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(R)-Terazosin is the R-enantiomer of Terazosin, which is a selective α1-adrenoceptor antagonist approved for use in treatment of symptoms of BPH (benign prostatic hyperplasia, an enlarged prostate).
| Targets |
α1-adrenoceptor
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|---|---|
| ln Vitro |
(R)-Terazosin has a low affinity with Ki values of 3.85 μM, 0.33 μM, and 0.37 μM for the α2a, α2B, and α2c adrenoceptors, respectively[1]. Understanding the functional role of adrenoceptor subtypes in different tissues may be facilitated by the use of (R)-terazosin as a probe. It might be able to distinguish between pharmacological effects mediated by distinct subtypes of α2-adrenoceptors in animal investigations using (R)-Terazosin, as it is a weaker antagonist at α2B sites than its enantiomer[1].
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| ln Vivo |
(R)-Terazosin exhibits antagonistic effects on the α1A and α2A receptors in the rat vas deferens, with pA2 values of 7.5 and 5.31, respectively[1].
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| Enzyme Assay |
Terazosin and its enantiomers, antagonists of alpha 1-adrenoceptors, were studied in radioligand binding and functional assays to determine relative potencies at subtypes of alpha 1- and alpha 2-adrenoceptors in vitro. The racemic compound and its enantiomers showed high and apparently equal affinity for subtypes of alpha 1-adrenoceptors with Kl values in the low nanomolar range, and showed potent antagonism of alpha 1-adrenoceptors in isolated tissues, with the enantiomers approximately equipotent to the racemate at each alpha 1-adrenoceptor subtype. At alpha 2b sites, R(+) terazosin bound less potently than either the S(-) enantiomer or racemate. R(+) terazosin was also less potent than the S(-) enantiomer or the racemate at rat atrial alpha 2B receptors. These agents were not significantly different in their potencies at alpha 2a or alpha 2A sites. Since the high affinity for alpha 2B sites of quinazoline-type alpha-adrenoceptor antagonists has been used to differentiate alpha 2-adrenoceptor subtypes, the low affinity of R(+) terazosin for these sites was unexpected. Because terazosin or its enantiomers are approximately equipotent at alpha 1-adrenoceptor subtypes, the lower potency of R(+) terazosin at alpha 2B receptors indicates a somewhat greater selectivity for alpha 1-compared to alpha 2B adrenoceptor subtypes. The possible pharmacological significance of this observation is discussed[1].
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| References |
| Molecular Formula |
C19H25N5O4
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|---|---|
| Molecular Weight |
387.4329
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| Exact Mass |
387.191
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| CAS # |
109351-34-0
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| Related CAS # |
Terazosin hydrochloride dihydrate;70024-40-7;(S)-Terazosin;109351-33-9;Terazosin;63590-64-7;Terazosin hydrochloride;63074-08-8
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| PubChem CID |
1398859
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| Appearance |
White to off-white solid powder
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| LogP |
1.64
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
4
|
| Heavy Atom Count |
28
|
| Complexity |
544
|
| Defined Atom Stereocenter Count |
1
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| SMILES |
COC1=C(C=C2C(=C1)C(=NC(=N2)N3CCN(CC3)C(=O)[C@H]4CCCO4)N)OC
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| InChi Key |
VCKUSRYTPJJLNI-CQSZACIVSA-N
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| InChi Code |
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-/m1/s1
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| Chemical Name |
[4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl]-[(2R)-oxolan-2-yl]methanone
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| Synonyms |
(R)-Terazosin; 109351-34-0; [4-(4-Amino-6,7-Dimethoxyquinazolin-2-Yl)piperazin-1-Yl][(2r)-Tetrahydrofuran-2-Yl]methanone; [4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl]-[(2R)-oxolan-2-yl]methanone; (R)-(4-(4-AMINO-6,7-DIMETHOXYQUINAZOLIN-2-YL)PIPERAZIN-1-YL)(TETRAHYDROFURAN-2-YL)METHANONE; TZN; Tocris-1506; 4o3f;
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~75 mg/mL (~193.58 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 7.5 mg/mL (19.36 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 75.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 7.5 mg/mL (19.36 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 75.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 7.5 mg/mL (19.36 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.5811 mL | 12.9056 mL | 25.8111 mL | |
| 5 mM | 0.5162 mL | 2.5811 mL | 5.1622 mL | |
| 10 mM | 0.2581 mL | 1.2906 mL | 2.5811 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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