79-57-2 Usage
Uses
Used in Clinical Medicine:
Oxytetracycline is used as a therapeutic agent for bacterial respiratory, periodontal, and urogenital tract diseases. It is the second most widely used antibiotic, after penicillins, in terms of total tons used each year.
Used in Plant Disease Control:
Oxytetracycline has seen significant usage in controlling plant diseases, acting as a broad-spectrum antibiotic to prevent the growth of or kill bacteria, fungi, and mycoplasma-like organisms.
Used as a Feed Amendment:
Oxytetracycline is used as a feed amendment for growth promotion in agricultural animals, including fish.
Used in Animal Health:
Oxytetracycline is used as a therapeutic agent for curing diseases of agricultural animals, including infections caused by chlamydia, mycoplasma organisms, propionebacterium acnes, haemophilus influenzae, and rickettsiae. It acts by inhibiting protein synthesis by binding to the 30S ribosomal subunit of the bacteria.
Used in Food-Additive Tolerances:
Food-additive tolerances are established for residues of tetracyclines in commodities of beef cattle, dairy cattle, calves, swine, sheep, chickens, turkeys, finfish, and lobster (21 CFR §556.500).
Physical and Chemical Properties
Isolated from the culture medium of Streptomyces fission; appears as a gray-yellow to yellow crystalline powder. Commonly in a form of hydrochloride; appears as yellow crystal, easily soluble in water, stable under acidic conditions but unstable in alkaline environment.
Its oxytetracycline appears as light yellow to dark yellow crystalline powder, insoluble in water. Adjusting the pH to over 8 or below 2 yields oxytetracycline sodium salt or hydrochloride, this is stable and easily soluble in water. The 10% aqueous solution should have a pH of 2.3 to 2.9.
Pharmacology
1. Pharmacodynamics; The drug is a tetracycline antibacterial drug with a broad spectrum of anti-pathogenic microorganisms; appears as a rapid bacteriostatic agent; exhibits bactericidal effect to some bacteria species at high concentration; have a slightly high potency than tetracycline for the treatment of intestinal infections (including amoebic dysentery).
Mechanism of action; The drug can specifically bind to the A site of the 30s subunit of the ribosomes in pathogens, preventing the binding of aminoacyl-tRNA to this position, thereby inhibiting the growth of the peptide chain and affecting the protein synthesis of bacteria or other pathogenic microorganisms .
Antibacterial spectrum The drug has strong antibacterial activity on Staphylococcus aureus, pneumococcus, Streptococcus pyogenes, Neisseria gonorrhoeae, meningococcal, Escherichia coli, Aerobacter aerogenes, Shigella, Yersinia and Listeria monocytogenes. It also has strong effect on rickettsia, mycoplasma, chlamydia, spirochetes, amoebae and some plasmodium and actinomyces.
2. Pharmacokinetic: oral absorption is not complete (absorb about 30% to 58%); single-dose oral administration of 1 g gives a peak plasma concentration of about 3.9mg / L. The drug is widely distributed after absorption, being capable to penetrate pleural effusion, ascites, can also be distributed in the liver, spleen, bone marrow, bone, dentin and enamel, and can reach a higher concentration in milk. The drug can penetrate through the placental barrier, but not easily through the blood - cerebrospinal fluid barrier. The drug has a distribution volume of 0.9 ~ 1.9L / kg, the protein binding rate of about 20% to 35%, half-life of 6 to 10 hours for people of normal renal function. It has a prolonged half-life for renal failure patients, being as long as 47 to 66 hours for anastomosis patients. The drug is mainly excreted through the glomerular filtration with 70% administered drug being discharged within 24 hours; non-absorbed drugs are excreted in the form of prototype. Hemodialysis can remove about 10% to 15% of the drug.
Adverse reactions
Bone; The medicine can be deposited in the teeth and bones, resulting in varying degrees of discoloration yellow teeth, enamel dysplasia and dental caries, and can cause bone dysplasia.
Oral administration of the gastrointestinal tract can cause nausea, vomiting, abdominal discomfort, abdominal distension, diarrhea and other gastrointestinal reactions; occasional esophagitis and esophageal ulcer reported in patients with bed rest immediately after taking medicine.
