TILMICOSIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C46H80N2O13
Molecular Weight	869.133
Optical Activity	UNSPECIFIED
Defined Stereocenters	19 / 19
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]4(O[C@H]1[C@@H](CCN2C[C@@H](C)C[C@@H](C)C2)C[C@@H](C)C(=O)\C=C\C(C)=C\[C@H](CO[C@@H]3O[C@H](C)[C@@H](O)[C@@H](OC)[C@H]3OC)[C@@H](CC)OC(=O)C[C@@H](O)[C@@H]1C)O[C@H](C)[C@@H](O)[C@@H]([C@H]4O)N(C)C

InChI

InChIKey=JTSDBFGMPLKDCD-XVFHVFLVSA-N

InChI=1S/C46H80N2O13/c1-13-36-33(24-57-46-44(56-12)43(55-11)40(53)31(8)59-46)19-25(2)14-15-34(49)28(5)20-32(16-17-48-22-26(3)18-27(4)23-48)42(29(6)35(50)21-37(51)60-36)61-45-41(54)38(47(9)10)39(52)30(7)58-45/h14-15,19,26-33,35-36,38-46,50,52-54H,13,16-18,20-24H2,1-12H3/b15-14+,25-19+/t26-,27+,28-,29+,30-,31-,32+,33-,35-,36-,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/ucm115928.pdf
Curator's Comment: description was created based on several sources, including http://www.fao.org/docrep/W4601E/w4601e0e.htm http://www.merckvetmanual.com/mvm/pharmacology/antibacterial_agents/macrolides.html

Tilmicosin is a macrolide antibiotic was prepared by chemical modifications of desmycosin, and is used in veterinary. It is recommended for treatment and prevention of pneumonia in cattle, sheep and pigs, associated with Pasteurella haemolytica, P. multocida, Actinobacillus pleuropneumoniae, mycoplasma species and other microorganisms found sensitive to this compound. Tilmicosin belongs to 16-membered ring group of class macrolides. The antimicrobial mechanism seems to be the same for all of the macrolides. They interfere with protein synthesis by reversibly binding to the 50S subunit of the ribosome. They appear to bind at the donor site, thus preventing the translocation necessary to keep the peptide chain growing. The effect is essentially confined to rapidly dividing bacteria and mycoplasmas. Macrolides are regarded as being bacteriostatic but demonstrate bactericidal activity at high concentrations.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial 70S ribosome 179 Target ID: CHEMBL2363135 Sources: http://www.merckvetmanual.com/mvm/pharmacology/antibacterial_agents/macrolides.html	Binding Agent 1064

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bovine respiratory disease 8 Sources: http://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/ucm115928.pdf	Curative		Approved 8429	MICOTIL 300 Approved Use For the treatment of bovine respiratory disease (BRD) and ovine respiratory disease (ORD) associated with Mannheimia (Pasteurella) haemolytica. For the control of respiratory disease in cattle at high risk of developing BRD associated with Mannheimia (Pasteurella) haemolytica. Launch Date 2005
Ovine respiratory disease 2 Sources: http://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/ucm115928.pdf	Curative		Approved 8429	MICOTIL 300 Approved Use For the treatment of bovine respiratory disease (BRD) and ovine respiratory disease (ORD) associated with Mannheimia (Pasteurella) haemolytica. For the control of respiratory disease in cattle at high risk of developing BRD associated with Mannheimia (Pasteurella) haemolytica. Launch Date 2005

PubMed

Title	Date	PubMed
Concentrations of tilmicosin in mammary gland secretions of dairy cows following subcutaneous administration of one or two doses of an experimental preparation of tilmicosin and its efficacy against intramammary infections caused by Staphylococcus aureus.	2016 Sep	27580103

Patents

Sample Use Guides

In Vivo Use Guide

for animasl only: 10 mg/kg body weight (BW)(1.5 mL per 100 lb BW), administered once

Route of Administration: Other

In Vitro Use Guide

The MIC95 of TILMICOSIN for the Actinobacillus pleuropneumoniae isolates was 6.25 ug/mL while for the Pasteurella multocida isolates it was 12.5 ug/mL

Name

Type

Language

TILMICOSIN

Official Name

English

TILMICOSIN [USP MONOGRAPH]

Common Name

English

TILMICOSIN [USAN]

Common Name

English

LY-177370

Code

English

TILMICOSIN [HSDB]

Common Name

English

Tilmicosin [WHO-DD]

Common Name

English

TILMICOSIN [MI]

Common Name

English

TILMICOSIN [USP-RS]

Common Name

English

4 SUP(A)-O-DE(2,6-DIDEOXY-3-C-METHYL-.ALPHA.-L-RIBO-HEXOPYRANOSYL)-20-DEOXO-20-(CIS-3,5-DIMETHYLPIPERIDINO)TYLOSIN

Common Name

English

NSC-759584

Code

English

tilmicosin [INN]

Common Name

English

MICOTIL

Brand Name

English

TILMICOSIN [GREEN BOOK]

Common Name

English

LY177370

Code

English

TYLOSIN, 4 SUP(A)-O-DE(2,6-DIDEOXY-3-C-METHYL-.ALPHA.-L-RIBO-HEXOPYRANOSYL)-20-DEOXO-20-(3,5-DIMETHYL-1-PIPERIDINYL)-, (20(CIS))-

Common Name

English

EL870

Code

English

EL-870

Code

English

TILMICOSIN [MART.]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QJ01FA91