U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of TAMSULOSIN HYDROCHLORIDE

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
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

Curator's Comment: Tamsulosin can across the blood-brain barrier.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
10.1 ng/mL
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
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
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
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
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
151 ng × h/mL
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
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
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
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
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
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
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
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
14.9 h
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
6%
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

Doses

DosePopulationAdverse 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:
unhealthy, 54 years
n = 1
Health Status: unhealthy
Condition: benign prostatic hyperplasia
Age Group: 54 years
Sex: M
Population Size: 1
Sources:
Disc. AE: Drug eruption...
AEs leading to
discontinuation/dose reduction:
Drug eruption (1 patient)
Sources:
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:
unhealthy
n = 492
Health Status: unhealthy
Population Size: 492
Sources:
Disc. AE: Abnormal ejaculation...
AEs leading to
discontinuation/dose reduction:
Abnormal ejaculation (1.6%)
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
unhealthy, 54 years
n = 1
Health Status: unhealthy
Condition: benign prostatic hyperplasia
Age Group: 54 years
Sex: M
Population Size: 1
Sources:
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:
unhealthy
n = 492
Health Status: unhealthy
Population Size: 492
Sources:
PubMed

PubMed

TitleDatePubMed
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
Efficacy and tolerability of drugs for treatment of benign prostatic hyperplasia.
2001
Our experience with the treatment of benign prostatic hyperplasia (BPH) with tamsulosin.
2001
Results of treatment with tamsulosin in men with acute urinary retention.
2001 Dec
A quantitative analysis of antagonism and inverse agonism at wild-type and constitutively active hamster alpha1B-adrenoceptors.
2001 Jan
alpha-Blockade improves symptoms suggestive of bladder outlet obstruction but fails to relieve it.
2001 Jan
Does the time of administration (morning or evening) affect the tolerability or efficacy of tamsulosin?
2001 Jan
Finasteride and tamsulosin used in benign prostatic hypertrophy: a review of the prescription-event monitoring data.
2001 Jun
Pharmacological effect of tamsulosin in relation to dog plasma and tissue concentrations: prostatic and urethral retention possibly contributes to uroselectivity of tamsulosin.
2001 Mar
Stimulatory effect of isoferulic acid on alpha1A-adrenoceptor to increase glucose uptake into cultured myoblast C2C12 cell of mice.
2001 May 14
Worldwide experience with alfuzosin and tamsulosin.
2001 Oct
Classical vs reverse pharmacology in drug discovery.
2001 Sep
Speedy elimination of ureterolithiasis in lower part of ureters with the alpha 1-blocker--Tamsulosin.
2002
Terazosin for benign prostatic hyperplasia.
2002
[The clinical efficacy of Naftopidil tablet in the treatment of benign prostatic hyperplasia].
2002
[Tamsulosin for the treatment of chronic abacterial prostatitis].
2002
Tamsulosin: a review of its pharmacology and therapeutic efficacy in the management of lower urinary tract symptoms.
2002
Tamsulosin: an update of its role in the management of lower urinary tract symptoms.
2002
Gateways to clinical trials.
2002 Dec
Terazosin for treating symptomatic benign prostatic obstruction: a systematic review of efficacy and adverse effects.
2002 Feb
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
Digoxin-drug interactions: study design and generalizability.
2002 Feb
Quantitation of tamsulosin in human plasma by liquid chromatography-electrospray ionization mass spectrometry.
2002 Feb 5
[Transition zone index in predicting therapeutic efficacy of benign prostatic hyperplasia].
2002 Jan
Quinazoline-derived alpha1-adrenoceptor antagonists induce prostate cancer cell apoptosis via an alpha1-adrenoceptor-independent action.
2002 Jan 15
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
alpha-Adrenoceptor antagonists in the treatment of benign prostate hyperplasia.
2002 Jul
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
Method for simultaneous recording of the prostatic contractile and urethral pressure responses in anesthetized rats and the effects of tamsulosin.
2002 Nov
Comparison of tamsulosin and finasteride for lower urinary tract symptoms associated with benign prostatic hyperplasia in Korean patients.
2002 Nov-Dec
Gateways to clinical trials.
2002 Oct
Prophylactic versus therapeutic alpha-blockers after permanent prostate brachytherapy.
2002 Oct
[alpha 1-receptor blockade in therapy of benign prostatic hyperplasia syndrome. Correct dosing for optimal effectiveness].
2002 Sep
[Comparative evaluation of the efficacy of using terazosin and tamsulosin in patients with benign prostatic hyperplasia].
2002 Sep-Oct
[Correction of urination disorders caused by benign prostatic hyperplasia in cardiac surgery].
2003
Effects of intrathecal injection of tamsulosin and naftopidil, alpha-1A and 1D adrenergic receptor antagonists, on bladder activity in rats.
2003 Apr
Priapism following ingestion of tamsulosin.
2003 Jun
A placebo-controlled pharmacodynamic and pharmacokinetic interaction study between tamsulosin and acenocoumarol.
2003 Mar
Quinazoline-based alpha 1-adrenoceptor antagonists induce prostate cancer cell apoptosis via TGF-beta signalling and I kappa B alpha induction.
2003 May 19
Patents

