Tylvalosin
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| Category | Antibiotics |
| Catalog number | BBF-05837 |
| CAS | 63409-12-1 |
| Molecular Weight | 1042.25 |
| Molecular Formula | C53H87NO19 |
| Purity | ≥95% |
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Description
Tylvalosin, a macrolide antibiotic, is active against S. aureus, E. coli, and P. multocidas with MICs of 2, 128, and 128 μg/mL, respectively. Tylvalosin (5 and 10 μg/mL) reduces LPS-induced production of proinflammatory cytokines, prostaglandin E2 (PGE2) and nitric oxide in RAW 264.7 cells. Preparations containing tylvalosin have been used for the treatment and metaphylaxis of enzootic pneumonia caused by M. hyopneumoniae in pigs.
Specification
| Related CAS | 63428-13-7 (tartrate) 63428-14-8 (HCl) 1453840-14-6 (phosphate) |
| Synonyms | 3-Acetate 4B-(3-methylbutanoate)-tylosin; 3-O-Acetyl-4''-O-isovaleryltylosin; Acetylisovaleryltylosin; 3-Acetyl-4''-isovaleryltylosin; AIV-tylosin; Tylosin acetate isovalerte; Oxacyclohexadeca-11,13-diene-7-acetaldehyde, 4-(acetyloxy)-15-[[(6-deoxy-2,3-di-O-methyl-β-D-allopyranosyl)oxy]methyl]-6-[[3,6-dideoxy-4-O-[2,6-dideoxy-3-C-methyl-4-O-(3-methyl-1-oxobutyl)-α-L-ribo-hexopyranosyl]-3-(dimethylamino)-β-D-glucopyranosyl]oxy]-16-ethyl-5,9,13-trimethyl-2,10-dioxo-, (4R,5S,6S,7R,9R,11E,13E,15R,16R)- |
| Storage | Store at -20°C |
| IUPAC Name | [(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6R)-6-[[(4R,5S,6S,7R,9R,11E,13E,15R,16R)-4-acetyloxy-16-ethyl-15-[[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-5,9,13-trimethyl-2,10-dioxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2,4-dimethyloxan-3-yl] 3-methylbutanoate |
| Canonical SMILES | CCC1C(C=C(C=CC(=O)C(CC(C(C(C(CC(=O)O1)OC(=O)C)C)OC2C(C(C(C(O2)C)OC3CC(C(C(O3)C)OC(=O)CC(C)C)(C)O)N(C)C)O)CC=O)C)C)COC4C(C(C(C(O4)C)O)OC)OC |
| InChI | InChI=1S/C53H87NO19/c1-16-38-36(26-65-52-49(64-15)48(63-14)44(60)31(7)67-52)22-28(4)17-18-37(57)29(5)23-35(19-20-55)46(30(6)39(69-34(10)56)24-41(59)70-38)73-51-45(61)43(54(12)13)47(32(8)68-51)72-42-25-53(11,62)50(33(9)66-42)71-40(58)21-27(2)3/h17-18,20,22,27,29-33,35-36,38-39,42-52,60-62H,16,19,21,23-26H2,1-15H3/b18-17+,28-22+/t29-,30+,31-,32-,33+,35+,36-,38-,39-,42+,43-,44-,45-,46-,47-,48-,49-,50+,51+,52-,53-/m1/s1 |
| InChI Key | KCJJINQANFZSAM-HZDSEHBESA-N |
Properties
| Appearance | Off-White to Pale Yellow Solid |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 1005.4±65.0°C (Predicted) |
| Melting Point | >105°C (dec.) |
| Density | 1.21±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Chloroform (Slightly), Methanol (Slightly) |
Reference Reading
1. Evaluation of the clinical efficacy of a water soluble formulation of tylvalosin in the control of enzootic pneumonia associated with Mycoplasma hyopneumoniae and Pasteurella multocida in pigs
Mark J Gnozzio, Annika Muller, Pascale Sierra, Cliff Ramage, Hafid A Benchaoui, Alfonso Lopez Rodriguez, Anna Catharina Berge, Rickie J Domangue, Ryan Saltzman Porcine Health Manag . 2020 Dec 4;6(1):39. doi: 10.1186/s40813-020-00177-9.
