Virginiamycin M1 (RP 12536) is a novel and potent macrocyclic lactone peptolide antibiotic derived from Streptomyces pristinaespiralis, a member of the streptogramin A group of antibiotics.
Physicochemical Properties
| Molecular Formula | C28H35N3O7 |
| Molecular Weight | 525.5934 |
| Exact Mass | 525.248 |
| CAS # | 21411-53-0 |
| Related CAS # | Pristinamycin;270076-60-3 |
| PubChem CID | 5354042 |
| Appearance | White to yellow solid powder |
| Density | 1.26 g/cm3 |
| Boiling Point | 825.2ºC at 760 mmHg |
| Melting Point | 165-170 °C |
| Flash Point | 452.9ºC |
| Vapour Pressure | 0mmHg at 25°C |
| Index of Refraction | 1.586 |
| LogP | 2.926 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 1 |
| Heavy Atom Count | 38 |
| Complexity | 1030 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | CC1/C=C\C(=O)NC/C=C\C(=C/C(CC(=O)CC2=NC(=CO2)C(=O)N3CCC=C3C(=O)OC1C(C)C)O)\C |
| InChi Key | DAIKHDNSXMZDCU-RLJJXFIZSA-N |
| InChi Code | InChI=1S/C28H35N3O7/c1-17(2)26-19(4)9-10-24(34)29-11-5-7-18(3)13-20(32)14-21(33)15-25-30-22(16-37-25)27(35)31-12-6-8-23(31)28(36)38-26/h5,7-10,13,16-17,19-20,26,32H,6,11-12,14-15H2,1-4H3,(H,29,34)/b7-5-,10-9-,18-13- |
| Chemical Name | (12Z,17Z,19Z)-21-hydroxy-11,19-dimethyl-10-propan-2-yl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.03,7]octacosa-1(27),6,12,17,19,25(28)-hexaene-2,8,14,23-tetrone |
| 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
| References | Complete conversion of antibiotic precursor to pristinamycin IIA by overexpression of Streptomyces pristinaespiralis biosynthetic genes. Nat Biotechnol. 1997 Apr;15(4):349-53. |
| Additional Infomation |
Pristinamycin IIA is a macrolide antibiotic, a member of the streptogramin A group of antibiotics, and one component of pristinamycin. It is produced by Streptomyces graminofaciens and other bacteria. Ostreogrycin a has been reported in Streptomyces pristinaespiralis and Streptomyces virginiae with data available. A specific streptogramin group A antibiotic produced by Streptomyces graminofaciens and other bacteria. See also: Streptogramin A (annotation moved to). Drug Indication For the treatment of bacterial infections. Mechanism of Action Virginiamycin M1 is a macrocyclic lactone antibiotic that acts syngeristically with the structurally unrelated cyclic depsipeptides more commonly known as the virginiamycins B (ostreogrycin B or streptogramin B) and S to inhibit peptide elongation. This is achieved by blocking formation of a peptide bond between the growing peptide chain (peptidyl-tRNA) linked to the 50S ribosome and aminoacyl-tRNA. Virginiamycin M1 has proven to be highly active against Gram positive bacteria, particularly methicillin-resistant S. aureus. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~100 mg/mL (~190.26 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 5 mg/mL (9.51 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 (9.51 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 (9.51 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 | 1.9026 mL | 9.5131 mL | 19.0262 mL | |
| 5 mM | 0.3805 mL | 1.9026 mL | 3.8052 mL | |
| 10 mM | 0.1903 mL | 0.9513 mL | 1.9026 mL |