Lasalocid sodium | CAS#25999-20-6 (sodium)| antibiotic

MedKoo Cat#: 598410 | Name: Lasalocid sodium

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Lasalocid is a cationic ionophore antibiotic obtained from Streptomyces lasaliensis that, among other effects, dissociates the calcium fluxes in muscle fibers. It is used as a coccidiostat, especially in poultry.

Chemical Structure

Lasalocid sodium

CAS#25999-20-6 (sodium)

Theoretical Analysis

MedKoo Cat#: 598410

Name: Lasalocid sodium

CAS#: 25999-20-6 (sodium)

Chemical Formula: C34H53NaO8

Exact Mass: 590.3819

Molecular Weight: 612.78

Elemental Analysis: C, 66.64; H, 8.72; Na, 3.75; O, 20.89

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 350.00	2 Weeks
25mg	USD 650.00	2 Weeks

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Related CAS #

73951-77-6 (acetate),62211-64-7 (anion) 25999-31-9 (free) 25999-20-6 (sodium) 83198-76-9 (potassium)

Synonym

Lasalocid; Bovatec R; Antibiotic X 537; Antibiotic X-537; Antibiotic X537; X537; X 537; X-537; Avatec; Bovatec; Lasalocid sodium; Lasalocid sodium salt; MT 2007; NSC 243046; Ro 2-2985; Sodium lasalocid; Sodium lasalocid A;

IUPAC/Chemical Name

Benzoic acid, 6-[(3R,4S,5S,7R)-7-[(2S,3S,5S)-5-ethyl-5-[(2R,5R,6S)-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-methyl-, monosodium salt

InChi Key

RDHDUYAKDYQPEW-HWLWSTNVSA-M

InChi Code

InChI=1S/C34H54O8.Na/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);/q;+1/p-1/t19-,21+,22+,23+,25+,26-,28+,31+,33-,34+;/m1./s1

SMILES Code

O=C([O-])C1=C(CC[C@@H](C)[C@H](O)[C@H](C)C([C@H](CC)[C@H]2O[C@@]([C@H]3CC[C@](O)(CC)[C@H](C)O3)(CC)C[C@@H]2C)=O)C=CC(C)=C1O.[Na+]

Appearance

Solid powder

Purity

Refer to the Certificate of Analysis

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Lasalocid sodium (Lasalocid-A sodium) treatment led to an increase in cell wall thickness, whilst the quantity and sugar composition of the cell wall remained unchanged in BY-2 cells.

In vitro activity:

Lasalocid protects cells from all toxins tested and impairs the drop of vesicular pH along the trafficking pathways that are required for toxin sorting and translocation to the cytoplasm. Lasalocid also has an impact on the cellular distribution of GOLPH4 and GOLPH2 Golgi markers. Other intracellular trafficking compartments positive for EEA1 and Rab9A display a modified cellular pattern. In conclusion, lasalocid protects cells from multiple deadly bacterial toxins by corrupting vesicular trafficking and Golgi stack homeostasis. Reference: Toxins (Basel). 2020 Jan 1;12(1):26. https://pubmed.ncbi.nlm.nih.gov/31906353/

In vivo activity:

In experiments of coronary blockade and reperfusion carried out in rat heart, it was found that when administered from 5 to 30 minutes prior to the induction of coronary blockade, at a concentration of 2 mg/kg of body weight, the ionophore (lasalocid) immediately, simultaneously, and completely interrupts the blood pressure decay, cardiac frequency increase, electrical ventricular tachycardia and fibrillation, as well as the fall of mitochondrial oxidative phosphorylation and decay of mitochondrial oxygen uptake provoked by the induced myocardial injury. Reference: Mol Cell Biochem. 2019 Mar;453(1-2):121-130. https://pubmed.ncbi.nlm.nih.gov/30191481/

