| Size | Price | Stock | Qty |
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| Targets |
α1-adrenoceptor
(R)-Terazosin targets α1-adrenoceptors, specifically the α1a, α1b, and α1d subtypes. It acts as a potent antagonist, with Ki values of 6.51 nM for α1a, 1.01 nM for α1b, and 1.97 nM for α1d. It has significantly lower affinity for α2-adrenoceptors. By blocking α1-adrenoceptors, it causes vasodilation, leading to a decrease in blood pressure, which is its primary therapeutic mechanism. |
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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].
In vitro, (R)-Terazosin is a potent antagonist of α1a, α1b, and α1d-adrenoceptors with Ki values of 6.51 nM, 1.01 nM, and 1.97 nM, respectively. It shows low affinity for α2a, α2b, and α2c adrenoceptors with Ki values of 3.85 μM, 0.33 μM, and 0.37 μM, respectively. Its activity is characterized by its ability to block α1-mediated vasoconstriction, making it a valuable tool for studying α1-adrenoceptor function. |
| 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].
In vivo, (R)-Terazosin is an α1-adrenoceptor antagonist used for its antihypertensive effects. As the active R-enantiomer of Terazosin, it is responsible for the therapeutic activity of the racemic mixture. By blocking α1-adrenoceptors in vascular smooth muscle, it causes vasodilation and lowers blood pressure. It is used clinically for the treatment of hypertension and benign prostatic hyperplasia. |
| 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].
In vitro receptor binding assays for (R)-Terazosin involve measuring its affinity for α1-adrenoceptor subtypes. Radioligand binding studies using ³H-prazosin are performed on membranes from cells expressing α1a, α1b, or α1d receptors. The compound is incubated with increasing concentrations, and Ki values of 6.51 nM, 1.01 nM, and 1.97 nM are determined. Selectivity is confirmed by testing against α2-adrenoceptors. |
| Cell Assay |
For in vitro cell-based assays, cells expressing α1-adrenoceptors are cultured and treated with (R)-Terazosin. Its antagonism is confirmed by its ability to block agonist (e.g., phenylephrine)-induced calcium signaling or contraction in vascular smooth muscle cells. Its effects on cell viability are measured using MTT assays. Its vasodilating properties can be assessed in isolated vascular ring preparations.
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| Animal Protocol |
In vivo animal studies with (R)-Terazosin are conducted in models of hypertension. The compound is administered orally or intravenously to hypertensive rats, and blood pressure is measured. Its effects on vascular resistance and heart rate are monitored. Its efficacy in treating benign prostatic hyperplasia is assessed in animal models of prostate enlargement.
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| ADME/Pharmacokinetics |
(R)-Terazosin (CAS: 109351-34-0) has a molecular weight of 387.43 g/mol and a molecular formula of C19H25N5O4. It is an active R-enantiomer of Terazosin and a potent α1-adrenoceptor antagonist. It is a solid and is typically stored as a powder. It is soluble in DMSO. It is an approved drug for the treatment of hypertension and benign prostatic hyperplasia.
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| Toxicity/Toxicokinetics |
(R)-Terazosin is an approved drug with an established safety profile. Common side effects include dizziness, headache, and fatigue, which are related to its vasodilating effects. It can cause postural hypotension, especially upon initiation of therapy. It is contraindicated in patients with a history of hypersensitivity to terazosin. It is a clinically used antihypertensive agent.
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| References | |
| Additional Infomation |
(R)-Terazosin is the active R-enantiomer of Terazosin and a potent antagonist of α1a, α1b, and α1d-adrenoceptors. It is used for the treatment of hypertension and benign prostatic hyperplasia. It is an approved drug in many countries.
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| 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
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| Heavy Atom Count |
28
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| Complexity |
544
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| 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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