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{{Short description|Chemical compound}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 400653238 |
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| verifiedrevid = 409090936 |
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| IUPAC_name = 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-<small>D</small>-allopyranoside |
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| IUPAC_name = 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-<small>D</small>-allopyranoside |
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| image = Tylosin structure.png |
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| image = Tylosin structure.svg |
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| CAS_number = 1401-69-0 |
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| ATCvet = yes |
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<!--Clinical data--> |
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| ATC_prefix = J01 |
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| tradename = Tylocine, Tylan |
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| ATC_suffix = FA90 |
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| Drugs.com = {{drugs.com|international|tylosin}} |
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| ATC_supplemental = {{ATCvet|J51|FA90}} |
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| PubChem = 5280440 |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| DrugBank = |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category = |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
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| KEGG = D02490 |
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| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| smiles = CN(C)2(O)(O(C)2O1C(C) (O)(O)(C)O1)O4(CC=O)C(C)C(=O)C=CC(C)=C (CO3O(C)(O)(OC)3OC)(CC)OC(=O)C(O)4C |
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| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> |
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| C=46 |H=77 |N=1 |O=17 |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| molecular_weight = 916.10 g/mol |
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| bioavailability = |
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| legal_status = |
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| routes_of_administration = |
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| protein_bound = |
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| metabolism = |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| protein_bound = |
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| metabolism = |
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| elimination_half-life = |
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| elimination_half-life = |
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| excretion = |
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| excretion = |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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<!--Identifiers--> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| pregnancy_category= |
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| CAS_number = 1401-69-0 |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
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| ATCvet = yes |
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| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| ATC_prefix = J01 |
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| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> |
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| ATC_suffix = FA90 |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| ATC_supplemental = {{ATCvet|J51|FA90}} |
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| legal_status = |
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| PubChem = 5280440 |
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| routes_of_administration = |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII = YEF4JXN031 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D02490 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 17658 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 42743 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 4444097 |
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| smiles = CC1(/C=C(/C=C/C(=O)(C((((CC(=O)O1)O)C)O2((((O2)C)O3C(((O3)C)O)(C)O)N(C)C)O)CC=O)C)\C)CO4((((O4)C)O)OC)OC |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 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 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = WBPYTXDJUQJLPQ-VMXQISHHSA-N |
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<!--Chemical data--> |
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| C=46 | H=77 | N=1 | O=17 |
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}} |
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'''Tylosin''' is a ]-class ] used in veterinary medicine. It has a broad spectrum of activity against ] organisms and a limited range of ] organisms.<ref name="Giguere">'''', by Steeve Giguere, P. M. Dowling, ISBN 9780813806563</ref> It is found naturally as a fermentation product of '']''.<ref name="marvistavet">, marvistavet.com</ref> |
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'''Tylosin''' is a ] ] and bacteriostatic feed additive used in veterinary medicine. It has a broad spectrum of activity against ] organisms and a limited range of ] organisms.<ref name="Giguere">{{cite book | chapter = Tylosin | chapter-url = https://books.google.com/books?id=lxmyfSave4IC&q=tylosin&pg=PA197 | title = Antimicrobial Therapy in Veterinary Medicine | vauthors = Giguere S, Dowling PM |date=2006 |publisher=Blackwell Pub |location=Ames, Iowa |isbn=978-0-8138-0656-3 |edition=4th }}</ref> It is found naturally as a fermentation product of '']''.<ref name="marvistavet">{{cite web | url = http://www.marvistavet.com/html/body_tylosin.html | archive-url = https://web.archive.org/web/20120510091437/http://www.marvistavet.com/html/body_tylosin.html | archive-date = 10 May 2012| title = Tylosin | work = marvistavet.com }}</ref> |
