Tylosin

Last updated
Tylosin
Tylosin structure.svg
Clinical data
Trade names Tylocine, Tylan
AHFS/Drugs.com International Drug Names
ATCvet code
Identifiers
  • [(2R,3R,4E,6E,9R,11R,12S,13S,14R) -12- {[3,6-dideoxy-4-O-(2,6-dideoxy-3-C-methyl-α-L-ribo-hexopyranosyl) -3- (dimethylamino)-β-D-glucopyranosyl]oxy}-2-ethyl-14-hydroxy-5, 9,13-trimethyl-8, 16-dioxo-11-(2-oxoethyl)oxacyclohexadeca-4,6-dien-3-yl]methyl 6-deoxy-2,3-di-O-methyl-β-D-allopyranoside
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
E number E713 (antibiotics) OOjs UI icon edit-ltr-progressive.svg
CompTox Dashboard (EPA)
ECHA InfoCard 100.014.322 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C46H77NO17
Molar mass 916.112 g·mol−1
3D model (JSmol)
  • CC[C@@H]1[C@H](/C=C(/C=C/C(=O)[C@@H](C[C@@H]([C@@H]([C@H]([C@@H](CC(=O)O1)O)C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C)O[C@H]3C[C@@]([C@H]([C@@H](O3)C)O)(C)O)N(C)C)O)CC=O)C)\C)CO[C@H]4[C@@H]([C@@H]([C@@H]([C@H](O4)C)O)OC)OC
  • InChI=1S/C46H77NO17/c1-13-33-30(22-58-45-42(57-12)41(56-11)37(52)26(5)60-45)18-23(2)14-15-31(49)24(3)19-29(16-17-48)39(25(4)32(50)20-34(51)62-33)64-44-38(53)36(47(9)10)40(27(6)61-44)63-35-21-46(8,55)43(54)28(7)59-35/h14-15,17-18,24-30,32-33,35-45,50,52-55H,13,16,19-22H2,1-12H3/b15-14+,23-18+/t24-,25+,26-,27-,28+,29+,30-,32-,33-,35+,36-,37-,38-,39-,40-,41-,42-,43+,44+,45-,46-/m1/s1 X mark.svgN
  • Key:WBPYTXDJUQJLPQ-VMXQISHHSA-N X mark.svgN
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Tylosin is a macrolide antibiotic and bacteriostatic feed additive used in veterinary medicine. It has a broad spectrum of activity against Gram-positive organisms and a limited range of Gram-negative organisms. [1] It is found naturally as a fermentation product of Streptomyces fradiae . [2]

Contents

Tylosin is used in veterinary medicine to treat bacterial infections in a wide range of species and has a high margin of safety. [3] It has also been used as a growth promotant in some species, and as a treatment for colitis in companion animals. [2]

Mode of action

Like other macrolides, tylosin has a bacteriostatic effect on susceptible organisms, caused by inhibition of protein synthesis through binding to the 50S subunit of the bacterial ribosome.[ citation needed ]

Spectrum of activity

Tylosin has a wide spectrum of activity against Gram-positive bacteria including Staphylococcus , Streptococcus , Corynebacterium , and Erysipelothrix . It has a much narrower Gram-negative spectrum of activity, but has been shown to be active against Campylobacter coli , and certain spirochaetes. [4] It has also been shown to be extremely active against Mycoplasma species isolated from both mammalian and avian hosts. [3] [5] The following represents MIC susceptibility data for a few medically significant pathogens:

Clinical use

Tylosin has been used to treat a variety of different diseases throughout the world. Differing formulations and licensing conditions mean it may not be a recognized method of treatment for certain conditions in certain countries. In general, tylosin is licensed for the treatment of infections caused by organisms susceptible to the drug, but it has also been used as a treatment of colitis in small animals, as a growth promotant in food-producing animals, and as a way of reducing epiphora (tear staining) around the eyes of white-faced dogs. [2] In these cases, the result is positive only when using the tylosin in the form of tartrate, a chelating porphyrin. No marketing authority exists for the use of other tylosin forms as a tear-stain remover, thus it is not legal to use it for such purposes; the exception is as a prescription-only medicine of last resort by veterinarians under the cascading rule (UK) or the extra-label use rule (US).[ citation needed ]

Examples of bacterial infections that could potentially be treated with tylosin include respiratory infections, metritis, and acute mastitis in cattle; mastitis in sheep and goats; enteritis, pneumonia, erysipelas, and infectious arthritis in swine; and soft-tissue infections in small animals. [1] [2] [4] [5] While tylosin may be one appropriate therapeutic choice in theory for the conditions listed above, many other antibiotics may be preferable for treating a specific infection, and tylosin will not be the first choice.

