Compound: tetracycline
SMILES: O=C1c2c(O)cccc2[C@](O)(C)[C@@H]3C1=C(O)[C@]4(O)C(=O)C(=C(O)[C@H]([C@@H]4C3)N(C)C)C(=O)N
InChIKey: OFVLGDICTFRJMM-WESIUVDSSA-N
Synonyms: tetracycline, 60-54-8, Deschlorobiomycin, Tsiklomitsin, Tetraciclina, Tetracyclinum, Sumycin, Abramycin, Ambramycin, Panmycin, Tetracyclin, Tetracyn, Cyclopar, Liquamycin, Omegamycin, Tetrazyklin, Agromicina, Ambramicina, Criseociclina, Purocyclina, Tetradecin, Tetraverine, Tsiklomistsin, Vetacyclinum, Tetrabon, Tetrafil, Cefracycline, Abricycline, Achromycin V, Biocycline, Ciclibion, Copharlan, Cyclomycin, Democracin, Lexacycline, Limecycline, Mericycline, Micycline, Orlycycline, Roviciclina, Solvocin, Tetracycl, Amycin, Veracin, SK-Tetracycline, Tetracycline II, Tetra-Co, Tetracycline I, Bio-tetra, CCRIS 9483, (4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide, Piracaps (base), Centet (base), (4S,4aS,5aS,12aS)-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide, NSC-108579, Cefracycline suspension, Liquamycin (Veterinary), F8VB5M810T, 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, (4S,4aS,5aS,6S,12aS)-, DTXSID7023645, Tetracycline base, CHEBI:27902, Tetracycline (internal use), Supramycin, Vetquamycin-324 (free base), MFCD00151232, (4S,4aS,5aS,6S,12aR)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide, E701, Achromycin (naphthacene derivative), (4S,4aS,5aS,6S,12aS)-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide, T-125, HSDB 3188, 6-Methyl-1,11-dioxy-2-naphthacenecarboxamide, Tetracyclinum [INN-Latin], Tetraciclina [INN-Spanish], Sumycin (TN), Tetracycline & VRC3375, UNII-F8VB5M810T, Economycin, Vetquamycin, Brodspec, Tetracycline (JAN/USP/INN), SR-01000000212, NSC108579, Tetrabid Organon, Ala-Tet, Tetracycline [USP:INN:BAN:JAN], (4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide, 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, (4S-(4alpha,4aalpha,5aalpha,6beta,12aalpha))-, EINECS 200-481-9, 60-54-8 (FREE BASE), Spectrum_001034, Tetracycline (Standard), Prestwick0_000140, Prestwick1_000140, Prestwick2_000140, Prestwick3_000140, Spectrum2_001329, Spectrum3_000565, Spectrum4_000352, Spectrum5_001112, TETRACYCLINE [MI], TETRACYCLINE [INN], TETRACYCLINE [JAN], EC 200-481-9, TETRACYCLINE [HSDB], SCHEMBL3098, TETRACYCLINE [VANDF], BSPBio_000220, BSPBio_001950, KBioGR_000783, KBioSS_001514, TETRACYCLINE [MART.], BIDD:GT0653, DivK1c_000827, Oxytetracycline EP Impurity B, SCHEMBL537050, TETRACYCLINE [WHO-DD], SPBio_001457, SPBio_002159, BPBio1_000242, DTXCID703645, orb1310175, SCHEMBL2116649, SCHEMBL2116661, SCHEMBL21271987, SCHEMBL29349464, SCHEMBL29734343, GTPL10927, HY-A0107R, KBio1_000827, KBio2_001514, KBio2_004082, KBio2_006650, KBio3_001450, Tetracycline - Bio-X trade mark, TETRACYCLINE [GREEN BOOK], NINDS_000827, DTXSID201371250, HMS2090B04, TETRACYCLINE [ORANGE BOOK], Tetracycline, >=98.0% (NT), TETRACYCLINE [EP MONOGRAPH], TETRACYCLINE [USP IMPURITY], 2-NAPHTHACENECARBOXAMIDE, 4-(DIMETHYLAMINO)-1,4,4A,5,5A,6,11,12A-OCTAHYDRO-3,6,10,12,12A-PENTAHYDROXY-6-METHYL-1,11-DIOXO-, (4S-(4.ALPHA.,4A.ALPHA.,5A.ALPHA.,6.BETA.,12A.ALPHA.))-, HY-A0107, PYLERA COMPONENT TETRACYCLINE, RKL10088, TETRACYCLINE [USP MONOGRAPH], Tetracycline, >=88.0% (HPLC), Tox21_300150, BDBM50237605, EBC-12827, s4490, T0912L, AKOS024277860, AKOS026749977, CS-8188, DB00759, Tetracycline dried down 2.5 microg/mL, CAS-60-54-8, IDI1_000827, NCGC00017323-03, NCGC00017323-04, NCGC00017323-05, NCGC00017323-07, NCGC00017323-15, NCGC00017323-16, NCGC00142507-02, NCGC00254063-01, 4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,1 0,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide, BT166207, DA-68063, ST019403, SBI-0051530.P003, LYMECYCLINE IMPURITY H [EP IMPURITY], NS00000577, T3971, C06570, D00201, EN300-374118, AB00053550-04, AB00053550_05, AB00053550_06, Q193045, SR-01000000212-3, Oxytetracycline EP Impurity B; Lymecycline EP Impurity H, Z2144222809, OXYTETRACYCLINE HYDROCHLORIDE IMPURITY B [EP IMPURITY], (4S,4aS,5aS,6S,12aR)-2-carbamoyl-4-(dimethylammonio)-6,10,11,12a-tetrahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracen-1-olate, (4S,6S,12aS,4aS,5aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,1 1-dioxo-4,5,6,12a,4a,5a-hexahydronaphthacene-2-carboxamide
Theoretical properties:
molecular_formula: C22H24N2O8
molecular_weight: 444.4 g/mol
exact_mass: 444.15326573 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 6
hydrogen_bond_acceptor_count: 9
rotatable_bond_count: 2
heavy_atom_count: 32
topological_polar_surface_area: 182 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Tetracycline (internal use) can cause developmental toxicity according to state or federal government labeling requirements.
chebi: A broad-spectrum polyketide antibiotic produced by the <em>Streptomyces genus</em> of actinobacteria.
chembl: TETRACYCLINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Tetracycline, sold under various brand names, is an antibiotic in the tetracyclines family of medications, used to treat a number of infections, including acne, cholera, brucellosis, plague, malaria, and syphilis. It is available in oral and topical formulations.
Common side effects include vomiting, diarrhea, rash, and loss of appetite. Other side effects include poor tooth development if used by children less than eight years of age, kidney problems, and sunburning easily. Use during pregnancy may harm the baby. It works by inhibiting protein synthesis in bacteria.
Tetracycline was patented in 1953 and was approved for prescription use in 1954. It is on the World Health Organization's List of Essential Medicines. Tetracycline is available as a generic medication.  Tetracycline was originally made from bacteria of the genus Streptomyces. The tetracycline name comes from the 4 hydrocarbon rings.