| Size | Price | Stock | Qty |
|---|---|---|---|
| 50mg |
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| 100mg |
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| Other Sizes |
| Targets |
Erythromycylamine targets the bacterial 50S ribosomal subunit, similar to other macrolide antibiotics. It binds to the 23S rRNA within the 50S subunit and inhibits protein synthesis by blocking the translocation step of translation. As a semi-synthetic analogue of erythromycin, it retains antibacterial activity while having different physicochemical properties. The introduction of the amino moiety increases the compound's polarity. Erythromycylamine is active against a variety of bacteria, including gram-positive and some gram-negative organisms.
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| ln Vitro |
In vitro, Erythromycylamine has excellent activity against Campylobacter, a type of bacteria that can cause diarrheal disease. It is active against a variety of bacteria, including strains of S. pyogenes, S. pneumoniae, L. monocytogenes, and B. pertussis. As the major active metabolite of dirithromycin, it contributes to the antibacterial activity of the parent drug. The compound's activity spectrum is similar to that of erythromycin.
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| ln Vivo |
In vivo, Erythromycylamine is the major active metabolite of dirithromycin. After oral administration of dirithromycin, it is converted to erythromycylamine, which is responsible for the antibacterial activity. The compound's increased polarity due to the amino moiety may be disadvantageous for in vivo use compared to erythromycin. However, it retains antibacterial activity and has been studied for its potential in treating various bacterial infections.
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| Enzyme Assay |
For in vitro antimicrobial susceptibility testing, bacterial strains are cultured in appropriate media and treated with erythromycylamine at various concentrations (0.01-100 µg/mL). Minimum inhibitory concentrations (MICs) are determined using broth microdilution or agar dilution methods according to CLSI guidelines. The compound's activity against different bacterial species is assessed by comparing MIC values to those of erythromycin and other macrolides.
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| Cell Assay |
For cell-based assays, mammalian cells are not typically used for evaluating macrolide antibiotics. Instead, bacterial cultures are used to assess antibacterial activity. Time-kill assays can be performed to evaluate the bactericidal or bacteriostatic activity of erythromycylamine. The compound's activity against intracellular bacteria can be assessed in infected cell lines.
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| Animal Protocol |
For in vivo efficacy studies, animal models of bacterial infection (such as murine pneumonia, sepsis, or skin infection models) would be used. Erythromycylamine would be administered via oral or intravenous routes at doses determined from pharmacokinetic studies. Bacterial loads in tissues would be measured by colony counting. Survival rates and clinical signs would be monitored. However, specific in vivo protocols for erythromycylamine have not been detailed.
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| ADME/Pharmacokinetics |
Erythromycylamine is soluble in ethanol, methanol, DMF, DMSO, and water. Storage is recommended at -20°C for long-term stability. As a semi-synthetic macrolide antibiotic, it is for research use only and is not intended for human or veterinary use. Standard laboratory safety precautions should be followed when handling this compound.
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| Toxicity/Toxicokinetics |
Toxicological data for erythromycylamine are available from the development of dirithromycin, as it is the major active metabolite. Macrolide antibiotics are generally well-tolerated, with common adverse effects including gastrointestinal disturbances. As a research compound, standard safety precautions should be followed when handling this compound. It is not intended for human use.
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| References |
:Antimicrob. Agents Chemother. 32(11), 1710-1719 (1988).
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| Additional Infomation |
(9S)-Erythromycin cycloamine is a macrolide antibiotic. It is formed by converting the keto group of erythromycin A into the corresponding imine, and then reducing it to give the corresponding amino compound (9S diastereomer).
Erythromycylamine is a semi-synthetic macrolide antibiotic and the major active metabolite of dirithromycin. It is active against a variety of bacteria including Campylobacter, S. pyogenes, S. pneumoniae, L. monocytogenes, and B. pertussis. The compound is a derivative of erythromycin with an amino group at the 9-position. Erythromycylamine is a research compound and is not approved for clinical use. |
| Molecular Formula |
C37H70N2O12
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|---|---|
| Molecular Weight |
734.97Synonym
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| Exact Mass |
734.493
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| CAS # |
26116-56-3
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| Related CAS # |
Erythromycylamine-d3;Erythromycylamine-13C,d3
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| PubChem CID |
83952
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| Appearance |
White to off-white solid powder
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| Density |
1.19g/cm3
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| Boiling Point |
810.3ºC at 760mmHg
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| Flash Point |
443.8ºC
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| Vapour Pressure |
2.15E-30mmHg at 25°C
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| Index of Refraction |
1.539
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| LogP |
2.244
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| Hydrogen Bond Donor Count |
6
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| Hydrogen Bond Acceptor Count |
14
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
51
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| Complexity |
1140
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| Defined Atom Stereocenter Count |
19
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| 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@@]([H])(C([H])([H])[H])[C@@]([H])([C@@]([H])(C([H])([H])[H])C(=O)O[C@]([H])(C([H])([H])C([H])([H])[H])[C@](C([H])([H])[H])([C@@]([H])([C@@]([H])(C([H])([H])[H])[C@]([H])([C@]([H])(C([H])([H])[H])C([H])([H])[C@@]1(C([H])([H])[H])O[H])N([H])[H])O[H])O[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]
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| InChi Key |
XCLJRCAJSCMIND-JCTYMORFSA-N
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| InChi Code |
InChI=1S/C37H70N2O12/c1-14-25-37(10,45)30(41)20(4)27(38)18(2)16-35(8,44)32(51-34-28(40)24(39(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/h18-32,34,40-42,44-45H,14-17,38H2,1-13H3/t18-,19-,20+,21+,22-,23+,24+,25-,26+,27+,28-,29+,30-,31+,32-,34+,35-,36-,37-/m1/s1
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| Chemical Name |
(3R,4S,5S,6R,7R,9R,10S,11S,12R,13S,14R)-10-amino-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-oxacyclotetradecan-2-one
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
DMSO: ~100 mg/mL (~136.1 mM; with ultrasonication)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (3.40 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween-80 + 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 DMSO stock solution (25.0 mg/mL) to 400 μL of PEG300 and mix well; then add 50 μL of Tween-80 and mix well; finally add 450 μL of physiological saline and 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: ≥ 2.5 mg/mL (3.40 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 DMSO stock solution (25.0 mg/mL) to 900 μL of 20% SBE-β-CD saline and mix well. 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: ≥ 2.5 mg/mL (3.40 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 DMSO stock solution (25.0 mg/mL) to 900 μL of corn oil and mix well. (Please use freshly prepared in vivo formulations for optimal results.) |
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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