Piperazine, 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-[(tetrahydro-2-furanyl)carbonyl]-, (S)-

Modify Date: 2023-02-19 17:23:18

Piperazine, 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-[(tetrahydro-2-furanyl)carbonyl]-, (S)- Structure
Piperazine, 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-[(tetrahydro-2-furanyl)carbonyl]-, (S)- structure
Common Name Piperazine, 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-[(tetrahydro-2-furanyl)carbonyl]-, (S)-
CAS Number 109351-33-9 Molecular Weight 387.43300
Density N/A Boiling Point N/A
Molecular Formula C19H25N5O4 Melting Point N/A
MSDS N/A Flash Point N/A

 Use of Piperazine, 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-[(tetrahydro-2-furanyl)carbonyl]-, (S)-


(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].

 Names

Name (S)-Terazosin
Synonym More Synonyms

  Biological Activity

Description (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].
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Target

Ki: 3.91 nM (α1a-adrenoceptor), 0.79 nM (α1b-adrenoceptor) and 1.16 nM (α1d-adrenoceptor); 729 nM (α2a-adrenoceptor), 3.5 nM (α2Ba-adrenoceptor) and 46.4 nM (α2c-adrenoceptor)[1]

In Vitro 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].
In Vivo (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].
References

[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.

 Chemical & Physical Properties

Molecular Formula C19H25N5O4
Molecular Weight 387.43300
Exact Mass 387.19100
PSA 103.04000
LogP 1.64090

 Synonyms

(-)-(S)-terazosin
S(-)-terazosin
S(-)-2-[4-[(tetrahydro-2-furanyl)carbonyl]-1-piperazinyl]-6,7-dimethoxy-4-quinazolinamine
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