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 2778		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 8429	FLOMAX Approved Use Flomax® (tamsulosin hydrochloride) capsules are indicated for the treatment of the signs and symptoms of benign prostatic hyperplasia (BPH) Launch Date 1997

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
Initial choices and final outcomes in lower urinary tract symptoms.	2001	11786676
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
Our experience with the treatment of benign prostatic hyperplasia (BPH) with tamsulosin.	2001	11433602
Effect of KMD-3213, an alpha1A-adrenoceptor antagonist, on the prostatic urethral pressure and blood pressure in male decerebrate dogs.	2001 Apr	11260350
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
Results of treatment with tamsulosin in men with acute urinary retention.	2001 Dec	11763483
Tamsulosin: current clinical experience.	2001 Dec	11750250
[The efficacy and safety of terazosin and tamsulosin in patients with urinary disturbance accompanying prostatic hypertrophy].	2001 Jan	11235215
Do we know everything about alpha-blockade in the management of lower urinary tract symptoms?	2001 Jan	11223696
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	11206183
A quantitative analysis of antagonism and inverse agonism at wild-type and constitutively active hamster alpha1B-adrenoceptors.	2001 Jan	11191834
[Omnic (tamsulosin) in the treatment of benign prostatic hyperplasia].	2001 Jan-Feb	11233228
A 6-month large-scale study into the safety of tamsulosin.	2001 Jun	11422021
Finasteride and tamsulosin used in benign prostatic hypertrophy: a review of the prescription-event monitoring data.	2001 Jun	11412215
Comparison of prazosin, terazosin and tamsulosin: functional and binding studies in isolated prostatic and vascular human tissues.	2001 Jun 1	11398170
Long-term, open-label, phase III multicenter study of tamsulosin in benign prostatic hyperplasia.	2001 Mar	11248621
Pharmacological effect of tamsulosin in relation to dog plasma and tissue concentrations: prostatic and urethral retention possibly contributes to uroselectivity of tamsulosin.	2001 Mar	11181895
Evaluating adverse cardiovascular effects of drug treatment for benign prostatic hyperplasia (BPH): methodological considerations.	2001 May	11337216
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
Tamsulosin as an effective treatment for reboxetine-associated urinary hesitancy.	2001 Nov	11712624
Long-term use of tamsulosin to treat lower urinary tract symptoms/benign prostatic hyperplasia.	2001 Oct	11547074
Classical vs reverse pharmacology in drug discovery.	2001 Sep	11589663
[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
Clinical characteristics of alpha-blocker responders in men with benign prostatic hyperplasia.	2002	12053024
Tamsulosin: an update of its role in the management of lower urinary tract symptoms.	2002	11790159
Citalopram-induced priapism.	2002 Apr	11939691
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
Spinal substance P immunoreactivity is enhanced by acute chemical stimulation of the rat prostate.	2002 Jan	11796311
Quinazoline-derived alpha1-adrenoceptor antagonists induce prostate cancer cell apoptosis via an alpha1-adrenoceptor-independent action.	2002 Jan 15	11809715
[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
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
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
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
[Experience in long term use of tamsulosin (Omnik) in patients with chronic prostatitis].	2002 Sep-Oct	12402767
[Generally effective for unstable bladder? Tamsulosin: application not limited to benign prostatic hyperplasia].	2003 Feb	12739514
Priapism following ingestion of tamsulosin.	2003 Jun	12771780

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 `Fri Dec 15 16:11:28 GMT 2023` Edited by `admin` on `Fri Dec 15 16:11:28 GMT 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

Tamsulosine

Common Name

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