Lasalocid
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| Category | Animal Health |
| Catalog number | BBF-02645 |
| CAS | 25999-31-9 |
| Molecular Weight | 590.80 |
| Molecular Formula | C34H53O8 |
| Purity | > 95% |
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Description
It is produced by the strain of Str. lasaliensis. It has anti-gram-positive bacteria, protozoa and mycobacterium activity. It is added to feed to prevent coccidiosis in chickens.
Specification
| Related CAS | 25999-20-6 (sodium) |
| Synonyms | Lasalocid A; Lasalocide; Lasalocidum; Antibiotic X 537A; 6-(7-(5-Ethyl-5-(5-ethyltetrahydro-5-hydroxy-6-methyl-2H-pyran-2-yl)tetrahydro-3-methyl-2-furanyl)-4-hydroxy-3,5-dimethyl-6-oxononyl)-2-hydroxy-3-methylbenzoic acid, (2R-(2alpha(2S*(3R*,4S*,5S*,7R*),3S*,5S*),5alpha,6beta))- |
| Shelf Life | 2 years |
| Storage | Store in a cool and dry place and at 0 - 4℃ for short term (days to weeks) or -134℃ for long term (months to years). |
| IUPAC Name | 6-[(3R,4S,5S,7R)-7-[(2S,3S,5S)-5-ethyl-5-[(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyloxan-2-yl]-3-methyloxolan-2-yl]-4-hydroxy-3,5-dimethyl-6-oxononyl]-2-hydroxy-3-methylbenzoic acid |
| Canonical SMILES | CCC(C1C(CC(O1)(CC)C2CCC(C(O2)C)(CC)O)C)C(=O)C(C)C(C(C)CCC3=C(C(=C(C=C3)C)O)C(=O)O)O |
| InChI | 1S/C34H54O8/c1-9-25(31-21(6)18-34(11-3,42-31)26-16-17-33(40,10-2)23(8)41-26)30(37)22(7)28(35)19(4)12-14-24-15-13-20(5)29(36)27(24)32(38)39/h13,15,19,21-23,25-26,28,31,35-36,40H,9-12,14,16-18H2,1-8H3,(H,38,39)/t19-,21+,22+,23+,25+,26-,28+,31+,33-,34+/m1/s1 |
| InChI Key | BBMULGJBVDDDNI-OWKLGTHSSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | Colorless Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Mycobacteria; Parasites |
| Boiling Point | 735.7±60.0°C (Predicted) |
| Melting Point | 110-114°C |
| Density | 1.119±0.06 g/cm3 (Predicted) |
| Solubility | Soluble in Methanol, Ethanol, DMSO |
Reference Reading
1.A meta-analysis of lasalocid effects on rumen measures, beef and dairy performance, and carcass traits in cattle.
Golder HM, Lean IJ. J Anim Sci. 2016 Jan;94(1):306-26. doi: 10.2527/jas.2015-9694.
The effects of lasalocid on rumen measures, beef and dairy performance, and carcass traits were evaluated using meta-analysis. Meta-regression was used to investigate sources of heterogeneity. Ten studies (20 comparisons) were used in the meta-analysis on rumen measures. Lasalocid increased total VFA and ammonia concentrations by 6.46 and 1.44 m, respectively. Lasalocid increased propionate and decreased acetate and butyrate molar percentage (M%) by 4.62, 3.18, and 0.83%, respectively. Valerate M% and pH were not affected. Meta-regression found butyrate M% linearly increased with duration of lasalocid supplementation (DUR; = 0.017). When >200 mg/d was fed, propionate and valerate M% were higher and acetate M% was lower ( = 0.042, = 0.017, and = 0.005, respectively). Beef performance was assessed using 31 studies (67 comparisons). Lasalocid increased ADG by 40 g/d, improved feed-to-gain ratio (F:G) by 410 g/kg, and improved feed efficiency (FE; combined measure of G:F and the inverse of F:G).
2.Analysis of lasalocid residues in grease and fat using liquid chromatography-mass spectrometry.
Clark SB1, Storey JM, Carr JR, Madson M. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2015;32(8):1243-8. doi: 10.1080/19440049.2015.1052572. Epub 2015 Jun 9.
A method for the determination of lasalocid, an antibiotic and coccidiostat, in grease and fat is described. The manufacture of lasalocid produces a grease-like residue as a waste byproduct. Recently this byproduct has been shown to have been illegally introduced into the animal feed chain. Therefore, a quantitative and confirmatory procedure to analyse for lasalocid in this matrix is needed. A portion of grease/oil sample was extracted into hexane-washed acetonitrile, and a portion of the extract was then applied to a carboxylic acid solid-phase extraction (SPE) column for concentration and clean-up. The SPE column was washed with additional hexane-washed acetonitrile and ethyl acetate/methanol, after which lasalocid was eluted with 10% ammoniated methanol. The eluate was evaporated to dryness, redissolved in (1:1) acetonitrile-water and filtered through a PTFE syringe filter. Confirmation and quantitation of lasalocid in the final extract employed a triple quadrupole LC-MS/MS.
3.Spectroscopic studies of the equilibrium between complexes of lasalocid acid with propargylamine and metal cations.
Rutkowski J1, Huczyński A2, Ratajczak-Sitarz M2, Katrusiak A2, Brzezinski B2, Bartl F3. Spectrochim Acta A Mol Biomol Spectrosc. 2015 Nov 5;150:704-11. doi: 10.1016/j.saa.2015.05.099. Epub 2015 Jun 9.
The molecular structure of 1:1 complex formed between the naturally occurring polyether ionophore, called lasalocid acid (LAS) and propargylamine (PROP) is studied by X-ray, FT-IR, (1)H NMR, (13)C NMR and ESI-MS methods. The complex formed between deprotonated LAS acid and protonated PROP molecule is stabilized by intra- and inter-molecular hydrogen bonds. The protons of the protonated amine group are hydrogen bonded to etheric and hydroxyl oxygen atoms of the LAS anion. The similarity of the FT-IR spectra of the LAS-PROP complex in solid state and in solution demonstrated that the molecular structures of the complex in both states are comparable. It is shown that LAS in solution can form concurrent complexes with metal cations (M=Li(+), Na(+), K(+)) and amine existing in equilibrium. Analysis of the structures of lasalocid complexes is important for a better understanding of the antibacterial and anticancer properties of lasalocid acid.
4.Development of intramammary delivery systems containing lasalocid for the treatment of bovine mastitis: impact of solubility improvement on safety, efficacy, and milk distribution in dairy cattle.
Wang W1, Song Y1, Petrovski K2, Eats P2, Trott DJ2, Wong HS2, Page SW3, Perry J2, Garg S1. Drug Des Devel Ther. 2015 Jan 22;9:631-42. doi: 10.2147/DDDT.S74731. eCollection 2015.
BACKGROUND: Mastitis is a major disease of dairy cattle. Given the recent emergence of methicillin-resistant Staphylococcus aureus as a cause of bovine mastitis, new intramammary (IMA) treatments are urgently required. Lasalocid, a member of the polyether ionophore class of antimicrobial agents, has not been previously administered to cows by the IMA route and has favorable characteristics for development as a mastitis treatment. This study aimed to develop an IMA drug delivery system (IMDS) of lasalocid for the treatment of bovine mastitis.
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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 ╳
