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-1 167 Target ID: CHEMBL2094251 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020579s016lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/11026539	Antagonist 2737		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 8307	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
Human cloned alpha1A-adrenoceptor isoforms display alpha1L-adrenoceptor pharmacology in functional studies.	1999 Apr 16	10334511
[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
alpha-Blockade improves symptoms suggestive of bladder outlet obstruction but fails to relieve it.	2001 Jan	11125359
[Omnic (tamsulosin) in the treatment of benign prostatic hyperplasia].	2001 Jan-Feb	11233228
Finasteride and tamsulosin used in benign prostatic hypertrophy: a review of the prescription-event monitoring data.	2001 Jun	11412215
Long-term, open-label, phase III multicenter study of tamsulosin in benign prostatic hyperplasia.	2001 Mar	11248621
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
Worldwide experience with alfuzosin and tamsulosin.	2001 Oct	11597528
Stimulatory effect of phenylephrine on the secretion of beta-endorphin from rat adrenal medulla in vitro.	2001 Oct 8	11695703
[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 overview.	2002 Apr	12022708
Citalopram-induced priapism.	2002 Apr	11939691
Painful ejaculation and urinary hesitancy in association with antidepressant therapy: relief with tamsulosin.	2002 Aug	12126873
Gateways to clinical trials.	2002 Dec	12616965
The use of alpha-adrenoceptor antagonists in lower urinary tract disease.	2002 Feb	11829730
Managing reboxetine-associated urinary hesitancy in a patient with major depressive disorder: a case study.	2002 Feb	11823898
Effect of fiduxosin, an antagonist selective for alpha(1A)- and alpha(1D)-adrenoceptors, on intraurethral and arterial pressure responses in conscious dogs.	2002 Feb	11805208
[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
Design of a multicenter randomized clinical trial for chronic prostatitis/chronic pelvic pain syndrome.	2002 Jun	12031372
Method for simultaneous recording of the prostatic contractile and urethral pressure responses in anesthetized rats and the effects of tamsulosin.	2002 Nov	12499584
Gateways to clinical trials.	2002 Oct	12500432
[Comparative evaluation of the efficacy of using terazosin and tamsulosin in patients with benign prostatic hyperplasia].	2002 Sep-Oct	12518668
[Correction of urination disorders caused by benign prostatic hyperplasia in cardiac surgery].	2003	12645203
Effects of intrathecal injection of tamsulosin and naftopidil, alpha-1A and 1D adrenergic receptor antagonists, on bladder activity in rats.	2003 Apr	12641149
[Generally effective for unstable bladder? Tamsulosin: application not limited to benign prostatic hyperplasia].	2003 Feb	12739514
Drug treatment of benign prostatic hyperplasia and hospital admission for BPH-related surgery.	2003 May	12705998

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 16 19:29:21 UTC 2022` Edited by `admin` on `Fri Dec 16 19:29:21 UTC 2022`
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