Lasalocid | CAS#25999-31-9 | antibiotic

MedKoo Cat#: 593077 | Name: Lasalocid

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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.

Chemical Structure

Lasalocid

CAS#25999-31-9 (free)

Theoretical Analysis

MedKoo Cat#: 593077

Name: Lasalocid

CAS#: 25999-31-9 (free)

Chemical Formula: C34H54O8

Exact Mass: 590.3819

Molecular Weight: 590.80

Elemental Analysis: C, 69.12; H, 9.21; O, 21.66

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

Avatec; Bovatec; Lasalocid sodium; Lasalocid sodium salt; MT 2007; NSC 243046; Ro 2-2985; Sodium lasalocid; Sodium lasalocid A;

IUPAC/Chemical Name

(2R-(2alpha(2S*(3R*,4S*,5S*,7R*)3S*,5S*),5alpha,6beta))-6-(7-(5-Ethyl-5-(5-ethyltetrahydro-5-hydroxy-6-methyl-2H-pyran-2-yl)tetrahydro-3-methyl-2-furyl)-4-hydroxy-3,5-dimethyl-6-oxononyl)-3-methylsalicylic acid

InChi Key

BBMULGJBVDDDNI-WELPDAJWSA-N

InChi Code

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?/m0/s1

SMILES Code

OC1=C(C)C=CC(CC[C@H](C)[C@H](O)[C@H](C)C([C@@H]([C@@H]2OC(C3CCC(O)(CC)[C@H](C)O3)(CC)CC2C)CC)=O)=C1C(O)=O

Appearance

Solid powder

Purity

>98% (or 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 (Lasalocid-A; Ionophore X-537A; Antibiotic X-537A) is an antibacterial agent and a coccidiostat, used in the feed additives.

