Editing Azithromycin (section)

{{Short description|Antibiotic}}
{{Distinguish|Erythromycin}}
{{Use dmy dates|date=June 2024}}
{{cs1 config |name-list-style=vanc |display-authors=6}}
{{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 =

<!-- Clinical data -->
| pronounce = 
| tradename = Zithromax, others<ref name=drugs.comINT/>
| Drugs.com = {{drugs.com|monograph|azithromycin}}
| MedlinePlus = a697037
| DailyMedID = Azithromycin
| pregnancy_AU = B1
| pregnancy_AU_comment =<ref name="Drugs.com pregnancy">{{cite web | title=Azithromycin Use During Pregnancy | website=Drugs.com | date=2 May 2019 | url=https://www.drugs.com/pregnancy/azithromycin.html | access-date=24 December 2019 | archive-date=18 June 2020 | archive-url=https://web.archive.org/web/20200618185520/https://www.drugs.com/pregnancy/azithromycin.html | url-status=live }}</ref>
| pregnancy_category = 
| routes_of_administration = [[Oral administration|By mouth]], [[intravenous therapy|intravenous]], [[Ophthalmic drug administration|eye drop]]s
| class = [[Macrolide antibiotic]]
| ATC_prefix = J01
| ATC_suffix = FA10
| ATC_supplemental = {{ATC|S01|AA26}} {{ATC|J01|RA07}}

<!-- Legal status -->
| legal_AU = S4
| legal_AU_comment = <ref>{{cite web | title=Zithromax azithromycin 500mg (as dihydrate) tablet blister pack (58797) | website=Therapeutic Goods Administration (TGA) | date=12 August 2022 | url=https://www.tga.gov.au/resources/artg/58797 | access-date=26 April 2024}}</ref>
| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F -->
| legal_BR_comment =
| legal_CA = Rx-only
| legal_CA_comment = <ref>{{cite web | title=Zithromax Product information | website=[[Health Canada]] | date=16 January 2013 | url=https://health-products.canada.ca/dpd-bdpp/info?lang=eng&code=43063 | access-date=26 April 2024}}</ref><ref>{{cite web | title=Drug and medical device highlights 2018: Helping you maintain and improve your health | website=[[Health Canada]] | date=14 October 2020 | url=https://www.canada.ca/en/health-canada/services/publications/drugs-health-products/drug-medical-device-highlights-2018.html | access-date=17 April 2024}}</ref>
| legal_DE = <!-- Anlage I, II, III or Unscheduled -->
| legal_DE_comment =
| legal_NZ = <!-- Class A, B, C -->
| legal_NZ_comment =
| legal_UK = POM
| legal_UK_comment = <ref>{{cite web | title=Zithromax Summary of Product Characteristics (SmPC) | website=(emc) | date=5 February 2024 | url=https://www.medicines.org.uk/emc/product/1073/smpc | access-date=26 April 2024}}</ref>
| legal_US = Rx-only
| legal_US_comment = <ref name="Zithromax FDA label" />
| legal_EU = Rx-only
| legal_EU_comment =<ref>{{cite web|url=https://www.ema.europa.eu/en/documents/psusa/azithromycin-list-nationally-authorised-medicinal-products-psusa/00010491/202004_en.pdf|title=List of nationally authorised medicinal products Active substance: azithromycin (systemic use formulations)|publisher=European Medicine Agency|date=14 January 2021|access-date=10 March 2023|url-status=live|archive-url=https://web.archive.org/web/20210818092015/https://www.ema.europa.eu/en/documents/psusa/azithromycin-list-nationally-authorised-medicinal-products-psusa/00010491/202004_en.pdf|archive-date=18 August 2021}}</ref>
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment =
| legal_status = <!-- For countries not listed above -->

<!-- Pharmacokinetic data -->
| bioavailability = 38% for 250 mg capsules
| protein_bound = 
| metabolism = [[Liver]]
| metabolites = 
| onset = 
| elimination_half-life = 68 h
| duration_of_action = 
| excretion = [[Bile duct]]<ref name="Zithromax FDA label" />

