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Azithromycin

Athanor · official

C38H72N2O12 · 749 g/mol

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

Also called Zithromax, Z-Pak, azalide, macrolide antibiotic

Drugs
Open in Athanor
The structure of Azithromycin
Drawn from its SMILES with RDKit
Harmful or irritantHealth hazardEnvironmental hazardDangerMay cause an allergic skin reaction · May cause allergy or asthma symptoms or breathing difficulties if inhaled · Causes damage to organs through prolonged or repeated exposure · Very toxic to aquatic life · Very toxic to aquatic life with long lasting effects

Names and identifiers

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
Synonyms
Zithromax, Z-Pak, azalide
+ 38 more

macrolide antibiotic, Hemomycin, Azithromycine, Azasite, Azithromycinum, Zitromax, Azenil, aziromycin, Azithrocin, Azitrocin, Macrozit, Azitromicina, Aruzilina, azithromycin anhydrous, Trozocina, Xithrone, Zithromac, Zythromax, Aziwin, DuraSite, CP 62993, Anhydrous azithromycin, Azyter, DTXSID8030760, J2KLZ20U1M, XZ-450, NSC643732, XZ 405, XZ 450, NSC-758625, Azithromycin (as dihydrate), CP-62,993, CHEBI:2955, DTXCID6010760, Azadose, Ultreon, N-Methyl-11-aza-10-deoxo-10-dihydroerythromycin A, 1-Oxa-6-azacyclopentadecan-15-one, 13-((2,6-dideoxy-3-C-methyl-3-O-methyl-alpha-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)-beta-D-xylo-hexopyranosyl)oxy)-, (2R-(2R*,3S*,4R*,5R*,8R*,10R*,11R*,12S*,13S*,14R*))-

Molecular formula
C38H72N2O12
Empirical formula
C19H36NO6
Molecular weight
749 g/mol
Exact mass
748.50853
CAS number
83905-01-5
PubChem CID
447043
Canonical SMILES
CCC1C(C(C(N(CC(CC(C(C(C(C(C(=O)O1)C)OC2CC(C(C(O2)C)O)(C)OC)C)OC3C(C(CC(O3)C)N(C)C)O)(C)O)C)C)C)O)(C)O
Isomeric 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]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)O)C)C)C)O)(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
Molfile

Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.

Physical properties

log P
log Kow = 4.02[1]
pKa
pKa = 8.74[1]

Each value as its source reports it, with the source's number after it (listed under References). Where several sources report a property, the row shows the value most of them agree on, the rule the app uses; open the values to see every one.

Calculated

Heavy atoms
52
Rings
3
Aromatic rings
0
Fraction sp³ carbons (Fsp3)
0.97
H-bond donors
5
H-bond acceptors
14
Rotatable bonds
7
TPSA (Ų)
180.1 computed here · PubChem 180
Formal charge
0
XLogP3
4 PubChem
Complexity
1150 PubChem
Stereocenters
18 definedCIP: C3: R · C7: R · C9: S · C11: R · C13: R · C17: S · C19: S · C22: S · C24: R · C26: S · C28: R · C31: R
Double-bond geometry
None specified
Point group
C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)

Elemental analysis

  • C60.94%
  • H9.69%
  • N3.74%
  • O25.63%

Isotope pattern

100%748.50943%749.51212%750.5152.3%751.517752.520

Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.

Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.

Predicted

log P
1.9 Crippen (Wildman and Crippen 1999)
log S (water solubility)
-5.22 ESOL (Delaney 2004), log mol/L
Synthetic accessibility
6.13 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

  • Molecular weight ≤ 500: 749
  • log P ≤ 5 (Crippen): 1.9
  • H-bond donors ≤ 5: 5
  • H-bond acceptors ≤ 10: 14

Breaks 2 of the four rules.

¹³C NMR shifts, predicted

Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.

Safety

Danger

Most widely reported: 122 company reports to ECHA. Source [2].

  • Harmful or irritant
  • Health hazard
  • Environmental hazard
  • H317May cause an allergic skin reaction (97.5% of reports)
  • H334May cause allergy or asthma symptoms or breathing difficulties if inhaled (96.7% of reports)
  • H372Causes damage to organs through prolonged or repeated exposure (28.7% of reports)
  • H400Very toxic to aquatic life (29.5% of reports)
  • H410Very toxic to aquatic life with long lasting effects (30.3% of reports)

Precautionary statements: P233, P260, P261, P264, P270, P271, P272, P273, P280, P284, P302+P352, P304+P340, P319, P321, P333+P317, P342+P316, P362+P364, P391, P403, P501

Storage

  • Store in tight container as defined in the usp-nf. This material should be handled and stored per label instructions to ensure product integrity.[1]
  • Store in tight, light-resistant container as defined in the usp-nf. This material should be handled and stored per label instructions to ensure product integrity. Store in a freezer.[1]
  • Commercially available azithromycin 250- or 500-mg tablets should be stored at 15-30 °C.[1]
  • Azithromycin powder in single-dose packets for oral suspension should be stored at 5-30 °C. Following reconstitution, the entire contents of the single-dose packet should be ingested immediately.10 Azithromycin powder for extended-release oral suspension should be stored at 30 °C or lower. Following reconstitution, azithromycin single-dose extended-release oral suspension should be stored in the original bottle at 25 °C but may be exposed to 15-30 °C. The reconstituted suspension should be consumed within 12 hours.[1]

Safety data sheets on the supplier’s page: LGC Standards, CymitQuimica, MuseChem.

Always read the supplier’s safety data sheet before working with it.

Spectra

Experimental spectra held by these sources; each link opens the source's own record.

Literature

Reading PubChem, OpenAlex and GSRS…

Bioactivity

Reading ChEMBL…

References

  1. [1]Hazardous Substances Data Bank (HSDB) · Public domain (US NLM) · via PubChem · retrieved 2026-10-14
  2. [2]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
  3. [3]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
  4. [4]NIST Mass Spectrometry Data Center · Linked only · via PubChem · retrieved 2026-10-14
  5. [5]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
  6. [6]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
  7. [7]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
  8. ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
  9. ·Literature on PubChem

Data last updated 2026-10-14.