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

Identification

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Name
Tylosin
Accession Number
DB11475
Type
Small Molecule
Groups
Vet approved
Description

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.

Structure
Thumb
Synonyms
  • Tilosina
  • Tylocine
  • Tylosin
  • Tylosin A
  • Tylosine
  • Tylosinum
Product Ingredients
IngredientUNIICASInChI Key
Tylosin phosphateNR75X12AFF1405-53-4NBOODGNJLRRJNA-IAGPQMRQSA-N
Tylosin tartrate5P4625C51T74610-55-2ICVKYYINQHWDLM-KBEWXLTPSA-N
International/Other Brands
Tylan
Categories
UNII
YEF4JXN031
CAS number
1401-69-0
Weight
Average: 916.1001
Monoisotopic: 915.519150043
Chemical Formula
C46H77NO17
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

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
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
(R)-warfarinThe serum concentration of (R)-warfarin can be increased when it is combined with Tylosin.
(S)-WarfarinThe serum concentration of (S)-Warfarin can be increased when it is combined with Tylosin.
3-isobutyl-1-methyl-7H-xanthineThe metabolism of 3-isobutyl-1-methyl-7H-xanthine can be decreased when combined with Tylosin.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Tylosin.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Tylosin.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Tylosin.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Tylosin.
7-DeazaguanineThe metabolism of 7-Deazaguanine can be decreased when combined with Tylosin.
7-ethyl-10-hydroxycamptothecinThe metabolism of 7-ethyl-10-hydroxycamptothecin can be decreased when combined with Tylosin.
7,9-DimethylguanineThe metabolism of 7,9-Dimethylguanine can be decreased when combined with Tylosin.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

References

General References
  1. Smith HW: Tylosin. Vet Rec. 1965 Nov 6;77(45):1342. [PubMed:5891431]
  2. Verbov J: Tylosin dermatitis. Contact Dermatitis. 1983 Jul;9(4):325-6. [PubMed:6225619]
  3. Morin RB, Gorman M, Hamill RL, Demarco PV: The structure of tylosin. Tetrahedron Lett. 1970 Nov;(54):4737-40. [PubMed:5500229]
  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. [PubMed:7649866]
  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. [PubMed:6501102]
  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. [PubMed:812238]
  7. Roberts R: Effect of feeding tylosin and tylosin and dimetridazole to cows. Vet Rec. 1981 May 16;108(20):446. [PubMed:7292915]
  8. Crossman PJ, Poyser MR: Effect of feeding tylosin and tylosin with dimetridazole to cows. Vet Rec. 1981 May 30;108(22):483. [PubMed:7257138]
  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. [PubMed:4682324]
  10. Atef M, Youssef SA, Atta AH, el-Maaz AA: Disposition of tylosin in goats. Dtsch Tierarztl Wochenschr. 1991 Dec;98(12):451-3. [PubMed:1790764]
  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. [PubMed:18836909]
  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. [PubMed:23013044]
  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. [PubMed:23352520]
  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. [PubMed:23397987]
  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. [PubMed:23398744]
  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. [PubMed:23928021]
  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. [PubMed:23985521]
  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. [PubMed:24063615]
  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. [PubMed:24113548]
  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. [PubMed:24201036]
  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. [PubMed:24270892]
  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. [PubMed:24393633]
  23. Caraffini S, Assalve D, Stingeni L, Lisi P: Tylosin, an airborne contact allergen in veterinarians. Contact Dermatitis. 1994 Nov;31(5):327-8. [PubMed:7867337]
External Links
KEGG Drug
D02490
KEGG Compound
C01457
ChemSpider
4444097
ChEBI
17658
ChEMBL
CHEMBL42743
HET
TYK
Wikipedia
Tylosin
PDB Entries
1k9m

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
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

Taxonomy

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
Aminoglycoside core / Macrolide / Disaccharide / Glycosyl compound / O-glycosyl compound / Oxane / Alpha-hydrogen aldehyde / Tertiary alcohol / 1,2-aminoalcohol / Amino acid or derivatives
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)

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Kuper JI, D'Aprile M: Drug-Drug interactions of clinical significance in the treatment of patients with Mycobacterium avium complex disease. Clin Pharmacokinet. 2000 Sep;39(3):203-14. [PubMed:11020135]

Drug created on February 25, 2016 12:04 / Updated on September 02, 2019 21:52