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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 of TAMSULOSIN

SMILES

CCOC1=CC=CC=C1OCCN[C@H](C)CC2=CC(=C(OC)C=C2)S(N)(=O)=O

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

Description

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 TargetPharmacologyConditionPotency
0.19 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
FLOMAX

Cmax

ValueDoseCo-administeredAnalytePopulation
9.015 ng/mL
0.4 mg single, oral
TAMSULOSIN plasma
Homo sapiens
8.8694 ng/mL
0.4 mg single, oral
TAMSULOSIN plasma
Homo sapiens
10.1 ng/mL
0.4 mg 1 times / day multiple, oral
TAMSULOSIN HYDROCHLORIDE plasma
Homo sapiens
17.1 ng/mL
0.4 mg 1 times / day multiple, oral
TAMSULOSIN HYDROCHLORIDE plasma
Homo sapiens
29.8 ng/mL
0.8 mg 1 times / day multiple, oral
TAMSULOSIN HYDROCHLORIDE plasma
Homo sapiens
29.1 ng/mL
0.8 mg 1 times / day multiple, oral
TAMSULOSIN HYDROCHLORIDE plasma
Homo sapiens
41.6 ng/mL
0.8 mg 1 times / day multiple, oral
TAMSULOSIN HYDROCHLORIDE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
148.9023 ng*h/mL
0.4 mg single, oral
TAMSULOSIN plasma
Homo sapiens
157.9455 ng*h/mL
0.4 mg single, oral
TAMSULOSIN plasma
Homo sapiens
137.0248 ng*h/mL
0.4 mg single, oral
TAMSULOSIN plasma
Homo sapiens
143.2749 ng*h/mL
0.4 mg single, oral
TAMSULOSIN plasma
Homo sapiens
151 ng × h/mL
0.4 mg 1 times / day multiple, oral
TAMSULOSIN HYDROCHLORIDE plasma
Homo sapiens
199 ng × h/mL
0.4 mg 1 times / day multiple, oral
TAMSULOSIN HYDROCHLORIDE plasma
Homo sapiens
440 ng × h/mL
0.8 mg 1 times / day multiple, oral
TAMSULOSIN HYDROCHLORIDE plasma
Homo sapiens
449 ng × h/mL
0.8 mg 1 times / day multiple, oral
TAMSULOSIN HYDROCHLORIDE plasma
Homo sapiens
557 ng × h/mL
0.8 mg 1 times / day multiple, oral
TAMSULOSIN HYDROCHLORIDE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
14.9 h
0.8 mg 1 times / day multiple, oral
TAMSULOSIN HYDROCHLORIDE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
6%
0.4 mg 1 times / day multiple, oral
TAMSULOSIN HYDROCHLORIDE plasma
Homo sapiens

PubMed

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.