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	163.19

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 612.78 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Mahtal N, Wu Y, Cintrat JC, Barbier J, Lemichez E, Gillet D. Revisiting Old Ionophore Lasalocid as a Novel Inhibitor of Multiple Toxins. Toxins (Basel). 2020 Jan 1;12(1):26. doi: 10.3390/toxins12010026. PMID: 31906353; PMCID: PMC7020423. 2. Kim KY, Kim SH, Yu SN, Park SG, Kim YW, Nam HW, An HH, Yu HS, Kim YW, Ji JH, Seo YK, Ahn SC. Lasalocid induces cytotoxic apoptosis and cytoprotective autophagy through reactive oxygen species in human prostate cancer PC-3 cells. Biomed Pharmacother. 2017 Apr;88:1016-1024. doi: 10.1016/j.biopha.2017.01.140. Epub 2017 Feb 6. PMID: 28178613. 3. Estrada-Orihuela SF, Ibarra-Pérez C. Lasalocid immediately and completely prevents the myocardial damage caused by coronary ischemia reperfusion in rat heart. Mol Cell Biochem. 2019 Mar;453(1-2):121-130. doi: 10.1007/s11010-018-3437-2. Epub 2018 Sep 6. PMID: 30191481; PMCID: PMC6394521.

In vitro protocol:

In vivo protocol:

1. Estrada-Orihuela SF, Ibarra-Pérez C. Lasalocid immediately and completely prevents the myocardial damage caused by coronary ischemia reperfusion in rat heart. Mol Cell Biochem. 2019 Mar;453(1-2):121-130. doi: 10.1007/s11010-018-3437-2. Epub 2018 Sep 6. PMID: 30191481; PMCID: PMC6394521.