<!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 83905-01-5
| CAS_supplemental = 
| PubChem = 55185
| IUPHAR_ligand = 6510
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00207
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10482163
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = J2KLZ20U1M
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07486
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 2955
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 529
| NIAID_ChemDB = 007311
| PDB_ligand = 
| synonyms = 9-deoxy-9α-aza-9α-methyl-9α-homoerythromycin A

<!-- Chemical and physical data -->
| IUPAC_name = (2''R'',3''S'',4''R'',5''R'',8''R'',10''R'',11''R'',12''S'',13''S'',14''R''<nowiki>)-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-15-oxo- 11-{[3,4,6-trideoxy-3-(dimethylamino)-β-</nowiki>D-''xylo''<nowiki>-hexopyranosyl]oxy}-1-oxa-6-azacyclopentadec-13-yl 2,6-dideoxy-3</nowiki>''C''-methyl-3-''O''-methyl-α-L-''ribo''-hexopyranoside
| C=38 | H=72 | N=2 | O=12
| 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
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| 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
| StdInChI_comment = 
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = MQTOSJVFKKJCRP-BICOPXKESA-N
| density = 
| density_notes = 
| melting_point = 
| melting_high = 
| melting_notes = 
| boiling_point = 
| boiling_notes = 
| solubility = 
| sol_units = 
| specific_rotation = 
}}

<!-- Definition and medical uses -->
'''Azithromycin''', sold under the brand names '''Zithromax''' (in oral form) and '''Azasite''' (as an eye drop), is an [[antibiotic]] medication used for the treatment of several [[bacterial infection]]s.<ref name=AHFS2015>{{cite web|title=Azithromycin|url=https://www.drugs.com/monograph/azithromycin.html|publisher=The American Society of Health-System Pharmacists|access-date=1 August 2015|url-status=live|archive-url=https://web.archive.org/web/20150905161757/http://www.drugs.com/monograph/azithromycin.html|archive-date=5 September 2015}}</ref> This includes [[otitis media|middle ear infections]], [[strep throat]], [[pneumonia]], [[traveler's diarrhea]], [[STI]] and certain other [[gastroenteritis|intestinal infections]].<ref name=AHFS2015/> Along with other medications, it may also be used for [[malaria]].<ref name=AHFS2015/> It is [[Drug administration|administered]] [[by mouth]], [[intravenously|into a vein]], or into the [[eye drops|eye]].<ref name=AHFS2015/>

<!-- Side effects and mechanism -->
Common side effects include [[nausea]], vomiting, [[diarrhea]] and upset stomach.<ref name=AHFS2015/> An [[allergic reaction]], such as [[anaphylaxis]], or a type of diarrhea caused by [[Clostridioides difficile infection|''Clostridioides difficile'']] is possible.<ref name=AHFS2015/> Azithromycin causes [[drug-induced QT prolongation|QT prolongation]] that may cause life-threatening arrhythmias such as [[torsades de pointes]].<ref name="pmid27928188">{{cite journal |vauthors=Dunker A, Kolanczyk DM, Maendel CM, Patel AR, Pettit NN |title=Impact of the FDA Warning for Azithromycin and Risk for QT Prolongation on Utilization at an Academic Medical Center |journal=Hosp Pharm |volume=51 |issue=10 |pages=830–833 |date=November 2016 |pmid=27928188 |pmc=5135431 |doi=10.1310/hpj5110-830 }}</ref> While some studies claim that no harm has been found with use during pregnancy,<ref name=AHFS2015/> more recent studies with mice during late pregnancy has shown adverse effects on embryonic testicular and neural development of prenatal azithromycin exposure (PAzE). However, there need to be more well-controlled studies in pregnant women.<ref name="Zithromax FDA label">{{cite web | title=Zithromax- azithromycin dihydrate tablet, film coated; Zithromax- azithromycin dihydrate powder, for suspension | website=DailyMed | date=29 September 2023 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=b749df83-49b0-433e-8a62-589a048dd716 | access-date=26 April 2024}}</ref> Its safety during [[breastfeeding]] is not confirmed, but it is likely safe.<ref name=Breast2015>{{cite web|title=Azithromycin use while Breastfeeding|url=https://www.drugs.com/breastfeeding/azithromycin.html|access-date=4 September 2015|url-status=live|archive-url=https://web.archive.org/web/20150905170054/http://www.drugs.com/breastfeeding/azithromycin.html|archive-date=5 September 2015}}</ref> Azithromycin is an [[azalide]], a type of [[macrolide]] antibiotic.<ref name=AHFS2015/> It works by decreasing the production of protein, thereby stopping bacterial growth.<ref name=AHFS2015/><ref>{{cite web |title=Azithromycin Stops The Growth of Bacteria |url=https://deutschemedz.de/azithromycin/ |access-date=24 December 2017 |language=de |archive-date=12 May 2020 |archive-url=https://web.archive.org/web/20200512060429/https://deutschemedz.de/azithromycin |url-status=live }}</ref>