Background:The efficacy of a water soluble formulation of tylvalosin (Aivlosin® 625 mg/g granules) was evaluated in the treatment and metaphylaxis of Enzootic Pneumonia (EP) in pigs. In all four trials, pigs in the tylvalosin group were administered 10 mg tylvalosin/kg bodyweight in drinking water daily for 5 consecutive days (TVN). In a single-challenge study, pigs were inoculated with lung homogenate containing Mycoplasma hyopneumoniae. In a dual challenge study, pigs were sequentially inoculated with pure culture of M. hyopneumoniae and Pasteurella multocida. Efficacy was evaluated based on reduction of lung lesions compared to unmedicated control pigs (CTL). In two field studies at European commercial farms with confirmed outbreaks of EP, treatment efficacy in clinically affected fatteners was evaluated based on improved clinical conditions compared to pigs treated with tylosin at 10 mg/kg by injection for 3 consecutive days (TYL). In these field trials, healthy in contact pigs were enrolled for metaphylaxis efficacy evaluation based on reduction in incidence of new clinical cases of respiratory disease compared to unmedicated pigs (CTL).Results:In the M. hyopneumoniae-only challenge study, pigs in TVN group had lower lung lesion scores than CTL (6.52 vs. 14.97; p < 0.001). In the dual challenge study with M. hyopneumoniae and P. multocida, pigs in TVN group had lower lung lesion scores than CTL (3.32 vs. 8.37; p < 0.01) and the recovery of both challenge bacteria from the lungs was lower in TVN compared with CTL group (p < 0.01). In field outbreaks of EP, multicentre analysis showed that 13 days after the start of medication, treatment success for TVN pigs was significantly better than for TYL pigs (80.0% vs 48.7% p = 0.03) and metaphylactic administration of TVN significantly reduced the incidence of new clinical cases (2.1% vs. 7.8%; p < 0.01) compared with unmedicated controls.Conclusions:Tylvalosin at 10 mg/kg daily for 5 days in drinking water was safe and effective in the treatment and metaphylaxis of EP in pigs associated with infections of M. hyopneumoniae either alone or in combination with P. multocida under both experimental challenge and field natural infection conditions.
2. Tylvalosin demonstrates anti-parasitic activity and protects mice from acute toxoplasmosis
Weifeng Yuan, Zhanhui Wang, Zhenwen Zhao, Xing Li, Xinghui Zhao, Xianyong Liu, Ting Xin, Hong Jia, Li Liu, Xiangfang Tang, Zhanzhong Zhao, Lin Liang Life Sci . 2022 Apr 1;294:120373. doi: 10.1016/j.lfs.2022.120373.
Aims:Toxoplasmosis, caused by Toxoplasma gondii (Tg), is one of the most prevalent zoonotic diseases worldwide. Currently, safe and efficient therapeutic options for this disease are still being developed, and are urgently needed. Tylvalosin (Tyl), a broad-spectrum third-generation macrolide, exhibits anti-bacterial, anti-viral, and anti-inflammatory properties. The present study aims to explore the anti-parasitic and immunomodulation activities of Tyl against Tg, and the underlying mechanism.Main methods:Adhesion, invasion, replication, proliferation, plaque, reversibility, immunofluorescence assays and transmission electron microscopy were utilized to determine the anti-Toxoplasma effect of Tyl. With acute toxoplasmosis model and rabies virus-induced brain inflammation model, the anti-toxoplasmosis and immunomodulation activities of Tyl were assessed by colorimetric assay, histopathological and Oil red O staining, and real-time quantitative PCR. The involved molecular mechanisms were investigated by western blotting and immunohistochemical staining.Key findings:Tyl (5 and 10 μg/ml) can inhibit Tg propagation, and damage its ultrastructure irreversibly. The combination of Tyl and Pyrimethamine (Pyr) exhibits a better synergistic effect. Tyl (50 and 100 mg/kg) treatment intraperitoneally can delay mice death and improve survival rate, accompanying the reduced histopathological score and parasite load in the indicated tissues, espically for ileum, liver, spleen, lung and brain. Furthermore, Tg can modulate host phospho-p38 MAPK (pp38), subtilisin/kexin-isozyme-1 (SKI-1)-sterol regulatory element binding protein-1 (SREBP-1) (SKI-1-SREBP-1) pathway and peroxisome proliferators-activated receptor δ (PPARδ), while Tyl is able to reverse these signal pathways close to normal levels.Significance:Our findings indicate that Tyl exhibits anti-Toxoplasma activity and protects mice from acute toxoplasmosis.
3. Use of tylvalosin in the control of porcine enzootic pneumonia
C Lasa, M Roozen, F J Pallarés, G Ramis Vet Rec Open . 2015 Jun 30;2(1):e000079. doi: 10.1136/vetreco-2014-000079.
Objectives:The purpose of this study was to investigate the efficacy of tylvalosin (Aivlosin Water Soluble Granules, ECO Animal Health) in drinking water for control of Mycoplasma hyopneumoniae (M hyo) on a farm with chronic enzootic pneumonia (EP) problems and high prevalence of mycoplasma-like lesions at slaughter.Design:On a 4000-sow farm in the southeast of Spain, 1500 animals of same age were randomly divided into two groups: 900 pigs in the treated group (TG) and 600 pigs in the non-treated control group (CG). TG was medicated for seven days with tylvalosin in drinking water (2.5 mg tylvalosin/kg bodyweight (BW)) at weaning (from 21st to 28th day of life) and a second treatment when moved to finisher barn (from 63rd to 70th day of life).Results:In the TG, there was a significant reduction in the severity (P<0.001) and number of animals with lung lesions (P<0.001) compared with CG. TG had an increased average daily gain and decreased average number of days in finishing. TG had a lower average carcase weight, but improved homogeneity. M hyo was not detected by q-PCR in samples, taken from lungs with characteristic EP lesions in the TG (0/9), in contrast to the CG (8/9 positive).Conclusions:A strategic medication with Aivlosin at 2.5 mg tylvalosin/kg BW in drinking water for seven days at weaning and when moved to finisher barn significantly reduces mycoplasma-like lung lesions and improves productivity parameters.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
