Chemical Component Summary

NameCLARITHROMYCIN
Identifiers(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-dimethylamino-3-hydroxy-6-methyl-oxan-2-yl]oxy-14-ethyl-12,13-dihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyl-oxan-2-yl]oxy-7-methoxy-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione
FormulaC38 H69 N O13
Molecular Weight747.953
TypeNON-POLYMER
Isomeric SMILESCC[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
InChIInChI=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
InChIKeyAGOYDEPGAOXOCK-KCBOHYOISA-N

Chemical Details

Formal Charge0
Atom Count121
Chiral Atom Count18
Bond Count123
Aromatic Bond Count0

Drug Info: DrugBank

DrugBank IDDB01211 
NameClarithromycin
Groups approved
DescriptionClarithromycin, a semisynthetic macrolide antibiotic derived from erythromycin, inhibits bacterial protein synthesis by binding to the bacterial 50S ribosomal subunit. Binding inhibits peptidyl transferase activity and interferes with amino acid translocation during the translation and protein assembly process. Clarithromycin may be bacteriostatic or bactericidal depending on the organism and drug concentration.
Synonyms
  • Clarithromycinum
  • Claritromicina
  • Clarithromycina
  • Clarithromycine
  • CLA
Brand Names
  • Mylan-clarithromycin
  • Clarithromycin extended release
  • Prevpac
  • Apo-clarithromycin
  • Teva-clarithromycin
IndicationAn alternative medication for the treatment of acute otitis media caused by <i>H. influenzae, M. catarrhalis, or S. pneumoniae</i> in patients with a history of type I penicillin hypersensitivity. Also for the treatment of pharyngitis and tonsillitis caused by susceptible <i>Streptococcus pyogenes</i>, as well as respiratory tract infections including acute maxillary sinusitis, acute bacterial exacerbations of chronic bronchitis, mild to moderate community-acquired pneuomia, Legionnaires' disease, and pertussis. Other indications include treatment of uncomplicated skin or skin structure infections, helicobacter pylori infection, duodenal ulcer disease, bartonella infections, early Lyme disease, and encephalitis caused by <i>Toxoplasma gondii</i> (in HIV infected patients in conjunction with pyrimethamine). Clarithromycin may also decrease the incidence of cryptosporidiosis, prevent the occurence of α-hemolytic (viridans group) streptococcal endocarditis, as well as serve as a primary prevention for <i>Mycobacterium avium</i> complex (MAC) bacteremia or disseminated infections (in adults, adolescents, and children with advanced HIV infection). Clarithromycin is indicated in combination with [vonoprazan] and [amoxicillin] as co-packaged triple therapy to treat _Helicobacter pylori_ (_H. pylori_) infection in adults.[L41695]
Categories
  • Alimentary Tract and Metabolism
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterials for Systemic Use
  • Antiinfectives for Systemic Use
ATC-Code
  • A02BD12
  • A02BD14
  • A02BD07
  • A02BD04
  • A02BD09
CAS number81103-11-9

Drug Targets

NameTarget SequencePharmacological ActionActions
50S ribosomal protein L10MALNLQDKQAIVAEVSEVAKGALSAVVADSRGVTVDKMTELRKAGREAGV...unknowninhibitor
Potassium voltage-gated channel subfamily H member 2MPVRRGHVAPQNTFLDTIIRKFEGQSRKFIIANARVENCAVIYCNDGFCE...unknown
Solute carrier organic anion transporter family member 1B1MDQNQHLNKTAEAQPSENKKTRYCNGLKMFLAALSLSFIAKTLGAIIMKS...unknown
Solute carrier organic anion transporter family member 1B3MDQHQHLNKTAESASSEKKKTRRCNGFKMFLAALSFSYIAKALGGIIMKI...unknown
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate,inhibitor
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 84029
ChEMBL CHEMBL1741
ChEBI CHEBI:3732
COD 2018369, 2018622, 2105812, 2001652