(S)-Terazosin

• CAT Number: M003867
• CAS Number: 109351-33-9
• Molecular Formula: C19H25N5O4
• Molecular Weight: 387.43
• Purity: ≥95%
• Synonyms: [4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl]-[(2S)-oxolan-2-yl]methanone
• InChI: InChI=1S/C19H25N5O4/c1-26-15-10-12-13(11-16(15)27-2)21-19(22-17(12)20)24-7-5-23(6-8-24)18(25)14-4-3-9-28-14/h10-11,14H,3-9H2,1-2H3,(H2,20,21,22)/t14-/m0/s1
• InChIKey: VCKUSRYTPJJLNI-AWEZNQCLSA-N
• SMILES: COC1=C(C=C2C(=C1)C(=NC(=N2)N3CCN(CC3)C(=O)C4CCCO4)N)OC

(S)-Terazosin is an active S-enantiomer of Terazosin. (S)-Terazosin is a potent and high-affinity α-adrenoceptor antagonist with Ki values of 3.91 nM, 0.79 nM and 1.16 nM for α1a, α1b and α1d-adrenoceptor, respectively. (S)-Terazosin also has high-affinity for α2a, α2B and α2c-adrenoceptor with Ki values of 729 nM, 3.5 nM and 46.4 nM, respectively[1].
The racemic compound and its enantiomers show high and apparently equal affinity for subtypes of α1-adrenoceptors with Ki values in the low nanomolar range, and showed potent antagonism of α1-adrenoceptors in isolated tissues, with the enantiomers approximately equipotent to the racemate at each α1-adrenoceptor subtype. At α2b sites, (R)-Terazosin binds less potently than either the (S)-Terazosin or racemate[1].
(S)-Terazosin shows antagonism of at rat atrial α2B receptor with a pEC30 of 6.93. (s)-Terazosin shows antagonism of at rat vas deferens α1A and α2A receptor with pA2 values of 8.3 and 6.12, respectively[1].

Reference

[1]. Hancock AA, et al. Actions of terazosin and its enantiomers at subtypes of alpha 1- and alpha 2-adrenoceptors in vitro. J Recept Signal Transduct Res. 1995 Sep-Dec;15(7-8):863-85.
 [Content Brief]