TULATHROMYCIN A

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C41H79N3O12
Molecular Weight	806.0789
Optical Activity	UNSPECIFIED
Defined Stereocenters	18 / 18
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]1(C[C@@](C)(OC)[C@](O)(CNCCC)[C@H](C)O1)O[C@H]2[C@H](C)[C@@H](O[C@]3([H])O[C@H](C)C[C@@H]([C@H]3O)N(C)C)[C@](C)(O)C[C@@H](C)CN[C@H](C)[C@@H](O)[C@](C)(O)[C@@H](CC)OC(=O)[C@@H]2C

InChI

InChIKey=GUARTUJKFNAVIK-QPTWMBCESA-N

InChI=1S/C41H79N3O12/c1-15-17-42-22-41(50)28(8)53-31(20-39(41,10)51-14)55-33-25(5)35(56-37-32(45)29(44(12)13)18-24(4)52-37)38(9,48)19-23(3)21-43-27(7)34(46)40(11,49)30(16-2)54-36(47)26(33)6/h23-35,37,42-43,45-46,48-50H,15-22H2,1-14H3/t23-,24-,25+,26-,27-,28+,29+,30-,31+,32-,33+,34-,35-,37+,38-,39-,40-,41+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C41H79N3O12
Molecular Weight	806.0789
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	18 / 18
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.zoetisus.com/products/pages/draxxinbeef/documents/draxxin-8.5x11-1pg-pi.pdf | http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/veterinary/000077/WC500063309.pdf

Tulathromycin A is a triamilide antibiotic. Exists as an equilibrium mixture of two isomeric forms, Tulathromycin A (90%) and B (10%). It acts by binding to a bacterial ribosome sub-unit thereby inhibiting protein synthesis. Tulathromycin mixture is indicated for the treatment of bovine and swine respiratory disease, infectious bovine keratoconjunctivitis, bovine foot rot (interdigital necrobacillosis). In one bovine respiratory disease field study, two calves treated with DRAXXIN (Tulathromycin mixture) exhibited transient hypersalivation. In one field study, one out of 40 pigs treated with DRAXXIN exhibited mild salivation that resolved in less than four hours. Cross resistance occurs with other macrolides. Do not administer simultaneously with antimicrobials with a similar mode of action such as other macrolides or lincosamides.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial 70S ribosome 179 Target ID: CHEMBL2363135 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22926570	Inhibitor 8297		0.26 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Bovine respiratory disease 8 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/veterinary/000077/WC500063309.pdf	Curative	Approved 8429	DRAXXIN Approved Use DRAXXIN Injectable Solution is indicated for the treatment of bovine respiratory disease (BRD) associated with Mannheimia haemolytica, Pasteurella multocida, Histophilus somni, and Mycoplasma bovis; and for the control of respiratory disease in cattle at high risk of developing BRD associated with Mannheimia haemolytica, Pasteurella multocida, Histophilus somni, and Mycoplasma bovis. Launch Date 2005
Swine respiratory disease 1 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/veterinary/000077/WC500063309.pdf	Curative	Approved 8429	DRAXXIN Approved Use DRAXXIN Injectable Solution is indicated for the treatment of swine respiratory disease (SRD) associated with Actinobacillus pleuropneumoniae, Pasteurella multocida, Bordetella bronchiseptica, Haemophilus parasuis, and Mycoplasma hyopneumoniae; and for the control of SRD associated with Actinobacillus pleuropneumoniae, Pasteurella multocida, and Mycoplasma hyopneumoniae in groups of pigs where SRD has been diagnosed. Launch Date 2005
Infectious bovine keratoconjunctivitis 1 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/veterinary/000077/WC500063309.pdf	Curative	Approved 8429	DRAXXIN Approved Use DRAXXIN Injectable Solution is indicated for the treatment of infectious bovine keratoconjunctivitis (IBK) associated with Moraxella Bovis. Launch Date 2007
Bovine foot rot 1 Sources: https://www.zoetisus.com/products/pages/draxxinbeef/documents/draxxin-8.5x11-1pg-pi.pdf	Curative	Approved 8429	DRAXXIN Approved Use DRAXXIN Injectable Solution is indicated for the treatment of bovine foot rot (interdigital necrobacillosis) associated with Fusobacterium necrophorum and Porphyromonas levii. Launch Date 2005

PubMed

Title	Date	PubMed
An analytical method for the analysis of tulathromycin, an equilibrating triamilide, in bovine and porcine plasma and lung.	2004 Apr 21	15080618
[Tulathromycin, a new antibiotic for farm animals].	2004 May 1	15156657
Pharmacokinetics and lung tissue concentrations of tulathromycin, a new triamilide antibiotic, in cattle.	2004 Spring	15150731
Ultratrace analysis of nine macrolides, including tulathromycin A (Draxxin), in edible animal tissues with minicolumn liquid chromatography tandem mass spectrometry.	2008 Oct 8	18778062

Patents

Sample Use Guides

In Vivo Use Guide

Cattle: Inject intramuscularly single dose in the neck at a dosage of 2.5 mg/kg (1.1 mL/100 lb) body weight (BW). Do not inject more than 10 mL per injection site. Swine: Inject intramuscularly as a single dose in the neck at a dosage of 2.5 mg/kg (0.25 mL/22 lb) BW. Do not inject more than 2.5 mL per injection site.

Route of Administration: Other

In Vitro Use Guide

Tulathromycin was found to have poor activity in vitro against R. equi isolates susceptible or resistant to macrolides, with MIC50 and MIC90 values >64 ug/mL for all isolates.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:20:53 GMT 2023` Edited by `admin` on `Fri Dec 15 16:20:53 GMT 2023`
Record UNII	897A3KN7AP
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TULATHROMYCIN A

Common Name

English

TULATHROMYCIN COMPONENT A

Common Name

English

CP-472295

Code

English

TULATHROMYCIN A [MI]

Common Name

English

CP-472,295

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C261