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Tylosin is used in veterinary medicine to treat bacterial infections in a wide range of species and has a high margin of safety.<ref name="Elanco">Tylan 200 Injectable - Product data sheet PA9063DENZP - Elanco Animal Health</ref> It has also been used as a growth promotant in some species, and as a treatment for colitis in companion animals.<ref name="marvistavet"/> |
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Tylosin is used in veterinary medicine to treat bacterial infections in a wide range of species and has a high margin of safety.<ref name="Elanco">{{cite web | title = Tylan 200 Injectable - Product data sheet PA9063DENZP | work = Elanco Animal Health | url = https://assets-eu-01.kc-usercontent.com/ad0f862a-9fb6-0162-80e8-2abe0fae68af/f03e9619-9ede-4b2f-b76b-b4e49430e389/Tylan_200_Injection_Label.pdf }}</ref> It has also been used as a growth promotant in some species, and as a treatment for colitis in companion animals.<ref name="marvistavet"/> |
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== Mode of action == |
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== Mode of action == |
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Like other macrolides, tylosin has a ] effect on susceptible organisms, caused by inhibition of protein synthesis through binding to the ] subunit of the bacterial ]. |
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Like other macrolides, tylosin has a ] effect on susceptible organisms, caused by inhibition of protein synthesis through binding to the ] subunit of the bacterial ].{{cn|date=March 2023}} |
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== Spectrum of activity == |
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== Spectrum of activity == |
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Tylosin has a wide spectrum of activity against gram positive bacteria including '']'', '']'', '']'', and '']''. It has a much narrower gram negative spectrum of activity, but has been shown to be active against '']'', and certain ]s.<ref name="drugs.com">, drugs.com</ref> It has also been shown to be extremely active against ''Mycoplasma'' species isolated from both mammalian and avian hosts.<ref name="Elanco"/><ref name="petplace">, petplace.com</ref> |
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Tylosin has a wide spectrum of activity against Gram-positive bacteria including '']'', '']'', '']'', and '']''. It has a much narrower Gram-negative spectrum of activity, but has been shown to be active against '']'', and certain ]s.<ref name="drugs.com">, drugs.com</ref> It has also been shown to be extremely active against ''Mycoplasma'' species isolated from both mammalian and avian hosts.<ref name="Elanco"/><ref name="petplace">{{cite web | url = http://www.petplace.com/drug-library/tylosin-tylan/page1.aspx | title = Tylosin-Tylan | work = petplace.com }}</ref> The following represents MIC susceptibility data for a few medically significant pathogens: |
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* ''Mycoplasma bovis'': 0.06 - 4 μg/ml{{cn|date=March 2023}} |
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* ''Staphylococcus aureus'': 0.5 - >128 μg/ml<ref>{{Cite web|url=http://antibiotics.toku-e.com/antimicrobial_1177_5.html|title = Tylosin | the Antimicrobial Index Knowledgebase - TOKU-E}}</ref> |
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== Clinical use == |
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== Clinical use == |
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Tylosin has been used to treat a variety of different diseases throughout the world. Differing formulations and licensing conditions will mean that 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 ] in small animals, as a growth promotant in food producing animals, and as a way of reducing ] (tear staining) around the eyes of white faced dogs.<ref name="marvistavet"/> No marketing authority exists for the use of tylosin as a tear stain remover and thus it is not legal to use it for such purposes- the exception being as a Prescription Only Medicine of last resort by vets under the Cascading Rule (UK) or the Extra Label rule (US). |
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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 ] in small animals, as a growth promotant in food-producing animals, and as a way of reducing ] (tear staining) around the eyes of white-faced dogs.<ref name="marvistavet"/> 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).{{cn|date=March 2023}} |
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Examples of bacterial infections that could potentially be treated with tylosin include respiratory infections, ], and acute ] in cattle; mastitis in sheep and goats; ], ], ], and infectious ] in swine; and soft tissue infections in small animals.<ref name="Giguere"/><ref name="marvistavet"/><ref name="drugs.com"/><ref name="petplace"/> |
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Examples of bacterial infections that could potentially be treated with tylosin include respiratory infections, ], and acute ] in cattle; mastitis in sheep and goats; ], ], ], and infectious ] in swine; and soft-tissue infections in small animals.<ref name="Giguere"/><ref name="marvistavet"/><ref name="drugs.com"/><ref name="petplace"/> |
