Milbemycin oxime

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Milbemycin oxime
Category Animal Health
Catalog number BBF-03816
CAS 129496-10-2
Molecular Weight 2194.78
Molecular Formula C126H176N4O28

Ordering Information

Catalog Number Size Price Stock Quantity
BBF-03816 500 mg $439 In stock
BBF-03816 1 g $523 In stock
BBF-03816 5 g $998 In stock

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Description

Milbemycin oxime is a semi-synthetic macrolide. As a nematocide and insecticide in veterinary medicine, it opens glutamate sensitive chloride channels in neurons of invertebrates that leads to paralysis by hyperpolarisation of these cells and signal transfer blocking. M1-family aminopeptidase: IC50 = 2.6 µM (Plasmodium falciparum 3D7); Bile acid transporter: IC50 = 3.6 µM (human); TGR5: IC50 = 36.4 µM (human); HCT-116: IC50 >50 µM (human); GBM: IC50 >50 µM (human)

Specification

Synonyms Milbemycin A 5-oxime; Milbemite; Trifexis; Interceptor; Milbe Mite
Shelf Life >2 years if stored properly
Storage Store at -20°C, Under inert atmosphere
IUPAC Name (1R,4S,5'S,6R,6'R,8R,10E,13R,14E,16E,20R,21E,24S)-6'-ethyl-24-hydroxy-21-hydroxyimino-5',11,13,22-tetramethylspiro[3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6,2'-oxane]-2-one
Canonical SMILES CCC1C(CCC2(O1)CC3CC(O2)CC=C(CC(C=CC=C4COC5C4(C(C=C(C5=NO)C)C(=O)O3)O)C)C)C.CC1CCC2(CC3CC(O2)CC=C(CC(C=CC=C4COC5C4(C(C=C(C5=NO)C)C(=O)O3)O)C)C)OC1C
InChI InChI=1S/C32H45NO7.C31H43NO7/c1-6-27-21(4)12-13-31(40-27)17-25-16-24(39-31)11-10-20(3)14-19(2)8-7-9-23-18-37-29-28(33-36)22(5)15-26(30(34)38-25)32(23,29)35;1-18-7-6-8-23-17-36-28-27(32-35)21(4)14-26(31(23,28)34)29(33)37-25-15-24(10-9-19(2)13-18)39-30(16-25)12-11-20(3)22(5)38-30/h7-10,15,19,21,24-27,29,35-36H,6,11-14,16-18H2,1-5H3;6-9,14,18,20,22,24-26,28,34-35H,10-13,15-17H2,1-5H3
InChI Key CKVMAPHTVCTEMM-UHFFFAOYSA-N
Source Semi-synthetic

Properties

Appearance White Powder
Application A broad spectrum insecticide; Used for treatment and prevention of heartworm in dogs and cats
Antibiotic Activity Spectrum parasites
Melting Point 169.6-177.4°C
Solubility Soluble in DMSO, not in water

Reference Reading

1.Efficacy of oral afoxolaner plus milbemycin oxime chewables against induced infestations with Dermacentor reticulatus in dogs
Steffen Rehbein & Josephus J. Fourie & Christa de Vos. Parasitol Res (2016) 115:1845–1851
In order to provide dog owners and veterinarians with products to be used conveniently for the treatment and/or control of multiple ectoparasites and endoparasites which may infest or infect dogs concurrently, the parasiticidal spectrum of NexGard® chewable tablets was extended through the combination of afoxolaner with the macrocyclic lactone, milbemycin oxime, in a novel braised beef-flavored chewable formulation (NexGard Spectra®). This formulation, with respect to its composition, is similar to the afoxolaner singleentity chewable tablet formulation except for the active ingredients. Milbemycin oxime was proven to be safe in dogs (Jung et al. 2002) and, when administered to dogs orally at a dose of 0.5 mg per kg body weight, to be efficacious against adult intestinal nematode infections and to prevent heartworm disease by interrupting the life cycle of Dirofilaria immitis (Nolan and Lok 2012). At that dose and route of administration, milbemycin oxime did not demonstrate activity against fleas and ticks in dogs (Snyder and Wiseman 2012; Merial, unpublished data). The interrelationship between milbemycin oxime and afoxolaner, however, was not known.

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