Clarithromycin

Clarithromycin
Clinical data
Trade names	Biaxin, others
Other names	6-O-methylerythromycin A
AHFS/Drugs.com	Monograph
MedlinePlus	a692005
License data	US DailyMed: Clarithromycin;
Pregnancy; category	AU: B3; ;
Routes of; administration	By mouth, intravenous
Drug class	Macrolides
ATC code	J01FA09 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); US: WARNINGRx-only; EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	50%
Protein binding	low binding
Metabolism	Liver
Elimination half-life	3–4 h
Identifiers
	IUPAC name (3R,4S,5S,6R,7R,9R,11S,12R,13S,14R)-6-{[(2S,3R,4S,6R) -4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy} -14-ethyl-12,13-dihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy -4-methoxy-4,6-dimethyloxan-2-yl]oxy}-7 -methoxy-3,5,7,9,11,13-hexamethyl -1-oxacyclotetradecane-2,10-dione;
CAS Number	81103-11-9 ;
PubChem CID	84029;
DrugBank	DB01211 ;
ChemSpider	10342604 ;
UNII	H1250JIK0A;
KEGG	D00276 ;
ChEMBL	ChEMBL1741 ;
CompTox Dashboard (EPA)	DTXSID3022829 ;
ECHA InfoCard	100.119.644
Chemical and physical data
Formula	C38H69NO13
Molar mass	747.964 g·mol−1
3D model (JSmol)	Interactive image;
	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;
	InChI InChI=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 ; Key:AGOYDEPGAOXOCK-KCBOHYOISA-N ;
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Clarithromycin, sold under the brand name Biaxin among others, is an antibiotic used to treat various bacterial infections.^[3] This includes strep throat, pneumonia, skin infections, H. pylori infection, and Lyme disease, among others.^[3] Clarithromycin can be taken by mouth as a tablet or liquid or can be infused intravenously.^[3]

Common side effects include nausea, vomiting, headaches, and diarrhea.^[3] Severe allergic reactions are rare.^[3] Liver problems have been reported.^[3] It may cause harm if taken during pregnancy.^[3] It is in the macrolide class and works by slowing down bacterial protein synthesis.^[3] 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.^[4]

Clarithromycin was developed in 1980 and approved for medical use in 1990.^[5]^[6] It is on the World Health Organization's List of Essential Medicines.^[7] Clarithromycin is available as a generic medication.^[3] It is made from erythromycin and is chemically known as 6-O-methylerythromycin.^[8]

^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
^ "Active substance: clarithromycin" (PDF). List of nationally authorised medicinal products. European Medicines Agency. 10 December 2020.
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ "Clarithromycin". The American Society of Health-System Pharmacists. Archived from the original on 3 September 2015. Retrieved 4 September 2015.
^ Mommersteeg MC, Nieuwenburg SA, Wolters LM, Roovers BH, van Vuuren HA, Verhaar AP, et al. (November 2023). "The use of non-invasive stool tests for verification of Helicobacter pylori eradication and clarithromycin resistance". United European Gastroenterol J. 11 (9): e894-903. doi:10.1002/ueg2.12473. PMC 10637120. PMID 37854002.
^ Greenwood D (2008). Antimicrobial drugs : chronicle of a twentieth century medical triumph (1 ed.). Oxford: Oxford University Press. p. 239. ISBN 978-0-19-953484-5. Archived from the original on 5 March 2016.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 498. ISBN 978-3-527-60749-5.
^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
^ Kirst HA (2012). Macrolide Antibiotics (2 ed.). Basel: Birkhäuser Basel. p. 53. ISBN 978-3-0348-8105-0. Archived from the original on 5 March 2016.

[FDA-AllBoxedWarnings-1] "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.

[List_of_nationally_authorised_medicinal_products-2020-2] "Active substance: clarithromycin" (PDF). List of nationally authorised medicinal products. European Medicines Agency. 10 December 2020.

[AHFS2015-3] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ "Clarithromycin". The American Society of Health-System Pharmacists. Archived from the original on 3 September 2015. Retrieved 4 September 2015.

[4] Mommersteeg MC, Nieuwenburg SA, Wolters LM, Roovers BH, van Vuuren HA, Verhaar AP, et al. (November 2023). "The use of non-invasive stool tests for verification of Helicobacter pylori eradication and clarithromycin resistance". United European Gastroenterol J. 11 (9): e894-903. doi:10.1002/ueg2.12473. PMC 10637120. PMID 37854002.

[Greenwood-2008-5] Greenwood D (2008). Antimicrobial drugs : chronicle of a twentieth century medical triumph (1 ed.). Oxford: Oxford University Press. p. 239. ISBN 978-0-19-953484-5. Archived from the original on 5 March 2016.

[Fischer-2006-6] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 498. ISBN 978-3-527-60749-5.

[WHO-2019-7] World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

[Kirst-2012-8] Kirst HA (2012). Macrolide Antibiotics (2 ed.). Basel: Birkhäuser Basel. p. 53. ISBN 978-3-0348-8105-0. Archived from the original on 5 March 2016.

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