(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

• ChemBase ID: 119603
• Molecular Formular: C38H72N2O12
• Molecular Mass: 748.98448
• Monoisotopic Mass: 748.50852575
• SMILES: [C@@H]1([C@@H]([C@H](C[C@H](O1)C)N(C)C)O)O[C@@H]1[C@H]([C@H]([C@H](C(=O)O[C@H]([C@]([C@@H]([C@@H](N(C[C@@H](C[C@]1(O)C)C)C)C)O)(O)C)CC)C)O[C@H]1C[C@]([C@H]([C@@H](O1)C)O)(OC)C)C
• Canonical SMILES: CC[C@@H]1OC(=O)[C@H](C)[C@H](O[C@@H]2O[C@@H](C)[C@@H]([C@](C2)(C)OC)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
• InChI: InChI=1S/C38H72N2O12/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/t20-,21-,22+,23-,24-,25+,26+,27-,28+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1
• InChIKey: MQTOSJVFKKJCRP-BICOPXKESA-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
• IUPAC Traditional name: azithromycin; (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
• Brand Name: Zithromax, Azithrocin, Azin
• Synonyms: (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-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 Dihydrate; CP-62993; XZ-450; Azitrocin; Ribotrex; Sumamed; Trozocina; Zithromaz; Zitromax; Azithromycin Dihydrate; 9-deoxy-9a-aza-9a-methyl-9a-homoerythromycin A; Azithromycin; (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-2-ethyl-3,4,10-trihydroxy-13-(((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethylt etrahydro-2H-pyran-2-yl)oxy)-3,5,6,8,10,12,14-heptameth yl-1-oxa-6-azacyclopentadecan-15-one; Trezid; Zithromax; Azithromycin

Database IDs

• CAS Number: 83905-01-5; 117772-70-0
• PubChem SID: 162102992
• PubChem CID: 447043; 55185
• CHEBI ID: 2955
• ATC CODE: S01AA26; J01FA10
• CHEMBL: 529
• Chemspider ID: 10482163
• DrugBank ID: DB00207
• KEGG ID: D07486
• Unique Ingredient Identifier: J2KLZ20U1M
• Wikipedia Title: Azithromycin
• Medline Plus: a697037

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: Chloroform; Ethanol,
• Apperance: White Solid
• Melting Point: 122-124°C

Safety Information

• Storage Condition: -20°C Freezer, Under inert atmosphere

Pharmacology Properties

• Admin Routes: Oral (capsule or suspension), intravenous, ophthalmic
• Bioavailability: 38% for 250 mg capsules
• Excretion: Biliary, renal (4.5%)
• Half Life: 68 h
• Metabolism: Hepatic
• Legal Status: Rx-only (US)
• Pregnancy Category: B (US); B1 (Australia)
• US Licence: Azithromycin
• Mechanism of Action: Protein synthesis inhibitor

Product Information

• Application(s): Antibacterial agent; Macrolide antibiotic

DETAILS

Toronto Research Chemicals - A927000

Semi-synthetic macrolide antibiotic; related to Erythromycin A. Antibacterial.

REFERENCES

• Langtry, H.D., et al.: Drugs, 56, 273 (1998)
• Eur. Pat., 1984, Pfizer, 109 253; CA, 101, 211651, (synth, props)
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• Kovacic-Bosnjak, N. et al., Chromatographia, 1988, 25, 999
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• Langtry, H.D. et al., Drugs, 1998, 56, 273-297, (rev)
• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 155
• Awan, A. et al., J.C.S. Perkin 2, 2000, 1645-1652, (pmr, conformn)