azithromycin

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

thumb|Azithromycin pills in Europe, with brand name Sumamed. Azithromycin, sold under the brand names Zithromax (in oral form) and Azasite (as an eye drop), is an antibiotic medication used to treat several bacterial infections. These include middle ear infections, strep throat, pneumonia, traveler's diarrhea, sexually transmitted infection, and certain other intestinal infections. Along with other medications, it may also be used for malaria. It is administered by mouth, into a vein, or as topical treatment for the eye.

AI overview

Azithromycin is an antibiotic medication sold under brand names like Zithromax that doctors prescribe to treat various bacterial infections, including strep throat, pneumonia, ear infections, and certain sexually transmitted infections. It can be taken by mouth, injected into a vein, or applied directly to the eye, and is sometimes used alongside other drugs to treat malaria.

AI-generated from the Wikipedia summary — may 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

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

Mass: 748.509

Show 4 more facts

chemical formula: C₃₈H₇₂N₂O₁₂
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
Commons category: Azithromycin

Sources (10)

via Wikidata · CC0

~27 min read

Article

19 sections

Contents

Medical uses
Bacterial susceptibility
Pregnancy and breastfeeding
Airway diseases
Adverse effects
Interactions
Colchicine
Drugs metabolized by CYP3A4
Pharmacology
Mechanism of action
Pharmacokinetics
History
Society and culture
Available forms
Usage
Brand names
Research
References
External links

{{Infobox drug | Watchedfields = changed | verifiedrevid = 458267362 | image = Azithromycin.svg | image_class = skin-invert-image | alt = | image2 = Azithromycin_3d_structure.png | image_class2 = bg-transparent | alt2 =