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Mizolastine (Mizollen; SL 85.0324; Mistalin; SL-850324; SL 850324; Mistamine; Mizolastina) is a histamine H1-receptor antagonist with anti-allergic effects. It has been used to treat hay fever (seasonal allergic rhinitis), hives, and other allergic reactions. It inhibits the histamine H1-receptor with an IC50 of 47 nM. A single daily dose of non-sedating antihistamine is mizolastine. It usually acts quickly and blocks H1 receptors. Just the binding of histamine to receptors is inhibited; mast cell release of histamine is not stopped. Tight lips and throat are possible side effects.
Physicochemical Properties
| Molecular Formula | C24H25FN6O | |
| Molecular Weight | 432.49 | |
| Exact Mass | 432.207 | |
| Elemental Analysis | C, 66.65; H, 5.83; F, 4.39; N, 19.43; O, 3.70 | |
| CAS # | 108612-45-9 | |
| Related CAS # | Mizolastine dihydrochloride;1056596-82-7;Mizolastine-13C,d3 | |
| PubChem CID | 65906 | |
| Appearance | White to off-white solid powder | |
| Density | 1.3±0.1 g/cm3 | |
| Melting Point | 217° | |
| Index of Refraction | 1.682 | |
| LogP | 3.42 | |
| Hydrogen Bond Donor Count | 1 | |
| Hydrogen Bond Acceptor Count | 5 | |
| Rotatable Bond Count | 5 | |
| Heavy Atom Count | 32 | |
| Complexity | 728 | |
| Defined Atom Stereocenter Count | 0 | |
| SMILES | FC1C([H])=C([H])C(=C([H])C=1[H])C([H])([H])N1C2=C([H])C([H])=C([H])C([H])=C2N=C1N1C([H])([H])C([H])([H])C([H])(C([H])([H])C1([H])[H])N(C1=NC([H])=C([H])C(N1[H])=O)C([H])([H])[H] |
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| InChi Key | PVLJETXTTWAYEW-UHFFFAOYSA-N | |
| InChi Code | InChI=1S/C24H25FN6O/c1-29(23-26-13-10-22(32)28-23)19-11-14-30(15-12-19)24-27-20-4-2-3-5-21(20)31(24)16-17-6-8-18(25)9-7-17/h2-10,13,19H,11-12,14-16H2,1H3,(H,26,28,32) | |
| Chemical Name | 2-[[1-[1-[(4-fluorophenyl)methyl]benzimidazol-2-yl]piperidin-4-yl]-methylamino]-1H-pyrimidin-6-one | |
| Synonyms |
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| 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 |
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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 H1 receptor ( IC50 = 47 nM ) |
| ln Vitro |
Mizolastine (1–10,000 nM; 0.5–6 h) inhibits the release of VEGF, KC, and TNF-α in mast cells[1]. Mizolastine (0.1 µM; 4 h) dramatically lowers the expression of KC, TNF-α, VEGF165, and VEGF120 mRNA in mast cells[1]. |
| ln Vivo | Mizolastine (0.3 mg/kg; p.o.; once daily for 7 days) suppresses expression of 5-LOX, cytosolic PLA2 (cPLA2), 5-LOX-activating protein, and LTB4 receptor mRNA. It also inhibits production of the 5-LOX AA (arachidonic acid) metabolite leukotriene B4 (LTB4) in the AA-induced inflammation model[2]. |
| Cell Assay |
Cell Line: Mast cells (from Kunming mice) Concentration: 1-10000 nM Incubation Time: 0.5-6 h Result: Markedly inhibited release of KC, VEGF and TNF-α in a time- and dose- dependent manner. |
| Animal Protocol |
Male Sprague-Dawley rats (specific-pathogen-free; 234-254 g; 7 to 8-week-old; rat paw edema model) 0.3 mg/kg Oral gavage; single daily for 7 days. |
| References |
[1]. The effect of mizolastine on expression of vascular endothelial cell growth factor, tumour necrosis factor-alpha and keratinocyte-derived chemokine in murine mast cells, compared with dexamethasone and loratadine. Clin Exp Dermatol . 2005 Mar;30(2):165-70. [2]. The anti-inflammatory effects of Yunnan Baiyao are involved in regulation of the phospholipase A2/arachidonic acid metabolites pathways in acute inflammation rat model. Mol Med Rep. 2017 Oct;16(4):4045-4053. [3]. Mizolastine: a review of its use in allergic rhinitis and chronic idiopathic urticaria. BioDrugs. 1998 Jul;10(1):41-63. |
| Additional Infomation |
Mizolastine is a member of benzimidazoles. Mizolastine is under investigation in clinical trial NCT01928316 (A Bioequivalence Study of Domestic (Made in China) and Imported Mizolastine Tablets in Healthy Volunteers). |
Solubility Data
| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.78 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 (5.78 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 (5.78 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 | 2.3122 mL | 11.5610 mL | 23.1219 mL | |
| 5 mM | 0.4624 mL | 2.3122 mL | 4.6244 mL | |
| 10 mM | 0.2312 mL | 1.1561 mL | 2.3122 mL |