Sample Use Guides

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
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 Thu Jul 06 00:00:59 UTC 2023
Edited
by admin
on Thu Jul 06 00:00:59 UTC 2023
Record UNII
11SV1951MR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TAMSULOSIN HYDROCHLORIDE
EP   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
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
Created by admin on Thu Jul 06 00:00:59 UTC 2023 , Edited by admin on Thu Jul 06 00:00:59 UTC 2023
Code System Code Type Description
RS_ITEM_NUM
1643260
Created by admin on Thu Jul 06 00:00:59 UTC 2023 , Edited by admin on Thu Jul 06 00:00:59 UTC 2023
PRIMARY
DAILYMED
11SV1951MR
Created by admin on Thu Jul 06 00:00:59 UTC 2023 , Edited by admin on Thu Jul 06 00:00:59 UTC 2023
PRIMARY
CHEBI
9399
Created by admin on Thu Jul 06 00:00:59 UTC 2023 , Edited by admin on Thu Jul 06 00:00:59 UTC 2023
PRIMARY
EPA CompTox
DTXSID2046628
Created by admin on Thu Jul 06 00:00:59 UTC 2023 , Edited by admin on Thu Jul 06 00:00:59 UTC 2023
PRIMARY
MERCK INDEX
M10451
Created by admin on Thu Jul 06 00:00:59 UTC 2023 , Edited by admin on Thu Jul 06 00:00:59 UTC 2023
PRIMARY Merck Index
FDA UNII
11SV1951MR
Created by admin on Thu Jul 06 00:00:59 UTC 2023 , Edited by admin on Thu Jul 06 00:00:59 UTC 2023
PRIMARY
SMS_ID
100000089670
Created by admin on Thu Jul 06 00:00:59 UTC 2023 , Edited by admin on Thu Jul 06 00:00:59 UTC 2023
PRIMARY
MESH
C088482
Created by admin on Thu Jul 06 00:00:59 UTC 2023 , Edited by admin on Thu Jul 06 00:00:59 UTC 2023
PRIMARY
PUBCHEM
5362376
Created by admin on Thu Jul 06 00:00:59 UTC 2023 , Edited by admin on Thu Jul 06 00:00:59 UTC 2023
PRIMARY
RXCUI
236495
Created by admin on Thu Jul 06 00:00:59 UTC 2023 , Edited by admin on Thu Jul 06 00:00:59 UTC 2023
PRIMARY RxNorm
DRUG BANK
DBSALT000978
Created by admin on Thu Jul 06 00:00:59 UTC 2023 , Edited by admin on Thu Jul 06 00:00:59 UTC 2023
PRIMARY
ChEMBL
CHEMBL836
Created by admin on Thu Jul 06 00:00:59 UTC 2023 , Edited by admin on Thu Jul 06 00:00:59 UTC 2023
PRIMARY
EVMPD
SUB04673MIG
Created by admin on Thu Jul 06 00:00:59 UTC 2023 , Edited by admin on Thu Jul 06 00:00:59 UTC 2023
PRIMARY
CAS
106463-17-6
Created by admin on Thu Jul 06 00:00:59 UTC 2023 , Edited by admin on Thu Jul 06 00:00:59 UTC 2023
PRIMARY
USAN
GG-3
Created by admin on Thu Jul 06 00:00:59 UTC 2023 , Edited by admin on Thu Jul 06 00:00:59 UTC 2023
PRIMARY
NCI_THESAURUS
C29486
Created by admin on Thu Jul 06 00:00:59 UTC 2023 , Edited by admin on Thu Jul 06 00:00:59 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY