875	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB3128875
MolPort	MolPort-003-850-388	https://www.molport.com/shop/molecule-link/MolPort-003-850-388
ZINC	ZINC000001530694	http://zinc15.docking.org/substances/ZINC000001530694
eMolecules	3716265	https://www.emolecules.com/cgi-bin/more?vid=3716265

PubMed

Title	Date	PubMed
Lower urinary tract symptoms: what are the implications for the patients?	2001	11786675
Potential mechanisms of action of superselective alpha(1)-adrenoceptor antagonists.	2001	11786674
Efficacy and tolerability of drugs for treatment of benign prostatic hyperplasia.	2001	11583366
Effect of tamsulosin hydrochloride on sympathetic hyperactivity in amyotrophic lateral sclerosis.	2001 Apr 12	11474551
Molecular cloning and functional expression of the guinea pig alpha(1a)-adrenoceptor.	2001 Aug 31	11527538
Stimulatory effect of isoferulic acid on alpha1A-adrenoceptor to increase glucose uptake into cultured myoblast C2C12 cell of mice.	2001 May 14	11474559
Review of orthostatic tests on the safety of tamsulosin, a selective alpha1A-adrenergic receptor antagonist, shows lack of orthostatic hypotensive effects.	2001 May-Jun	11471862
[A case of heparin-induced thrombocytopenia after transurethral resection of prostate during anticoagulant therapy].	2001 Nov	11766370
Long-term use of tamsulosin to treat lower urinary tract symptoms/benign prostatic hyperplasia.	2001 Oct	11547074
Stimulatory effect of phenylephrine on the secretion of beta-endorphin from rat adrenal medulla in vitro.	2001 Oct 8	11695703
Speedy elimination of ureterolithiasis in lower part of ureters with the alpha 1-blocker--Tamsulosin.	2002	12549635
Terazosin for benign prostatic hyperplasia.	2002	12519611
[The clinical efficacy of Naftopidil tablet in the treatment of benign prostatic hyperplasia].	2002	12491697
[Tamsulosin for the treatment of chronic abacterial prostatitis].	2002	12479050
Tamsulosin: a review of its pharmacology and therapeutic efficacy in the management of lower urinary tract symptoms.	2002	11950378
Tamsulosin: an update of its role in the management of lower urinary tract symptoms.	2002	11790159
Tamsulosin: an overview.	2002 Apr	12022708
Citalopram-induced priapism.	2002 Apr	11939691
Long-term risk of re-treatment of patients using alpha-blockers for lower urinary tract symptoms.	2002 Apr	11912399
Successful treatment of reboxetine-induced urinary hesitancy with tamsulosin.	2002 Apr	11872327
Painful ejaculation and urinary hesitancy in association with antidepressant therapy: relief with tamsulosin.	2002 Aug	12126873
Gateways to clinical trials.	2002 Dec	12616965
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	11846858
Digoxin-drug interactions: study design and generalizability.	2002 Feb	11846856
[A comparative study assessing clinical effects of naftopidil and tamsulosin hydrochloride on benign prostatic hyperplasia].	2002 Jan	11868386
[Transition zone index in predicting therapeutic efficacy of benign prostatic hyperplasia].	2002 Jan	11842535
Tamsulosin for treating lower urinary tract symptoms compatible with benign prostatic obstruction: a systematic review of efficacy and adverse effects.	2002 Jan	11743300
Managing benign prostatic hyperplasia.	2002 Jul 1	12126034
[Tamsulosin with or without Serenoa repens in benign prostatic hyperplasia: the OCOS trial].	2002 Jun	12189745
[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	12189744
[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	12094707
Method for simultaneous recording of the prostatic contractile and urethral pressure responses in anesthetized rats and the effects of tamsulosin.	2002 Nov	12499584
Comparison of tamsulosin and finasteride for lower urinary tract symptoms associated with benign prostatic hyperplasia in Korean patients.	2002 Nov-Dec	12526285
Prophylactic versus therapeutic alpha-blockers after permanent prostate brachytherapy.	2002 Oct	12385927
Identification of binding sites of prazosin, tamsulosin and KMD-3213 with alpha(1)-adrenergic receptor subtypes by molecular modeling.	2002 Oct 11	12270758
Gateways to Clinical Trials.	2002 Sep	12428432
[alpha 1-receptor blockade in therapy of benign prostatic hyperplasia syndrome. Correct dosing for optimal effectiveness].	2002 Sep	12426862
[Drug therapy of benign prostatic hyperplasia syndrome with alpha 1-receptor blockers. Basic principles and clinical results].	2002 Sep	12426859
[Comparison of prazosin, terazosin and tramsulosin: functional and binding studies in isolated prostatic and vascular human tissues].	2002 Sep	12384622
[Comparative evaluation of the efficacy of using terazosin and tamsulosin in patients with benign prostatic hyperplasia].	2002 Sep-Oct	12518668
[Experience in long term use of tamsulosin (Omnik) in patients with chronic prostatitis].	2002 Sep-Oct	12402767
Tamsulosin for benign prostatic hyperplasia.	2003	12535426
Effects of intrathecal injection of tamsulosin and naftopidil, alpha-1A and 1D adrenergic receptor antagonists, on bladder activity in rats.	2003 Apr	12641149
Doxazosin and terazosin suppress prostate growth by inducing apoptosis: clinical significance.	2003 Apr	12629407
A randomized, double-blind crossover study of tamsulosin and controlled-release doxazosin in patients with benign prostatic hyperplasia.	2003 Jan	12614248
Priapism following ingestion of tamsulosin.	2003 Jun	12771780
Combination treatment with an alpha-blocker plus an anticholinergic for bladder outlet obstruction: a prospective, randomized, controlled study.	2003 Jun	12771763
Anoikis induction by quinazoline based alpha 1-adrenoceptor antagonists in prostate cancer cells: antagonistic effect of bcl-2.	2003 Mar	12576871
Drug treatment of benign prostatic hyperplasia and hospital admission for BPH-related surgery.	2003 May	12705998
Quinazoline-based alpha 1-adrenoceptor antagonists induce prostate cancer cell apoptosis via TGF-beta signalling and I kappa B alpha induction.	2003 May 19	12771931

Patents

Sample Use Guides

In Vivo Use Guide

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

Tamsulosin at concentrations of 0.1 and 1 uM directly inhibited MCh-induced contractility of pregnant rat ureters.

Name

Type

Language

TAMSULOSIN

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