SKU: O008  / 
    CAS Number: 14206-58-7

    4-Epi-Oxytetracycline, EvoPure®

    $286.00

    4-Epi-Oxytetracycline, EvoPure® (oxytetracycline-related compound A) is an oxytetracycline metabolite and impurity found in commercial oxytetracycline. This highly pure metabolite can be used as a secondary reference standard during stability studies of oxytetracycline. It can also be used to study the degradation pathway and products of tetracyclines.

    4-Epi-Oxytetracycline, EvoPure® is very slightly soluble in water, methanol, and DMSO.

    We also offer:

    • α-Epi-Oxytetracycline, EvoPure® (Oxytetracycline-related compound A)(O009)
    • β-Apo-Oxytetracycline, EvoPure® (Oxytetracycline-related compound E)(O010)
    Application 4-Epi-oxytetracycline can be used as a secondary reference standard.
    Mechanism of Action Oxytetracycline causes inhibition of protein synthesis. It binds to the 30S ribosomal subunit and prevents the amino-acyl tRNA from binding to the A site of the ribosome.

    In an acellular model system of protein synthesis using ribosomes from tetracycline-sensitive and resistant strains of E. coli in the synthesis of polyphenylalanine, Oxytetracycline showed inhibitory activity along with minocycline. 4-Epi-oxytetracycline and beta-apo-oxytetracycline had competing properties with respect to oxytetracycline at the stage of penetration through the cell membrane but did not, however, suppress the synthesis of polyphenylalanine.
    Spectrum Broad-spectrum, including Gram-negative and Gram-positive bacteria. It has only ~5% of the potency of oxytetracycline against S. aureus.
    Microbiology Applications 4-Epi-oxytetracycline can be used to prepare S. aureus and E. coli selective media.
    Molecular Formula C22H24N2O9
    References

    Beliavskaia et al. (1976)  Study of the mechanism of action of minocycline and of certain other tetracycline group compounds. Antibiotiki, 21(3): 242 - 245

    Halling-Sorensen B, Sengelov G and Tjornelund J (2002)  Toxicity of tetracyclines and tetracycline degradation products to environmentally relevant bacteria, including selected tetracycline-resistant bacteria. Arch. Environ. Contam. Toxicol. 42(3):263-271  PMID  11910453

    Lykkeberg AK, Halling-Sørensen B, Cornett C, Tjørnelund J and Honoré HS (2004)   Quantitative analysis of Oxytetracycline and its impurities by LC-MS-MS. J. Pharm. Biomed. Anal. 34(2):325-332  PMID 15013146

    Richeng X et al (2010)  Hydrolysis and photolysis of Oxytetracycline in aqueous solution. J. Environ. Sci. and Health 45:73-81  PMID 20390934

