(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 dihydrate

• ChemBase ID: 154613
• Molecular Formular: C38H76N2O14
• Molecular Mass: 785.01504
• Monoisotopic Mass: 784.52965512
• SMILES: CC[C@H]1[C@@]([C@@H]([C@H](N(C[C@@H](C[C@@]([C@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]1C[C@@]([C@H]([C@@H](O1)C)O)(C)OC)C)O[C@H]1[C@@H]([C@H](C[C@H](O1)C)N(C)C)O)(C)O)C)C)C)O)(C)O.O.O
• Canonical SMILES: CC[C@@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@H]([C@@H](O2)C)O)[C@H](C)[C@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@](C[C@H](CN([C@@H]([C@H]([C@]1(C)O)O)C)C)C)(C)O.O.O
• InChI: InChI=1S/C38H72N2O12.2H2O/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;2*1H2/t20-,21-,22+,23-,24-,25+,26+,27-,28+,29-,30+,31-,32+,33-,35+,36-,37-,38-;;/m1../s1
• InChIKey: SRMPHJKQVUDLQE-KUJJYQHYSA-N

NAMES AND DATABASE IDS

Names

• 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 dihydrate
• IUPAC Traditional name: azithromycin dihydrate
• Synonyms: N-Methyl-11-aza-10-deoxo-10-dihydroerythromycin A; CP-62993; Azithromycin dihydrate; 阿齐霉素 二水合物

Database IDs

• CAS Number: 117772-70-0
• MDL Number: MFCD01862248
• PubChem SID: 162248751
• PubChem CID: 3033819

CALCULATED PROPERTIES

• Acid pKa: 12.428324
• H Acceptors: 13
• H Donor: 5
• LogD (pH = 5.5): -4.14965
• LogD (pH = 7.4): -1.2309437
• Log P: 2.4447815
• Molar Refractivity: 194.1082 cm^3
• Polarizability: 79.00683 Å^3
• Polar Surface Area: 180.08 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL
• Apperance: off-white powder

Safety Information

• Storage Condition: protect from light
• RTECS: RN6960000
• German water hazard class: 3
• Storage Temperature: -20°C; room temp

Product Information

• Purity: ≥98% (HPLC)
• Pharmacopeia Traceability: traceable to PhEur Y0000307; traceable to USP 1046056
• Empirical Formula (Hill Notation): C38H72N2O12 · 2H2O

DETAILS

Sigma Aldrich - PZ0007

Legal Information
Sold for research purposes under agreement from Pfizer Inc.
Biochem/physiol Actions
Azithromycin dihydrate is a macrolide antibiotic, azalide subclass. It binds to the 50S subunit of the 70S bacterial ribosomes and inhibits RNA-dependent protein synthesis in bacterial cells. Azithromycin also has anti-immunomodulatory/anti-inflammatory properties, which make it useful in treating cystic fibrosis.

Sigma Aldrich - 57947

Biochem/physiol Actions
Azithromycin dihydrate is a macrolide antibiotic, azalide subclass. It binds to the 50S subunit of the 70S bacterial ribosomes and inhibits RNA-dependent protein synthesis in bacterial cells. Azithromycin also has anti-immunomodulatory/anti-inflammatory properties, which make it useful in treating cystic fibrosis.