Moxidectin

Basic Info

Common NameMoxidectin(F05784)
2D Structure
FRCD IDF05784
CAS Number113507-06-5
PubChem CID9832912
FormulaC37H53NO8
IUPAC Name

None

InChI Key

YZBLFMPOMVTDJY-LSGXYNIPSA-N

InChI

InChI=1S/C37H53NO8/c1-21(2)14-25(6)33-26(7)31(38-42-8)19-36(46-33)18-29-17-28(45-36)13-12-23(4)15-22(3)10-9-11-27-20-43-34-32(39)24(5)16-30(35(40)44-29)37(27,34)41/h9-12,14,16,21-22,26,28-30,32-34,39,41H,13,15,17-20H2,1-8H3/b10-9+,23-12+,25-14+,27-11+,38-31+/t22-,26-,28+,29-,30-,32+,33+,34+,36-,37+/m0/s1

Canonical SMILES

CC1CC(=CCC2CC(CC3(O2)CC(=NOC)C(C(O3)C(=CC(C)C)C)C)OC(=O)C4C=C(C(C5C4(C(=CC=C1)CO5)O)O)C)C

Isomeric SMILES

C[C@@H]\1C/C(=C/C[C@@H]2C[C@@H](C[C@@]3(O2)C/C(=N\OC)/[C@@H]([C@H](O3)/C(=C/C(C)C)/C)C)OC(=O)[C@@H]4C=C([C@H]([C@@H]5[C@]4(/C(=C/C=C1)/CO5)O)O)C)/C

Synonyms
        
            Moxidectin
        
            ProHeart 6
        
            113507-06-5
        
            UNII-NGU5H31YO9
        
            Cydectin
        
            NGU5H31YO9
        
            Moxidectine [INN-French]
        
            Moxidectinum [INN-Latin]
        
            Moxidectina [INN-Spanish]
        
            C37H53NO8
Classifies
                

                  
                    Veterinary Drug
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassPhenylpropanoids and polyketides
ClassMacrolides and analogues
SubclassMilbemycins
Intermediate Tree NodesNot available
Direct ParentMilbemycins
Alternative Parents
Molecular FrameworkAliphatic heteropolycyclic compounds
SubstituentsMilbemycin - Ketal - Oxane - Tertiary alcohol - Tetrahydrofuran - Carboxylic acid ester - Lactone - Oxime ether - Secondary alcohol - Acetal - Carboxylic acid derivative - Dialkyl ether - Ether - Monocarboxylic acid or derivatives - Oxacycle - Organoheterocyclic compound - Organopnictogen compound - Organic oxygen compound - Carbonyl group - Alcohol - Organonitrogen compound - Organooxygen compound - Organic oxide - Hydrocarbon derivative - Organic nitrogen compound - Aliphatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as milbemycins. These are a group of macrolides with a structure containing a 16-membered lactone ring fused to a 1,7-dioxaspiroundecane ring system and to either a benzofuran (or hydrogenated derivative thereof). In some cases (e.g. Milbemycin E), the tetrahydrofuranyl ring is missing. Milbemycins can be o-glycosylated at C13 to form Avermectins. Milbemycins are produced by Streptomyces species.

