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Davercin (Erythromycin cyclocarbonate), an Erythromycin derivative, is a potent bacteriostatic antibiotic macrolide produced by Streptomyces erythreus and is active against Gram-positive and some Gram-negative microorganisms. It inhibits protein synthesis by binding to 50S ribosomal subunits. This binding process inhibits peptidyl transferase activity and interferes with translocation of amino acids during translation and assembly of proteins.
Physicochemical Properties
| Molecular Formula | C38H65NO14 |
| Molecular Weight | 759.9210 |
| Exact Mass | 759.441 |
| Elemental Analysis | C, 60.06; H, 8.62; N, 1.84; O, 29.47 |
| CAS # | 55224-05-0 |
| Related CAS # |
114-07-8 (free); 3521-62-8 (estolate); 16667-03-1 (glutamate); 30010-41-4 (aspartate); 7704-67-8 (thiocyante); 1264-62-6 (Ethylsuccinate); 914076-30-5 (ethyl carbonate); 55224-05-0 (cyclocarbonate); 33396-29-1 (Erythromycin A enol ether); 59319-72-1 (Erythromycin A dihydrate) |
| PubChem CID | 10033072 |
| Appearance | White to off-white solid powder; Colorless solution (in ethanol, 100mg/mL) |
| Density | 1.22 g/cm3 |
| Boiling Point | 859.8ºC at 760 mmHg |
| Index of Refraction | 1.534 |
| LogP | 2.967 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 15 |
| Rotatable Bond Count | 7 |
| Heavy Atom Count | 53 |
| Complexity | 1300 |
| Defined Atom Stereocenter Count | 18 |
| SMILES | O([C@@]1([H])[C@@]([H])([C@]([H])(C([H])([H])[C@@]([H])(C([H])([H])[H])O1)N(C([H])([H])[H])C([H])([H])[H])O[H])[C@@]1([H])[C@@](C([H])([H])[H])(C([H])([H])[C@@]([H])(C([H])([H])[H])C([C@]([H])(C([H])([H])[H])[C@]2([H])[C@@](C([H])([H])[H])([C@@]([H])(C([H])([H])C([H])([H])[H])OC([C@]([H])(C([H])([H])[H])[C@]([H])([C@]1([H])C([H])([H])[H])O[C@@]1([H])C([H])([H])[C@](C([H])([H])[H])([C@]([H])([C@]([H])(C([H])([H])[H])O1)O[H])OC([H])([H])[H])=O)OC(=O)O2)=O)O[H] |
| InChi Key | NKLGIWNNVDPGCA-ZDYKNUMJSA-N |
| InChi Code | InChI=1S/C38H65NO14/c1-14-25-38(10)32(52-35(44)53-38)20(4)27(40)18(2)16-36(8,45)31(51-34-28(41)24(39(11)12)15-19(3)47-34)21(5)29(22(6)33(43)49-25)50-26-17-37(9,46-13)30(42)23(7)48-26/h18-26,28-32,34,41-42,45H,14-17H2,1-13H3/t18-,19-,20+,21+,22-,23+,24+,25-,26+,28-,29+,30+,31-,32-,34+,36-,37-,38-/m1/s1 |
| Chemical Name | (3aR,4R,7R,8S,9S,10R,11R,13R,15R,15aR)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-11-hydroxy-8-(((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-3a,7,9,11,13,15-hexamethyldecahydro-6H-[1,3]dioxolo[4,5-c][1]oxacyclotetradecine-2,6,14(7H)-trione |
| Synonyms | Erythromycin A; Erythromycin A 11,12-carbonate; Erythromycin A cyclic carbonate; Davercin; |
| 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 | Macrolide |
| ln Vitro | Erythromycin is used to treat infections of the skin and soft tissues in addition to gastrointestinal, genital, and respiratory tract infections. Since the first generation of macrolides, which had low toxicity and good tolerability, are unstable in acidic media, erythromycin, with its ten chiral centers and two sugar substituents (L-cladinose and D-desosamine), is a good starting point for numerous medicinal chemistry efforts to improve its biological profile (better activity, higher stability, and improved bioavailability[1]. |
| ln Vivo | Macrolides, as a class of natural or semisynthetic products, express their antibacterial activity primarily by reversible binding to the bacterial 50S ribosomal subunits and by blocking nascent proteins' progression through their exit tunnel in bacterial protein biosynthesis. Generally considered to be bacteriostatic, they may also be bactericidal at higher doses. The discovery of azithromycin from the class of macrolides, as one of the most important new drugs of the 20th century, is presented as an example of a rational medicinal chemistry approach to drug design, applying classical structure-activity relationship that will illustrate an impressive drug discovery success story. However, the microorganisms have developed several mechanisms to acquire resistance to antibiotics, including macrolide antibiotics. The primary mechanism for acquiring bacterial resistance to macrolides is a mutation of one or more nucleotides from the binding site. Although azithromycin is reported to show different, two-step process of the inhibition of ribosome function of some species, more detailed elaboration of that specific mode of action is needed. New macrocyclic derivatives, which could be more potent and less prone to escape bacterial resistance mechanisms, are also continuously evaluated. A novel class of antibiotic compounds-macrolones, which are derived from macrolides and comprise macrocyclic moiety, linker, and either free or esterified quinolone 3-carboxylic group, show excellent antibacterial potency towards key erythromycin-resistant Gram-positive and Gram-negative bacterial strains, with possibly decreased potential of bacterial resistance to macrolides[1]. |
| References |
[1]. From Erythromycin to Azithromycin and New Potential Ribosome-Binding Antimicrobials. Antibiotics (Basel). 2016 Sep 1;5(3). pii: E29. |
| Additional Infomation | Davercin is an aminoglycoside. |
Solubility Data
| Solubility (In Vitro) |
DMSO : 100 mg/mL (131.59 mM) Ethanol : 100 mg/mL |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 3 mg/mL (3.95 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 30.0 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: ≥ 3 mg/mL (3.95 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 30.0 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: ≥ 3 mg/mL (3.95 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 30.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 4: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 3 mg/mL (3.95 mM) (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.3159 mL | 6.5796 mL | 13.1593 mL | |
| 5 mM | 0.2632 mL | 1.3159 mL | 2.6319 mL | |
| 10 mM | 0.1316 mL | 0.6580 mL | 1.3159 mL |