Azithromycin monohydrateProduct ingredient for Azithromycin
- Name
- Azithromycin monohydrate
- Drug Entry
- Azithromycin
Azithromycin is a broad-spectrum macrolide antibiotic with a long half-life and a high degree of tissue penetration 3. It was initially approved by the FDA in 1991 4.
It is primarily used for the treatment of respiratory, enteric and genitourinary infections and may be used instead of other macrolides for some sexually transmitted and enteric infections. It is structurally related to erythromycin 2.
Azithromycin [9-deoxo-9a-aza-9a-methyl-9a-homoerythromycin] is a part of the azalide subclass of macrolides, and contains a 15-membered ring, with a methyl-substituted nitrogen instead of a carbonyl group at the 9a position on the aglycone ring, which allows for the prevention of its metabolism. This differentiates azithromycin from other types of macrolides 4.
In March 2020, a small study was funded by the French government to investigate the treatment of COVID-19 with a combination of azithromycin and the anti-malaria drug hydroxychloroquine. The results were positive, all patients taking the combination were virologically cured within 6 days of treatment, however, larger studies are required.9
- Accession Number
- DBSALT001208
- Structure
Structure for Azithromycin monohydrate (DBSALT001208)
- Synonyms
- Not Available
- UNII
- JTE4MNN1MD
- CAS Number
- 121470-24-4
- Weight
- Average: 767.011
Monoisotopic: 766.519090451 - Chemical Formula
- C38H74N2O13
- InChI Key
- HQUPLSLYZHKKQT-WVVFQGGUSA-N
- InChI
- InChI=1S/C38H72N2O12.H2O/c1-15-27-38(10,46)31(42)24(6)40(13)19-20(2)17-36(8,45)33(52-35-29(41)26(39(11)12)16-21(3)48-35)22(4)30(23(5)34(44)50-27)51-28-18-37(9,47-14)32(43)25(7)49-28;/h20-33,35,41-43,45-46H,15-19H2,1-14H3;1H2/t20-,21-,22+,23-,24-,25+,26+,27-,28+,29-,30+,31-,32+,33-,35+,36-,37-,38-;/m1./s1
- IUPAC Name
- (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-3,4,10-trihydroxy-13-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one hydrate
- SMILES
- O.CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@](C)(O)C[C@@H](C)CN(C)[C@H](C)[C@@H](O)[C@]1(C)O
- External Links
- ChemSpider
- 8072677
- ChEMBL
- CHEMBL1200502
- Predicted Properties
Property Value Source Water Solubility 0.514 mg/mL ALOGPS logP 3.03 ALOGPS logP 2.44 Chemaxon logS -3.2 ALOGPS pKa (Strongest Acidic) 12.43 Chemaxon pKa (Strongest Basic) 9.57 Chemaxon Physiological Charge 2 Chemaxon Hydrogen Acceptor Count 13 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 180.08 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 194.11 m3·mol-1 Chemaxon Polarizability 82.26 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon