Compound: azithromycin
SMILES: O=C1O[C@@H]([C@@](O)([C@H](O)[C@H](N(C[C@@H](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)(O)C)C)C)C)C)CC
InChIKey: MQTOSJVFKKJCRP-BICOPXKESA-N
Synonyms: azithromycin, Zithromax, 83905-01-5, Hemomycin, Azithromycine, Azasite, Azithromycinum, Zitromax, Azenil, aziromycin, Azitrocin, Azitromicina, Aruzilina, Azithrocin, azithromycin anhydrous, Macrozit, Trozocina, Xithrone, Zithromac, Zythromax, Aziwin, DuraSite, CP 62993, Anhydrous azithromycin, Azyter, J2KLZ20U1M, XZ-450, DTXSID8030760, XZ 405, XZ 450, NSC-758625, Azithromycin (as dihydrate), CP-62,993, CHEBI:2955, DTXCID6010760, Azadose, Ultreon, N-Methyl-11-aza-10-deoxo-10-dihydroerythromycin A, NSC643732, 1-Oxa-6-azacyclopentadecan-15-one, 13-((2,6-dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl)oxy)-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-11-((3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl)oxy)-, (2R-(2R*,3S*,4R*,5R*,8R*,10R*,11R*,12S*,13S*,14R*))-, Clamelle, Sunamed, (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl)oxy)-2-ethyl-3,4,10-trihydroxy-13-(((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl)oxy)-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one, (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-((2S,3R,4S,6R)-4-dimethylamino-3-hydroxy-6-methyloxan-2-yl)oxy-2-ethyl-3,4,10-trihydroxy-13-((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl)oxy-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one, (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-[(2S,3R,4S,6R)-4-dimethylamino-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one, (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-3,4,10-trihydroxy-13-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one, Dihydrate, Azithromycin, RefChem:6386, Monohydrate, Azithromycin, F94OW58Y8V, J01FA10, S01AA26, CP62993, N-methyl-11-aza-10-deoxy-10-dihydroerythromycin A, (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-13-((2,6-Dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl)oxy)-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-11-((3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl)oxy)-1-oxa-6-azacyclopentade, Azythromycin, Sumamed, Zmax, Azithromycine [French], Azithromycinum [Latin], CP-62993, (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-2-ethyl-3,4,10-trihydroxy-13-(((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one, 9-Deoxo-9a-aza-9a-methyl-9a-homoerythromycin A, C38H72N2O12, (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one, Toraseptol, Azithromycin (INN), NCGC00090753-01, Aritromicina, Mixoterin, Zithrax, Zitrotek, Aziwok, Aztrin, Setron, Zitrim, Tobil, Zifin, Zeto, Zmas, MFCD00873574, Zithromax IV, AZITHROMYCIN [INN], Azithromycin hydrate, (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-15-oxo-11-{[3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl]oxy}-1-oxa-6-azacyclopentadecan-13-yl 2,6-dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranoside, Z-Pak, Aritromicina [Spanish], Azitromicine, Trulimax, DRG-0104, yl-1-oxa-6-azacyclopentadecan-15-one, (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydropyran-2-yl]oxy-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one, SMR000471864, ZIT, Azithromycin (Zithromax), CAS-83905-01-5, CCRIS 1961, HSDB 7205, Z-Pak (Azithromycin), Azithromycin (anhydrous), SR-05000002067, UNII-J2KLZ20U1M, BRN 5387583, Azithramycine, Zithromycin, Azifast, Azigram, Azimakrol, Azitromin, Zentavion, etrahydro-2H-pyran-2-yl)oxy)-3,5,6,8,10,12,14-heptameth, Azitrocin;, Ribotrex;, Azithromycin [USAN:INN:BAN], Sumamed;, Azithromycin (AIDS Initiative), Spiramycin CRS, Trezid;, Azithromycin CRS, Zmax SR, (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-2-ethyl-3,4,10-trihydroxy-13-(((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethylt, Azasite (TN), Zitromax Avium 600, Azitromicina [Spanish], Spectrum_000307, DCH3, Spectrum2_001582, Spectrum3_000653, Spectrum4_000186, Spectrum5_001867, AZITHROMYCIN [MI], GlyTouCan:G62804SW, CHEMBL529, AZITHROMYCIN [HSDB], EC 617-500-5, Azithromycin [EP monograph], SCHEMBL23481, BSPBio_002285, KBioGR_000731, KBioSS_000787, (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-13-((2,6-Dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl)oxy)-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-11-((3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl)oxy)-1-oxa-6-azacyclopentadecan-15-one, MLS001055353, MLS001066331, MLS001201763, MLS001304005, MLS001332499, MLS001332500, AZITHROMYCIN [WHO-DD], BIDD:GT0792, DivK1c_000233, SPECTRUM1503679, SPBio_001544, GTPL6510, orb1300799, Azithromycin, analytical standard, HMS500L15, KBio1_000233, KBio2_000787, KBio2_003355, KBio2_005923, KBio3_001505, MSK7816, NINDS_000233, HMS1922G12, HMS2094M11, HMS2232M10, HMS3259D10, ALBB-038592, G62804SW, AZITHROMYCIN [USP MONOGRAPH], Tox21_111008, Tox21_201011, Azithromycin & Tumor Necrosis Factor, BDBM50373918, CCG-39360, HB4336, MSK7816-100M, AKOS015895044, AD29657, DB00207, NC00712, NSC 758625, IDI1_000233, NCGC00090753-02, NCGC00090753-03, NCGC00090753-04, NCGC00090753-06, NCGC00258564-01, AC-16014, CP62,993, HY-17506, SY077628, First International Standard for Spiramycin, SBI-0206706.P001, Spiramycin 1000 microg/mL in Acetonitrile, A2076, Azithromycin Solution in Methanol, 100ug/mL, CP-62993-3, NS00000204, A-9941, C06838, D07486, N46072, AB00698251-10, AB00698251_11, Q165399, Azithromycin, Antibiotic for Culture Media Use Only, SR-05000002067-1, SR-05000002067-2, BRD-K74501079-001-15-7, BRD-K74501079-001-18-1, Z1558483766, Azithromycin, European Pharmacopoeia (EP) Reference Standard, Azithromycin Identity, United States Pharmacopeia (USP) Reference Standard, (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-((2S,3R,4S,6R)-, Azithromycin for peak identification, European Pharmacopoeia (EP) Reference Standard, Azithromycin for system suitability, European Pharmacopoeia (EP) Reference Standard, (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)-2-ethyl-3,4,10-trihydroxy-13-((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yloxy)-3,5,6,8,10,12,14-heptamethy..., (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-15-oxo-11-{[3,4,6-trideoxy-3-(dimethylamino)-b-D-xylo-hexopyranosyl]oxy}-1-oxa-6-azacyclopentadecan-13-yl 2,6-dideoxy-3-C-methyl-3-O-methyl-a-L-ribo-hexopyranoside, (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)13-((2,6-Dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl)oxy)-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-11-((3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl)oxy)-1-oxa-6-azacyclopentadecan-15-one, [2R-(2R*,3S*,4R*,5R*,8R*,10R*,11R*,12S*,13S*,14R*)]-13-[(2,6-Dideoxy-3-C-methyl-3-O-methyl-.alpha.-L-ribo-hexopyranosyl)oxy]-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-11-[[3,4,6-
Theoretical properties:
molecular_formula: C38H72N2O12
molecular_weight: 749.0 g/mol
exact_mass: 748.50852574 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 5
hydrogen_bond_acceptor_count: 14
rotatable_bond_count: 7
heavy_atom_count: 52
topological_polar_surface_area: 180 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Amorphous solid
color: Amorphous solid
solubility: soluble in ethanol and DSMO, minimally soluble in water
Descriptions:
{"pubchem": "Azithromycin is a macrolide antibiotic useful for the treatment of bacterial infections. It has a role as a xenobiotic, an antibacterial drug and an environmental contaminant. It is a conjugate base of an azithromycin(2+).", "chebi": "A macrolide antibiotic useful for the treatment of bacterial infections.", "chembl": "AZITHROMYCIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Azithromycin, sold under the brand names Zithromax (in oral form) and Azasite (as an eye drop), is an antibiotic medication used to treat several bacterial infections. These include middle ear infections, strep throat, pneumonia, traveler's diarrhea, sexually transmitted infection, and certain other intestinal infections. Along with other medications, it may also be used for malaria. It is administered by mouth, into a vein, or as topical treatment for the eye.\nCommon side effects include nausea, vomiting, diarrhea and upset stomach. An allergic reaction, such as anaphylaxis, or a type of diarrhea caused by Clostridioides difficile is possible. Azithromycin causes QT prolongation that may cause life-threatening arrhythmias such as torsades de pointes. While some studies claim that no harm has been found with use during pregnancy, more recent studies with mice during late pregnancy has shown adverse effects on embryonic testicular and neural development of prenatal azithromycin exposure (PAzE). However, there need to be more well-controlled studies in pregnant women. Its safety during breastfeeding is not confirmed, but it is likely safe. Azithromycin is an azalide, a type of macrolide antibiotic. It works by decreasing the production of protein, thereby stopping bacterial growth.\nAzithromycin was discovered in Croatia in 1980 by the pharmaceutical company Pliva and approved for medical use in 1988. It is on the World Health Organization's List of Essential Medicines. The World Health Organization lists it as an example under \"Macrolides and ketolides\" in its Critically Important Antimicrobials for Human Medicine (designed to help manage antimicrobial resistance). It is available as a generic medication and is sold under many brand names worldwide. In 2023, it was the 64th most commonly prescribed medication in the United States, with more than 10 million prescriptions.\n\n"}