LASALOCID SODIUM

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C34H53O8.Na
Molecular Weight	612.7696
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 10
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].CC[C@H]([C@H]1O[C@@](CC)(C[C@@H]1C)[C@H]2CC[C@](O)(CC)[C@H](C)O2)C(=O)[C@@H](C)[C@@H](O)[C@H](C)CCC3=CC=C(C)C(O)=C3C([O-])=O

InChI

InChIKey=RDHDUYAKDYQPEW-HWLWSTNVSA-M

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

HIDE SMILES / InChI

Molecular Formula	C34H53O8
Molecular Weight	589.7798
Charge	-1
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	10 / 10
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	Na
Molecular Weight	22.98976928
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.drugs.com/pro/bovatec.html | https://www.fda.gov/OHRMS/DOCKETS/98fr/141129fi.pdf | http://www.ema.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2009/11/WC500014596.pdf | https://www.ncbi.nlm.nih.gov/pubmed/28178613

Lasalocid is a polyether ionophore with potent antibacterial activity. Lasalocid was developed as an animal health product for treatment of coccidia. Lasalocid is able to form neutral complexes with monovalent and divalent cations and transport the ions through apolar phase (including lipid bilayer membranes). Interestingly, lasalocid can also transport larger organic cations, e.g. protonated dopamine. Lasalocid is used for the prevention of coccidiosis caused by Eimeria tenella, E. necatrix, E. acervulina, E. brunetti, E. mivati, and E. maxima, and for increased rate of weight gain and improved feed efficiency in broiler chickens. Also used for control of coccidiosis caused by Eimeria bovis and E. zuernii in cattle up to 800 lbs. and for prevention of coccidiosis caused by Eimeria ovina, E. crandallis, E. ovinoidalis (E. ninakohlyakimovae), E. parva and E. intricata in sheep maintained in confinement. Lasalocid has being shown to induce cytotoxic apoptosis and cytoprotective autophagy through reactive oxygen species in human prostate cancer PC-3 cells. Lasalocid should be useful in the search for new potential chemotherapeutic agents for understanding the molecular mechanisms of anticancer in prostate cancer cells.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Staphylococcus aureus 70 Target ID: CHEMBL352 Sources: https://web.archive.org/web/20171115064750/https://www.fda.gov/ucm/groups/fdagov-public/@fdagov-av-gen/documents/document/ucm071990.pdf	Inhibitor 8504
Apoptosis 156 Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28178613	Activator 1447

