TAMSULOSIN HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H28N2O5S.ClH
Molecular Weight	444.973
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.CCOC1=C(OCCN[C@H](C)CC2=CC(=C(OC)C=C2)S(N)(=O)=O)C=CC=C1

InChI

InChIKey=ZZIZZTHXZRDOFM-XFULWGLBSA-N

InChI=1S/C20H28N2O5S.ClH/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);1H/t15-;/m1./s1

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Clinical comparison of selective and non-selective alpha 1A-adrenoceptor antagonists for bladder outlet obstruction associated with benign prostatic hyperplasia: studies on tamsulosin and terazosin in Chinese patients. The Chinese Tamsulosin Study Group.	1998	10503165
Human cloned alpha1A-adrenoceptor isoforms display alpha1L-adrenoceptor pharmacology in functional studies.	1999 Apr 16	10334511
Tamsulosin for the treatment of benign prostatic hypertrophy.	2000 Feb	10676828
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
Molecular cloning and functional expression of the guinea pig alpha(1a)-adrenoceptor.	2001 Aug 31	11527538
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
[Omnic (tamsulosin) in the treatment of benign prostatic hyperplasia].	2001 Jan-Feb	11233228
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
Terazosin for benign prostatic hyperplasia.	2002	12519611
Clinical characteristics of alpha-blocker responders in men with benign prostatic hyperplasia.	2002	12053024
Successful treatment of reboxetine-induced urinary hesitancy with tamsulosin.	2002 Apr	11872327
Gateways to clinical trials.	2002 Dec	12616965
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
Biochemical and functional characterization of alpha-adrenergic receptors in the rabbit vagina.	2002 Nov 1	12377271
Prophylactic versus therapeutic alpha-blockers after permanent prostate brachytherapy.	2002 Oct	12385927
Gateways to Clinical Trials.	2002 Sep	12428432
[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
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 `Fri Dec 16 20:34:02 UTC 2022` Edited by `admin` on `Fri Dec 16 20:34:02 UTC 2022`
Record UNII	11SV1951MR
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TAMSULOSIN HYDROCHLORIDE

Official Name

English

TAMSULOSIN HCL

Common Name

English

LY253351

Code

English

YM-12617-1

Code

English

TAMSULOSIN HYDROCHLORIDE [USP MONOGRAPH]

Common Name

English

YM617

Code

English

LY-253351

Code

English

TAMSULOSIN HYDROCHLORIDE [USP-RS]

Common Name

English

YM-617

Code

English

FLOMAX

Brand Name

English

TAMSULOSIN HYDROCHLORIDE [USAN]

Common Name

English

TAMSULOSIN HYDROCHLORIDE COMPONENT OF JALYN

Brand Name

English

TAMSULOSIN HYDROCHLORIDE [EP MONOGRAPH]

Common Name

English

TAMSULOSIN HYDROCHLORIDE [JAN]

Common Name

English

TAMSULOSIN HYDROCHLORIDE [MART.]

Common Name

English

TAMSULOSIN HYDROCHLORIDE [ORANGE BOOK]

Common Name

English

Tamsulosin hydrochloride [WHO-DD]

Common Name

English

(-)-(R)-5-(2-((2-(O-ETHOXYPHENOXY)ETHYL)AMINO)PROPYL)-2-METHOXYBENZENESULFONAMIDE MONOHYDROCHLORIDE

Common Name

English

R-(-)-YM-12617

Code

English

TAMSULOSIN HYDROCHLORIDE [VANDF]

Common Name

English

JALYN COMPONENT TAMSULOSIN HYDROCHLORIDE

Brand Name

English

TAMSULOSIN HYDROCHLORIDE [USP IMPURITY]

Common Name

English

BENZENESULFONAMIDE, 5-(2-((2-(2-ETHOXYPHENOXY)ETHYL)AMINO)PROPYL)-2-METHOXY-, MONOHYDROCHLORIDE, (R)-

Common Name

English

HARNAL

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29713