Liver; in rare cases, serum bilirubin, alkaline phosphatase and aminotransferase increase. Long-term medication can cause liver damage, usually leading to hepatic steatosis. People of liver and renal insufficiency, late pregnancy and women receiving high-dose intravenous administration are more likely to suffer. Occasionally also cause both pancreatic inflammation together with liver toxicity.
Renal; in rare cases, blood urea nitrogen content increase. Patients with significant renal impairment may have aggravating azotemia, hyperphosphatemia and acidosis.
Allergic reaction cases are less than penicillin. It can cause drug fever or rash, the latter can exhibit rash, urticaria, erythema multiforme, eczema-like erythema; can also cause photosensitive dermatitis. In addition, anaphylactic shock, asthma, purpura, etc. are also occasionally reported.
Long-term use in blood can cause abnormal lymphocytes, granulocytic granules, hemolytic anemia, thrombocytopenia and neutropenia.
Superinfection; Long-term medication can induce drug-resistant Staphylococcus aureus, Gram-negative bacteria and fungi, which lead to the infections in digestive tract, respiratory and urinary tract infections with sepsis occurring in severe cases.
Dysbacteriosis; long-term medication can also reduce the body's normal bacteria population, resulting in vitamin deficiency, fungal breeding, dry mouth, sore throat, angular cheilitis, glossitis, dark brown tongue or discoloration.
Central nervous system; it has been reported of the cases of benign increased intracranial pressure, manifested as headache, vomiting, optic disc edema and so on.
Drugs interactions
Quinolones: not suitable for combination usage with reduced efficacy and increased side effects.
Cephalosporins: oxytetracycline can reduce the antibacterial effect of cephalosporins.
Chlortetracycline, kanamycin, olaquindox, enramycin, North rifampin, furinomycin, flavomycin: incompatibility; oxytetracycline are incompatible with the latter combination.
Tylosin and other macrolides: combination yields synergistic effect.
Polymyxin: combination with oxytetracycline enhances the absorption of the latter, leading to synergistic effect.
Penicillins: Antagonistic effect.
Metronidazole: combination can reduce the effect of metronidazole, reducing the efficacy.
Sodium bicarbonate: increase the pH of oxytetracycline; reduce the dissociation degree and absorption rate.
Magnesium sulfate: oxytetracycline can form chelate with magnesium ions; reduce its own absorption and curative effect.
TMP: significant synergistic effect.
Vitamin C: The latter can inactivate oxytetracycline; oxytetracycline in turn causes faster excretion of vitamin C in the urine. Not suitable.
Drugs and feeds containing calcium, magnesium, aluminum and other cationic; prevent the absorption of oxytetracycline and reduce its efficacy.
Sodium sulfate: In order to avoid the effect of metal cations in feed; adding appropriate amount of sodium sulfate in the feed can improve the absorption of oxytetracycline and improve the curative effect.
Diuretics: Combination can increase blood urea nitrogen, leading to increased renal toxicity.
Berberine: combination can enhance antibacterial effect.
Vitamin B complex: reduce the effect of oxytetracycline.
Bacitracin: incompatibility should not be combined.
Food, milk: oxytetracycline, when used with food, milk, the blood concentration is only 20% of that in the cases of fasting drug administration with remarkably compromised antibacterial effect.
Trace elements: block the absorption of oxytetracycline, reduce the effect.
Therapeutic Function
Antibiotic
Antimicrobial activity
It is slightly less active than other tetracyclines against
most common pathogenic bacteria.
Pharmaceutical Applications
A fermentation product of certain strains of Streptomyces rimosus,
supplied as the dihydrate or hydrochloride for oral or parenteral
administration.
Pharmacokinetics
Oral absorption： c.60%
Cmax 500 mg oral： 3–4 mg/L after 2–4 h
Plasma half-life： c.9 h
Volume of distribution： c.1.8 L/kg
Plasma protein binding： 20–35%
Oxytetracycline is moderately well absorbed from the upper
gastrointestinal tract. Food decreases plasma levels by approximately
50%. Although widely distributed in the tissues, it achieves lower concentrations than related agents such as minocycline.
Sputum concentrations of 1 mg/L have been recorded
on a daily dosage of 2 g. Approximately 60% is excreted in the
urine and the half-life is prolonged in renal insufficiency.
Clinical Use
It offers no unique therapeutic advantages, although it is one
of the cheaper preparations.
