File:Azithromycin.svg · Wikimedia Commons · See Wikimedia Commons
azithromycin
Sign in to saveAlso 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.
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 Ų
- 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
~27 min read
Encyclopedic overview
19 sectionsContents
- 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 =
| pronounce = | tradename = Sumamed, Hemomicin, Zithromax, others | Drugs.com = | MedlinePlus = a697037 | DailyMedID = Azithromycin | pregnancy_AU = B1 | pregnancy_AU_comment = | pregnancy_category = | routes_of_administration = By mouth, intravenous, eye drops | class = Macrolide antibiotic | ATC_prefix = J01 | ATC_suffix = FA10 | ATC_supplemental =
Excerpted from Wikipedia’s “azithromycin” article, available under the CC BY-SA 4.0 licence.