TAMSULOSIN

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

Structure Search

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

HIDE SMILES / InChI

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

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-1 169 Target ID: CHEMBL2094251 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020579s016lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/11026539	Antagonist 2760		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 8360	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
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
Clinical characteristics of alpha-blocker responders in men with benign prostatic hyperplasia.	2002	12053024
Tamsulosin: a review of its pharmacology and therapeutic efficacy in the management of lower urinary tract symptoms.	2002	11950378
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
Effects of intrathecal injection of tamsulosin and naftopidil, alpha-1A and -1D adrenergic receptor antagonists, on bladder activity in rats.	2002 Aug 2	12123863
Gateways to clinical trials.	2002 Dec	12616965
[Alpha 1-adrenoceptor antagonists for treatment of prostatic hyperplsia].	2002 Dec	12599599
Quantitation of tamsulosin in human plasma by liquid chromatography-electrospray ionization mass spectrometry.	2002 Feb 5	11863298
[A comparative study assessing clinical effects of naftopidil and tamsulosin hydrochloride on benign prostatic hyperplasia].	2002 Jan	11868386
Tamsulosin: effect on quality of life in 2740 patients with lower urinary tract symptoms managed in real-life practice in Spain.	2002 Jan-Feb	11957763
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 Jan-Feb	11921497
alpha-Adrenoceptor antagonists in the treatment of benign prostate hyperplasia.	2002 Jul	12037374
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
Decrease of ultrasound estimated bladder weight during tamsulosin treatment in patients with benign prostatic enlargement.	2002 Jun	12161944
Design of a multicenter randomized clinical trial for chronic prostatitis/chronic pelvic pain syndrome.	2002 Jun	12031372
[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
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 May	12074791
Method for simultaneous recording of the prostatic contractile and urethral pressure responses in anesthetized rats and the effects of tamsulosin.	2002 Nov	12499584
Biochemical and functional characterization of alpha-adrenergic receptors in the rabbit vagina.	2002 Nov 1	12377271
Comparison of tamsulosin and finasteride for lower urinary tract symptoms associated with benign prostatic hyperplasia in Korean patients.	2002 Nov-Dec	12526285
Gateways to clinical trials.	2002 Oct	12500432
Effects of KMD-3213, a uroselective alpha 1A-adrenoceptor antagonist, on the tilt-induced blood pressure response in normotensive rats.	2002 Oct	12419883
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
[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
[Correction of urination disorders caused by benign prostatic hyperplasia in cardiac surgery].	2003	12645203
Tamsulosin for benign prostatic hyperplasia.	2003	12535426
Nocturia and benign prostatic hyperplasia.	2003 Apr	12670566
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
[Generally effective for unstable bladder? Tamsulosin: application not limited to benign prostatic hyperplasia].	2003 Feb	12739514
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
A placebo-controlled pharmacodynamic and pharmacokinetic interaction study between tamsulosin and acenocoumarol.	2003 Mar	12630984
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.

Substance Class	Chemical Created by `admin` on `Wed Jul 05 23:39:01 UTC 2023` Edited by `admin` on `Wed Jul 05 23:39:01 UTC 2023`
Record UNII	G3P28OML5I
Record Status	`Validated (UNII)`
Record Version

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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

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

Tamsulosin [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QG04CA52