Erythromycin A Dihydrate
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| Category | Antibiotics |
| Catalog number | BBF-04082 |
| CAS | 59319-72-1 |
| Molecular Weight | 769.95 |
| Molecular Formula | C37H67NO13.2H2O |
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Description
A highly purified form of erythromycin A, a major component found in erythromycin.
Specification
| Synonyms | Erythromycin A (dihydrate) |
| Storage | Store at 2-8°C |
| IUPAC Name | (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione;dihydrate |
| Canonical SMILES | CCC1C(C(C(C(=O)C(CC(C(C(C(C(C(=O)O1)C)OC2CC(C(C(O2)C)O)(C)OC)C)OC3C(C(CC(O3)C)N(C)C)O)(C)O)C)C)O)(C)O.O.O |
| InChI | InChI=1S/C37H67NO13.2H2O/c1-14-25-37(10,45)30(41)20(4)27(39)18(2)16-35(8,44)32(51-34-28(40)24(38(11)12)15-19(3)47-34)21(5)29(22(6)33(43)49-25)50-26-17-36(9,46-13)31(42)23(7)48-26;;/h18-26,28-32,34,40-42,44-45H,14-17H2,1-13H3;2*1H2/t18-,19-,20+,21+,22-,23+,24+,25-,26+,28-,29+,30-,31+,32-,34+,35-,36-,37-;;/m1./s1 |
| InChI Key | IWGQNYZQLVGGCS-INORWZNNSA-N |
Properties
| Boiling Point | 818.4°C at 760 mmHg |
Reference Reading
1. Solid-state investigations of erythromycin A dihydrate: structure, NMR spectroscopy, and hygroscopicity
S R Byrn, J G Stowell, R R Pfeiffer, P H Toma, G A Stephenson J Pharm Sci . 1997 Nov;86(11):1239-44. doi: 10.1021/js9701667.
The crystal structures of the commercially available form of erythromycin A dihydrate and clarithromycin anhydrate, in addition to the structure of erythromycin B dihydrate, are reported in this paper. In light of the crystallographic data, analysis of the structural information provides insight into the physical properties of these pharmaceuticals. The propensity of these pharmaceuticals to form solvated structures is discussed and the hygroscopicity of erythromycin A dihydrate is investigated. Solid-state 13C NMR was used to monitor changes that occur when the dihydrate form of erythromycin A is stored under conditions of low relative humidity. Although erythromycin A dihydrate retains its crystallographic order at low humidity, as indicated by its X-ray powder diffraction pattern, the local chemical environment is dramatically influenced by the loss of the water molecules and results in dramatic changes in its solid-state 13C NMR spectrum.
2. Physical characterization of erythromycin: anhydrate, monohydrate, and dihydrate crystalline solids
A J Vanderwielen, A C Sarapu, P D Rahn, P V Allen J Pharm Sci . 1978 Aug;67(8):1087-93. doi: 10.1002/jps.2600670816.
Hot-stage microscopy, thermoanalytical methods, and X-ray powder diffraction were used to demonstrate that crystalline erythromycin dihydrate converts to the crystalline anhydrate via a noncrystalline intermediate. X-ray powder diffraction, IR spectral, thermogravimetric, and differential thermal analyses were used to characterize the monohydrate material. The flow interrupt technique, a procedure recently developed to deal with low surface area samples, was employed successfully in obtaining isotherms and specific surface areas for the monohydrate and anhydrate. The relative dissolution rates of the various hydrates were determined in an aqueous solution (0.01 M phosphate buffer, pH 7.5) at 37 degrees. The results showed a significant difference in the dissolution rate of the dihydrate compared to the monohydrate and anhydrate.
3. Properties of erythromycin-loaded polymeric dicalcium phosphate dehydrate bone graft substitute
Paula Dietz, Bin Wu, David Markel, Weiping Ren, Tong Shi, Therese Bou-Akl, Angelica Guardia J Orthop Res . 2021 Nov;39(11):2446-2454. doi: 10.1002/jor.24979.
A self-setting, injectable polymeric dicalcium phosphate dehydrate bone graft substitute that is mechanically strong and has excellent cohesion was developed. We assessed the performance of erythromycin-loaded polymeric dicalcium phosphate dehydrate cement. Its properties include drug release, growth inhibition against Staphylococcus aureus and biocompatibility with osteoblastic MC3T3 cells. The impact of erythromycin loading on cement injectability, setting time, and mechanical strength were also evaluated. A sustained, low burst release of erythromycin was observed. Eluents collected from erythromycin-loaded cement showed a considerable zone of inhibition for up to 28 days. Direct contact of erythromycin-loaded cement discs with agar plate showed a similarly sizable zone of inhibition for up to 22 days. Degraded ceramic residues had strong zones of inhibition as well. While the erythromycin-loaded cement was injectable, a notable delay of the setting time was observed (49.2 ± 6.8 min) as compared with control (drug-free cement, 12.2 ± 2.6 min). A slight increase in compressive strength (60.83 ± 6.28 MPa) was observed in erythromycin-loaded cement as compared with control (59.41 ± 6.48 MPa). Erythromycin-loaded cement was biocompatible although reduced cell growth was observed in the presence of the cement eluent. We propose that the bactericidal efficacy of erythromycin-loaded cement was caused by the combined effects of erythromycin released and exposed on the contact surface of degrading ceramics. Our data may elucidate the future application of polymeric dicalcium phosphate dehydrate bone graft substitute for the treatment of orthopedic infections and opportunities to use other antibiotics and applications considering its comparable handling and mechanical strength to poly (methyl methacrylate) cements.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
