CHEBI:9398 - tamsulosin

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ChEBI Name tamsulosin
ChEBI ID CHEBI:9398
Definition A 5-(2-{[2-(2-ethoxyphenoxy)ethyl]amino}propyl)-2-methoxybenzenesulfonamide that has (R)-configuration. A specific α1 adrenoceptor antagonist used (generally as its hydrochloride salt, tamsulosin hydrochloride) in the treatment of prostatic hyperplasia, chronic prostatitis, urinary retention, and help with the passage of kidney stones.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C20H28N2O5S
Net Charge 0
Average Mass 408.514
Monoisotopic Mass 408.172
InChI 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
InChIKey DRHKJLXJIQTDTD-OAHLLOKOSA-N
SMILES C=1C=C(OCCN[C@@H](CC2=CC=C(C(=C2)S(N)(=O)=O)OC)C)C(=CC1)OCC
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): alpha-adrenergic antagonist
An agent that binds to but does not activate alpha-adrenergic receptors thereby blocking the actions of endogenous or exogenous alpha-adrenergic agonists. alpha-Adrenergic antagonists are used in the treatment of hypertension, vasospasm, peripheral vascular disease, shock, and pheochromocytoma.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
alpha-adrenergic antagonist
An agent that binds to but does not activate alpha-adrenergic receptors thereby blocking the actions of endogenous or exogenous alpha-adrenergic agonists. alpha-Adrenergic antagonists are used in the treatment of hypertension, vasospasm, peripheral vascular disease, shock, and pheochromocytoma.
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ChEBI Ontology
Outgoing tamsulosin (CHEBI:9398) has role α-adrenergic antagonist (CHEBI:37890)
tamsulosin (CHEBI:9398) has role antineoplastic agent (CHEBI:35610)
tamsulosin (CHEBI:9398) is a 5-(2-{[2-(2-ethoxyphenoxy)ethyl]amino}propyl)-2-methoxybenzenesulfonamide (CHEBI:142546)
tamsulosin (CHEBI:9398) is conjugate base of tamsulosin(1+) (CHEBI:142544)
tamsulosin (CHEBI:9398) is enantiomer of ent-tamsulosin (CHEBI:142548)
Incoming rac-tamsulosin (CHEBI:142552) has part tamsulosin (CHEBI:9398)
tamsulosin(1+) (CHEBI:142544) is conjugate acid of tamsulosin (CHEBI:9398)
ent-tamsulosin (CHEBI:142548) is enantiomer of tamsulosin (CHEBI:9398)
IUPAC Name
5-[(2R)-2-{[2-(2-ethoxyphenoxy)ethyl]amino}propyl]-2-methoxybenzenesulfonamide
INNs Sources
tamsulosin ChemIDplus
tamsulosina ChemIDplus
tamsulosine ChemIDplus
tamsulosinum ChemIDplus
Synonyms Sources
(−)-tamsulosin ChEBI
(R)-(−)-tamsulosin ChEBI
(R)-5-(2-((2-(2-ethoxyphenoxy)ethyl)amino)propyl)-2-methoxybenzenesulfonamide ChemIDplus
Tamsulosin KEGG COMPOUND
Manual Xrefs Databases
2562 DrugCentral
C07124 KEGG COMPOUND
D08560 KEGG DRUG
DB00706 DrugBank
EP34432 Patent
Tamsulosin Wikipedia
US4703063 Patent
View more database links
Registry Numbers Types Sources
106133-20-4 CAS Registry Number KEGG COMPOUND
106133-20-4 CAS Registry Number ChemIDplus
6896059 Reaxys Registry Number Reaxys
6896059 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
2891044 PubMed citation Europe PMC
29728928 PubMed citation Europe PMC
29737501 PubMed citation Europe PMC
29913020 PubMed citation Europe PMC
29971698 PubMed citation Europe PMC
29974124 PubMed citation Europe PMC
30174141 PubMed citation Europe PMC
30360332 PubMed citation Europe PMC
Last Modified
12 November 2018