| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| 25mg | |||
| Other Sizes |
| Targets |
beta1- and beta2-Adrenergic Receptors. 4-Hydroxypropranolol acts as a non-selective competitive antagonist of beta1- and beta2-adrenergic receptors. It blocks the effects of endogenous catecholamines (epinephrine, norepinephrine) at these receptors, leading to decreased heart rate, reduced cardiac output, lowered blood pressure, and bronchodilation. This metabolite also exhibits antioxidant properties at micromolar concentrations.
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| ln Vitro |
4-Hydroxypropranolol blocks beta1-adrenergic receptors with a pA2 value of 8.24, indicating potency comparable to propranolol. It is approximately equipotent to the parent drug in inhibiting isoprenaline-induced tachycardia and vasodilation. It also possesses membrane-stabilizing (local anesthetic) activity and reduces platelet aggregation in vitro at therapeutic concentrations.
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| ln Vivo |
In vivo, 4-hydroxypropranolol exhibits beta-blocking properties similar to propranolol in animal models. Intravenous administration antagonizes isoprenaline-induced increases in heart rate and blood pressure in rats and dogs with an ED50 of approximately 0.1-0.5 mg/kg. The metabolite contributes to the overall pharmacological effect of propranolol in humans, particularly after chronic oral dosing.
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| Enzyme Assay |
Radioligand binding assays are performed using membrane preparations from CHO cells expressing human beta1- or beta2-adrenergic receptors. Membranes (20-50 microg protein) are incubated with [3H]-CGP-12177 as the radioligand and varying concentrations of 4-hydroxypropranolol in 50 mM Tris-HCl buffer (pH 7.4) for 60 minutes at 25degC. Nonspecific binding is determined with 10 microM propranolol. Bound and free radioligands are separated by filtration through GF/B filters, and bound radioactivity is measured by liquid scintillation counting. IC50 values are converted to Ki using the Cheng-Prusoff equation.
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| Cell Assay |
Isolated rat thoracic aorta rings (3-4 mm) are mounted in organ baths containing Krebs-Henseleit buffer (pH 7.4) at 37degC, bubbled with 95% O2/5% CO2. Rings are pre-contracted with 10-⁶ M phenylephrine to achieve stable tone, then cumulative concentration-response curves to isoprenaline (10-⁹ to 10-⁵ M) are generated in the absence or presence of 4-hydroxypropranolol (10-⁹ to 10-⁶ M, 30 min pre-incubation). Relaxation responses are recorded isometrically, and pA2 values are calculated by Schild plot analysis of the rightward shift in isoprenaline concentration-response curves.
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| Animal Protocol |
Male Sprague-Dawley rats (250-300 g) are anesthetized with urethane (1.2 g/kg i.p.). The femoral artery is cannulated for mean arterial blood pressure (MAP) and heart rate (HR) measurement, and the femoral vein is cannulated for drug administration. Isoprenaline (0.5 microg/kg i.v.) is administered as a bolus to induce tachycardia. After baseline responses are established, 4-hydroxypropranolol is administered intravenously (0.03-1 mg/kg), and the inhibition of isoprenaline-induced tachycardia is recorded. The ED50 for beta-blockade is determined from dose-response curves.
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| ADME/Pharmacokinetics |
4-Hydroxypropranolol is an active metabolite with high hepatic extraction. In humans, the plasma concentration of this metabolite is approximately 10-30% of the parent drug after oral propranolol administration. It has an elimination half-life of 2-4 hours, shorter than propranolol (4-6 hours). Due to significant first-pass metabolism, propranolol has an oral bioavailability of ~25%, and approximately 60% of an oral dose is recovered in urine as metabolites including 4-hydroxypropranolol.
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| Toxicity/Toxicokinetics |
4-Hydroxypropranolol exhibits a safety profile comparable to propranolol. As a non-selective beta-blocker, it may cause bradycardia, hypotension, bronchospasm (contraindicated in asthma), and central nervous system effects including fatigue and depression. This compound is a research standard and not intended for human therapeutic use, so human toxicity data are limited to its role as a metabolite.
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| References |
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| Additional Infomation |
Propranolol was the first clinically useful beta-adrenoceptor antagonist and was approved by the FDA in 1967. 4-Hydroxypropranolol is primarily used in research as an analytical reference standard for drug metabolism studies, bioequivalence testing, and investigations of propranolol's pharmacokinetics. The compound is also valuable for studying the role of CYP2D6 polymorphisms in propranolol disposition and response.
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| Molecular Formula |
C16H21NO3.HCL
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|---|---|
| Molecular Weight |
311.80378
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| Exact Mass |
311.128
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| CAS # |
14133-90-5
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| Related CAS # |
4-Hydroxypropranolol-d7 hydrochloride;1219804-03-1;4-Hydroxypropranolol-d7;1219908-86-7
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| PubChem CID |
3014810
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.168g/cm3
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| Boiling Point |
487.5ºC at 760mmHg
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| Melting Point |
156-158ºC
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| Flash Point |
248.6ºC
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| LogP |
3.476
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
21
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| Complexity |
285
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| Defined Atom Stereocenter Count |
0
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| SMILES |
Cl.CC(NCC(COC1=CC=C(O)C2=CC=CC=C12)O)C
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| InChi Key |
ROUJENUXWIFONU-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C16H21NO3.ClH/c1-11(2)17-9-12(18)10-20-16-8-7-15(19)13-5-3-4-6-14(13)16;/h3-8,11-12,17-19H,9-10H2,1-2H3;1H
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| Chemical Name |
4-[2-hydroxy-3-(propan-2-ylamino)propoxy]naphthalen-1-ol;hydrochloride
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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 | 3.2072 mL | 16.0359 mL | 32.0718 mL | |
| 5 mM | 0.6414 mL | 3.2072 mL | 6.4144 mL | |
| 10 mM | 0.3207 mL | 1.6036 mL | 3.2072 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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