Editing Clarithromycin (section)

{{Short description|Antibiotic medication}}
{{Use dmy dates|date=March 2024}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 457457495
| image = Clarithromycin structure.svg
| image_class = skin-invert-image
| width = 250
| alt = 
| image2 = Clarithromycin-from-xtal-3D-bs-17.png
| image_class2 = bg-transparent
| alt2 =

<!--Clinical data-->
| tradename = Biaxin, others
| Drugs.com = {{drugs.com|monograph|clarithromycin}}
| MedlinePlus = a692005
| DailyMedID = Clarithromycin
| pregnancy_AU = B3
| pregnancy_AU_comment = 
| pregnancy_category= 
| routes_of_administration = [[Oral administration|By mouth]], [[intravenous]]
| class = [[Macrolides]]
| ATC_prefix = J01
| ATC_suffix = FA09

<!--Legal status-->
| legal_AU = S4
| legal_CA          = Rx-only
| legal_CA_comment  = <ref>{{cite web | title=Biaxin BID Product information | website=[[Health Canada]] | date=30 August 2016 | url=https://health-products.canada.ca/dpd-bdpp/info?lang=eng&code=12779 | access-date=16 February 2025}}</ref><ref>{{cite web | title=Biaxin Product information | website=[[Health Canada]] | date=8 April 2016 | url=https://health-products.canada.ca/dpd-bdpp/info?lang=eng&code=18066 | access-date=16 February 2025}}</ref><ref>{{cite web | title=Biaxin XL Product information | website=[[Health Canada]] | date=16 September 2020 | url=https://health-products.canada.ca/dpd-bdpp/info?lang=eng&code=68745 | access-date=16 February 2025}}</ref>
| legal_US = Rx-only
| legal_EU = Rx-only
| legal_EU_comment = <ref name="List of nationally authorised medicinal products-2020">{{cite web | title = Active substance: clarithromycin | work = List of nationally authorised medicinal products | publisher = European Medicines Agency | date = 10 December 2020 | url = https://www.ema.europa.eu/documents/psusa/clarithromycin-list-nationally-authorised-medicinal-products-psusa/00000788/202004_en.pdf }}</ref>
| legal_status = Rx-only

<!--Pharmacokinetic data-->
| bioavailability = 50%
| protein_bound = Low binding
| metabolism = [[Liver]]
| metabolites = 
| elimination_half-life = 3–4 h
| excretion = 

<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 81103-11-9
| PubChem = 84029
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01211
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 10342604
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = H1250JIK0A
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00276
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1741
| synonyms = 6-''O''-Methylerythromycin A

<!--Chemical data-->
| IUPAC_name = (3''R'',4''S'',5''S'',6''R'',7''R'',9''R'',11''S'',12''R'',13''S'',14''R'')-6-<nowiki/>{[(2''S'',3''R'',4''S'',6''R'') -4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy} -14-ethyl-12,13-dihydroxy-4-<nowiki/>{[(2''R'',4''R'',5''S'',6''S'')-5-hydroxy -4-methoxy-4,6-dimethyloxan-2-yl]oxy}-7 -methoxy-3,5,7,9,11,13-hexamethyl -1-oxacyclotetradecane-2,10-dione
| C=38 | H=69 | N=1 | O=13
| SMILES = CC[C@@H]1[C@@]([C@@H]([C@H](C(=O)[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)OC)C)C)O)(C)O
|  StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C38H69NO13/c1-15-26-38(10,45)31(42)21(4)28(40)19(2)17-37(9,47-14)33(52-35-29(41)25(39(11)12)16-20(3)48-35)22(5)30(23(6)34(44)50-26)51-27-18-36(8,46-13)32(43)24(7)49-27/h19-27,29-33,35,41-43,45H,15-18H2,1-14H3/t19-,20-,21+,22+,23-,24+,25+,26-,27+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1
|  StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = AGOYDEPGAOXOCK-KCBOHYOISA-N
}}
<!-- Definition and medical uses -->
'''Clarithromycin''', sold under the brand name '''Biaxin''' among others, is an [[antibiotic]] used to treat various [[bacterial]] infections.<ref name=AHFS2015>{{cite web|title=Clarithromycin|url=https://www.drugs.com/monograph/clarithromycin.html|publisher=The American Society of Health-System Pharmacists|access-date=4 September 2015|url-status=live|archive-url=https://web.archive.org/web/20150903071907/http://www.drugs.com/monograph/clarithromycin.html|archive-date=3 September 2015}}</ref> This includes [[strep throat]], [[pneumonia]], skin infections, ''[[Helicobacter pylori|H. pylori]]'' infection, and [[Lyme disease]], among others.<ref name=AHFS2015/> Clarithromycin can be taken by mouth as a tablet or liquid or can be infused intravenously.<ref name=AHFS2015/>

<!-- Side effects and mechanism -->
Common side effects include nausea, vomiting, headaches, and diarrhea.<ref name=AHFS2015/> Severe [[allergic reaction]]s are rare.<ref name=AHFS2015/> Liver problems have been reported.<ref name=AHFS2015/> It may cause harm if taken during [[pregnancy]].<ref name=AHFS2015/> It is in the [[macrolide]] class and works by slowing down bacterial [[protein synthesis]].<ref name=AHFS2015/> Clarithromycin resistance is already a major challenge to healthcare systems and such resistance is spreading, leading to recommendations to test the susceptibility of pathogenic organisms to the antibiotic before commencing clarithromycin therapy.<ref> {{cite journal | vauthors = Mommersteeg MC, Nieuwenburg SA, Wolters LM, Roovers BH, van Vuuren HA, Verhaar AP, Bruno MJ, Kuipers EJ, Peppelenbosch MP, Spaander MC, Fuhler GM | title =  The use of non-invasive stool tests for verification of Helicobacter pylori eradication and clarithromycin resistance. | journal =  United European Gastroenterol J | volume = 11 | issue = 9 | pages = e894-903| date = November 2023 | pmid = 37854002 | pmc = 10637120 | doi = 10.1002/ueg2.12473 | doi-access = free}}</ref>

<!-- History, society and culture -->
Clarithromycin was developed in 1980 and approved for medical use in 1990.<ref name="Greenwood-2008">{{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=1 |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.ca/books?id=i4_FZHmzjzwC&pg=PA239|archive-date=5 March 2016}}</ref><ref name="Fischer-2006">{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=978-3-527-60749-5 |page=498 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA498 }}</ref> It is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<ref name="WHO-2019">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO | hdl-access=free }}</ref> Clarithromycin is available as a generic medication.<ref name=AHFS2015/> It is made from [[erythromycin]] and is chemically known as 6-O-methylerythromycin.<ref name="Kirst-2012">{{cite book| vauthors = Kirst HA |title=Macrolide Antibiotics|date=2012|publisher=Birkhäuser Basel |location=Basel |isbn=978-3-0348-8105-0 |page=53 |edition=2 |url=https://books.google.com/books?id=8Vn2BwAAQBAJ&pg=PA53 |url-status=live |archive-url= https://web.archive.org/web/20160305031148/https://books.google.ca/books?id=8Vn2BwAAQBAJ&pg=PA53 |archive-date=5 March 2016}}</ref>