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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.
Physicochemical Properties
| Molecular Formula | C13H20N2O2 | |
| Molecular Weight | 236.31 | |
| Exact Mass | 236.152 | |
| 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 | |
| PubChem CID | 65859 | |
| Appearance | White to off-white solid powder | |
| Density | 1.2±0.1 g/cm3 | |
| Boiling Point | 412.7±34.0 °C at 760 mmHg | |
| Melting Point | 102-106ºC | |
| Flash Point | 220.9±24.3 °C | |
| Vapour Pressure | 0.0±1.0 mmHg at 25°C | |
| Index of Refraction | 1.577 | |
| LogP | 0.46 | |
| Hydrogen Bond Donor Count | 2 | |
| Hydrogen Bond Acceptor Count | 4 | |
| Rotatable Bond Count | 4 | |
| Heavy Atom Count | 17 | |
| Complexity | 212 | |
| Defined Atom Stereocenter Count | 1 | |
| SMILES | O([H])[C@]([H])(C([H])([H])O[H])C([H])([H])N1C([H])([H])C([H])([H])N(C2C([H])=C([H])C([H])=C([H])C=2[H])C([H])([H])C1([H])[H] |
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| 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 | |
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| 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 |
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| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | Histamine receptor | ||
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| 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. |
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| Additional Infomation |
Levodropropizine is a member of the class of N-arylpiperazines that is N-phenylpiperazine in which the amino hydrogen is replaced by a 2,3-dihydroxypropyl group (the S-enantiomer). A peripherally acting antitussive drug that is used as an alternative to opioids. It has a role as an antitussive. It is a N-alkylpiperazine, a N-arylpiperazine and a secondary alcohol. Levodropropizine is under investigation in clinical trial NCT01573663 (A Drug-Drug Interaction Study of Ambroxol and Levodropropizine). |
Solubility Data
| Solubility (In Vitro) |
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| 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. 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 |