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Labetalol HCl (AH-5158 HCl; Sch-15719W)

Alias: AH-5158 hydrochloride; Sch-15719W; AH5158 hydrochloride; Sch15719W; AH 5158 hydrochloride; Sch 15719W; Normodyne; Trandate; Albetol; Apo-Labetalol; Dilevalol
Cat No.:V1102 Purity: ≥98%
Labetalol HCl (ch15719W; AH5158; Normodyne, Albetol, Trandate, Apo-Labetalol, Dilevalol), the hydrochloride salt of Labetalol, is a competitive and dual antagonist of alpha1-adrenergic and beta-adrenergic receptors with potential antihypertensive properties.
Labetalol HCl (AH-5158 HCl; Sch-15719W)
Labetalol HCl (AH-5158 HCl; Sch-15719W) Chemical Structure CAS No.: 32780-64-6
Product category: Adrenergic Receptor
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1g
2g
5g
10g
Other Sizes

Other Forms of Labetalol HCl (AH-5158 HCl; Sch-15719W):

  • Labetalol-d6 hydrochloride
  • Labetalol (hydrochloride)-d5
  • Labetalol (AH-5158; Sch-15719W)
Official Supplier of:
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Labetalol HCl (ch15719W; AH5158; Normodyne, Albetol, Trandate, Apo-Labetalol, Dilevalol), the hydrochloride salt of Labetalol, is a competitive and dual antagonist of alpha1-adrenergic and beta-adrenergic receptors with potential antihypertensive properties. The medication labetalol was approved to treat hypertension.

Biological Activity I Assay Protocols (From Reference)
Targets
α1-adrenergic receptor; β-adrenergic receptor
Toxicity/Toxicokinetics
Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation
Because of the low levels of labetalol in breastmilk, amounts ingested by the infant are small and would not be expected to cause any adverse effects in fullterm breastfed infants. No special precautions are required in most infants. However, other agents may be preferred while nursing a preterm infant. Labetalol may predispose nursing mothers to Raynaud’s phenomenon of the nipple.
◉ Effects in Breastfed Infants
One investigator reported that no adverse effects occurred in breastfed infants whose mothers were taking labetalol in doses of 330 to 800 mg daily.
A 26-week premature infant weighing 640 grams developed sinus bradycardia (80 to 90 bpm) and isolated atrial premature beats after nasogastric feeding with mother's pumped breastmilk began on day 8 of life. The mother was taking labetalol 300 mg twice daily by mouth for hypertension. Bradycardia and premature beats resolved within 24 hours of substitution of formula for breastmilk. No other causes for bradycardia could be identified. One untimed sample of the mother's breastmilk contained 710 mcg/L of labetalol. Although the authors estimated the infant's dose to be 100 mg/kg daily, a recalculation using their data indicates that the infant's dose was only 100 mcg/kg daily.
A 2-month-old infant was being breastfed exclusively by a mother taking labetalol 100 mg twice daily. The infants electrocardiogram had a regular heart rate, but borderline prolonged QT. The infant was started on propranolol 1 mg/kg daily for infantile hemangioma. One month later, the infant had a normal QT interval. A second infant was exclusively breastfed by a mother taking labetalol 150 mg twice daily and nifedipine 60 mg daily. The infant was started on propranolol 0.6 mg/kg daily for infantile hemangioma. The propranolol dose was increased over 2 weeks to 3.4 mg/kg daily. The infant had some sleeping difficulties with the higher propranolol dose, but no other symptoms.
◉ Effects on Lactation and Breastmilk
Intravenous labetalol can increase serum prolactin in men and non-nursing women, although the increase is greater in women. Oral labetalol does not increase serum prolactin. The maternal prolactin level in a mother with established lactation may not affect her ability to breastfeed.
A woman with a history of symptoms of Raynaud's phenomenon developed Raynaud's phenomenon of the nipples when treated for pregnancy-induced hypertension with labetalol 100 mg twice daily. She breastfed for 5 weeks, but nursing caused pain in her nipples. In a subsequent pregnancy, similar symptoms occurred during treatment with labetalol 100 mg twice daily. Discontinuing labetalol eliminated the nipple pain in both instances.
A pregnant woman was treated on two occasions with intravenous labetalol for pre-eclampsia. On each occasion, she reported a burning sensation of the nipples. While continuing on labetalol, sustained-release nifedipine was added to her regimen and the burning of the nipple did not return.
References

[1]. Expert Opin Drug Saf . 2015 Mar;14(3):453-61.