1: Wang W, Song Y, Petrovski K, Eats P, Trott DJ, Wong HS, Page SW, Perry J, Garg S. 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. Drug Des Devel Ther. 2015 Jan 22;9:631-42. doi: 10.2147/DDDT.S74731. eCollection 2015. PubMed PMID: 25653501; PubMed Central PMCID: PMC4310348. 2: Clark SB, Storey JM, Carr JR, Madson M. Analysis of lasalocid residues in grease and fat using liquid chromatography-mass spectrometry. 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. PubMed PMID: 26054429. 3: Žižek S, Dobeic M, Pintarič Š, Zidar P, Kobal S, Vidrih M. Degradation and dissipation of the veterinary ionophore lasalocid in manure and soil. Chemosphere. 2015 Nov;138:947-51. doi: 10.1016/j.chemosphere.2014.12.032. Epub 2014 Dec 30. PubMed PMID: 25556006. 4: Anderson RC, Harvey RB, Wickersham TA, MacDonald JC, Ponce CH, Brown M, Pinchak WE, Osterstock JB, Krueger N, Nisbet DJ. Effect of distillers feedstuffs and lasalocid on Campylobacter carriage in feedlot cattle. J Food Prot. 2014 Nov;77(11):1968-75. doi: 10.4315/0362-028X.JFP-14-169. PubMed PMID: 25364932. 5: Huczyński A, Janczak J, Rutkowski J, Brzezinski B. Spectroscopic, crystallographic and theoretical studies of lasalocid complex with ammonia and benzylamine. Spectrochim Acta A Mol Biomol Spectrosc. 2014 May 5;125:297-307. doi: 10.1016/j.saa.2014.01.083. Epub 2014 Jan 24. PubMed PMID: 24562161. 6: Wong FT, Hotta K, Chen X, Fang M, Watanabe K, Kim CY. Epoxide hydrolase-lasalocid a structure provides mechanistic insight into polyether natural product biosynthesis. J Am Chem Soc. 2015 Jan 14;137(1):86-9. doi: 10.1021/ja511374k. Epub 2014 Dec 31. PubMed PMID: 25535803. 7: Dzikamunhenga RS, Wilberts B, Yaeger M, Burrough E, Hostetter J, Bender H, Larson W, Griffith RW. Safety evaluation of lasalocid use in Chinese ring-necked pheasants (Phasianus colchicus). Avian Dis. 2013 Jun;57(2):188-91. PubMed PMID: 24689172. 8: Golder HM, Lean IJ. A meta-analysis of lasalocid effects on rumen measures, beef and dairy performance, and carcass traits in cattle. J Anim Sci. 2016 Jan;94(1):306-26. doi: 10.2527/jas.2015-9694. PubMed PMID: 26812337. 9: Murakoshi F, Takeuchi M, Inomata A, Horimoto T, Ito M, Suzuki Y, Kato K. Administration of lasalocid-NA is preventive against cryptosporidiosis of newborn calves. Vet Rec. 2014 Oct 11;175(14):353. doi: 10.1136/vr.102508. Epub 2014 Aug 25. PubMed PMID: 25155027. 10: Radko L, Cybulski W, Rzeski W. Cytoprotective effect of silybin against lasalocid-induced toxicity in HepG2 cells. Pol J Vet Sci. 2013;16(2):275-82. PubMed PMID: 23971195. 11: Žižek S, Zidar P. Toxicity of the ionophore antibiotic lasalocid to soil-dwelling invertebrates: avoidance tests in comparison to classic sublethal tests. Chemosphere. 2013 Jul;92(5):570-5. doi: 10.1016/j.chemosphere.2013.04.007. Epub 2013 Apr 29. PubMed PMID: 23635534. 12: Radko L, Cybulski W, Rzeski W. The protective effect of silybin against lasalocid cytotoxic exposure on chicken and rat cell lines. Biomed Res Int. 2013;2013:783519. doi: 10.1155/2013/783519. Epub 2012 Dec 30. PubMed PMID: 23509777; PubMed Central PMCID: PMC3591103. 13: Rutkowski J, Huczyński A, Ratajczak-Sitarz M, Katrusiak A, Brzezinski B, Bartl F. Spectroscopic studies of the equilibrium between complexes of lasalocid acid with propargylamine and metal cations. Spectrochim Acta A Mol Biomol Spectrosc. 2015;150:704-11. doi: 10.1016/j.saa.2015.05.099. Epub 2015 Jun 9. PubMed PMID: 26093967. 14: Tkáčiková S, Kožárová I, Mačanga J, Levkut M. Determination of lasalocid residues in the tissues of broiler chickens by liquid chromatography-tandem mass spectrometry. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2012;29(5):761-9. doi: 10.1080/19440049.2011.653987. Epub 2012 Feb 27. PubMed PMID: 22369356. 15: Minami A, Oguri H, Watanabe K, Oikawa H. Biosynthetic machinery of ionophore polyether lasalocid: enzymatic construction of polyether skeleton. Curr Opin Chem Biol. 2013 Aug;17(4):555-61. doi: 10.1016/j.cbpa.2013.06.004. Epub 2013 Jun 21. Review. PubMed PMID: 23796908. 16: Huczyński A, Rutkowski J, Borowicz I, Wietrzyk J, Maj E, Brzezinski B. One-pot synthesis and cytotoxicity studies of new Mannich base derivatives of polyether antibiotic--lasalocid acid. Bioorg Med Chem Lett. 2013 Sep 15;23(18):5053-6. doi: 10.1016/j.bmcl.2013.07.040. Epub 2013 Jul 26. PubMed PMID: 23932361. 17: Minami A, Shimaya M, Suzuki G, Migita A, Shinde SS, Sato K, Watanabe K, Tamura T, Oguri H, Oikawa H. Sequential enzymatic epoxidation involved in polyether lasalocid biosynthesis. J Am Chem Soc. 2012 May 2;134(17):7246-9. doi: 10.1021/ja301386g. Epub 2012 Apr 20. PubMed PMID: 22506807. 18: Decloedt A, Verheyen T, De Clercq D, Sys S, Vercauteren G, Ducatelle R, Delahaut P, van Loon G. Acute and long-term cardiomyopathy and delayed neurotoxicity after accidental lasalocid poisoning in horses. J Vet Intern Med. 2012 Jul-Aug;26(4):1005-11. doi: 10.1111/j.1939-1676.2012.00933.x. Epub 2012 Apr 21. PubMed PMID: 22519686. 19: Vandenberge V, Delezie E, Huyghebaert G, Delahaut P, Pierret G, De Backer P, Croubels S, Daeseleire E. Transfer of the coccidiostats monensin and lasalocid from feed at cross-contamination levels to whole egg, egg white and egg yolk. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2012;29(12):1881-92. doi: 10.1080/19440049.2012.719641. Epub 2012 Sep 10. PubMed PMID: 22963507. 20: Huczyński A, Rutkowski J, Brzezinski B, Bartl F. Synthesis, FT-IR, ¹H, ¹³CNMR, ESI MS and PM5 studies of a new Mannich base of polyether antibiotic - Lasalocid acid and its complexes with Li⁺, Na⁺ and K⁺ cations. Spectrochim Acta A Mol Biomol Spectrosc. 2013 Mar;104:497-504. doi: 10.1016/j.saa.2012.11.106. Epub 2012 Dec 8. PubMed PMID: 23287734.