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While tylosin may be one appropriate therapeutic choice in theory for the conditions listed above, there are many other antibiotics that may be preferable for treating a specific infection, and Tylosin will not be the first choice. |
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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. |
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It is also used as a growth promoter for a variety of terrestrial and aquatic animals grown for human consumption(Hirsch et al. 1999) |
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It is also used as a growth promoter for a variety of terrestrial and aquatic animals grown for human consumption.<ref name="pmid28708">{{cite journal | vauthors = Palmer FJ, Sawyers TM | title = Hyperparathyroidism, chemodectoma, thymoma, and myasthenia gravis | journal = Archives of Internal Medicine | volume = 138 | issue = 9 | pages = 1402–3 | date = September 1978 | pmid = 28708 | doi = 10.1001/archinte.1978.03630340072022| url = }}</ref> |
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== Available forms == |
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== Available forms == |
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Tylosin is available in injectable, intramammary, and oral formulations with different product ranges available in different countries.<ref name="Giguere"/> |
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Tylosin is available in injectable, intramammary, and oral formulations with different product ranges available in different countries.<ref name="Giguere"/> |
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== Composition == |
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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.<ref name="pmid10705554">{{cite journal | vauthors = Loke ML, Ingerslev F, Halling-Sørensen B, Tjørnelund J | title = Stability of Tylosin A in manure containing test systems determined by high performance liquid chromatography | journal = Chemosphere | volume = 40 | issue = 7 | pages = 759–65 | date = April 2000 | pmid = 10705554 | doi = 10.1016/s0045-6535(99)00450-6 | bibcode = 2000Chmsp..40..759L }}</ref> |
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== Precautions and contraindications == |
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== Precautions and contraindications == |
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Administration of tylosin should be avoided in animals with a known hypersensitivity to the product, or to other macrolides.<ref name="petplace"/> |
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Administration of tylosin should be avoided in animals with a known hypersensitivity to the product, or to other macrolides.<ref name="petplace"/> |
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Oral administration can result in diarrhoea and gastrointestinal disturbance. This is particularly true of horses, such that it can be fatal.<ref>, americanlivestock.com</ref> Tylosin also has a foul taste that is difficult to disguise. |
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Oral administration can result in diarrhoea and gastrointestinal disturbance. This is particularly true of horses, such that it can be fatal.<ref>{{cite web | url = http://www.americanlivestock.com/pc-1359-123-tylan-200-injectable.aspx | archive-url = https://web.archive.org/web/20111006022641/http://www.americanlivestock.com/pc-1359-123-tylan-200-injectable.aspx | archive-date = 6 October 2011 | title = Tylan | work = americanlivestock.com }}</ref> Tylosin also has a foul taste that is difficult to disguise. |
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The injectable formulations of tylosin can cause pain, inflammation, and itchiness around the injection site. |
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The injectable formulations of tylosin can cause pain, inflammation, and itchiness around the injection site.{{cn|date=March 2023}} |
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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. |
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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.{{cn|date=March 2023}} |
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== Drug interactions == |
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== Drug interactions == |
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Tylosin may increase digitalis blood levels and thus its toxicity,<ref name="petplace"/> and may be antagonistic to ] or ]s. |
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Tylosin may increase digitalis blood levels, thus its toxicity,<ref name="petplace"/> and may be antagonistic to ] or ]s. |
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Colorimetric assays of serum ALT and AST may be falsely elevated by macrolide antibiotics. |
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Colorimetric assays of serum ALT and AST may be falsely elevated by macrolide antibiotics.{{cn|date=March 2023}} |
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== See also == |
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* ] |
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== References == |
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== References == |
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{{reflist}} |
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{{reflist}} |
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{{Protein synthesis inhibitor antibiotics}} |
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Hirsch R, Ternes T, Haberer K, Kratz KL (1999). Occurrence of antibiotics in the aquatic environment. ''The Science of the total environment'', 225:109-118. |
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