Description
Tetracycline is an antibiotic produced by various Streptomyces such as Str. viridifaciens BL-567201 and Str. aureofacies NRRL 2209. It has antibacterial and mycobacterial activity, and has cross-resistance with oxytetracycline and chlortetracycline. Human serum does not affect its antibacterial activity. It has the effect of inhibiting large viruses and the main gram. It is widely used in clinics to treat chlamydia, rickettsia, mycoplasma and bacterial infections.
Synonyms
Oxytetracycline EP Impurity B; (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; Abramycin; Achromycin; (-)-Tetracycline; 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)-; 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-(4α,4aα,5aα,6β,12aα)]-; NSC 108579; Dispatetrin; Economycin; Biocycline; Cytome; Limecycline; Medocycline; Veracin; Oxytetracycline Dihydrate EP Impurity B; Oxytetracycline Hydrochloride EP Impurity B
IUPAC Name
(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
Molecular Formula
C22H24N2O8
Canonical SMILES
O=C(N)C=1C(=O)C2(O)C(O)=C3C(=O)C=4C(O)=CC=CC4C(O)(C)C3CC2C(C1O)N(C)C
InChI
InChI=1S/C22H24N2O8/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28/h4-6,9-10,15,25,27-28,31-32H,7H2,1-3H3,(H2,23,30)/t9-,10-,15-,21+,22-/m0/s1
InChIKey
OFVLGDICTFRJMM-WESIUVDSSA-N
Boiling Point
790.6±60.0°C at 760 mmHg
Melting Point
170-173°C(dec.)
Solubility
Soluble in ethanol, methanol, DMF or DMSO. Limited water solubility.
Appearance
Yellow Crystal
Application
Antibiotics, Tetracycline; protein synthesis inhibitors
Toxicity
LD50 = 808mg/kg (oral, mice).