Tylosin monotartrate

Tylosin monotartrate

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Tylosin monotartrate
Category Antibiotics
Catalog number BBF-03943
CAS 74610-55-2
Molecular Weight 1066.19
Molecular Formula C50H83NO23
Purity >98%

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Description

Tylosin tartrate is a macrolide antibiotic produced by Streptomyces. Tylosin tartrate is an antimicrobial for gram-positive bacteria and mycoplasma. It can be used to prevent and treat respiratory diseases such as mycoplasma pneumonia, pleuropneumonia, swine pneumonia, Haemophilus parasuis, streptococcus suis, and other tissue infections.

Specification

Related CAS 1401-69-0 (free base) 1405-54-5 (x-tartrate) 1405-53-4 (phosphate) 8075-70-5 (Deleted CAS) 61913-18-6 (Deleted CAS) 65608-64-2 (Deleted CAS)
Synonyms Tylosin, (2R,3R)-2,3-dihydroxybutanedioate (1:1); Tylosin, (2R,3R)-2,3-dihydroxybutanedioate (1:1) (salt); Tylosin, [R-(R*,R*)]-2,3-dihydroxybutanedioate (1:1) (salt); Pharmasin; Tylan Injectable; Tylan Soluble; Tylosin tartrate
Storage Store at -20°C
IUPAC Name (2R,3R)-2,3-dihydroxybutanedioic acid;2-[(4R,5S,6S,7R,9R,11E,13E,15R,16R)-6-[(2R,3R,4R,5S,6R)-5-[(2S,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-16-ethyl-4-hydroxy-15-[[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-5,9,13-trimethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde
Canonical SMILES CCC1C(C=C(C=CC(=O)C(CC(C(C(C(CC(=O)O1)O)C)OC2C(C(C(C(O2)C)OC3CC(C(C(O3)C)O)(C)O)N(C)C)O)CC=O)C)C)COC4C(C(C(C(O4)C)O)OC)OC.C(C(C(=O)O)O)(C(=O)O)O
InChI InChI=1S/C46H77NO17.C4H6O6/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;5-1(3(7)8)2(6)4(9)10/h14-15,17-18,24-30,32-33,35-45,50,52-55H,13,16,19-22H2,1-12H3;1-2,5-6H,(H,7,8)(H,9,10)/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-;1-,2-/m11/s1
InChI Key ICVKYYINQHWDLM-KBEWXLTPSA-N

Properties

Appearance Off-white to Yellow Powder
Antibiotic Activity Spectrum Gram-positive bacteria; mycoplasma
Melting Point 140-146°C
Solubility Soluble in Chloroform (Slightly), Methanol (Slightly), Water

Reference Reading

1.Sub-MIC Tylosin Inhibits Streptococcus suis Biofilm Formation and Results in Differential Protein Expression.
Wang S1, Yang Y1, Zhao Y1, Zhao H2, Bai J1, Chen J1, Zhou Y1, Wang C1, Li Y1. Front Microbiol. 2016 Mar 30;7:384. doi: 10.3389/fmicb.2016.00384. eCollection 2016.
Streptococcus suis (S.suis) is an important zoonotic pathogen that causes severe diseases in humans and pigs. Biofilms of S. suis can induce persistent infections that are difficult to treat. In this study, the effect of tylosin on biofilm formation of S. suis was investigated. 1/2 minimal inhibitory concentration (MIC) and 1/4 MIC of tylosin were shown to inhibit S. suis biofilm formation in vitro. By using the iTRAQ strategy, we compared the protein expression profiles of S. suis grown with sub-MIC tylosin treatment and with no treatment. A total of 1501 proteins were identified by iTRAQ. Ninety-six differentially expressed proteins were identified (Ratio > ±1.5, p < 0.05). Several metabolism proteins (such as phosphoglycerate kinase) and surface proteins (such as ABC transporter proteins) were found to be involved in biofilm formation. Our results indicated that S. suis metabolic regulation, cell surface proteins, and virulence proteins appear to be of importance in biofilm growth with sub-MIC tylosin treatment.
2.Comparison of agar dilution and antibiotic gradient strip test with broth microdilution for susceptibility testing of swine Brachyspira species.
Mirajkar NS1, Gebhart CJ2. J Vet Diagn Invest. 2016 Mar;28(2):133-43. doi: 10.1177/1040638716629154.
Production-limiting diseases in swine caused by Brachyspira are characterized by mucohemorrhagic diarrhea (B. hyodysenteriae and "B. hampsonii") or mild colitis (B. pilosicoli), while B. murdochii is often isolated from healthy pigs. Emergence of novel pathogenic Brachyspira species and strains with reduced susceptibility to commonly used antimicrobials has reinforced the need for standardized susceptibility testing. Two methods are currently used for Brachyspira susceptibility testing: agar dilution (AD) and broth microdilution (BMD). However, these tests have primarily been used for B. hyodysenteriae and rarely for B. pilosicoli. Information on the use of commercial susceptibility testing products such as antibiotic gradient strips is lacking. Our main objective was to validate and compare the susceptibility results, measured as the minimum inhibitory concentration (MIC), of 6 antimicrobials for 4 Brachyspira species (B. hyodysenteriae, "B.
3.Quantifying Attachment and Antibiotic Resistance of from Conventional and Organic Swine Manure.
Zwonitzer MR, Soupir ML, Jarboe LR, Smith DR. J Environ Qual. 2016 Mar;45(2):609-17. doi: 10.2134/jeq2015.05.0245.
Broad-spectrum antibiotics are often administered to swine, contributing to the occurrence of antibiotic-resistant bacteria in their manure. During land application, the bacteria in swine manure preferentially attach to particles in the soil, affecting their transport in overland flow. However, a quantitative understanding of these attachment mechanisms is lacking, and their relationship to antibiotic resistance is unknown. The objective of this study is to examine the relationships between antibiotic resistance and attachment to very fine silica sand in collected from swine manure. A total of 556 isolates were collected from six farms, two organic and four conventional (antibiotics fed prophylactically). Antibiotic resistance was quantified using 13 antibiotics at three minimum inhibitory concentrations: resistant, intermediate, and susceptible. Of the 556 isolates used in the antibiotic resistance assays, 491 were subjected to an attachment assay.
4.Examination of the Aerobic Microflora of Swine Feces and Stored Swine Manure.
Whitehead TR, Cotta MA. J Environ Qual. 2016 Mar;45(2):604-8. doi: 10.2134/jeq2015.05.0248.
Understanding antibiotic resistance in agricultural ecosystems is critical for determining the effects of subtherapeutic and therapeutic uses of antibiotics for domestic animals. This study was conducted to ascertain the relative levels of antibiotic resistance in the aerobic bacterial population to tetracycline, tylosin, and erythromycin. Swine feces and manure samples were plated onto various agar media with and without antibiotics and incubated at 37°C. Colonies were counted daily. Randomly selected colonies were isolated and characterized by 16S rRNA sequence analyses and additional antibiotic resistance and biochemical analyses. Colonies were recovered at levels of 10 to 10 CFU mL for swine slurry and 10 to 10 CFU g swine feces, approximately 100-fold lower than numbers obtained under anaerobic conditions. Addition of antibiotics to the media resulted in counts that were 60 to 80% of those in control media without added antibiotics.

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