Tetracycline
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Category | Antibiotics |
Catalog number | BBF-03503 |
CAS | 60-54-8 |
Molecular Weight | 444.43 |
Molecular Formula | C22H24N2O8 |
Purity | >98% by HPLC |
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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.
Specification
Related CAS | 6591-49-7 (Deleted CAS) 929020-51-9 (Deleted CAS) 1172112-85-4 (Deleted CAS) |
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 |
Storage | Store at -20°C |
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 |
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 |
InChI Key | OFVLGDICTFRJMM-WESIUVDSSA-N |
Source | Streptomyces sp. |
Properties
Appearance | Yellow Crystal |
Application | Antibiotics, Tetracycline; protein synthesis inhibitors |
Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; mycobacteria |
Boiling Point | 790.6±60.0°C at 760 mmHg |
Melting Point | 170-173°C(dec.) |
Density | 1.64±0.1 g/cm3 |
Solubility | Soluble in ethanol, methanol, DMF or DMSO. Limited water solubility. |
LogP | -1.3 |
Toxicity
Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
Mechanism Of Toxicity | Tetracyclines target the 28S small subunit of the mitochondrial ribosome thereby deactivation mitochondrial protein synthesis. As a result tetracyclines are cytotoxic to the most metabolically active cells or tissues including the heart, liver, thymus and bone-marrow. The likely target of most tetracyclines is the 12S rRNA molecule in the mitochondrial ribosome, which is analogous to the 16S rRNA in bacterial ribosomes. |
Toxicity | LD50 = 808mg/kg (oral, mice). |
Reference Reading
Spectrum
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C22H24N2O8
Molecular Weight (Monoisotopic Mass): 444.1533 Da
Molecular Weight (Avergae Mass): 444.4346 Da
LC-MS/MS Spectrum - LC-ESI-QFT , negative
Experimental Conditions
Ionization Mode: negative
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C22H24N2O8
Molecular Weight (Monoisotopic Mass): 444.1533 Da
Molecular Weight (Avergae Mass): 444.4346 Da
13C NMR Spectrum
Experimental Conditions
Nucleus: 13C
Frequency: 100
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2