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Lasalocid

Lasalocid structure

CAS No:
25999-31-9
Formula:
C34H54O8
Chemical Name:
Lasalocid
Synonyms:
Lasalocid;Lasalocid A;6-{7-[(5S)-5-((6S,5R)-5-Ethyl-5-hydroxy-6-methylperhydro-2H-pyran-2-yl)-5-ethyl-3-methyloxolan-2-yl](4S,5S,3R,7R)-4-hydroxy-3,5-dimethyl-6-oxononyl}-2-hydroxy-3-methylbenzoic acid;Aids003766;Aids-003766;Nsc243046 (sodium salt);X 537A, Lasalocid A;[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
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

Lasalocid is a polyether antibiotic used for prevention and treatment of coccidiosis in poultry. It has a role as a coccidiostat, a bacterial metabolite and an ionophore. It is a monohydroxybenzoic acid, a beta-hydroxy ketone, a secondary alcohol, a member of oxolanes, a monocarboxylic acid, a member of oxanes, a tertiary alcohol and a polyether antibiotic. It is a conjugate acid of a lasalocid(1-).|Lasalocid is an agent that presents antibacterial and coccidiostat activities. It is produced by strains of Streptomyces lasaliensis.|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.

Lasalocid is an ionophore antibiotic isolated from certainStreptomycessp. and used in veterinary practice as a coccidiostat for gastrointestinal parasites. Lasalocid cytotoxicity targets cell metabolism, demonstrating EC50values in the range of 7-20 μM in viability assays using chicken hepatoma LMH cells and rat myoblast L6 cells.

Lasalocid is one of the polyether ionophore antibiotics and was found in the culture broth of Streptomyces lasaliensis by Hoffmann-La Roche in 195. It shows activity against gram-positive bacteria, including Mycobacterium and Streptomyces, and also against anaerobic bacteria, but it has no activity against gramnegative bacteria or fungi. Lasalocid also shows strong anticoccidial activity, and it stimulates propionic acid formation in the rumen. It is used for prophylaxis and for therapy of coccidial infections in poultry and as a feed additive for growth promotion in cattle.

Lasalocid Basic Attributes

Molecular Weight：

590.79

Exact Mass：

590.79

EC Number：

247-401-9

UNII：

W7V2ZZ2FWB

DSSTox ID：

DTXSID9048485

Color/Form：

White to Off-White

Characteristics

PSA：

133.52000

XLogP3：

5.84220

Density：

1.119±0.06 g/cm3(Predicted)

Melting Point：

110-114°; mp 100-109° (unsharp)

Boiling Point：

735.7±60.0 °C(Predicted)

Flash Point：

224.8ºC

Vapor Pressure：

1.01E-22mmHg at 25°C

Toxicity：

LD50 in mice (mg/kg): 40 i.p. (Berger); also reported as LD50 in mice (mg/kg): 146 orally, 64 i.p., J. W. Westley, "Antibiotics (Polyether)" in Kirk-Othmer Encyclopedia of Chemical TechnologyVol. 3(Interscience, New York, 3rd ed., 1978) p 61

PKA：

3.15±0.39(Predicted)

Critical Temperature & Pressure：

-20°C Freezer, Under inert atmosphere

Safety Information

GHS Classification：

|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P264, P270, P301+P310, P321, P330, P405, and P501|Aggregated GHS information provided by 195 companies from 2 notifications to the ECHA C&L Inventory.|Warning|H316: Causes mild skin irritation [Warning Skin corrosion/irritation]|P264, P280, P305+P351+P338, P332+P313, and P337+P313|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P260, P264, P270, P280, P281, P301+P310, P302+P352, P305+P351+P338, P308+P313, P309+P311, P312, P314, P321, P322, P330, P337+P313, P363, P405, and P501

Drug Information

MeSH：

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)|Agents useful in the treatment or prevention of COCCIDIOSIS in man or animals. (See all compounds classified as Coccidiostats.)|Chemical agents that increase the permeability of biological or artificial lipid membranes to specific ions. Most ionophores are relatively small organic molecules that act as mobile carriers within membranes or coalesce to form ion permeable channels across membranes. Many are antibiotics, and many act as uncoupling agents by short-circuiting the proton gradient across mitochondrial membranes. (See all compounds classified as Ionophores.)

MeSH Entry Terms：

Avatec

Lasalocid Use and Manufacturing

Uses

Lasalocid is a polyether ionophore with potent antibacterial activity isolated from Streptomyces lasaliensis, first reported in 1951. 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 an anticancer supplement agent comprising of polyether antibiotic for treating brain tumors, also inhibits mitochondrial GPD2 activity and elicits anti-proliferative effects on cancer cells.

Use Classification：

Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients|Veterinary Drug -> ANTIMICROBIAL_AGENT; -> JECFA Functional Classes|Polyketides [PK] -> Polyether antibiotics [PK09]|Pharmaceuticals

Food Additive Classes：

Veterinary Drug -> ANTIMICROBIAL_AGENT;

Computed Properties

Molecular Weight:590.8
XLogP3:6.4
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:13
Exact Mass:590.38186868
Monoisotopic Mass:590.38186868
Topological Polar Surface Area:134
Heavy Atom Count:42
Complexity:910
Defined Atom Stereocenter Count:10
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes