TYLOSIN PHOSPHATE

First approved in 2009

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C46H77NO17.H3O4P
Molecular Weight	1014.0953
Optical Activity	UNSPECIFIED
Defined Stereocenters	21 / 21
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OP(O)(O)=O.[H][C@@]1(C[C@@](C)(O)[C@@H](O)[C@H](C)O1)O[C@@H]2[C@@H](C)O[C@@]([H])(O[C@H]3[C@@H](CC=O)C[C@@H](C)C(=O)\C=C\C(C)=C\[C@H](CO[C@@H]4O[C@H](C)[C@@H](O)[C@@H](OC)[C@H]4OC)[C@@H](CC)OC(=O)C[C@@H](O)[C@@H]3C)[C@H](O)[C@H]2N(C)C

InChI

InChIKey=NBOODGNJLRRJNA-IAGPQMRQSA-N

InChI=1S/C46H77NO17.H3O4P/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;1-5(2,3)4/h14-15,17-18,24-30,32-33,35-45,50,52-55H,13,16,19-22H2,1-12H3;(H3,1,2,3,4)/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

HIDE SMILES / InChI

Description
Sources: http://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/ucm091554.pdf
Curator's Comment: Description was created based on several sources, including https://www.elanco.us/labels/Swine/Tylan_Soluble.pdf

Tylosin (trade names Tylocine, Tylan) is a bacteriostat 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. It is found naturally as a fermentation product of Streptomyces fradiae. It is a macrolide antibiotic. Tylosin is used in veterinary medicine to treat bacterial infections in a wide range of species and has a high margin of safety. Tylosin is certified by the FDA but is only approved for use in livestock such as cattle, chickens, swine, and turkeys. The FDA has prohibited the use of tylosin in dogs and cats, except where it is specifically prescribed by a veterinarian. Tylosin has a bacteriostatic effect on susceptible organisms, caused by inhibition of protein synthesis through binding to the 50S subunit of the bacterial ribosome.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Mycoplasma sp. 1220 growth 4 Target ID: Mycoplasma sp. 1220 growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/27543140	Inhibitor 8297
Staphylococcus aureus growth 27 Target ID: Staphylococcus aureus growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/14711312	Inhibitor 8297
E. coli growth 6 Target ID: E. coli growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/14711312	Inhibitor 8297
Streptococcus pneumoniae growth 20 Target ID: Streptococcus pneumoniae growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/14711312	Inhibitor 8297
Pasteurella multocida growth 4 Target ID: Pasteurella multocida growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/9135031	Inhibitor 8297
Fusobacterium necrophorum growth 4 Target ID: Fusobacterium necrophorum growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/3398001	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bovine respiratory complex 4 Sources: http://www.accessdata.fda.gov/spl/data/20c69938-ade4-46eb-adb6-710165f92002/20c69938-ade4-46eb-adb6-710165f92002.xml	Curative		Approved 8429	Tylan 200 Approved Use In beef cattle and non-lactating dairy cattle, Tylan 200 Injection is indicated for use in the treatment of bovine respiratory complex (shipping fever, pneumonia) usually associated with Pasteurella multocida and Actinomyces pyogenes; foot rot (necrotic pododermatitis) and calf diphtheria caused by Fusobacterium necrophorum and metritis caused by Actinomyces pyogenes. In swine, Tylan 200 Injection is indicated for use in the treatment of swine arthritis caused by Mycoplasma hyosynoviae; swine pneumonia caused by Pasteurella spp; swine erysipelas caused by Erysipelothrix rhusiopathiae; swine dysentery associated with Treponema hyodysenteriae when followed by appropriate medication in the drinking water and/or feed. Launch Date 2010
Calf diphtheria 6 Sources: http://www.accessdata.fda.gov/spl/data/20c69938-ade4-46eb-adb6-710165f92002/20c69938-ade4-46eb-adb6-710165f92002.xml	Curative		Approved 8429	Tylan 200 Approved Use In beef cattle and non-lactating dairy cattle, Tylan 200 Injection is indicated for use in the treatment of bovine respiratory complex (shipping fever, pneumonia) usually associated with Pasteurella multocida and Actinomyces pyogenes; foot rot (necrotic pododermatitis) and calf diphtheria caused by Fusobacterium necrophorum and metritis caused by Actinomyces pyogenes. In swine, Tylan 200 Injection is indicated for use in the treatment of swine arthritis caused by Mycoplasma hyosynoviae; swine pneumonia caused by Pasteurella spp; swine erysipelas caused by Erysipelothrix rhusiopathiae; swine dysentery associated with Treponema hyodysenteriae when followed by appropriate medication in the drinking water and/or feed. Launch Date 2010

PubMed

Title	Date	PubMed
Anti-infective drug use in relation to the risk of agranulocytosis and aplastic anemia. A report from the International Agranulocytosis and Aplastic Anemia Study.	1989 May	2785785

Patents

Sample Use Guides

In Vivo Use Guide

BEEF CATTLE AND NON-LACTATING DAIRY CATTLE—Inject intramuscularly 8 mg per pound of body weight one time daily (1 mL per 6.25 pounds). Treatment should be continued 24 hours following remission of disease signs, not to exceed 5 days. SWINE—Inject intramuscularly 4 mg per pound of body weight (1 mL per 12.5 pounds) twice daily. Treatment should be continued 24 hours following remission of disease signs, not to exceed 3 days. Do not inject more than 5 mL per site.

Route of Administration: Intramuscular

In Vitro Use Guide

Tylosin yielded MIC50 value for Mycoplasma sp. 1220 strain isolated from geese in Hungary - 8 ug/ml

Name

Type

Language

TYLOSIN PHOSPHATE

Common Name

English

TYLOSIN PHOSPHATE (SALT)

Common Name

English

TYLOSIN PHOSPHATE [GREEN BOOK]

Common Name

English

TYLOSIN A PHOSPHATE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C261