It is also used as a growth promoter for a variety of terrestrial and aquatic animals grown for human consumption. [7]

Available forms

Tylosin is available in injectable, intramammary, and oral formulations with different product ranges available in different countries. [1]

Composition

Tylosin is a mixture of four major components: tylosins A, B, C, and D. Tylosin A is considered the major component of tylosin (comprises about 90% of tylosin); however, tylosins B, C, and D contribute to the overall potency of tylosin. [8]

Precautions and contraindications

Administration of tylosin should be avoided in animals with a known hypersensitivity to the product, or to other macrolides. [5]

Oral administration can result in diarrhoea and gastrointestinal disturbance. This is particularly true of horses, such that it can be fatal. [9] Tylosin also has a foul taste that is difficult to disguise.

The injectable formulations of tylosin can cause pain, inflammation, and itchiness around the injection site.[ citation needed ]

Since tylosin has a relatively poor spectrum of activity against Gram-negative organisms, it may not be a sensible therapeutic choice in the treatment of infections caused by unknown, potentially unsusceptible organisms.[ citation needed ]

Drug interactions

Tylosin may increase digitalis blood levels, thus its toxicity, [5] and may be antagonistic to chloramphenicol or lincosamides.

Colorimetric assays of serum ALT and AST may be falsely elevated by macrolide antibiotics.[ citation needed ]

See also

Related Research Articles

<span class="mw-page-title-main">Ampicillin</span> Antibiotic

Ampicillin is an antibiotic belonging to the aminopenicillin class of the penicillin family. The drug is used to prevent and treat a number of bacterial infections, such as respiratory tract infections, urinary tract infections, meningitis, salmonellosis, and endocarditis. It may also be used to prevent group B streptococcal infection in newborns. It is used by mouth, by injection into a muscle, or intravenously.

<span class="mw-page-title-main">Macrolide</span> Class of natural products

Macrolides are a class of mostly natural products with a large macrocyclic lactone ring to which one or more deoxy sugars, usually cladinose and desosamine, may be attached. The lactone rings are usually 14-, 15-, or 16-membered. Macrolides belong to the polyketide class of natural products. Some macrolides have antibiotic or antifungal activity and are used as pharmaceutical drugs. Rapamycin is also a macrolide and was originally developed as an antifungal, but is now used as an immunosuppressant drug and is being investigated as a potential longevity therapeutic.

<span class="mw-page-title-main">Methicillin</span> Antibiotic medication

Methicillin (USAN), also known as meticillin (INN), is a narrow-spectrum β-lactam antibiotic of the penicillin class.

<span class="mw-page-title-main">Clindamycin</span> Antibiotic

Clindamycin is an antibiotic medication used for the treatment of a number of bacterial infections, including osteomyelitis (bone) or joint infections, pelvic inflammatory disease, strep throat, pneumonia, acute otitis media, and endocarditis. It can also be used to treat acne, and some cases of methicillin-resistant Staphylococcus aureus (MRSA). In combination with quinine, it can be used to treat malaria. It is available by mouth, by injection into a vein, and as a cream or a gel to be applied to the skin or in the vagina.

<span class="mw-page-title-main">Nitrofurantoin</span> Antibacterial drug

Nitrofurantoin is an antibacterial medication used to treat urinary tract infections, but it is not as effective for kidney infections. It is taken by mouth.

<span class="mw-page-title-main">Amoxicillin/clavulanic acid</span> Combination antibiotic drug

Amoxicillin/clavulanic acid, also known as co-amoxiclav or amox-clav, sold under the brand name Augmentin, among others, is an antibiotic medication used for the treatment of a number of bacterial infections. It is a combination consisting of amoxicillin, a β-lactam antibiotic, and potassium clavulanate, a β-lactamase inhibitor. It is specifically used for otitis media, streptococcal pharyngitis, pneumonia, cellulitis, urinary tract infections, and animal bites. It is taken by mouth or by injection into a vein.

Mycoplasma pneumonia is a form of bacterial pneumonia caused by the bacterium Mycoplasma pneumoniae.

<span class="mw-page-title-main">Cefepime</span> Fourth-generation Cephalosporin Antibiotic

Cefepime is a fourth-generation cephalosporin antibiotic. Cefepime has an extended spectrum of activity against Gram-positive and Gram-negative bacteria, with greater activity against both types of organism than third-generation agents. A 2007 meta-analysis suggested when data of trials were combined, mortality was increased in people treated with cefepime compared with other β-lactam antibiotics. In response, the U.S. Food and Drug Administration (FDA) performed their own meta-analysis which found no mortality difference.

<span class="mw-page-title-main">Cefadroxil</span> Antibiotic

Cefadroxil is a broad-spectrum antibiotic of the cephalosporin type, effective in Gram-positive and Gram-negative bacterial infections. It is a bactericidal antibiotic.

