tamsulosin   

GtoPdb Ligand ID: 488

Synonyms: (-)-YM617 | Flomax® | LY-253351 | Omnic® | tamsulosin hydrochloride
tamsulosin is an approved drug (FDA (1997))
Compound class: Synthetic organic
Comment: Tamsulosin is a selective α1A-adrenoceptor antagonist drug.
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: tamsulosin

2D Structure
Click here for structure editor
Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 11
Topological polar surface area 108.26
Molecular weight 408.17
XLogP 2.32
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES CCOc1ccccc1OCCNC(Cc1ccc(c(c1)S(=O)(=O)N)OC)C
Isomeric SMILES CCOc1ccccc1OCCN[C@@H](Cc1ccc(c(c1)S(=O)(=O)N)OC)C
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
InChI Key DRHKJLXJIQTDTD-OAHLLOKOSA-N
References
1. Chang DJ, Chang TK, Yamanishi SS, Salazar FH, Kosaka AH, Khare R, Bhakta S, Jasper JR, Shieh IS, Lesnick JD et al.. (1998)
Molecular cloning, genomic characterization and expression of novel human alpha1A-adrenoceptor isoforms.
FEBS Lett., 422 (2): 279-83. [PMID:9490024]
2. Daniels DV, Gever JR, Jasper JR, Kava MS, Lesnick JD, Meloy TD, Stepan G, Williams TJ, Clarke DE, Chang DJ et al.. (1999)
Human cloned alpha1A-adrenoceptor isoforms display alpha1L-adrenoceptor pharmacology in functional studies.
Eur. J. Pharmacol., 370 (3): 337-43. [PMID:10334511]
3. Ford AP, Daniels DV, Chang DJ, Gever JR, Jasper JR, Lesnick JD, Clarke DE. (1997)
Pharmacological pleiotropism of the human recombinant alpha1A-adrenoceptor: implications for alpha1-adrenoceptor classification.
Br. J. Pharmacol., 121 (6): 1127-35. [PMID:9249248]
4. Furyk JS, Chu K, Banks C, Greenslade J, Keijzers G, Thom O, Torpie T, Dux C, Narula R. (2016)
Distal Ureteric Stones and Tamsulosin: A Double-Blind, Placebo-Controlled, Randomized, Multicenter Trial.
Ann Emerg Med, 67 (1): 86-95.e2. [PMID:26194935]
5. Shibata K, Foglar R, Horie K, Obika K, Sakamoto A, Ogawa S, Tsujimoto G. (1995)
KMD-3213, a novel, potent, alpha 1a-adrenoceptor-selective antagonist: characterization using recombinant human alpha 1-adrenoceptors and native tissues.
Mol. Pharmacol., 48 (2): 250-8. [PMID:7651358]
6. Williams TJ, Blue DR, Daniels DV, Davis B, Elworthy T, Gever JR, Kava MS, Morgans D, Padilla F, Tassa S et al.. (1999)
In vitro alpha1-adrenoceptor pharmacology of Ro 70-0004 and RS-100329, novel alpha1A-adrenoceptor selective antagonists.
Br. J. Pharmacol., 127 (1): 252-8. [PMID:10369480]