SDZ-220-581 (SDZ-220581; SDZ220581) is a novel and potent competitive antagonist of NMDA glutamate receptor subtype(pKi= 7.7) with the potential to be used for Parkinson's disease.
Physicochemical Properties
| Molecular Formula | C16H17CLNO5P |
| Molecular Weight | 369.7378 |
| Exact Mass | 369.053 |
| CAS # | 174575-17-8 |
| Related CAS # | SDZ 220-581 Ammonium salt;179411-94-0;SDZ 220-581 hydrochloride;179411-93-9 |
| PubChem CID | 128019 |
| Appearance | Light yellow to yellow solid powder |
| Density | 1.5±0.1 g/cm3 |
| Boiling Point | 613.3±65.0 °C at 760 mmHg |
| Flash Point | 324.7±34.3 °C |
| Vapour Pressure | 0.0±1.9 mmHg at 25°C |
| Index of Refraction | 1.637 |
| LogP | 0.89 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 6 |
| Heavy Atom Count | 24 |
| Complexity | 485 |
| Defined Atom Stereocenter Count | 1 |
| SMILES | C1=CC=C(C(=C1)C2=CC(=CC(=C2)CP(=O)(O)O)C[C@@H](C(=O)O)N)Cl |
| InChi Key | VBRJFXSFCYEZMQ-HNNXBMFYSA-N |
| InChi Code | InChI=1S/C16H17ClNO5P/c17-14-4-2-1-3-13(14)12-6-10(8-15(18)16(19)20)5-11(7-12)9-24(21,22)23/h1-7,15H,8-9,18H2,(H,19,20)(H2,21,22,23)/t15-/m0/s1 |
| Chemical Name | (2S)-2-amino-3-[3-(2-chlorophenyl)-5-(phosphonomethyl)phenyl]propanoic acid |
| Synonyms | SDZ220-581. SDZ-220581 SDZ 220-581 SDZ-220-581 |
| 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 |
| 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
| ln Vivo | Male OF-1 mice were dose-dependently protected against maximal electroshock epileptic seizures (MES) by treatment with SDZ 220-581 (3.2–32 mg/kg; p.o.; for 24 hours). The quick onset and extended duration of action of SDZ 220-581 are characteristics of its protective duration [1]. |
| Animal Protocol |
Animal/Disease Models: Male OF-1 mouse (18-26g) [1] Doses: 3.2mg/kg, 10mg/kg, 32mg/kg Route of Administration: Oral administration; Route of Administration: Oral administration. 24-hour Experimental Results: Dose-dependent protection of mice from maximal electroshockable seizures (MES) following oral administration. |
| References |
[1]. Urwyler S, Campbell E, Fricker G, Biphenyl-derivatives of 2-amino-7-phosphono-heptanoic acid, a novel class of potent competitive N-methyl-D-aspartate receptor antagonists--II. Pharmacological characterization in vivo. Neuropharmacology. 1996 Jun;35(6):65. [2]. In vitro characterisation of the novel positive allosteric modulators of the mGlu₅ receptor, LSN2463359 and LSN2814617, and their effects on sleep architecture and operant responding in the rat. Neuropharmacology. 2013 Jan;64:224-39. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~8.57 mg/mL (~23.18 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.76 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 (6.76 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 (6.76 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 | 2.7046 mL | 13.5230 mL | 27.0460 mL | |
| 5 mM | 0.5409 mL | 2.7046 mL | 5.4092 mL | |
| 10 mM | 0.2705 mL | 1.3523 mL | 2.7046 mL |