<span class="mw-page-title-main">Lincomycin</span> Chemical compound

Lincomycin is a lincosamide antibiotic that comes from the actinomycete Streptomyces lincolnensis. A related compound, clindamycin, is derived from lincomycin by using thionyl chloride to replace the 7-hydroxy group with a chlorine atom with inversion of chirality. It was released for medical use in September 1964.

<span class="mw-page-title-main">Marbofloxacin</span> Chemical compound

Marbofloxacin is a carboxylic acid derivative third generation fluoroquinolone antibiotic. It is used in veterinary medicine under the brand names Marbocyl, Forcyl, Marbo vet and Zeniquin. A formulation of marbofloxacin combined with clotrimazole and dexamethasone is available under the name Aurizon.

<span class="mw-page-title-main">Cefotiam</span> Chemical compound

Cefotiam is a parenteral third-generation cephalosporin antibiotic. It has broad-spectrum activity against Gram-positive and Gram-negative bacteria. As a beta-lactam, its bactericidal activity results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins.

<span class="mw-page-title-main">Cefquinome</span> Chemical compound

Cefquinome is a fourth-generation cephalosporin with pharmacological and antibacterial properties valuable in the treatment of coliform mastitis and other infections. It is only used in veterinary applications.

<span class="mw-page-title-main">Enrofloxacin</span> Chemical compound

Enrofloxacin, sold under the brand name Baytril, among others, is a fluoroquinolone antibiotic used for the treatment of animals. It is a bactericidal agent.

<span class="mw-page-title-main">Cefoxitin</span> Chemical compound

Cefoxitin is a second-generation cephamycin antibiotic developed by Merck & Co., Inc. from Cephamycin C in the year following its discovery, 1972. It was synthesized in order to create an antibiotic with a broader spectrum. It is often grouped with the second-generation cephalosporins. Cefoxitin requires a prescription and as of 2010 is sold under the brand name Mefoxin by Bioniche Pharma, LLC. The generic version of cefoxitin is known as cefoxitin sodium.

<span class="mw-page-title-main">Oleandomycin</span> Chemical compound

Oleandomycin is a macrolide antibiotic. It is synthesized from strains of Streptomyces antibioticus. It is weaker than erythromycin.

<span class="mw-page-title-main">Spiramycin</span> Chemical compound

Spiramycin is a macrolide antibiotic and antiparasitic. It is used to treat toxoplasmosis and various other infections of soft tissues. Although used in Europe, Canada and Mexico, spiramycin is still considered an experimental drug in the United States, but can sometimes be obtained by special permission from the FDA for toxoplasmosis in the first trimester of pregnancy. Another treatment option are a combination of pyrimethamine and sulfadiazine.

<span class="mw-page-title-main">Mastitis in dairy cattle</span>

Bovine mastitis is the persistent, inflammatory reaction of the udder tissue due to physical trauma or microorganisms infections. Mastitis, a potentially fatal mammary gland infection, is the most common disease in dairy cattle in the United States and worldwide. It is also the most costly disease to the dairy industry. Milk from cows suffering from mastitis has an increased somatic cell count. Prevention and control of mastitis requires consistency in sanitizing the cow barn facilities, proper milking procedure and segregation of infected animals. Treatment of the disease is carried out by penicillin injection in combination with sulphar drug.

Mycoplasma bovis is one of 126 species of genus Mycoplasma. It is the smallest living cell and anaerobic organism in nature. It does not contain any cell wall and is therefore resistant to penicillin and other beta lactam antibiotics.

References

  1. 1 2 3 Giguere S, Dowling PM (2006). "Tylosin". Antimicrobial Therapy in Veterinary Medicine (4th ed.). Ames, Iowa: Blackwell Pub. ISBN   978-0-8138-0656-3.
  2. 1 2 3 4 "Tylosin". marvistavet.com. Archived from the original on 10 May 2012.
  3. 1 2 "Tylan 200 Injectable - Product data sheet PA9063DENZP" (PDF). Elanco Animal Health.
  4. 1 2 Tylosin, drugs.com
  5. 1 2 3 4 "Tylosin-Tylan". petplace.com.
  6. ↑ "Tylosin | the Antimicrobial Index Knowledgebase - TOKU-E".
  7. ↑ Palmer FJ, Sawyers TM (September 1978). "Hyperparathyroidism, chemodectoma, thymoma, and myasthenia gravis". Archives of Internal Medicine. 138 (9): 1402–3. doi:10.1001/archinte.1978.03630340072022. PMID   28708.
  8. ↑ Loke ML, Ingerslev F, Halling-Sørensen B, Tjørnelund J (April 2000). "Stability of Tylosin A in manure containing test systems determined by high performance liquid chromatography". Chemosphere. 40 (7): 759–65. Bibcode:2000Chmsp..40..759L. doi:10.1016/s0045-6535(99)00450-6. PMID   10705554.
  9. ↑ "Tylan". americanlivestock.com. Archived from the original on 6 October 2011.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.