Levodropropizine (DF-526)

Alias:
Cat No.:V1225 Purity: ≥98%
Levodropropizine [(S)-(-)-Dropropizine; DF 526; DF-526; DF526; Levotuss], the S-isomer of dropropizine, is a histamine receptor inhibitor used as a cough suppressant.
Levodropropizine (DF-526) Chemical Structure CAS No.: 99291-25-5
Product category: Histamine 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
25g
Other Sizes

Other Forms of Levodropropizine (DF-526):

  • Dropropizine
Official Supplier of:
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Levodropropizine [(S)-(-)-Dropropizine; DF 526; DF-526; DF526; Levotuss], the S-isomer of dropropizine, is a histamine receptor inhibitor used as a cough suppressant. It inhibits the histamine receptor and has anti-allergic properties, which lessen coughing.

Biological Activity I Assay Protocols (From Reference)
Targets
Histamine receptor
ln Vitro

In vitro activity: Levodropropizine binds to alpha-adrenergic and H1-histaminic receptors with affinity.

ln Vivo
Levodropropizine does not cause physical dependence in rats and has less potent central sedative effects than racemate. Levodropropizine (15 mg/kg, intraperitoneally) decreases the length of apnea as well as the C-fiber'sreactionto phenylbiguanide. In pulmonary fibers, LVDP-induced suppression of the C-fibre response to PBG averages 50%, whereas in non-pulmonary fibers, it is 25%. Anaesthetized guinea pigs and rabbits demonstrate good antitussive activity when levodropropizine is administered. When it comes to inducing coughing in rabbits and guinea pigs, levodropropizine (i.v.) is similar to dropropizine and 1/10 to 1/20 as active as codeine. Orally administered levodropropizine has similar effects to dropropizine and codeine in terms of preventing coughing brought on by irritant aerosols. When electrically induced cough is given to guinea pigs, codeine (5 μg/50 μl i.c.v.) significantly reduces coughing, but levodropropizine (40 μg/50 μL i.c.v.) does not. A peripheral site of action associated with sensory neuropeptides is observed with levodropropizine. In the rat trachea, levodropropizine (10 mg/kg, 50 mg/kg, and 200 mg/kg) decreases the extravasation of Evans blue dye triggered by capsaicin in a dose-dependent manner. Levodropropizine (200 mg/kg) also prevents extravasation triggered by substance P, but it has no effect on extravasation triggered by platelet activating factor.
Animal Protocol
15 mg/kg, 10 mg/kg, 50 mg/kg and 200 mg/kg; i.v.
Rats
References

[1]. Levodropropizine for treating cough in adult and children: a meta-analysis of published studies. Multidiscip Respir Med. 2015 May 31;10(1):19.

[2]. Effects of four antitussives on airway neurogenic inflammation in a guinea pig model of chronic cough induced by cigarette smoke exposure. Inflamm Res. 2013 Dec;62(12):1053-61.

[3]. Levodropropizine suppresses seizure activity in rats with pentylenetetrazol-induced epilepsy. Epilepsy Res. 2019 Feb;150:32-37.

[4]. Levodropropizine reduces capsaicin- and substance P-induced plasma extravasation in the rat trachea. Eur J Pharmacol. 1993 Oct 12;243(1):1-6.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C13H20N2O2
Molecular Weight
236.31
Exact Mass
236.15
Elemental Analysis
C, 66.07; H, 8.53; N, 11.85; O, 13.54
CAS #
99291-25-5
Related CAS #
Dropropizine; 17692-31-8; Levodropropizine-d8
Appearance
Solid powder
SMILES
C1CN(CCN1C[C@@H](CO)O)C2=CC=CC=C2
InChi Key
PTVWPYVOOKLBCG-ZDUSSCGKSA-N
InChi Code
InChI=1S/C13H20N2O2/c16-11-13(17)10-14-6-8-15(9-7-14)12-4-2-1-3-5-12/h1-5,13,16-17H,6-11H2/t13-/m0/s1
Chemical Name
(2S)-3-(4-phenylpiperazin-1-yl)propane-1,2-diol
Synonyms

(S)-(-)-Dropropizine; DF-526; Levodropropizine; DF 526; DF526; Levotuss

HS Tariff Code
2934.99.03.00
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 Data
Solubility (In Vitro)
DMSO: ~47 mg/mL (~198.9 mM)
Water: ~15 mg/mL (~63.5 mM)
Ethanol: ~47 mg/mL (~198.9 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (10.58 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 (10.58 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 (10.58 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.


Solubility in Formulation 4: 50 mg/mL (211.59 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.2317 mL 21.1586 mL 42.3173 mL
5 mM 0.8463 mL 4.2317 mL 8.4635 mL
10 mM 0.4232 mL 2.1159 mL 4.2317 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

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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?
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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:
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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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
NCT01573663 Completed Drug: Ambroxol
Drug: Levodropropizine
Healthy Hanmi Pharmaceutical
Company Limited
February 2012 Phase 1
NCT01416480 Completed Drug: Theobromine 300mg
Drug: Levodropropizine 10mg
Acute Bronchitis Ahn-Gook Pharmaceuticals Co.,Ltd May 2010 Phase 3
Biological Data
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