WAY-151932 (also known as VNA-932; WAY-VNA 932) is a novel and potent vasopressin V2-receptor agonist with IC50 of 80.3 nM and 778 nM in human-V2 binding and V1a binding assay. Small molecule agonists and antagonists of the V(2)-vasopressin receptor have been discovered and have undergone clinical trials.
Physicochemical Properties
| Molecular Formula | C23H19N4OCL |
| Molecular Weight | 402.87616 |
| Exact Mass | 402.124 |
| Elemental Analysis | C, 68.57; H, 4.75; Cl, 8.80; N, 13.91; O, 3.97 |
| CAS # | 220460-92-4 |
| PubChem CID | 5311500 |
| Appearance | White to off-white solid powder |
| Density | 1.3±0.1 g/cm3 |
| Boiling Point | 630.6±55.0 °C at 760 mmHg |
| Flash Point | 335.1±31.5 °C |
| Vapour Pressure | 0.0±1.8 mmHg at 25°C |
| Index of Refraction | 1.692 |
| LogP | 5.5 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 2 |
| Heavy Atom Count | 29 |
| Complexity | 603 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | O=C(C1=CC=C(N2N=C(C)C=C2)C=C1Cl)N3CC4=CC=CN4CC5=CC=CC=C53 |
| InChi Key | VLENVJZOHAXBBV-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C23H19ClN4O/c1-15-10-12-28(26-15)16-8-9-18(20(24)13-16)23(29)22-19-6-2-3-7-21(19)25-14-17-5-4-11-27(17)22/h2-5,7-13,25H,6,14H2,1H3 |
| Chemical Name | [2-chloro-4-(3-methylpyrazol-1-yl)phenyl]-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl)methanone |
| Synonyms | VNA932, VNA 932, VNA-932; WAY-151932; VNA-932; 220460-92-4; WAY-VNA-932; VNA932; CC7IZ88XD2; [2-chloro-4-(3-methylpyrazol-1-yl)phenyl]-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl)methanone; UNII-CC7IZ88XD2; VNA-932; WAY-VNA 932; WAY-VNA-932; WAY VNA 932; WAY VNA-932; WAYVNA 932 |
| 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 | Vasopressin V2-receptor (IC50 = 80.3 nM and 778 nM) |
| ln Vitro | WAY-151932 (VNA-932) has an EC50 of 0.74±0.07 nM and dose-dependently induces cAMP production in LV2 cells expressing hV2 receptors [2]. |
| ln Vivo | Oral administration of WAY-151932 (VNA-932) to conscious rats loaded with water results in a rise in osmotic pressure and a dose-dependent decrease in urine production (ED50=0.14 mg/kg, 2.5% starch in water vehicle) without altering the excretion curve of urine electrolytes[2]. |
| References |
[1]. Identification and synthesis of major metabolites of Vasopressin V2-receptor agonist WAY-151932, and antagonist, Lixivaptan. Bioorg Med Chem Lett. 2007 Nov 1;17(21):5796-800. [2]. Pyridobenzodiazepines: a novel class of orally active, vasopressin V2 receptor selective agonists. Bioorg Med Chem Lett. 2006 Feb 15;16(4):954-9. |
| Additional Infomation |
WAY-151932; VNA-932; 220460-92-4; WAY-VNA-932; VNA932; CC7IZ88XD2; [2-chloro-4-(3-methylpyrazol-1-yl)phenyl]-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl)methanone; UNII-CC7IZ88XD2; [1] Our efforts in seeking low molecular weight agonists of the antidiuretic peptide hormone arginine vasopressin (AVP) have led to the identification of the clinical candidate WAY-151932 (VNA-932). Further exploration of the structural requirements for agonist activity has provided another class of potent, orally active, non-peptidic vasopressin V2 receptor selective agonists exemplified by the 5,11-dihydro-pyrido[2,3-b][1,5]benzodiazepine as a candidate for further development.[2] |
Solubility Data
| Solubility (In Vitro) | DMSO : ~200 mg/mL (~496.43 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 5 mg/mL (12.41 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 50.0 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: ≥ 5 mg/mL (12.41 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 50.0 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: ≥ 5 mg/mL (12.41 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 50.0 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 | 2.4821 mL | 12.4106 mL | 24.8213 mL | |
| 5 mM | 0.4964 mL | 2.4821 mL | 4.9643 mL | |
| 10 mM | 0.2482 mL | 1.2411 mL | 2.4821 mL |