آزیترومایسین

Also known as Sumamed, XZ-450, Sunamed, ZMax, CP-62993, Zithromax, Azimakrol, Azitromin

ترکیب شیمیایی

OverviewAI-generated

Azithromycin is a chemical compound with the formula C₃₈H₇₂N₂O₁₂. It has a mass of 748.509 and a weight of 749.0. The substance possesses a charge of 0 and an xlogp value of 4. Its topological polar surface area is 180, with 5 hydrogen bond donors and 14 hydrogen bond acceptors.

The compound is associated with a Commons category titled "Azithromycin" and is referenced by 304 other encyclopedia articles. A search for azithromycin in PubMed yields a count of 15644.

Synthesized by Vinony from 15 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Key facts

Drug.IUPAC_name: (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-15-oxo-11-{[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy}-1-oxa-6-azacyclopentadec-13-yl 2,6-dideoxy-3-C,3-O-dimethyl-α-L-ribo-hexopyranoside
Drug.C: 38
Drug.H: 72
Drug.N: 2
Drug.O: 12
Drug.SMILES: CN(C)[C@H]3C[C@@H](C)O[C@@H](O[C@@H]2[C@@H](C)[C@H](O[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1)[C@@H](C)C(=O)O[C@H](CC)[C@@](C)(O)[C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@]2(C)O)[C@@H]3O
Drug.StdInChI: 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
Drug.StdInChIKey: MQTOSJVFKKJCRP-BICOPXKESA-N
Drug.Watchedfields: changed
Drug.verifiedrevid: 458267362
Drug.image: Azithromycin.svg
Drug.image_class: skin-invert-image
Drug.image2: Azithromycin_3d_structure.png
Drug.image_class2: bg-transparent
Drug.tradename: Sumamed, Hemomicin, Zithromax, others
Drug.MedlinePlus: a697037
Drug.DailyMedID: Azithromycin
Drug.pregnancy_AU: B1

via Wikipedia infobox

Chemical data

Formula: C38H72N2O12
Molecular weight: 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
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
InChIKey: MQTOSJVFKKJCRP-BICOPXKESA-N
XLogP: 4
Polar surface area: 180 Å²
H-bond donors: 5
H-bond acceptors: 14
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1991
Admin. routes: oral, parenteral, topical
Indications: urethritis, chronic obstructive pulmonary disease, infection, Otitis media

via ChEMBL · EBI

Research

15,644 papers

Azithromycin: The First Broad-spectrum Therapeutic.European journal of medicinal chemistry · 2020
Azithromycin.Profiles of drug substances, excipients, and related methodology · 2014
Azithromycin clinical pharmacokinetics.Clinical pharmacokinetics · 1993
Azithromycin.Current problems in dermatology · 1996
Should we still use azithromycin for gonorrhoea treatment?Sexual health · 2019

via PubMed

Wikidata facts

Subclass of: alkaloid
Mass: 748.509
Manufacturer: Pfizer
Has use: medication

Show 8 more facts

significant drug interaction: digoxin
chemical formula: C₃₈H₇₂N₂O₁₂
medical condition treated: COVID-19
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
subject has role: protein synthesis inhibitor
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
Commons category: Azithromycin
legal status (medicine): boxed warning