Conditions

Condition	Modality	Highest Phase	Product
Coccidiosis 45 Sources: https://web.archive.org/web/20171115070543/https://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/ucm064879.pdf	Curative	Approved 8583	Bovatec Approved Use CATTLE: For improved feed efficiency and increased rate of weight gain when used in medicated feeds for cattle fed in confinement for slaughter. For increased rate of weight gain when used in medicated feeds for pasture cattle (slaughter, stocker, feeder cattle, and dairy and beef replacement heifers). For control of coccidiosis caused by Eimeria bovis and E. zuernii in cattle up to 800 lbs. SHEEP: For prevention of coccidiosis caused by Eimeria ovina, E. crandallis, E. ovinoidalis (E. ninakohlyakimovae), E. parva and E. intricata in sheep maintained in confinement. Launch Date 2006
Prostate cancer 186 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28178613	Primary	Basic research	Unknown Approved Use Unknown
Cryptosporidiosis 10 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10856813 https://www.ncbi.nlm.nih.gov/pubmed/10499272	Curative	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Simultaneous determination of polyether ionophores, macrolides and lincosamides in hen eggs by liquid chromatography-electrospray ionization tandem mass spectrometry using a simple solvent extraction.	2010-12-03	21056719
Evaluation of potential carryover effects associated with limit feeding of gravid Holstein heifers.	2010-11	20965353
Selection of single chain variable fragment (scFv) antibodies from a hyperimmunized phage display library for the detection of the antibiotic monensin.	2010-08-31	20600077
Lasalocid awareness and sampling in Scotland.	2010-06	20155555
Intriguing substrate tolerance of epoxide hydrolase Lsd19 involved in biosynthesis of the ionophore antibiotic lasalocid A.	2010-05-21	20394359
An unusual thioesterase promotes isochromanone ring formation in ajudazol biosynthesis.	2010-05-17	20432424
Direct aqueous supercritical fluid extraction coupled on-line with liquid chromatography-tandem mass spectrometry for the analysis of polyether ionophore antibiotics in water.	2010-05-14	20381053
Synthesis of marine polycyclic polyethers via endo-selective epoxide-opening cascades.	2010-03-19	20411125
The effect of commonly used anticoccidials and antibiotics in a subclinical necrotic enteritis model.	2010-02	20390538
Inhaled Anesthetics Promote Albumin Dimerization through Reciprocal Exchange of Subdomains.	2010	21188076
Retrospective study of salinomycin toxicosis in 66 cats.	2010	20445777
Multi-residue confirmatory method for the determination of twelve coccidiostats in chicken liver using liquid chromatography tandem mass spectrometry.	2009-11-13	19481216
Validation of a multi-residue liquid chromatography-tandem mass spectrometry confirmatory method for 10 anticoccidials in eggs according to Commission Decision 2002/657/EC.	2009-11-13	19442981
[Determination of 5 polyether antibiotics in chicken tissues by liquid chromatography-electrospray ionization tandem mass spectrometry].	2009-11	20352937
The activity and compatibility of the antibiotic tiamulin with other drugs in poultry medicine--A review.	2009-11	19834086
Giardia duodenalis in feedlot cattle from the central and western United States.	2009-10-02	19799795
Effects of organophosphate phenyl saligenin phosphate and polyether carboxylic ionophore lasalocid on motor nerve conduction velocity, neuropathy target esterase enzyme activity, and clinical ataxia in chickens.	2009-06	19778211
Fast liquid chromatography/multiple-stage mass spectrometry of coccidiostats.	2009-05	19308967
Effects of ionophores and antibiotics on in vitro hydrogen sulfide production, dry matter disappearance, and total gas production in cultures with a steam-flaked corn-based substrate with or without added sulfur.	2009-05	19213713
Monensin causes dose dependent inhibition of Mycobacterium avium subspecies paratuberculosis in radiometric culture.	2009-02-09	19338684
Identification of a gene cluster of polyether antibiotic lasalocid from Streptomyces lasaliensis.	2009-01	19129623
Responses of plasma acetate metabolism to hop (Humulus lupulus L.) in sheep.	2009	19365576
Analysis of specific mutants in the lasalocid gene cluster: evidence for enzymatic catalysis of a disfavoured polyether ring closure.	2008-12-15	19025863
Efficacy of lasalocid against coccidiosis in Chinese ring-necked pheasants.	2008-12	19166054
Epoxide hydrolase Lsd19 for polyether formation in the biosynthesis of lasalocid A: direct experimental evidence on polyene-polyepoxide hypothesis in polyether biosynthesis.	2008-09-17	18710235
Determination of ionophore coccidiostats in feedingstuffs by liquid chromatography-tandem mass spectrometry Part I. Application to targeted feed.	2008-08-05	18440174
Doubly compensated multiplicity-edited HSQC experiments utilizing broadband inversion pulses.	2008-07	18383431
Determination of lasalocid sodium in animal feeds and premixes by reversed-phase liquid chromatography: collaborative study.	2008-06-24	18567291
Antimicrobial use on 24 beef farms in Ontario.	2008	18505199
Rubidium(I) monensinate dihydrate.	2007-12-12	21200506
Effects of lasalocid or monensin supplementation on digestion, ruminal fermentation, blood metabolites, and milk production of lactating dairy cows.	2007-12	18024764
Sorption and degradation in soils of veterinary ionophore antibiotics: monensin and lasalocid.	2007-08	17702333
Mucosal mast cell proteases are involved in colonic permeability alterations and subsequent bacterial translocation in endotoxemic rats.	2007-07	17510603
Efficacy of some anticoccidial drugs for treating coccidial enteritis of the common carp caused by Goussia carpelli (Apicomplexa: Eimeriidae).	2007-03	17385557
Changes in net portal nutrient flux in response to weaning transition and ionophore supplementation in dairy calves.	2007-03	17297108
An Irish perspective on Cryptosporidium. Part 2.	2006-09-01	21851686
Effects of weaning and ionophore supplementation on selected blood metabolites and growth in dairy calves.	2006-09	16899694
Pharmacologic reductions of total tau levels; implications for the role of microtubule dynamics in regulating tau expression.	2006-07-26	16930453
Efficacy of ionophores in cattle diets for mitigation of enteric methane.	2006-07	16775074
Simultaneous determination of four coccidiostats in eggs and broiler meat: validation of an LC-MS/MS method.	2006-05	16644594
Effect of ionophore supplementation on the incidence of Escherichia coli O157:H7 and Salmonella and antimicrobial susceptibility of fecal coliforms in Stocker cattle.	2006	16972777
Incidence of residues of nine anticoccidials in eggs.	2005-11	16332635
Resistance to anticoccidial drugs of Dutch avian Eimeria spp. field isolates originating from 1996, 1999 and 2001.	2003-08	17585463
Efficacy of lasalocid against murine Pneumocystis carinii pneumonitis.	1997-01	8980779
Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro.	1996-12	9039272
Putative anticryptosporidial agents tested with an immunodeficient mouse model.	1994-04	8031061
Anticryptosporidial activity of lasalocid and other ionophorous antibiotics in immunosuppressed rats.	1993-12	8245548
Assessment of candidate anticryptosporidial agents in an immunosuppressed rat model.	1993-03	8440946
Anti-cryptosporidial drug activity screened with an immunosuppressed rat model.	1991-11-01	1818183
Chemotherapeutic effect of azithromycin and lasalocid on Cryptosporidium infection in mice.	1991-11-01	1667931

Patents

Sample Use Guides

In Vivo Use Guide

Poultry: feed additive the substance is given continuously to chicken from day 0 up to 16 weeks at dose rates of 75 to 125 mg/kg feed with a withdrawal period of 5 days and to turkeys at dose rates of 90 to 125 mg/kg feed up to a maximum age of 12 weeks and with a withdrawal period of 5 days. For veterinary medicine lasalocid sodium is intended to be used in birds for the prevention of coccidiosis caused by Eimeria spp. The intended doses in feed are 75 to 125 mg/kg for fattening chickens, 90 to 125 mg/kg for turkeys and 90 to 120 mg/kg for pheasants, partridges and quails.

Route of Administration: Oral

In Vitro Use Guide

Lasalocid demonstrated antimicrobial activity against the major Gram-positive mastitis pathogens including S. aureus (MIC range 0.5-8 ug/mL).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:18:02 GMT 2025` Edited by `admin` on `Mon Mar 31 18:18:02 GMT 2025`
Record UNII	W2S5C71Y3G
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LASALOCID SODIUM

Common Name

English

NSC-243046

Preferred Name

English

LASALOCID SODIUM [GREEN BOOK]

Common Name

English

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-, SODIUM SALT (1:1)

Common Name

English

LASALOCID SODIUM [MART.]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C258