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Submit ReviewAzithromycin
Description: Antibiotic; inhibits 50S ribosomal subunit formation and elongation at transpeptidation
Alternative Names: CP 62993
Chemical Name: 13-[(2,6-Dideoxy-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranosyl)oxy]-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-11-[[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy]-1-oxa-6-azacyclopentadecan-15-one
Purity: ≥99% (HPLC)
Biological Activity for Azithromycin
Azithromycin is a macrolide antibiotic. Inhibits 50S ribosomal subunit formation and elongation at transpeptidation step in gram-positive and gram-negative organisms. Orally active with improved pharmacokinetics over erythromycin in mouse models. Inhibits autophagy. Predicted to disrupt binding of SARS-CoV-2 spike protein to ACE2.
Licensing Information
Sold for research purposes under agreement from Pfizer Inc.
Compound Libraries for Azithromycin
Azithromycin is also offered as part of the Tocriscreen 2.0 Max, Tocriscreen Antiviral Library and Tocriscreen FDA-Approved Drugs. Find out more about compound libraries available from Tocris.
Technical Data for Azithromycin
| M. Wt | 748.98 |
| Formula | C38H72N2O12 |
| Storage | Store at -20°C |
| Purity | ≥99% (HPLC) |
| CAS Number | 83905-01-5 |
| PubChem ID | 447043 |
| InChI Key | MQTOSJVFKKJCRP-BICOPXKESA-N |
| Smiles | [H][C@@]1(O[C@@H]([C@H](C)[C@@H](O[C@@]3([H])[C@H](O)[C@@H](N(C)C)C[C@@H](C)O3)[C@](C)(O)C[C@@H](C)C2)[C@@H](C)C(O[C@H](CC)[C@](O)(C)[C@H](O)[C@@H](C)N2C)=O)O[C@@H](C)[C@H](O)[C@](C)(OC)C1 |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for Azithromycin
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 74.9 | 100 | |
| ethanol | 74.9 | 100 |
Preparing Stock Solutions for Azithromycin
The following data is based on the product molecular weight 748.98. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.34 mL | 6.68 mL | 13.35 mL |
| 5 mM | 0.27 mL | 1.34 mL | 2.67 mL |
| 10 mM | 0.13 mL | 0.67 mL | 1.34 mL |
| 50 mM | 0.03 mL | 0.13 mL | 0.27 mL |
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Product Datasheets for Azithromycin
References for Azithromycin
References are publications that support the biological activity of the product.
Retsema et al (1987) Spectrum and mode of action of azithro. (CP-62,993), a new 15-membered-ring macrolide with improved potency against gram-negative organisms. Antimicrob.Agents Chemother. 31 1939 PMID: 2449865
Girard et al (1987) Pharmacokinetic and in vivo studies with azithro. (CP-62,993), a new macrolide with extended half-life and excellent tissue distribution. Antimicrob.Agents Chemother. 31 1948 PMID: 2830841
Champney and Burdine (1995) Macrolide antibiotics inhibit 50S ribosomal subunit assembly in Bacillus subtilis and Staphylococcus aureas. Antimicrob.Agents Chemother. 39 2141 PMID: 8540733
Galluzzi et al (2017) Pharmacological modulation of autophagy: therapeutic potential and persisting obstacles. Nat.Rev.Drug.Discov. PMID: 28529316
Sandeep and McGregor et al (2020) Energetics based modeling of hydroxychloroquine and azithromycin binding to the SARS-CoV-2 spike (S) protein - ACE2 complex. ChemRxiv - Paper not yet peer reviewed.
If you know of a relevant reference for Azithromycin, please let us know.
View Related Products by Target
Keywords: Azithromycin, Azithromycin supplier, Macrolides, antibiotics, Inhibits, inhibitors, 50S, ribosomal, subunit, formation, elongation, transpeptidation, gram, positive, negative, CP62993, Pfizer, CP, 62993, DNA,, RNA, and, Protein, Synthesis, Antibiotics, Autophagy, COVID-19, Coronavirus, 3771, Tocris Bioscience
3 Citations for Azithromycin
Citations are publications that use Tocris products. Selected citations for Azithromycin include:
Broad and Sanger (2013) The antibiotic azithro. is a motilin receptor agonist in human stomach: comparison with erythro. Br J Pharmacol 168 1859 PMID: 23190027
Palmer et al (2018) Nonoptimal Gene Expression Creates Latent Potential for Antibiotic Resistance. Mol Biol Evol 35 2669 PMID: 30169679
Groote et al (2018) Optimization and Lead Selection of Benzothiazole Amide Analogs Toward a Novel Antimycobacterial Agent. Front Microbiol 9 2231 PMID: 30294313
Do you know of a great paper that uses Azithromycin from Tocris? Please let us know.
Reviews for Azithromycin
Average Rating: 5 (Based on 1 Review.)
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Human tissue pharmacology.
By
John Broad on 01/05/2018
Assay Type: In Vitro
Species: Human
Human EFS GI smooth muscle assay
Use at 100-300uM for efficacy as motilin agonist
Literature in this Area
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