    MIC Bacillus cereus (ATCC 10702)| 1 - ?| 1302| Bacillus pumilus (ATCC 14884)| 2 - ?| 1302| Bacillus pumilus (ATCC 14884)| 2 - ?| 1183| Bacillus subtilis| 16 - ?| 1183| Bacillus subtilis| 16 - ?| 1183| Brochothrix thermosphacta| 124 - ?| 861| Burkholderia mallei (Pakistan)| ? - ?| 655| Clavibacter michiganensis subsp. michiganensis (185. 2. 1)| 4 - ?| 727| Clavibacter michiganensis subsp. michiganensis (C 8.2)| 4 - ?| 727| Clavibacter michiganensis subsp. michiganensis (IVIA-613)| 4 - ?| 727| Clavibacter michiganensis subsp. michiganensis (IVIA-873)| 4 - ?| 727| Diplococcus pneumoniae| 0.04 - 0.4| 1413| Enterococcus faecalis| 0.78 - >100| 1030| Enterococcus faecalis (broiler isolate)| 0.78 - >100| 1030| Enterococcus faecalis (cattle isolate)| 1.56 - >100| 1030| Enterococcus faecalis (pig isolate)| 0.78 - >100| 1030| Enterococcus faecium| 0.39 - >100| 1030| Enterococcus faecium (broiler isolate)| 0.39 - >100| 1030| Enterococcus faecium (cattle isolate)| 0.39 - >100| 1030| Enterococcus faecium (pig isolate)| 0.39 - >100| 1030| Enterococcus hirae| 0.39 - >100| 1030| Enterococcus sp. (Uraguay)| ≤0.25 - 2| 1391| Escherichia coli (ATCC 25922)| 0.25 - 2| 1127| Escherichia coli (K12 LE140)| 1.95 - ?| 1265| Escherichia coli (O157:H7)| 70 - ?| 861| Flavobacterium columnare| 15.63 - ?| 1347| Fusobacterium necrophorum| 0.03 - 4.1| 1444| Haemophilus influenzae| 1.6 - 6.3| 1413| Haemophilus parasuis (Spain)| 0.25 - 16| 768| Haemophilus parasuis (UK)| 0.25 - 16| 768| Klebsiella pneumonia (ATCC 10031)| 16 - ?| 1183| Listeria monocytogenes| 58 - ?| 861| Micrococcus kristinae| 1 - ?| 1302| Micrococcus kristinae| 4 - ?| 1183| Micrococcus luteus| 4 - ?| 1183| Mycoplasma bovis (Britain)| 1 - 128| 598| Mycoplasma bovis (Italy)| 0.12 - 4| 598| Mycoplasma bovis (Netherlands)| 8 - >64| 598| Mycoplasma gallisepticum| 0.05 - 200| 599| Mycoplasma gallisepticum (1975-1989)| 0.12 - 1| 606| Mycoplasma gallisepticum (1990-2000)| 0.05 - 200| 606| Mycoplasma gallisepticum (41-91)| 0.125 - ?| 595| Mycoplasma gallisepticum (ATCC 15302)| 0.125 - ?| 595| Mycoplasma hyopneumoniae| 0.25 - 4| 760| Mycoplasma hyopneumoniae| 0.12 - 2| 761| Mycoplasma hyopneumoniae (ATCC 25634)| 0.12 - ?| 594| Mycoplasma hyopneumoniae (ATCC 25634)| 0.12 - ?| 594| Mycoplasma hyopneumoniae (ATCC 25634)| 1 - ?| 594| Mycoplasma hyopneumoniae (field isolate + final)| 0.12 - >2| 761| Mycoplasma hyopneumoniae (field isolate + initial)| 0.03 - 2| 761| Mycoplasma hyopneumoniae (Final reading + Belgian)| 0.12 - >2| 594| Mycoplasma hyopneumoniae (Initial reading + Belgian)| 0.03 - 2| 594| Mycoplasma hyopneumoniae (J-strain + final)| 1 - ?| 761| Mycoplasma hyopneumoniae (J-strain + initial)| 0.12 - ?| 761| Mycoplasma hyosynoviae| 0.5 - >4| 1513| Mycoplasma iowae (1990-2000)| 0.025 - 100| 606| Mycoplasma iowae (90168)| 0.25 - ?| 595| Mycoplasma iowae (I 695)| 0.25 - ?| 595| Mycoplasma meleagridis (1975-1989)| 0.3 - 5| 606| Mycoplasma meleagridis (1990-2000)| 0.05 - 25| 606| Mycoplasma synoviae| 0.025 - 100| 599| Mycoplasma synoviae (1975-1989)| 0.06 - 0.08| 606| Mycoplasma synoviae (1990-2000)| 0.025 - 100| 606| Mycoplasma synoviae (WVU 1853)| 0.125 - ?| 595| Nocardia asteroides| 25 - 100| 1404| Paenibacillus larvae| 0.016 - 0.031| 1353| Pasteurella haemolytica| >64 - ?| 1022| Proteus vulgaris| 64 - ?| 1183| Proteus vulgaris (ATCC 6830)| 16 - ?| 1302| Proteus vulgaris (CSIR 0030)| 32 - ?| 1183| Pseudomonas aeruginosa (ATCC 19582)| 8 - ?| 1302| Pseudomonas flourescens| 40 - ?| 861| Salmonella enterica| 112 - ?| 861| Salmonella spp.| 2 - ?| 1302| Shigella flexneri| 1 - ?| 1302| Staphylococcus (coagulase-negative + Uruguay)| ≤0.25 - >64| 1391| Staphylococcus aureus| 76 - ?| 861| Staphylococcus aureus (ATCC 6538)| 4 - ?| 1183| Staphylococcus aureus (ATCC 6538)| 4 - ?| 1302| Staphylococcus aureus (OKOH1)| 1 - ?| 1302| Staphylococcus aureus (Uruguay)| ≤0.25 - >64| 1391| Staphylococcus epidermidis| 4 - ?| 1183| Streptococcus agalactiae (Uruguay)| ≤0.25 - 2| 1391| Streptococcus dysgalactiae (Uruguay)| >4 - >64| 1391| Streptococcus faecalis (ATCC 29212)| 8 - ?| 1183| Streptococcus iniae| 10 - ?| 1341| Streptococcus pneumonia (ATCC 6303 + quinolone-susceptible)| 0.5 - ?| 437| Streptococcus pneumonia (ATCC 7257 + quinolone-resistant)| 0.125 - ?| 437| Streptococcus uberis (Uruguay)| ≤0.25 - 64| 1391| Treponema hyodysenteriae| 0.78 - 25| 1427| Vibrio cholerae| 56 - ?| 861| Vibrio harveyi| 0.78 - ?| 1428|