NAV

Tylosin

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Tylosin
DrugBank Accession Number
DB11475
Background

Tylosin is a bacteriostatic macrolide antibiotic and 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. Tylosin is produced as a fermentation product of Streptomyces fradiae.

Type
Small Molecule
Groups
Vet approved
Structure
Similar Structures
Weight
Average: 916.1001
Monoisotopic: 915.519150043
Chemical Formula
C46H77NO17
Synonyms
  • Tilosina
  • Tylocine
  • Tylosin
  • Tylosin A
  • Tylosine
  • Tylosinum

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Tylosin.
AcetyldigitoxinThe serum concentration of Acetyldigitoxin can be increased when it is combined with Tylosin.
AlfentanilThe serum concentration of Alfentanil can be increased when it is combined with Tylosin.
AlprazolamThe serum concentration of Alprazolam can be increased when it is combined with Tylosin.
AmbroxolThe risk or severity of methemoglobinemia can be increased when Tylosin is combined with Ambroxol.
AminophyllineThe metabolism of Aminophylline can be decreased when combined with Tylosin.
ArticaineThe risk or severity of methemoglobinemia can be increased when Tylosin is combined with Articaine.
AtorvastatinThe risk or severity of adverse effects can be increased when Tylosin is combined with Atorvastatin.
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Tylosin.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Tylosin is combined with Benzocaine.
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Tylosin phosphateNR75X12AFF1405-53-4NBOODGNJLRRJNA-IAGPQMRQSA-N
Tylosin tartrate5P4625C51T74610-55-2ICVKYYINQHWDLM-KBEWXLTPSA-N
International/Other Brands
Tylan

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Aminoglycosides
Alternative Parents
Macrolides and analogues / Disaccharides / O-glycosyl compounds / Oxanes / Alpha-hydrogen aldehydes / Tertiary alcohols / 1,2-aminoalcohols / Trialkylamines / Amino acids and derivatives / Carboxylic acid esters
show 10 more
Substituents
1,2-aminoalcohol / Acetal / Alcohol / Aldehyde / Aliphatic heteromonocyclic compound / Alpha-hydrogen aldehyde / Amine / Amino acid or derivatives / Aminoglycoside core / Carbonyl group
show 24 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
macrolide antibiotic, monosaccharide derivative, enone, disaccharide derivative, aldehyde, leucomycin (CHEBI:17658) / Macrolides and lactone polyketides, Macrolides (C01457) / Macrolides and lactone polyketides (LMPK04000004)
Affected organisms
Not Available

Chemical Identifiers

UNII
YEF4JXN031
CAS number
1401-69-0
InChI Key
WBPYTXDJUQJLPQ-VMXQISHHSA-N
InChI
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
IUPAC Name
2-[(4R,5S,6S,7R,9R,11E,13E,15R,16R)-6-{[(2R,3R,4R,5S,6R)-5-{[(2S,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy}-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-16-ethyl-4-hydroxy-15-({[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxy}methyl)-5,9,13-trimethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde
SMILES
CC[C@H]1OC(=O)C[C@@H](O)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)[C@@H](O[C@H]3C[C@@](C)(O)[C@@H](O)[C@H](C)O3)[C@@H]([C@H]2O)N(C)C)[C@@H](CC=O)C[C@@H](C)C(=O)\C=C\C(\C)=C\[C@@H]1CO[C@@H]1O[C@H](C)[C@@H](O)[C@@H](OC)[C@H]1OC

References

General References
  1. Smith HW: Tylosin. Vet Rec. 1965 Nov 6;77(45):1342. [Article]
  2. Verbov J: Tylosin dermatitis. Contact Dermatitis. 1983 Jul;9(4):325-6. [Article]
  3. Morin RB, Gorman M, Hamill RL, Demarco PV: The structure of tylosin. Tetrahedron Lett. 1970 Nov;(54):4737-40. [Article]
  4. Bobillot S, Bakos T, Sarda P, Thang TT, Ming L, Olesker A, Lukacs G: Chemical modification of tylosin. J Antibiot (Tokyo). 1995 Jul;48(7):667-70. [Article]
  5. Omura S, Matsubara H, Tsuzuki K, Nakagawa A: Chemical modification of tylosin. Thioether derivatives of tylosin and demycarosyltylosin. J Antibiot (Tokyo). 1984 Sep;37(9):1007-15. [Article]
  6. Urbanova Z, Zahradnikova M, Schovanek V, Polak L, Rabas P, Sechser T, Svandova E, Raskova H, Raska K, Janovska D, Gutova M, Sverak V, Belinger A, Vanecek J, Zima L: [Effect of tylosin in pigs]. Vet Med (Praha). 1975 May;20(5):251-60. [Article]
  7. Roberts R: Effect of feeding tylosin and tylosin and dimetridazole to cows. Vet Rec. 1981 May 16;108(20):446. [Article]
  8. Crossman PJ, Poyser MR: Effect of feeding tylosin and tylosin with dimetridazole to cows. Vet Rec. 1981 May 30;108(22):483. [Article]
  9. Massey EH, Dennen DW: Tylosin-urea adduct related to tylosin stability in cattle feed. J Agric Food Chem. 1973 Jan-Feb;21(1):112-4. [Article]
  10. Atef M, Youssef SA, Atta AH, el-Maaz AA: Disposition of tylosin in goats. Dtsch Tierarztl Wochenschr. 1991 Dec;98(12):451-3. [Article]
  11. Lilia G, Aguilera R, Cortes-Cuevas A, Rosario C, Sumano H: Circadian serum concentrations of tylosin in broilers after feed or water medication. Br Poult Sci. 2008 Sep;49(5):619-24. doi: 10.1080/00071660802357033. [Article]
  12. Gaudin V, Hedou C, Verdon E: Validation of two ELISA kits for the screening of tylosin and streptomycin in honey according to the European decision 2002/657/EC. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2013;30(1):93-109. doi: 10.1080/19440049.2012.722696. Epub 2012 Sep 26. [Article]
  13. Ali M, Wang JJ, DeLaune RD, Seo DC, Dodla SK, Hernandez AB: Effect of redox potential and pH status on degradation and adsorption behavior of tylosin in dairy lagoon sediment suspension. Chemosphere. 2013 Jun;91(11):1583-9. doi: 10.1016/j.chemosphere.2012.12.050. Epub 2013 Jan 24. [Article]
  14. Holman DB, Chenier MR: Impact of subtherapeutic administration of tylosin and chlortetracycline on antimicrobial resistance in farrow-to-finish swine. FEMS Microbiol Ecol. 2013 Jul;85(1):1-13. doi: 10.1111/1574-6941.12093. Epub 2013 Mar 11. [Article]
  15. Pinckney JL, Hagenbuch IM, Long RA, Lovell CR: Sublethal effects of the antibiotic tylosin on estuarine benthic microalgal communities. Mar Pollut Bull. 2013 Mar 15;68(1-2):8-12. doi: 10.1016/j.marpolbul.2013.01.006. Epub 2013 Feb 8. [Article]
  16. Buss M, Fessler AT, Turnidge J, Peters T, Schwarz S: Quality control ranges for tylosin 30 mug and 15 mug discs applicable to Staphylococcus aureus ATCC(R) 25923. J Antimicrob Chemother. 2014 Jan;69(1):277-80. doi: 10.1093/jac/dkt309. Epub 2013 Aug 8. [Article]
  17. Garcia-Sanchez L, Garzon-Zuniga MA, Buelna G, Moeller-Chavez GE, Noyola A, Avilez-Flores M, Estrada-Arriaga EB: Occurrence of tylosin in swine wastewater in Mexico. Water Sci Technol. 2013;68(4):894-900. doi: 10.2166/wst.2013.323. [Article]
  18. Kolanovic BS, Bilandzic N, Varenina I, Bozic D: Tylosin content in meat and honey samples over a two-year period in Croatia. J Immunoassay Immunochem. 2014;35(1):37-47. doi: 10.1080/15321819.2013.784198. [Article]
  19. Mitchell SM, Ullman JL, Teel AL, Watts RJ, Frear C: The effects of the antibiotics ampicillin, florfenicol, sulfamethazine, and tylosin on biogas production and their degradation efficiency during anaerobic digestion. Bioresour Technol. 2013 Dec;149:244-52. doi: 10.1016/j.biortech.2013.09.048. Epub 2013 Sep 20. [Article]
  20. Pei Z, Yang S, Li L, Li C, Zhang S, Shan XQ, Wen B, Guo B: Effects of copper and aluminum on the adsorption of sulfathiazole and tylosin on peat and soil. Environ Pollut. 2014 Jan;184:579-85. doi: 10.1016/j.envpol.2013.09.038. Epub 2013 Nov 5. [Article]
  21. Khaliq S, Ghauri MA, Akhtar K: Characterization of mutations in regulatory genes of Tyl cluster leading to overexpression of tylosin in mutant gamma-1 of Streptomyces fradiae NRRL-2702. Appl Microbiol Biotechnol. 2014 Jan;98(2):785-93. doi: 10.1007/s00253-013-5317-8. Epub 2013 Nov 24. [Article]
  22. Lerner U, Amram E, Ayling RD, Mikula I, Gerchman I, Harrus S, Teff D, Yogev D, Lysnyansky I: Acquired resistance to the 16-membered macrolides tylosin and tilmicosin by Mycoplasma bovis. Vet Microbiol. 2014 Jan 31;168(2-4):365-71. doi: 10.1016/j.vetmic.2013.11.033. Epub 2013 Dec 14. [Article]
  23. Caraffini S, Assalve D, Stingeni L, Lisi P: Tylosin, an airborne contact allergen in veterinarians. Contact Dermatitis. 1994 Nov;31(5):327-8. [Article]
KEGG Drug
D02490
KEGG Compound
C01457
ChemSpider
4444097
RxNav
995505
ChEBI
17658
ChEMBL
CHEMBL42743
ZINC
ZINC000252441679
PDBe Ligand
TYK
Wikipedia
Tylosin
PDB Entries
1k9m

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Powder
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.211 mg/mLALOGPS
logP1.46ALOGPS
logP2.32Chemaxon
logS-3.6ALOGPS
pKa (Strongest Acidic)12.45Chemaxon
pKa (Strongest Basic)7.2Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count17Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area238.67 Å2Chemaxon
Rotatable Bond Count13Chemaxon
Refractivity232.21 m3·mol-1Chemaxon
Polarizability98.12 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Drug created at February 25, 2016 19:04 / Updated at April 20, 2021 00:38