Additional Infomation
Labetalol hydrochloride is a member of salicylamides.
Labetalol Hydrochloride is the hydrochloride form of labetalol, a third generation selective alpha-1-adrenergic antagonist and non-selective beta-adrenergic antagonist with vasodilatory and antihypertensive properties. Labetalol competitively binds to alpha-1-adrenergic receptors in vascular smooth muscle, thereby inhibiting the adrenergic stimulation of endothelial cell function and vasoconstriction in peripheral blood vessels. This agent also binds to beta-receptors in the bronchial and vascular smooth muscle, resulting in a decrease in adrenergic stimulation. The result is a decrease in resting and exercise heart rates, cardiac output, and in both systolic and diastolic blood pressure, thereby resulting in vasodilation, and negative chronotropic and inotropic cardiac effects.
A salicylamide derivative that is a non-cardioselective blocker of BETA-ADRENERGIC RECEPTORS and ALPHA-1 ADRENERGIC RECEPTORS.
See also: Labetalol (has active moiety); Hydrochlorothiazide; labetalol hydrochloride (component of).
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C19H25CLN2O3
Molecular Weight
364.866404294968
Exact Mass
364.16
Elemental Analysis
C, 62.55; H, 6.91; Cl, 9.72; N, 7.68; O, 13.15
CAS #
32780-64-6
Related CAS #
Labetalol; 36894-69-6; Labetalol hydrochloride (Standard); 32780-64-6
PubChem CID
71412
Appearance
White to off-white crystalline powder
Density
1.2±0.1 g/cm3
Boiling Point
552.7±50.0 °C at 760 mmHg
Melting Point
187-189°
Flash Point
288.1±30.1 °C
Vapour Pressure
0.0±1.6 mmHg at 25°C
Index of Refraction
1.609
LogP
2.31
Hydrogen Bond Donor Count
5
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
8
Heavy Atom Count
25
Complexity
385
Defined Atom Stereocenter Count
0
SMILES
O=C(N)C1=CC(C(O)CNC(C)CCC2=CC=CC=C2)=CC=C1O.[H]Cl
InChi Key
WQVZLXWQESQGIF-UHFFFAOYSA-N
InChi Code
InChI=1S/C19H24N2O3.ClH/c1-13(7-8-14-5-3-2-4-6-14)21-12-18(23)15-9-10-17(22)16(11-15)19(20)24;/h2-6,9-11,13,18,21-23H,7-8,12H2,1H3,(H2,20,24);1H
Chemical Name
2-hydroxy-5-[1-hydroxy-2-(4-phenylbutan-2-ylamino)ethyl]benzamide;hydrochloride
Synonyms
AH-5158 hydrochloride; Sch-15719W; AH5158 hydrochloride; Sch15719W; AH 5158 hydrochloride; Sch 15719W; Normodyne; Trandate; Albetol; Apo-Labetalol; Dilevalol
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

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: ≥ 38 mg/mL (~104.2 mM)
Water: ~8 mg/mL
Ethanol: ~7 mg/mL
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.85 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 25.0 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: ≥ 2.5 mg/mL (6.85 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 25.0 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.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (6.85 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.7407 mL 13.7035 mL 27.4070 mL
5 mM 0.5481 mL 2.7407 mL 5.4814 mL
10 mM 0.2741 mL 1.3704 mL 2.7407 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.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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.

Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT05551104 Recruiting Drug: Oral Nifedipine
Drug: Oral Labetalol
Postpartum Complication
Maternal Hypertension
Loma Linda University December 2023 Not Applicable
NCT04298034 Recruiting Drug: Labetalol, Nifedipine Preeclampsia
Hypertension in Pregnancy
Medical College of Wisconsin July 17, 2020 Phase 3
NCT04755764 Recruiting Drug: Labetalol
Drug: Atenolol
Drug: Nifedipine
Systolic Hypertension
Pregnancy Related
Marshall University March 3, 2021 N/A
NCT05309460 Not yet recruiting Drug: Labetalol Oral Tablet
Drug: NIFEdipine ER
Postpartum Preeclampsia
Hypertension in Pregnancy
Nebraska Methodist Health
System
June 6, 2022 Phase 4
NCT06093893 Not yet recruiting Drug: Dexmedetomidine
Drug: Nicardipine
Hypotensive Anesthesia
Orthognathic Surgery
Boston Medical Center March 2024 Phase 4
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