Compound: clarithromycin
SMILES: O=C1O[C@@H]([C@@](O)([C@H](O)[C@H](C(=O)[C@H](C)C[C@]([C@@H]([C@H]([C@@H]([C@H]1C)O[C@@H]2O[C@H]([C@H](O)[C@@](C2)(OC)C)C)C)O[C@@H]3O[C@@H](C[C@@H]([C@H]3O)N(C)C)C)(OC)C)C)C)CC
InChIKey: AGOYDEPGAOXOCK-KCBOHYOISA-N
Synonyms: clarithromycin, 81103-11-9, Biaxin, 6-O-Methylerythromycin, Klaricid, Clarithromycine, Erythromycin, 6-O-methyl-, 6-O-Methylerythromycin a, Macladin, Klacid, Veclam, Abbott-56268, Zeclar, Mavid, Naxy, Claritromicina, Cyllind, Clarithromycinum, TE-031, Biaxin XL, A-56268, Clarithromycin identity, Clarosip, DTXSID3022829, Klaricid XL, TE031, Clarithromycin extended release, NSC-758704, H1250JIK0A, CHEBI:3732, DTXCID40820062, A56268, (3R,4S,5S,6R,7R,9R,11R,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-oxacyclotetradecane-2,10-dione, Clarithromycin [USAN:USP:INN:BAN:JAN], Clarithromycin (USAN:USP:INN:BAN:JAN), Klaricid adult, Klaricid paed, Mycifor xl, Xetinin xl, Clarie xl, Febzin xl, NSC643733, Biaxin Xl Pac, Klaricid i.v., (3R,4S,5S,6R,7R,9R,11R,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-oxacyclotetradecane-2,10-dione, Klaricid 500, TE 031, RefChem:5694, Clarithromycin 500 mg, A 56268, J01FA09, (2R,3S,4S,5R,6R,8R,10R,11R,12S,13R)-5-(3,4,6-Trideoxy-3-dimethylamino-beta-D-xylo-hexopyranosyloxy)-3-(2,6-dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyloxy)-11,12-dihydroxy-6-methoxy-2,4,6,8,10,12-hexamethyl-9-oxopentadecan-13-olide, 617-200-4, 658-034-2, Clathromycin, Clarith, Kofron, MFCD00865140, (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-14-ethyl-12,13-dihydroxy-4-(((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-7-methoxy-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione, C38H69NO13, Abbotic, Astromen, Bicrolid, Clacine, Clambiotic, Claribid, Claricide, Claridar, Claripen, Fromilid, Heliclar, Klaciped, Mabicrol, Clacee, Clacid, Clarem, Crixan, Cyllid, Klabax, Klarid, Klarin, Maclar, Helas, Adel, Biaxin filmtab, Klax, Biaxin HP, Biaxin xl filmtab, Klaricid Pediatric, thyloxacyclotetradecane-2,10-dione, 116836-41-0, DRG-0099, Klaricid H.P., (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-14-ethyl-12,13-dihydroxy-4-(((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-7-methoxy-3,5,7,9,11,13-hexame, (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-14-ethyl-12,13-dihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydropyran-2-yl]oxy-7-methoxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione, CTY, SMR000466382, Clarithromycine [INN-French], Clarithromycinum [INN-Latin], Claritromicina [INN-Spanish], CAS-81103-11-9, SR-05000001992, clarithromycina, UNII-H1250JIK0A, Resclar, CCRIS 8833, Klaricid;, Macladin;, Cyllind;, Biaxin;, Klacid;, Veclam;, HSDB 8055, Mavid;Naxy;, Clarithromycin CRS, NCGC00095117-01, Biaxin (TN), Clarithromycin - EP, Clarithromycin-13CD3, Spectrum_000089, CPD000466382, SpecPlus_000559, 6-O-methyl erythromycin, O(6)-methylerythromycin, Spectrum2_001668, Spectrum3_001667, Spectrum4_000629, Spectrum5_001729, GlyTouCan:G47274QG, 6-0-methylerythromycin A, Clarithromycin 100 microg/mL in Acetonitrile, CLARITHROMYCIN [MI], CHEMBL1741, CLARITHROMYCIN [INN], CLARITHROMYCIN [JAN], SCHEMBL38125, BSPBio_003453, KBioGR_001218, KBioSS_000509, MLS000759516, MLS001201751, MLS001424066, BIDD:GT0200, CLARITHROMYCIN [VANDF], DivK1c_006655, SPECTRUM1504231, SPBio_001855, CLARITHROMYCIN [MART.], Lactoferrin B & Clarithromycin, Lactoferrin H & Clarithromycin, orb1308632, orb3139464, CLARITHROMYCIN [USP-RS], CLARITHROMYCIN [WHO-DD], Clarithromycin (Biaxin, Klacid), Clarithromycin & Interleukin-12, CLM & IL-12, GTPL10903, KBio1_001599, KBio2_000509, KBio2_003077, KBio2_005645, KBio3_002673, ANX-015, MSK7814, SDP-015, Clarithromycin (JP18/USP/INN), Clarithromycin, >=95% (HPLC), Clarithromycin, >=98% (HPLC), HMS1922H09, HMS2051G18, HMS2090O11, HMS2094M05, HMS2231A08, HMS3715J17, Pharmakon1600-01504231, (3R,4S,5S,6R,7R,9R,11R,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-oxacyclotetradecane-2,10-dion, G47274QG, CLARITHROMYCIN [ORANGE BOOK], Tox21_111429, Tox21_202903, BDBM50404044, CCG-39086, CLARITHROMYCIN [EP MONOGRAPH], CLARITHROMYCIN [USP IMPURITY], LMPK04000014, MSK7814-100M, NSC758704, s2555, CLARITHROMYCIN [USP MONOGRAPH], AKOS015894242, MSK7814-1000M, PREVPAC COMPONENT CLARITHROMYCIN, AC20469, AC72406, CS-2576, DB01211, NC00140, NSC 758704, CLARITHROMYCIN IDENTITY [USP-RS], NCGC00178054-01, NCGC00178054-06, NCGC00260449-01, AC171875, HY-17508, SY077491, Clarithromycin for peak identification CRS, SBI-0206716.P001, C2220, NS00098550, C06912, Clarithromycin Solution in Methanol, 100ug/mL, D00276, F14975, AB00053394-10, AB00053394-12, AB00053394-13, AB00053394_14, AB00053394_15, Clarithromycin Solution in Methanol, 1000ug/mL, Q118551, SR-05000001992-1, SR-05000001992-2, BRD-K49668410-001-07-1, BRD-K49668410-001-16-2, BRD-K49668410-001-18-8, Z1515385076, Clarithromycin, European Pharmacopoeia (EP) Reference Standard, Clarithromycin, United States Pharmacopeia (USP) Reference Standard, Clarithromycin Identity, United States Pharmacopeia (USP) Reference Standard, Clarithromycin for peak identification, European Pharmacopoeia (EP) Reference Standard, Clarithromycin, Pharmaceutical Secondary Standard; Certified Reference Material, (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-((2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)-14-ethyl-12,13-dihydroxy-4-((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yloxy)-7-methoxy-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione, (3R,4S,5S,6R,7R,9R,11R,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, (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-14-ethyl-12,13-dihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy}-7-methoxy-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione (non-preferred name), (3R,4S,5S,6R,7R,9R,11S, 12R,13S,14S)-6-{[(2S,3R,4S,6R)- 4-dimethylamino-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-12,13-dihydroxy- 4-{[(2R,4S,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
Theoretical properties:
molecular_formula: C38H69NO13
molecular_weight: 748.0 g/mol
exact_mass: 747.47689126 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 4
hydrogen_bond_acceptor_count: 14
rotatable_bond_count: 8
heavy_atom_count: 52
topological_polar_surface_area: 183 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Colorless needles from chloroform + diisopropyl ether (1:2) ... Also reported as crystals from ethanol
color: Colorless needles from chloroform + diisopropyl ether (1:2) ... Also reported as crystals from ethanol
Descriptions:
pubchem: Clarithromycin can cause developmental toxicity according to state or federal government labeling requirements.
chebi: The 6-<em>O</em>-methyl ether of erythromycin A, clarithromycin is a macrolide antibiotic used in the treatment of respiratory-tract, skin and soft-tissue infections. It is also used to eradicate <em>Helicobacter pylori</em> in the treatment of peptic ulcer disease. It prevents bacteria from growing by interfering with their protein synthesis.
chembl: CLARITHROMYCIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Clarithromycin, sold under the brand name Biaxin among others, is an antibiotic used to treat various bacterial infections. This includes strep throat, pneumonia, skin infections, H. pylori infection, and Lyme disease. Clarithromycin can be taken by mouth as a tablet or liquid or can be infused intravenously.
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 slowing down bacterial protein synthesis. 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.
Clarithromycin was developed in 1980 and approved for medical use in 1990. It is on the World Health Organization's List of Essential Medicines. Clarithromycin is available as a generic medication. It is made from erythromycin and is chemically known as 6-O-methylerythromycin.