TILDIPIROSIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C41H71N3O8
Molecular Weight	734.0177
Optical Activity	UNSPECIFIED
Defined Stereocenters	12 / 12
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]4(O[C@H]1[C@@H](CCN2CCCCC2)C[C@@H](C)C(=O)\C=C\C(C)=C\[C@H](CN3CCCCC3)[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=HNDXPZPJZGTJLJ-UEJFNEDBSA-N

InChI=1S/C41H71N3O8/c1-8-35-32(26-44-20-13-10-14-21-44)23-27(2)15-16-33(45)28(3)24-31(17-22-43-18-11-9-12-19-43)40(29(4)34(46)25-36(47)51-35)52-41-39(49)37(42(6)7)38(48)30(5)50-41/h15-16,23,28-32,34-35,37-41,46,48-49H,8-14,17-22,24-26H2,1-7H3/b16-15+,27-23+/t28-,29+,30-,31+,32-,34-,35-,37+,38-,39-,40-,41+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C41H71N3O8
Molecular Weight	734.0177
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	12 / 12
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.merck-animal-health-usa.com/products/zuprevo/overview.aspx | http://www.ema.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2010/10/WC500097539.pdf

Tildipirosin is a semisynthetic derivative of the naturally occurring 16-membered macrolide tylosin. Tildipirosin is intended for parenteral treatment of respiratory disease in cattle and swine. Tildipirosin will be administered as a single-dose injection: subcutaneously in cattle and intramuscularly in swine. The anticipated optimal clinical dose is 4 mg/kg bw. Tildipirosin is not used in human medicine. It is marketed under the brand name Zuprevo. As for other macrolides, the antimicrobial activity of tildipirosin is due to its binding to the ribosomal 50S subunit of bacterial cells thereby inhibiting bacterial protein synthesis. The in vitro antimicrobial activity against Gram-negative and Gram-positive pathogens indicates that tildipirosin is effective against a range of bacterial pathogens frequently associated with bovine and swine respiratory disease. Comparison of minimum inhibitory versus bactericidal concentrations shows that generally the antimicrobial action of tildipirosin is bacteriostatic.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial 70S ribosome 179 Target ID: CHEMBL2363135 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2010/10/WC500097539.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/22926570 \| https://www.ncbi.nlm.nih.gov/pubmed/22563863	Inhibitor 8297		0.23 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bovine respiratory disease 8 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2010/10/WC500097539.pdf	Curative		Approved 8429	ZUPREVO Approved Use For the treatment of bovine respiratory disease (BRD) associated with Mannheimia haemolytica, Pasteurella multocida, and Histophilus somni in beef and non-lactating dairy cattle, and for the control of respiratory disease in beef and non-lactating dairy cattle at high risk of developing BRD associated with Mannheimia haemolytica, Pasteurella multocida, and Histophilus somni. Launch Date 2012

PubMed

Title	Date	PubMed
Clinical disease and lung lesions in calves experimentally inoculated with Histophilus somni five days after metaphylactic administration of tildipirosin or tulathromycin.	2016 Apr	27027834
Pharmacokinetics of tildipirosin in pig tonsils.	2016 Apr	26935349
A microbiological assay to estimate the antimicrobial activity of parenteral tildipirosin against foodborne pathogens and commensals in the colon of beef cattle and pigs.	2016 Jun	26538405

Patents

Sample Use Guides

In Vivo Use Guide

Inject subcutaneously as a single dose in the neck at a dosage of 4 mg/kg (1 mL/100 lb) body weight (BW). Do not inject more than 10 mL per injection site.

Route of Administration: Other

In Vitro Use Guide

MICs of tildipirosin were determined according to CLSI standards and VICH GL 36 against 10 isolates from 10 bacterial groups sourced from the faecal microbiota of healthy unmedicated human volunteers. The MICs ranged from 0.5 to greater than 128 ug/ml. The MIC50 values were 2 ug/ml for Clostridium and Fusobacterium, 4 ug/ml for E. coli, 8 ug/ml for Enterococcus, 16 ug/ml for Bifidobacterium, 32 ug/ml for Eubacterium, Bacteroides fragilis, and other Bacteroides species, and >128 ug/ml for Gram-positive anaerobic cocci (“Peptostreptococcus”) and Lactobacillus.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 01:37:01 GMT 2023` Edited by `admin` on `Sat Dec 16 01:37:01 GMT 2023`
Record UNII	S795AT66JB
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TILDIPIROSIN

Official Name

English

TILDIPIROSIN [USAN]

Common Name

English

ZUPREVO COMPONENT TILDIPIROSIN

Brand Name

English

TILDIPIROSIN [EMA EPAR VETERINARY]

Common Name

English

tildipirosin [INN]

Common Name

English

TILDIPIROSIN [MI]

Common Name

English

TILDIPIROSIN COMPONENT OF ZUPREVO

Brand Name

English

ZUPREVO

Brand Name

English

TILDIPIROSIN [GREEN BOOK]

Common Name

English

TYLONOLIDE, 20-DEOXO-23-DEOXY-5-O-(3,6-DIDEOXY-3-(DIMETHYLAMINO)-.BETA.-D- GLUCOPYRANOSYL)-20,23-DI-1-PIPERIDINYL-

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 556.733