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 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| |