Side effects
Gastrointestinal intolerance is responsible for most side
effects, and tends to be more severe than with other tetracyclines.
Esophageal irritation may result from the local
effects of the swallowed drug. Potentially serious adverse
reactions have included neuromuscular paralysis following
intravenous administration to patients with myasthenia
gravis. Thrombocytopenic purpura and lupus erythematosus
syndrome have been reported, although a direct role for the
drug in the latter remains uncertain. Apart from the effect on
nitrogen balance common to many tetracyclines, a metabolic
effect on glucose homeostasis has been noted in type 1 diabetes
mellitus. Allergic contact sensitivity
reactions have also
been reported.
Synthesis
Oxytetracycline, 4-dimethylamino-1,4,4a,5,5a,6,11,12a-octahydro-
3,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-2-naphthacencarboxamide (32.3.2), is synthesized biosynthetically as a result of the activity of actinomycete S. rimosus.
Veterinary Drugs and Treatments
Oxytetracycline products are approved for use in dogs and cats (no
known products are being marketed, however), calves, non-lactating
dairy cattle, beef cattle, swine, fish, and poultry. For more information,
refer to the Doses section, below.
Drug interactions
Potentially hazardous interactions with other drugs
Anticoagulants: possibly enhanced anticoagulant
effect of coumarins and phenindione.
Oestrogens: possibly reduced contraceptive effects of
oestrogens (risk probably small).
Retinoids: possible increased risk of benign
intracranial hypertension with tetracyclines and
retinoids - avoid.
Metabolism
Metabolism is negligible. The tetracyclines are excreted
in the urine and in the faeces. Renal clearance is by
glomerular filtration. Up to 60% of an intravenous dose of
tetracycline, and up to 55% of an oral dose, is eliminated
unchanged in the urine. The tetracyclines are excreted in
the bile, where concentrations 5-25 times those in plasma
can occur. There is some enterohepatic reabsorption and
considerable quantities occur in the faeces after oral doses.
Toxicity evaluation
Tetracycline is a potent inhibitor of bacterial protein
biosynthesis, with less activity on mammalian cells. It
binds to the 30S and 50S bacterial ribosomal subunits,
and it inhibits the binding of aminoacyl–tRNA and the
termination factors RF1 and RF2 to the A site of bacterial
ribosomes (21). Acute oral LD50 for mice >7 g/kg; for rats
>10 g/kg, acute intravenous 100 ～ 200 mg/kg. Tlm for
black bass: 250 ppm (24 h).
Check Digit Verification of cas no
The CAS Registry Mumber 79-57-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 9 respectively; the second part has 2 digits, 5 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 79-57:
(4*7)+(3*9)+(2*5)+(1*7)=72
72 % 10 = 2
So 79-57-2 is a valid CAS Registry Number.
InChI:InChI=1/C22H26N2O8/c1-21(31)9-5-4-6-10(25)11(9)17(27)12-13(21)18(28)14-15(24(2)3)16(26)8(20(23)30)7-22(14,32)19(12)29/h4-6,13-15,18,25-26,28-29,31-32H,7H2,1-3H3,(H2,23,30)/t13?,14-,15+,18?,21-,22+/m1/s1
79-57-2Relevant articles and documents
Characterization of a robust cold-adapted and thermostable laccase from Pycnoporus sp. SYBC-L10 with a strong ability for the degradation of tetracycline and oxytetracycline by laccase-mediated oxidation
Tian, Qiaopeng,Dou, Xin,Huang, Lin,Wang, Lei,Meng, Di,Zhai, Lixin,Shen, Yu,You, Cuiping,Guan, Zhengbing,Liao, Xiangru
, (2020)
A native laccase (Lac-Q) with robust cold-adapted and thermostable characteristics from the white-rot fungus Pycnoporus sp. SYBC-L10 was purified, characterized, and used in antibiotic treatments. Degradation experiments revealed that Lac-Q at 10.0 U mL?1 coupled with 1.0 mmol L?1 ABTS could degrade 100% of the tetracycline or oxytetracycline (50 mg L?1) within 5 min with a static incubation at 0 °C (pH 6.0). The presence of the Mn2+ ion inhibited the removal rate of tetracycline and oxytetracycline by the Lac-Q–ABTS system, and the presence of Al3+, Cu2+, and Fe3+ accelerated the removal rate of tetracycline and oxytetracycline by the Lac-Q–ABTS system. Furthermore, seven transformation products of oxytetracycline (namely TP 445, TP 431, TP 413, TP 399, TP 381, TP 367, and TP 351) were identified during the Lac-Q-mediated oxidation process by using UPLC–MS/MS. A possible degradation pathway including deamination, demethylation, and dehydration was proposed. Furthermore, the growth inhibition of Bacillus altitudinis SYBC hb4 and E. coli by tetracycline antibiotics revealed that the antimicrobial activity was significantly reduced after treatment with the Lac-Q–ABTS system. Finally, seven transformation products of oxytetracycline (namely TP 445, TP 431, TP 413, TP 399, TP 381, TP 367, and TP 351) were identified during the Lac-Q-mediated oxidation process by using UPLC–MS/MS. A possible degradation pathway including deamination, demethylation, and dehydration was proposed. These results suggest that the Lac-Q–ABTS system shows a great potential for the treatment of antibiotic wastewater containing different metal ions at various temperatures.
