| Size | Price | |
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| 500mg | ||
| 1g | ||
| Other Sizes |
Oxprenolol (Ba-39089) is a novel and potent beta blocker with intrinsic sympathomimetic activity. It can be used for the treatment of angina pectoris, abnormal heart rhythms, and high blood pressure. It inhibits β-adrenergic receptor (β-AR) with a Ki of 7.10 nM in a radioligand binding assay using rat heart muscle.
| Targets |
β-adrenoceptor ( Ki = 7.1 nM )
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|---|---|
| ln Vitro |
Oxprenolol is lipophilic[3]. The permeability rate constant of oxiprenolol across human abdominal skin is 1.54 ± 1.54×10-3 cm/h [3].
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| ln Vivo |
Peak plasma drug levels within the normal therapeutic range are produced along with effective beta-blockade when oxiprenolol (200 mg/kg/day; po; daily for 3 weeks) is administered[2].
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| Enzyme Assay |
Binding characteristics of the beta-blockers and beta-agonists with the beta-adrenoceptors were investigated in 3H-dihydroalprenolol (3H-DHA) binding to rat heart membranes treated with neuraminidase. When 60% of the total sialic acid content in the membranes was removed, reproducibility of the binding assay became much better than was attainable without neuraminidase treatment, and the maximum density of beta-adrenoceptors was increased. These data suggest that the binding of the test compounds with the beta-adrenergic receptors in cardiac muscle was under the influence of the sialic acid of the glycocalyx of the membrane. The 3H-DHA binding sites in membranes treated with neuraminidase showed a strict stereo-specificity when tested with propranolol. The ranking order of inhibition of beta-antagonists or agonists is: dl-propranolol > Oxprenolol > than alprenolol > pindolol > YM-09538 > labetalol > acebutolol > atenolol > metoprolol > sotalol > butoxamine > practolol as antagonists or l-isoproterenol > l-epinephrine > l-norepinephrine as agonists. A good correlation (r = 0.91, P less than 0.001) was observed between the Ki values observed by the present binding assay and the pA2 observed in the guinea-pig atria relative to the positive inotropic effect by Bieth et al. (Br. J. Pharmacol. 68, 563-569, 1980), indicating that the present method will be useful for screening new beta-adrenergic receptor antagonists or agonists. [1]
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| Animal Protocol |
Animal/Disease Models: Male rats (230 to 300 g body wt) of the Wistar strain[2]
Doses: 200 mg/kg Route of Administration: Administered po (oral gavage) daily for 3 weeks Experimental Results: This dosage produced effective beta-blockade. |
| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
Oral bioavailability is 20-70%. Metabolism / Metabolites Hepatic. Oxoprenolol has known human metabolites that include Oxprenolol glucuronide. Biological Half-Life 1-2 hours |
| Toxicity/Toxicokinetics |
4631 human TDLo oral 50 mg/kg CARDIAC: PULSE RATE; CARDIAC: OTHER CHANGES; LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES British Medical Journal., 1(776), 1977
4631 mouse LD50 oral 375 mg/kg United States Patent Document., #5326774 4631 mouse LD50 intraperitoneal 170 mg/kg LUNGS, THORAX, OR RESPIRATION: DYSPNEA Polish Journal of Pharmacology and Pharmacy., 25(145), 1973 4631 mouse LD50 intravenous 20 mg/kg United States Patent Document., #5326774 71172 women LDLo oral 90 mg/kg BEHAVIORAL: GENERAL ANESTHETIC; CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION); LUNGS, THORAX, OR RESPIRATION: CYANOSIS British Medical Journal., 1(552), 1977 71172 rat LD50 oral 214 mg/kg Arzneimittel-Forschung. Drug Research., 35(1236), 1985 [PMID:2866775] 71172 rat LD50 intraperitoneal 147 mg/kg BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Kiso to Rinsho. Clinical Report., 7(3131), 1973 71172 rat LD50 subcutaneous 940 mg/kg BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD; BEHAVIORAL: ATAXIA; LUNGS, THORAX, OR RESPIRATION: DYSPNEA Arzneimittel-Forschung. Drug Research., 18(164), 1968 [PMID:5695373] 71172 rat LD50 intravenous 33 mg/kg BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD; BEHAVIORAL: ATAXIA; LUNGS, THORAX, OR RESPIRATION: DYSPNEA Arzneimittel-Forschung. Drug Research., 18(164), 1968 [PMID:5695373] |
| References |
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| Additional Infomation |
1-(propan-2-ylamino)-3-(2-prop-2-enoxyphenoxy)-2-propanol is an aromatic ether.
