Tulathromycin A

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Tulathromycin A
Category Antibiotics
Catalog number BBF-04301
CAS 217500-96-4
Molecular Weight 806.08
Molecular Formula C41H79N3O12
Purity 98% by HPLC

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BBF-04301 5 g $298 In stock

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Description

Tulathromycin A is a triamilide antibiotic used for the treatment of bovine and porcine respiratory disease. It exists as an equilibrium mixture of two isomeric forms, Tulathromycin A (90%) and B (10%).

Specification

Synonyms Tulathromycin; Draxxin; 1-Oxa-6-azacyclopentadecan-15-one,13-[[2,6-dideoxy-3-C-methyl-3-O-methyl-4-C-[(propylamino)methyl]-a-L-ribo-hexopyranosyl]oxy]-2-ethyl-3,4,10-trihydroxy-3,5,8,10,12,14-hexamethyl-11-[[3,4,6-trideoxy-3-(dimethylamino)-b-D-xylo-hexopyranosyl]oxy]-, (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-
Storage Store at -20°C
IUPAC Name (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyl-5-(propylaminomethyl)oxan-2-yl]oxy-3,5,8,10,12,14-hexamethyl-1-oxa-6-azacyclopentadecan-15-one
Canonical SMILES CCCNCC1(C(OC(CC1(C)OC)OC2C(C(C(CC(CNC(C(C(C(OC(=O)C2C)CC)(C)O)O)C)C)(C)O)OC3C(C(CC(O3)C)N(C)C)O)C)C)O
InChI 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
InChI Key GUARTUJKFNAVIK-QPTWMBCESA-N

Properties

Appearance White to Off-white Solid
Application Anti-Bacterial Agents
Boiling Point 853.8±65.0°C (Predicted)
Melting Point 186-188°C
Density 1.17 g/cm3
Solubility Slightly soluble in DMSO, Methanol

Reference Reading

1. Tulathromycin: an overview of a new triamilide antibiotic for livestock respiratory disease
Nigel A Evans Vet Ther . 2005 Summer;6(2):83-95.
Tulathromycin is a novel triamilide antimicrobial that has been approved for use in the treatment and prevention of bovine respiratory disease and the treatment of swine respiratory disease in the European Union and the United States. The agent penetrates gram-negative bacteria well, and it exhibits mixed bacteriostatic and bactericidal activity. Tulathromycin is formulated as a ready-to-use, sterile aqueous solution, and the packaged concentration of 100 mg tulathromycin/ml allows low-volume dosing. This agent is characterized by rapid absorption from the injection site, extensive distribution to tissue, and slow elimination, thereby providing high, prolonged drug concentration in the lungs. Studies show that a single dose of tulathromycin is effective in treating cattle and swine with respiratory disease and in preventing high-risk cattle from developing respiratory disease.
2. Antimalarial activity of tulathromycin in a murine model of malaria
Nathan W Schmidt, Joshua E Denny, Nicolas Villarino Antimicrob Agents Chemother . 2015;59(6):3672-4. doi: 10.1128/AAC.02858-14.
There is an urgent need for new antimalarial agents and strategies to treat and control malaria. This study shows an antiplasmodium effect of tulathromycin in mice infected with Plasmodium yoelii. The administration of tulathromycin around the time of infection prevented the progression of disease in 100% of the animals. In addition, highly parasitized mice treated with tulathromycin showed a decreased parasite burden and cleared the parasite faster than did untreated infected mice.
3. Pharmacokinetic/Pharmacodynamic Relationships of Tulathromycin Against Actinobacillus pleuropneumoniae in a Porcine Tissue Cage Infection Model
Yuzhou Ling, Huanzhong Ding, Yanzhe Wei, Xiangguang Shen, Lihua Yao, Lan Yang Front Vet Sci . 2022 Mar 28;9:822432. doi: 10.3389/fvets.2022.822432.
Tulathromycin is a semi-synthetic macrolide antibiotic that is highly effective in treating respiratory tract bacterial infections. We evaluated thein vivoantibacterial activity of tulathromycin againstActinobacillus pleuropneumoniaein piglets and determined its pharmacokinetic/pharmacodynamic (PK/PD) relationships using a tissue cage infection model.A. pleuropneumoniae(108CFU/ml) was exposed to tulathromycin via intramuscular injection followed by a collection of cage tissue fluids at various intervals. The percentage of time the drug concentration remained above the minimum inhibitory concentration (MIC) divided by the dosing interval (%T > MIC) was the best PK/PD index to describe the antibacterial efficacy of tulathromycin (R2= 0.9421). The %T > MIC values required to achieve 1 - log10CFU/ml reductions and bactericidal activity (3 - log10CFU/ml reduction) were 50.8 and 96.38%, respectively. These results demonstrated that maintaining %T > MIC above 96.38% achieved bactericidal activity and thereby optimized the clinical dosage.

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