Design and optimization of an enzymatic membrane reactor for tetracycline degradation
De Cazes,Belleville,Petit,Llorca,Rodríguez-Mozaz,De Gunzburg,Barceló,Sanchez-Marcano
, p. 146 - 152 (2014/12/09)
The tetracycline, antibiotic considered as a recalcitrant pollutant, was successfully depleted from model aqueous solutions by immobilized laccase from Trametes versicolor in an enzymatic membrane reactor. The results obtained show that tetracycline is depleted from water solutions at room temperature and without adding any extra chemicals. The degradation of tetracycline in aqueous solutions at 20 mg L-1 during 24 h, with equivalent amounts of free or immobilized biocatalyst, allowed reaching a tetracycline degradation yield of 56% with an enzymatic membrane whereas it was only of 30% with free laccase. This result highlights the good reactivity and stability of the immobilized enzyme for the degradation of tetracycline. Moreover, the enzymatic membrane reactor was able to reach a constant degradation rate of 0.34 mg of tetracycline per hour during 10 days.
Compositions and methods for treating hemorrhagic virus infections and other disorders
-
, (2008/06/13)
Cytokine-receptor and cytokine antagonist-enriched blood-dervided compositions and methods of preparing and using the compositions are provided. Also provided are compositions and methods for the treatment or prevention of disorders, especially acute inflammatory disorders involving pathological responses of the immune system, such as viral hemorrhagic diseases, sepsis, rheumatoid arthritis and other autoimmune disorders, acute cardiovascular events, flare-ups and acute phases of multiple sclerosis, wasting disorders and other disorders involving deleterious expression of cytokines and other factors, including tumor necrosis factor (TNF) and interleukin-1 (IL-1) are provided.
Biodegradable ionic matrix of variable internal polarity with grafted polymer
-
, (2008/06/13)
The present invention relates to a particulate biodegradable matrix comprising a biodegradable and hydrophilic core with a base of carbohydrate or polyol or polyamine matrix, cross-linked and derived in the mass by variable amounts of ionic groups; a hydrophilic polymer layer associated with the central core by chemical, for example ionic, interaction; and surface molecules or polymers grafted on the external polymer layer by covalent bonds.
Drug releasing surgical implant or dressing material
-
, (2008/06/13)
A surgical implant or external wound dressing which functions as both a hemostat and a device to safely and effectively deliver any of a number of pharmaceuticals to targeted tissue at a controlled rate is disclosed. The device generally comprises a carrier in the form of fibers, sutures, fabrics, cross-linked solid foams or bandages, a pharmaceutical in solid micoparticulate form releasably bound to the carrier fibers, and a lipid adjuvant which aids the binding of the microparticles to the fibers as well as their function in the body.
Lipid matrix carriers for use in drug delivery systems
-
, (2008/06/13)
Lipid matrix carriers are described which provide for the sustained release of bioactive agents in vivo or in vitro. The properties of the lipid matrix carriers of the present invention include high entrapment efficiencies; release of entrapped compounds in their active form; biodegradability and avoidance of vascular occlusion in vivo; and avoidance of sequestration of the bioactive agent in the liver and spleen.
