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Tylosin

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]

Tylosin
Clinical data
Trade namesTylocine, Tylan
AHFS/Drugs.comInternational 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
  • 1401-69-0 Y
PubChem CID
  • 5280440
ChemSpider
  • 4444097 N
UNII
  • YEF4JXN031
KEGG
  • D02490 Y
ChEBI
  • CHEBI:17658 N
ChEMBL
  • ChEMBL42743 N
E numberE713 (antibiotics)
CompTox Dashboard (EPA)
  • DTXSID3043996
ECHA InfoCard100.014.322
Chemical and physical data
FormulaC46H77NO17
Molar mass916.112 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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 N
  • Key:WBPYTXDJUQJLPQ-VMXQISHHSA-N N
 NY (what is this?)  (verify)

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 edit

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 edit

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:

  • Mycoplasma bovis: 0.06 - 4 μg/ml[citation needed]
  • Staphylococcus aureus: 0.5 - >128 μg/ml[6]

Clinical use edit

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 edit

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

Composition edit

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 edit

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 edit

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 edit

References edit

  1. ^ a b c Giguere S, Dowling PM (2006). "Tylosin". Antimicrobial Therapy in Veterinary Medicine (4th ed.). Ames, Iowa: Blackwell Pub. ISBN 978-0-8138-0656-3.
  2. ^ a b c d . marvistavet.com. Archived from the original on 10 May 2012.
  3. ^ a b "Tylan 200 Injectable - Product data sheet PA9063DENZP" (PDF). Elanco Animal Health.
  4. ^ a b Tylosin, drugs.com
  5. ^ a b c d "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. ^ . americanlivestock.com. Archived from the original on 6 October 2011.

tylosin, macrolide, antibiotic, bacteriostatic, feed, additive, used, veterinary, medicine, broad, spectrum, activity, against, gram, positive, organisms, limited, range, gram, negative, organisms, found, naturally, fermentation, product, streptomyces, fradiae. 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 TylosinClinical dataTrade namesTylocine TylanAHFS Drugs comInternational Drug NamesATCvet codeQJ01FA90 WHO QJ51FA90 WHO IdentifiersIUPAC name 2R 3R 4E 6E 9R 11R 12S 13S 14R 12 3 6 dideoxy 4 O 2 6 dideoxy 3 C methyl a L ribo hexopyranosyl 3 dimethylamino b 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 b D allopyranosideCAS Number1401 69 0 YPubChem CID5280440ChemSpider4444097 NUNIIYEF4JXN031KEGGD02490 YChEBICHEBI 17658 NChEMBLChEMBL42743 NE numberE713 antibiotics CompTox Dashboard EPA DTXSID3043996ECHA InfoCard100 014 322Chemical and physical dataFormulaC 46H 77N O 17Molar mass916 112 g mol 13D model JSmol Interactive imageSMILES 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 OCInChI 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 NKey WBPYTXDJUQJLPQ VMXQISHHSA N N N Y what is this verify 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 Contents 1 Mode of action 2 Spectrum of activity 3 Clinical use 4 Available forms 5 Composition 6 Precautions and contraindications 7 Drug interactions 8 See also 9 ReferencesMode of action editLike 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 editTylosin 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 Mycoplasma bovis 0 06 4 mg ml citation needed Staphylococcus aureus 0 5 gt 128 mg ml 6 Clinical use editTylosin 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 editTylosin is available in injectable intramammary and oral formulations with different product ranges available in different countries 1 Composition editTylosin 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 editAdministration 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 editTylosin 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 editTylvalosinReferences edit a b c Giguere S Dowling PM 2006 Tylosin Antimicrobial Therapy in Veterinary Medicine 4th ed Ames Iowa Blackwell Pub ISBN 978 0 8138 0656 3 a b c d Tylosin marvistavet com Archived from the original on 10 May 2012 a b Tylan 200 Injectable Product data sheet PA9063DENZP PDF Elanco Animal Health a b Tylosin drugs com a b c d Tylosin Tylan petplace com Tylosin the Antimicrobial Index Knowledgebase TOKU E 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 Loke ML Ingerslev F Halling Sorensen B Tjornelund 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 Tylan americanlivestock com Archived from the original on 6 October 2011 Retrieved from https en wikipedia org w index php title Tylosin amp oldid 1189787707, wikipedia, wiki, book, books, library,

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