| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
|
||
| 10mg |
|
||
| 25mg |
|
||
| 50mg |
|
||
| 100mg | |||
| Other Sizes |
| Targets |
α1a-adrenoceptor ( Ki = 3.91 nM ); α1b-adrenoceptor ( Ki = 0.79 nM ); α1d-adrenoceptor ( Ki = 1.16 nM ); α2a-adrenoceptor ( Ki = 729 nM ); α2Ba-adrenoceptor ( Ki = 3.5 nM ); α2c-adrenoceptor ( Ki = 46.4 nM )
(S)-Terazosin targets α₁-adrenergic receptors, which are G protein-coupled receptors expressed in the peripheral vasculature and the prostate. By blocking these receptors, (S)-Terazosin inhibits the vasoconstrictive effects of norepinephrine, leading to vasodilation and a reduction in peripheral vascular resistance. In the prostate, blockade of α₁-adrenergic receptors relaxes smooth muscle in the bladder neck and prostate, improving urine flow and reducing symptoms of BPH. The (S)-enantiomer is the active form of terazosin, with higher affinity for the receptor than the (R)-enantiomer. |
|---|---|
| ln Vitro |
The racemic compound and both of its enantiomers exhibit strong and seemingly equal affinity for α1-adrenoceptor subtypes with Ki values in the low nanomolar range. In isolated tissues, the enantiomers also demonstrate potent antagonistic effects on α1-adrenoceptors, with the enantiomers roughly equipotent to the racemate at each subtype. Racemate or (S)-Terazosin binds more potently at α2b sites than (R)-Terazosin[1].
In vitro, (S)-Terazosin has been characterized for its binding affinity and functional activity at α₁-adrenergic receptors. The compound demonstrates high affinity for α₁A, α₁B, and α₁D receptor subtypes, with Ki values in the low nanomolar range. In functional assays, (S)-Terazosin acts as a competitive antagonist, inhibiting norepinephrine-induced contraction of vascular smooth muscle and prostate tissue. The (S)-enantiomer is significantly more potent than the (R)-enantiomer, consistent with its pharmacological activity. |
| ln Vivo |
(S)-Terazosin exhibits antagonistic effects on a rat atrial α2B receptor, sporting a pEC30 of 6.93. (s)-Terazosin exhibits antagonistic effects on the α1A and α2A receptors in the rat vas deferens, with corresponding pA2 values of8.3 and 6.12.[1]
In vivo, (S)-Terazosin has been shown to effectively lower blood pressure in hypertensive patients and improve urinary symptoms in patients with BPH. The compound's antihypertensive effects are mediated by vasodilation and a reduction in peripheral vascular resistance. In patients with BPH, (S)-Terazosin relaxes smooth muscle in the prostate and bladder neck, improving urine flow and reducing obstructive symptoms. The compound's clinical efficacy has been established through numerous clinical trials. |
| 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 (S)-Terazosin are performed using membrane preparations from cells expressing human α₁-adrenergic receptor subtypes. Radiolabeled ligands, such as [³H]-prazosin, are used in competition binding assays. The compound is incubated with the receptor membranes and the radioligand, and the bound radioactivity is measured using a scintillation counter. The Ki values are calculated from the displacement curves. Functional activity is assessed using second messenger assays or tissue contraction assays. |
| Cell Assay |
In vitro cellular experiments for (S)-Terazosin are performed using cell lines expressing α₁-adrenergic receptors. The compound's effects on receptor-mediated signaling pathways are assessed by measuring changes in intracellular calcium levels or cAMP accumulation. The potency and efficacy of (S)-Terazosin as an antagonist are determined from concentration-response curves. These experiments are essential for characterizing the compound's functional activity and selectivity.
|
| Animal Protocol |
In vivo animal studies for (S)-Terazosin are conducted using rodent models. The compound is administered via oral gavage or intravenous injection. Antihypertensive efficacy is assessed by measuring blood pressure using telemetry or tail-cuff methods. The effects on prostate smooth muscle tone are assessed using in vivo urodynamic studies. The compound's safety and tolerability are also assessed by monitoring body weight and clinical signs.
|
| ADME/Pharmacokinetics |
Terazosin is rapidly absorbed following oral administration, with peak plasma concentrations achieved within 1-2 hours. It has a half-life of approximately 9-12 hours, allowing for once-daily dosing. The compound is extensively metabolized in the liver, primarily by cytochrome P450 enzymes, and its metabolites are excreted via the biliary and renal routes. The pharmacokinetic profile of terazosin supports its clinical use in hypertension and BPH.
|
| Toxicity/Toxicokinetics |
The toxicity profile of terazosin has been characterized in preclinical and clinical studies. Common adverse effects include dizziness, headache, and asthenia, which are related to its vasodilatory effects. Postural hypotension and syncope can occur, particularly after the first dose. The compound's safety in humans has been established through its widespread clinical use. Terazosin is generally well-tolerated, with a favorable safety profile.
|
| References | |
| Additional Infomation |
Terazosin is a quinazoline-based α₁-adrenergic receptor antagonist used for the treatment of hypertension and benign prostatic hyperplasia. The (S)-enantiomer is the pharmacologically active component, with higher affinity for the receptor than the (R)-enantiomer. Terazosin's clinical efficacy has been established through numerous clinical trials, and it remains an important therapeutic option for patients with hypertension and BPH. Its safety and tolerability profile supports its continued use in clinical practice.
|
| Molecular Formula |
C19H25N5O4
|
|---|---|
| Molecular Weight |
387.432904005051
|
| Exact Mass |
387.191
|
| CAS # |
109351-33-9
|
| Related CAS # |
Terazosin hydrochloride dihydrate; 70024-40-7; (R)-Terazosin; 109351-34-0; Terazosin; 63590-64-7; Terazosin hydrochloride; 63074-08-8
|
| PubChem CID |
969465
|
| Appearance |
White to off-white solid
|
| LogP |
1.64
|
| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
8
|
| Rotatable Bond Count |
4
|
| Heavy Atom Count |
28
|
| Complexity |
544
|
| Defined Atom Stereocenter Count |
1
|
| SMILES |
O1CCC[C@H]1C(N1CCN(C2N=C(C3C=C(C(=CC=3N=2)OC)OC)N)CC1)=O
|
| InChi Key |
VCKUSRYTPJJLNI-AWEZNQCLSA-N
|
| 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-/m0/s1
|
| Chemical Name |
[4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl]-[(2S)-oxolan-2-yl]methanone
|
| Synonyms |
(S)-Terazosin; (S)-Terazocin; 109351-33-9; [4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl]-[(2S)-oxolan-2-yl]methanone; Piperazine, 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-[(tetrahydro-2-furanyl)carbonyl]-, (S)-; (S)-(4-(4-Amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl)(tetrahydrofuran-2-yl)methanone; NCGC00016903-01; MLS001165675; BIDD:GT0682;
|
| HS Tariff Code |
2934.99.9001
|
| 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)
|
| Solubility (In Vitro) |
DMSO: ~150 mg/mL (~387.2 mM)
|
|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| 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.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT05855577 | Not yet recruiting | Drug: Terazosin | Parkinson Disease Gait Analysis |
I.R.C.C.S. Fondazione Santa Lucia | December 2023 | Phase 4 |
| NCT02046395 | Completed | Drug: amlodipine, hydralazine, terazosin or hydrochlorothiazide |
Type 2 Diabetes Hypertension |
Tulane University School of Medicine |
January 2012 | Phase 4 |
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
