DPI-201-106 [(±)-SDZ-201 106] is a novel and potent inhibitor of the TTX-resistant h1 Na channel which is cardioselective. It acts by inhibiting the L-type calcium current, and inward and delayed rectifier potassium currents. As a cardiotonic agent, it has a synergistic sarcolemmal and intracellular mechanism of action.
Physicochemical Properties
| Molecular Formula | C29H30N4O2 |
| Molecular Weight | 466.58 |
| Exact Mass | 466.237 |
| Elemental Analysis | C, 74.65; H, 6.48; N, 12.01; O, 6.86 |
| CAS # | 97730-95-5 |
| Related CAS # | 97730-95-5 (racemic);78573-14-5 (malonate);78573-15-6 (mesylate);161468-21-9 (mesylate 1:1); 97749-21-8 (S-isomer); 97749-20-7 (R-isomer); |
| PubChem CID | 5190 |
| Appearance | White to off-white solid powder |
| Density | 1.29g/cm3 |
| Boiling Point | 702.6ºC at 760mmHg |
| Flash Point | 378.7ºC |
| Index of Refraction | 1.692 |
| LogP | 4.062 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 8 |
| Heavy Atom Count | 35 |
| Complexity | 672 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | N#CC1NC2=CC=CC(OCC(CN3CCN(C(C4=CC=CC=C4)C4=CC=CC=C4)CC3)O)=C2C=1 |
| InChi Key | BYBYHCOEAFHGJL-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C29H30N4O2/c30-19-24-18-26-27(31-24)12-7-13-28(26)35-21-25(34)20-32-14-16-33(17-15-32)29(22-8-3-1-4-9-22)23-10-5-2-6-11-23/h1-13,18,25,29,31,34H,14-17,20-21H2 |
| Chemical Name | 4-[3-(4-benzhydrylpiperazin-1-yl)-2-hydroxypropoxy]-1H-indole-2-carbonitrile |
| Synonyms | DPI-201-106 (±)-SDZ-201 106 DPI201-106 DPI-201106 DPI 201106 DPI201106 SDZ201 106 SDZ-201106 SDZ 201 106DPI 201-106SDZ 201106 SDZ201106 |
| 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
| Targets |
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| ln Vitro | With an EC50 of 0.2 nM, DPI 201-106 raises the Ca2+-sensitivity of peeled fibers from porcine trabecula septomarginalis[2]. Between 0.1 and 3 μM, DPI 201-106 has concentration-dependent positive inotropic effects in the left atria of guinea pigs and rats, as well as in the papillary muscles of kittens, rabbits, and guinea pigs, and in the Langendorff perfused hearts of rabbits[2]. | |
| ln Vivo | DPI 201-106 0.2 mg/kg iv increases left ventricular dP/dtmax in dogs under anesthesia. DPI 201-106 is administered up to a cumulative dose of 12.22 mg/kg iv in sedated cats that had received digoxin pretreatment [3]. | |
| References |
[1]. DPI 201-106, a novel cardioactive agent. Combination of cAMP-independent positive inotropic, negative chronotropic, action potential prolonging and coronary dilatory properties. Naunyn Schmiedebergs Arch Pharmacol.1985 May;329(3):316-. [2]. Interaction of DPI 201-106 with cardiac glycosides. J Cardiovasc Pharmacol. 1989 Feb;13(2):342-7. [3]. Identification of a cardiac sodium channel insensitive to synthetic modulators. J Cardiovasc Pharmacol Ther. 2001 Apr;6(2):201-12. |
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| Additional Infomation | 4-[3-[4-(diphenylmethyl)-1-piperazinyl]-2-hydroxypropoxy]-1H-indole-2-carbonitrile is a diarylmethane. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~250 mg/mL (~535.83 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (4.46 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 20.8 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: ≥ 2.08 mg/mL (4.46 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 20.8 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: ≥ 2.08 mg/mL (4.46 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 20.8 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 | 2.1433 mL | 10.7163 mL | 21.4326 mL | |
| 5 mM | 0.4287 mL | 2.1433 mL | 4.2865 mL | |
| 10 mM | 0.2143 mL | 1.0716 mL | 2.1433 mL |