(Rac)-Tamsulosin
(Rac)-Tamsulosin (YM12617 (free base); (Rac)-LY253351 (free base)) is an isomer of Tamsulosin (HY-B0661). (Rac)-Tamsulosin is a sulfonamide phenethylamine derivative and a competitive antagonist of selective post-synaptic α1-adrenoceptors. (Rac)-Tamsulosin inhibits CYP3A4 activity in a non-competitive, enantiomer-specific manner, with an IC50 and Ki of 6.75 μM. (Rac)-Tamsulosin produces dose-dependent hypotension, preferentially antagonizing α1-adrenoceptor-mediated pressor responses, and inhibits α2-adrenoceptor-mediated pressor responses at high doses. (Rac)-Tamsulosin can be used in research related to various diseases such as metabolism.
For research use only. We do not sell to patients.
- CAS No.: 94666-07-6
- Formula: C20H28N2O5S
- Molecular Weight:408.51
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Storage:Powder -20°C, 3 years ; In solvent -80°C, 6 months , -20°C, 1 month
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Biological Activity
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Chemical Information
- Purity & Documentation
- References
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Help & FAQs
All Adrenergic Receptor Isoforms
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Biological Activity
Description
IC50 & Target
[1]|
α1-adrenergic receptor |
CYP3A4 6.75 μM (Ki) |
CYP3A4 6.75 μM (IC50) |
In Vitro
(Rac)-Tamsulosin (10-10 M-100 μM; 24 h) exhibits no cytotoxicity against AZ-AhR, AZ-GR or LS174T cell lines even at concentrations as high as 100 μM; it shows only weak AhR inhibitory activity in AZ-AhR cells at the concentration of 100 μM[1].
(Rac)-Tamsulosin (10-10 M-100 μM; 24 h) acts as a weak agonist of PXR in transiently transfected LS174T cells, exerting significant activation at a concentration of 100 μM, but it is not a potent PXR antagonist[1].
(Rac)-Tamsulosin acts as a noncompetitive inhibitor of CYP3A4-mediated testosterone 6β-hydroxylation in human liver microsomes, with a Ki value of 6.75 μM; its potency is weaker than that of the R-enantiomer but stronger than that of the S-enantiomer[2].
(Rac)-Tamsulosin weakly inhibits CYP3A4-mediated midazolam 10-hydroxylation in human liver microsomes, with an IC50 greater than 100 μM[2].
(Rac)-Tamsulosin binds to α1-adrenergic receptors labeled with 3H-prazosin in rat brain cell membranes, with a pKi value of 9.78, and shows 8100-fold higher selectivity for α1-adrenergic receptors over α2-adrenergic receptors. It also binds to labeled α2-adrenergic receptors, with a pKi value of 5.87[3].
(Rac)-Tamsulosin ((±)-YM-12617) acts as a competitive antagonist of Phenylephrine (HY-B0769)-induced contraction mediated by post-junctional α1-adrenergic receptors in isolated rabbit thoracic aorta, with a pA2 value of 9.88. It shows 8300-fold higher selectivity for α1-adrenergic receptors over α2-adrenergic receptors. It also functions as a competitive antagonist of UK-14304 (HY-B0659)-induced pre-synaptic α2-adrenergic receptors in electrically stimulated longitudinal muscle of guinea pig ileum, with a pA2 value of 5.96[3].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:AZ-AhR (human hepatoma HepG2-derived), AZ-GR (human cervix carcinoma HeLa-derived), LS174T human colon adenocarcinoma
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Concentration:10−10 M, 10−9 M, 10−8 M, 10−7 M, 10−6 M, 10−5 M, 10−4 M
100 μM (with receptor activators) -
Incubation Time:24 h
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Result:Exhibited no cytotoxicity in any of the cell lines tested at concentrations up to 100 μM.
Showed no significantly different cytotoxicity when combined with receptor activators compared to its cytotoxicity alone.
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Cell Line:LS174T human colon adenocarcinoma
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Concentration:100 μM
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Incubation Time:24 h
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Result:Did not significantly induce CYP3A4 mRNA expression, unlike rifampicin (10 μM) which caused an ~81-fold induction.
In Vivo
(Rac)-Tamsulosin (i.v.) dose-dependently reduces blood pressure in anesthetized normotensive rats, with an intravenous ED20 value of 1.75 μg/kg corresponding to a 20% decrease in mean blood pressure[3].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Chemical Information
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CAS No. 94666-07-6
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Appearance Solid
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Molecular Weight 408.51
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Formula C20H28N2O5S
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SMILES
O=S(N)(C1=CC(CC(C)NCCOC2=C(OCC)C=CC=C2)=CC=C1OC)=O
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Synonyms
YM12617 free base; (Rac)-LY253351 free base
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Powder -20°C 3 years In solvent -80°C 6 months -20°C 1 month
Purity & Documentation
References
[1]. Novotna A, et al. Profiling of enantiopure drugs towards aryl hydrocarbon (AhR), glucocorticoid (GR) and pregnane X (PXR) receptors in human reporter cell lines. Chemico-biological interactions. 2014 Feb 05;208:64-76. [Content Brief]
[2]. Krasulova K, et al. Enantiospecific effects of chiral drugs on cytochrome P450 inhibition in vitro. Xenobiotica; the fate of foreign compounds in biological systems. 2016;46(4):315-24. [Content Brief]
[3]. Honda K, et al. Further studies on (+/-)-YM-12617, a potent and selective alpha 1-adrenoceptor antagonist and its individual optical enantiomers. Naunyn-Schmiedeberg's archives of pharmacology. 1987 Sep;336(3):295-302. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
(Rac)-Tamsulosin Related Classifications
HY-B0661D Related Classifications
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