<!-- Society and culture -->
Azithromycin was discovered in Yugoslavia (present day [[Croatia]]) in 1980 by the pharmaceutical company [[Pliva]] and approved for medical use in 1988.<ref>{{cite book| vauthors = Greenwood D |title=Antimicrobial drugs : chronicle of a twentieth century medical triumph|date=2008|publisher=Oxford University Press|location=Oxford|isbn=978-0-19-953484-5|page=239|edition= 1st |url=https://books.google.com/books?id=i4_FZHmzjzwC&pg=PA239|url-status=live|archive-url=https://web.archive.org/web/20160305044428/https://books.google.com/books?id=i4_FZHmzjzwC&pg=PA239|archive-date=5 March 2016}}</ref><ref name=Fis2006>{{cite book |vauthors=Alapi EM, Fischer J |veditors=Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=Wiley-Vch Verlag GmbH & Co. KGaA |location=Weinheim |isbn=978-3-527-31257-3 |page=498 |chapter=Table of Selected Analogue Classes |chapter-url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA498 |access-date=2 April 2020 |archive-date=14 January 2023 |archive-url=https://web.archive.org/web/20230114140343/https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA498 |url-status=live }}</ref> It is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<ref name="WHO23rd">{{cite book | vauthors = ((World Health Organization)) | title = The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023) | year = 2023 | hdl = 10665/371090 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2023.02 | hdl-access=free }}</ref> The World Health Organization lists it as an example under "Macrolides and ketolides" in its ''Critically Important Antimicrobials for Human Medicine'' (designed to help manage [[antimicrobial resistance]]).<ref>{{cite book | vauthors=((World Health Organization)) | year=2018 | title=Critically important antimicrobials for human medicine | edition=6th revision | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | hdl=10665/312266 | id=License: CC BY-NC-SA 3.0 IGO | isbn=978-92-4-151552-8 | hdl-access=free }}</ref> It is available as a [[generic medication]]<ref name=Ric2015>{{cite book| vauthors = Hamilton R |title=Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition|date=2015|publisher=Jones & Bartlett Learning|isbn=978-1-284-05756-0}}</ref> and is sold under many brand names worldwide.<ref name=drugs.comINT>{{cite web|title=Azithromycin International Brands|url=https://www.drugs.com/international/azithromycin.html|publisher=Drugs.com|access-date=27 February 2017|url-status=live|archive-url=https://web.archive.org/web/20170228085651/https://www.drugs.com/international/azithromycin.html|archive-date=28 February 2017}}</ref> In 2022, it was the 78th most commonly prescribed medication in the United States, with more than 8{{nbsp}}million prescriptions.<ref name="Top 300">{{cite web | title=The Top 300 of 2022 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=30 August 2024 | archive-date=30 August 2024 | archive-url=https://web.archive.org/web/20240830202410/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref name="Azithromycin Drug Usage Statistics">{{cite web | title = Azithromycin Drug Usage Statistics, United States, 2013 - 2022 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Azithromycin | access-date = 30 August 2024 }}</ref>