Clarithromycin

Clarithromycin

Clinical data
Trade names	Biaxin
AHFS/Drugs.com	Monograph
MedlinePlus	a692005
Pregnancy category	C (USA) B3 (Aus)
Routes of administration	by mouth, intravenous
ATC code	J01FA09 (WHO)
Legal status
Legal status	prescription only
Pharmacokinetic data
Bioavailability	50%
Protein binding	low binding
Metabolism	hepatic
Biological 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 Y
PubChem (CID)	5284534
DrugBank	DB01211 Y
ChemSpider	10342604 N
UNII	H1250JIK0A Y
KEGG	D00276 Y
ChEMBL	CHEMBL1741 N
ECHA InfoCard	100.119.644
Chemical and physical data
Formula	C38H69NO13
Molar mass	747.953 g/mol
3D model (Jmol)	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 N Key:AGOYDEPGAOXOCK-KCBOHYOISA-N N
NY (what is this?)

Clarithromycin, sold under the brand name Biaxin, is an antibiotic used to treat various bacterial infections. This includes strep throat, pneumonia, skin infections, H. pylori infection, and Lyme disease, among others. Clarithromycin can be taken by mouth as a pill or liquid.

Common side effects include nausea, vomiting, headaches, and diarrhea. Severe allergic reactions are rare. Liver problems have been reported. It may cause harm if taken during pregnancy. It is in the macrolide class and works by decreasing protein production of some bacteria.

Clarithromycin was developed in 1980. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. Clarithromycin is available as a generic medication. The wholesale cost in the developing world is between 0.13 and 0.79 USD per dose. In the United States it is moderately expensive at 50 to 100 USD for a course of treatment. It is made from erythromycin and is chemically known as 6-O-methylerythromycin.

Clarithromycin is primarily used to treat a number of bacterial infections including: pneumonia, Helicobacter pylori and as an alternative to penicillin in strep throat. Other uses include: cat scratch disease and other infections due to bartonella, cryptosporidiosis, as a second line agent in Lyme disease and toxoplasmosis. It may also be used to prevent bacterial endocarditis in those who cannot take penicillin. It is effective against upper and lower respiratory tract infections, skin and soft tissue infections and helicobacter pylori infections associated with duodenal ulcers.