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	169.26

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 590.80 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: Xia M, Huang R, Shi Q, Boyd WA, Zhao J, Sun N, Rice JR, Dunlap PE, Hackstadt AJ, Bridge MF, Smith MV, Dai S, Zheng W, Chu PH, Gerhold D, Witt KL, DeVito M, Freedman JH, Austin CP, Houck KA, Thomas RS, Paules RS, Tice RR, Simeonov A. Comprehensive Analyses and Prioritization of Tox21 10K Chemicals Affecting Mitochondrial Function by in-Depth Mechanistic Studies. Environ Health Perspect. 2018 Jul 26;126(7):077010. doi: 10.1289/EHP2589. eCollection 2018 Jul. PubMed PMID: 30059008. 2: Hickey EE, Wong HS, Khazandi M, Ogunniyi AD, Petrovski KR, Garg S, Page SW, O'Handley R, Trott DJ. Repurposing Ionophores as novel antimicrobial agents for the treatment of bovine mastitis caused by Gram-positive pathogens. J Vet Pharmacol Ther. 2018 Jul 4. doi: 10.1111/jvp.12674. [Epub ahead of print] PubMed PMID: 29971788. 3: Zhao X, Wang B, Xie K, Liu J, Zhang Y, Wang Y, Guo Y, Zhang G, Dai G, Wang J. Development and comparison of HPLC-MS/MS and UPLC-MS/MS methods for determining eight coccidiostats in beef. J Chromatogr B Analyt Technol Biomed Life Sci. 2018 Jun 15;1087-1088:98-107. doi: 10.1016/j.jchromb.2018.04.044. Epub 2018 Apr 30. PubMed PMID: 29730532. 4: Pietruk K, Olejnik M, Posyniak A. Coccidiostats in milk: development of a multi-residue method and transfer of salinomycin and lasalocid from contaminated feed. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2018 Aug;35(8):1508-1518. doi: 10.1080/19440049.2018.1461256. Epub 2018 Jun 6. PubMed PMID: 29648988. 5: de Souza KA, Cooke RF, Schubach KM, Brandão AP, Schumaher TF, Prado IN, Marques RS, Bohnert DW. Performance, health and physiological responses of newly weaned feedlot cattle supplemented with feed-grade antibiotics or alternative feed ingredients. Animal. 2018 Mar 26:1-8. doi: 10.1017/S1751731118000551. [Epub ahead of print] PubMed PMID: 29576039. 6: Mahtal N, Brewee C, Pichard S, Visvikis O, Cintrat JC, Barbier J, Lemichez E, Gillet D. Screening of a Drug Library Identifies Inhibitors of Cell Intoxication by CNF1. ChemMedChem. 2018 Apr 6;13(7):754-761. doi: 10.1002/cmdc.201700631. Epub 2018 Feb 27. PubMed PMID: 29359495. 7: Hurst JJ, Wallace JS, Aga DS. Method development for the analysis of ionophore antimicrobials in dairy manure to assess removal within a membrane-based treatment system. Chemosphere. 2018 Apr;197:271-279. doi: 10.1016/j.chemosphere.2018.01.028. Epub 2018 Jan 9. PubMed PMID: 29353677. 8: Steverding D, Huczyński A. Trypanosoma brucei: trypanocidal and cell swelling activities of lasalocid acid. Parasitol Res. 2017 Nov;116(11):3229-3233. doi: 10.1007/s00436-017-5624-6. Epub 2017 Sep 27. PubMed PMID: 28956164; PubMed Central PMCID: PMC5660140. 9: Flythe MD, Kagan IA, Wang Y, Narvaez N. Hops (Humulus lupulus L.) Bitter Acids: Modulation of Rumen Fermentation and Potential As an Alternative Growth Promoter. Front Vet Sci. 2017 Aug 21;4:131. doi: 10.3389/fvets.2017.00131. eCollection 2017. Review. PubMed PMID: 28871284; PubMed Central PMCID: PMC5566628. 10: Annunziata L, Visciano P, Stramenga A, Colagrande MN, Campana G, Scortichini G, Migliorati G, Compagnone D. Determination of regulatory ionophore coccidiostat residues in feedstuffs at carry-over levels by liquid chromatography-mass spectrometry. PLoS One. 2017 Aug 9;12(8):e0182831. doi: 10.1371/journal.pone.0182831. eCollection 2017. PubMed PMID: 28792977; PubMed Central PMCID: PMC5549955. 11: Crane AR, Redden RR, Swanson KC, Howard BM, Frick TJ, Maddock-Carlin KR, Schauer CS. Effects of dried distiller's grains and lasalocid inclusion on feedlot lamb growth, carcass traits, nutrient digestibility, ruminal fluid volatile fatty acid concentrations, and ruminal hydrogen sulfide concentration. J Anim Sci. 2017 Jul;95(7):3198-3205. doi: 10.2527/jas.2017.1369. PubMed PMID: 28727092. 12: Robertson AS, Iben LG, Wei C, Meredith JE Jr, Drexler DM, Banks M, Vite GD, Olson RE, Thompson LA, Albright CF, Ahlijanian MK, Toyn JH. Synergistic inhibition of Aβ production by combinations of γ-secretase modulators. Eur J Pharmacol. 2017 Oct 5;812:104-112. doi: 10.1016/j.ejphar.2017.07.019. Epub 2017 Jul 8. PubMed PMID: 28690193. 13: Barrios MA, Da Costa M, Kimminau E, Fuller L, Clark S, Pesti G, Beckstead R. Relationship Between Broiler Body Weights, Eimeria maxima Gross Lesion Scores, and Microscores in Three Anticoccidial Sensitivity Tests. Avian Dis. 2017 Jun;61(2):237-241. doi: 10.1637/11518-102116-Reg.1. PubMed PMID: 28665718. 14: Knight EC, Trott DJ, Page SW, Garg S, Zhang Q, Song Y, Ebrahimie E, Mills PC, Shipstone MA. In vitro comparison of the dermal penetration of three different topical formulations containing lasalocid. Vet Dermatol. 2017 Aug;28(4):342-e74. doi: 10.1111/vde.12379. Epub 2017 May 3. PubMed PMID: 28470877. 15: Liu X, Xie S, Ni T, Chen D, Wang X, Pan Y, Wang Y, Huang L, Cheng G, Qu W, Liu Z, Tao Y, Yuan Z. Magnetic solid-phase extraction based on carbon nanotubes for the determination of polyether antibiotic and s-triazine drug residues in animal food with LC-MS/MS. J Sep Sci. 2017 Jun;40(11):2416-2430. doi: 10.1002/jssc.201700017. Epub 2017 May 4. PubMed PMID: 28402029. 16: Barreto F, Ribeiro C, Hoff RB, Costa TD. A simple and high-throughput method for determination and confirmation of 14 coccidiostats in poultry muscle and eggs using liquid chromatography - quadrupole linear ion trap - tandem mass spectrometry (HPLC-QqLIT-MS/MS): Validation according to European Union 2002/657/EC. Talanta. 2017 Jun 1;168:43-51. doi: 10.1016/j.talanta.2017.02.007. Epub 2017 Feb 3. PubMed PMID: 28391864. 17: 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. PubMed PMID: 28178613. 18: Thabet A, Zhang R, Alnassan AA, Daugschies A, Bangoura B. Anticoccidial efficacy testing: In vitro Eimeria tenella assays as replacement for animal experiments. Vet Parasitol. 2017 Jan 15;233:86-96. doi: 10.1016/j.vetpar.2016.12.005. Epub 2016 Dec 11. PubMed PMID: 28043393. 19: Sartori ED, Canellas LC, Pereira GR, Moojen FG, Carvalho HR, Barcellos JO. Performance of beef heifers supplemented with sodium lasalocid. Trop Anim Health Prod. 2017 Feb;49(2):273-279. doi: 10.1007/s11250-016-1188-1. Epub 2016 Dec 12. PubMed PMID: 27957652. 20: Gerhold RW, Fuller AL, McDougald LR. Coccidiosis in the Chukar Partridge ( Alectoris chukar ): A Survey of Coccidiosis Outbreaks and a Test of Anticoccidial Drugs Against Eimeria kofoidi. Avian Dis. 2016 Dec;60(4):752-757. PubMed PMID: 27902917.