A beta-adrenergic antagonist used in the treatment of hypertension, angina pectoris, arrhythmias, and anxiety. Oxprenolol is a lipophilic, nonselective beta-adrenergic receptor antagonist with anti-arrhythmic, anti-anginal and antihypertensive activities. Oxprenolol competitively binds to and blocks beta-1 adrenergic receptors in the heart, thereby decreasing cardiac contractility and rate. This leads to a reduction in cardiac output and lowers blood pressure. In addition, oxprenolol prevents the release of renin, a hormone secreted by the kidneys that causes constriction of blood vessels. A beta-adrenergic antagonist used in the treatment of hypertension, angina pectoris, arrhythmias, and anxiety. Drug Indication Used in the treatment of hypertension, angina pectoris, arrhythmias, and anxiety. Mechanism of Action Like other beta-adrenergic antagonists, oxprenolol competes with adrenergic neurotransmitters such as catecholamines for binding at sympathetic receptor sites. Like propranolol and timolol, oxprenolol binds at beta(1)-adrenergic receptors in the heart and vascular smooth muscle, inhibiting the effects of the catecholamines epinephrine and norepinephrine and decreasing heart rate, cardiac output, and systolic and diastolic blood pressure. It also blocks beta-2 adrenergic receptors located in bronchiole smooth muscle, causing vasoconstriction. By binding beta-2 receptors in the juxtaglomerular apparatus, oxprenolol inhibits the production of renin, thereby inhibiting angiotensin II and aldosterone production. Oxprenolol therefore inhibits the vasoconstriction and water retention due to angiotensin II and aldosterone, respectively. Pharmacodynamics Oxprenolol is a non-selective beta blocker with some intrinsic sympathomimetic activity. Oxprenolol is a lipophilic molecule and hence, it is able to cross the blood-brain barrier. As such, it is associated with a higher incidence of CNS-related side effects than hydrophilic ligands such as atenolol, sotalol and nadolol. Oxprenolol is an potent beta-blocker and should not be administered to asthmatics because it can cause irreversible airway failure and inflammation. Oxprenolol is a lipophilic, nonselective beta-adrenergic receptor antagonist with anti-arrhythmic, anti-anginal and antihypertensive activities. Oxprenolol competitively binds to and blocks beta-1 adrenergic receptors in the heart, thereby decreasing cardiac contractility and rate. This leads to a reduction in cardiac output and lowers blood pressure. In addition, oxprenolol prevents the release of renin, a hormone secreted by the kidneys that causes constriction of blood vessels. A beta-adrenergic antagonist used in the treatment of hypertension, angina pectoris, arrhythmias, and anxiety. In the present study, as a continuation of a previous one in which two β-blockers celiprolol and bisoprolol were reported (Modamio et al., 1998), transdermal permeation properties across human skin in vitro of propranolol, Oxprenolol, metoprolol and atenolol were compared (including also both celiprolol and bisoprolol), and the potential of each individual drug studied assessed. In addition, correlations between physicochemical parameters of β-blockers chosen, were established, especially lipophilicity expressed as intrinsic partition coefficient, in order to determine whether optimal permeability, and so the predictive potential of these physicochemical parameters can be established. [3] |
| Molecular Formula |
C15H23NO3
|
|---|---|
| Molecular Weight |
265.34802
|
| Exact Mass |
265.168
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| Elemental Analysis |
C, 67.90; H, 8.74; N, 5.28; O, 18.09
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| CAS # |
6452-71-7
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| Related CAS # |
Oxprenolol hydrochloride;6452-73-9;Oxprenolol-d7;1189805-10-4
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| PubChem CID |
4631
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.0479 (rough estimate)
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| Boiling Point |
408.57°C (rough estimate)
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| Melting Point |
78-80°
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| Index of Refraction |
1.5000 (estimate)
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| LogP |
2.38
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| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
4
|
| Rotatable Bond Count |
9
|
| Heavy Atom Count |
19
|
| Complexity |
246
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
C=CCOC1=CC=CC=C1OCC(CNC(C)C)O
|
| InChi Key |
CEMAWMOMDPGJMB-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C15H23NO3/c1-4-9-18-14-7-5-6-8-15(14)19-11-13(17)10-16-12(2)3/h4-8,12-13,16-17H,1,9-11H2,2-3H3
|
| Chemical Name |
1-(propan-2-ylamino)-3-(2-prop-2-enoxyphenoxy)propan-2-ol
|
| Synonyms |
oxprenolol; 6452-71-7; dl-Oxprenolol; Coretal; (+-)-Oxprenolol; Osprenololo [DCIT]; Oxprenololum; Oxprenololum [INN-Latin];
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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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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|---|---|
| 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 | 3.7686 mL | 18.8430 mL | 37.6861 mL | |
| 5 mM | 0.7537 mL | 3.7686 mL | 7.5372 mL | |
| 10 mM | 0.3769 mL | 1.8843 mL | 3.7686 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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