Properties

Property NameProperty Value
Molecular Weight639.83
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count9
Rotatable Bond Count3
Complexity1340
Monoisotopic Mass639.377
Exact Mass639.377
XLogP4.3
Formal Charge0
Heavy Atom Count46
Defined Atom Stereocenter Count10
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count5
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB-0.8767
Human Intestinal AbsorptionHIA+0.9507
Caco-2 PermeabilityCaco2-0.6304
P-glycoprotein SubstrateSubstrate0.7577
P-glycoprotein InhibitorInhibitor0.7582
Inhibitor0.8387
Renal Organic Cation TransporterNon-inhibitor0.6967
Distribution
Subcellular localizationMitochondria0.5842
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8261
CYP450 2D6 SubstrateNon-substrate0.8339
CYP450 3A4 SubstrateSubstrate0.7713
CYP450 1A2 InhibitorNon-inhibitor0.8263
CYP450 2C9 InhibitorNon-inhibitor0.7768
CYP450 2D6 InhibitorNon-inhibitor0.9168
CYP450 2C19 InhibitorNon-inhibitor0.7276
CYP450 3A4 InhibitorNon-inhibitor0.8005
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8097
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9874
Non-inhibitor0.8251
AMES ToxicityNon AMES toxic0.6021
CarcinogensNon-carcinogens0.9079
Fish ToxicityHigh FHMT0.9809
Tetrahymena Pyriformis ToxicityHigh TPT0.9812
Honey Bee ToxicityHigh HBT0.7533
BiodegradationNot ready biodegradable0.9678
Acute Oral ToxicityIII0.6010
Carcinogenicity (Three-class)Non-required0.4891
Model Value Unit
Absorption
Aqueous solubility-3.6391LogS
Caco-2 Permeability0.6524LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.7766LD50, mol/kg
Fish Toxicity0.8666pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.7045pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Muscle Of SheepUnited States5oppb
Liver Of SheepUnited States200ppb
Fat Of SheepUnited States300ppb
Muscle Of CattleUnited States5oppb
Liver Of CattleUnited States200ppb
Fat Of CattleUnited States300ppb
MilkJapan0.04ppm
Other Terrestrial Mammals,Edible Offal(Excep Deer)Japan0.05ppm
Deer,Edible OffalJapan0.2ppm
Cattle,Edible OffalJapan0.5ppm
Other Terrestrial Mammals,Kidney(Except Sheep And Deer)Japan0.05ppm
Other Terrestrial Mammals,Liver(Except Sheep And Deer)Japan0.1ppm
Other Terrestrial Mammals,Fat(Except Sheep And Deer)Japan0.5ppm
Other Terrestrial Mammals,Muscle(Except Sheep And Deer)Japan0.05ppm
Deer,KidneyJapan0.05ppm
Sheep,KidneyJapan0.05ppm
Cattle,KidneyJapan0.05ppm
Sheep,LiverJapan0.10ppm
Cattle,LiverJapan0.10ppm
Deer,FatJapan0.50ppm

References

TitleJournalDatePubmed ID
Effects of the Antiparasitic Drug Moxidectin in Cattle Dung on Zooplankton and Benthic Invertebrates and its Accumulation in a Water-Sediment System.Arch Environ Contam Toxicol2018 Aug29846763
A multi-country study to assess the effect of a treatment with moxidectin pour-onduring the dry period on milk production in dairy cows.Vet Parasitol2017 Apr 1528259556
The Anthelmintic Ingredient Moxidectin Negatively Affects Seed Germination ofThree Temperate Grassland Species.PLoS One2016 Nov 1527846249
Multiresidue method for simultaneous analysis of aflatoxin M1, avermectins, organophosphate pesticides and milbemycin in milk by ultra-performance liquid chromatography coupled to tandem mass spectrometry.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2016 Jun27144891
P-gp substrate-induced neurotoxicity in an Abcb1a knock-in/Abcb1b knock-out mouse model with a mutated canine ABCB1 targeted insertion.Res Vet Sci2013 Jun23186803
Relative neurotoxicity of ivermectin and moxidectin in Mdr1ab (-/-) mice and effects on mammalian GABA(A) channel activity.PLoS Negl Trop Dis201223133688
Fecal egg count reductions and performance effect of Dectomax, Cydectin, andCydectin plus Synanthic as used in feedlot steers.Vet Ther2007 Winter18183550
Combining the effects of supplementary feeding and copper oxide needles for thecontrol of gastrointestinal nematodes in browsing goats.Vet Parasitol2007 May 1517400391
Improving resilience against natural gastrointestinal nematode infections inbrowsing kids during the dry season in tropical Mexico.Vet Parasitol2006 Jan 3016203095
Endectocide use in cattle and fecal residues: environmental effects in Canada.Can J Vet Res2006 Jan16548326
The effect of supplementary feeding on the resilience and resistance of browsing Criollo kids against natural gastrointestinal nematode infections during therainy season in tropical Mexico.Vet Parasitol2004 Oct 515381302