Moxidectin

HCID 9832912

Daten werden ergänzt – meist innerhalb einer Minute fertig

Grundinformationen

CAS
113507-06-5
Standard-SMILES
CO/N=C1\C[C@]2(C[C@@H]3C[C@@H](C/C=C(\C)C[C@@H](C)/C=C/C=C4\CO[C@@H]5[C@H](O)C(C)=C[C@@H](C(=O)O3)[C@]45O)O2)O[C@H](/C(C)=C/C(C)C)[C@H]1C
InChIKey
YZBLFMPOMVTDJY-LSGXYNIPSA-N
Summenformel
C37H53NO8
Durchschnittliche Molmasse
639,8 g/mol
Monoisotopische Masse
639,37711766

Überblick

Moxidectin is a milbemycin.

Namen und Bezeichner

Bevorzugter Name
Moxidectin
IUPAC
(1R,4S,4'E,5'S,6R,6'S,8R,10E,13R,14E,16E,20R,21R,24S)-21,24-dihydroxy-4'-methoxyimino-5',11,13,22-tetramethyl-6'-[(E)-4-methylpent-2-en-2-yl]spiro[3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6,2'-oxane]-2-one

Namen und Synonyme

Moxidectin113507-06-5MoxidectinaMoxidectineMoxidectinumCydectinProHeart 6NGU5H31YO9CL 301,423NSC-760424(1R,4S,4'E,5'S,6R,6'S,8R,10E,13R,14E,16E,20R,21R,24S)-21,24-dihydroxy-4'-methoxyimino-5',11,13,22-tetramethyl-6'-[(E)-4-methylpent-2-en-2-yl]spiro[3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6,2'-oxane]-2-oneCL-301,423
Weitere Namen anzeigen
ADVOCATE COMPONENT MOXIDECTINTauramoxMoxiSolvProHeartDTXSID5037577Milbemycin B, 5-O-demethyl-28-deoxy-25-((1E)-1,3-dimethyl-1-butenyl)-6,28-epoxy-23-(methoxyimino)-, (6R,23E,25S)-Quest Gel(1R,4S,4'E,5'S,6R,6'S,8R,10E,13R,14E,16E,20R,21R,24S)-21,24-dihydroxy-4'-methoxyimino-5',11,13,22-tetramethyl-6'-((E)-4-methylpent-2-en-2-yl)spiro(3,7,19-trioxatetracyclo(15.6.1.14,8.020,24)pentacosa-10,14,16,22-tetraene-6,2'-oxane)-2-one

Datenbank-Bezeichner

CAS
113507-06-5
PubChem CID
9832912
DTXSID
DTXSID5037577
ChEMBL
CHEMBL2104415
ChEBI
CHEBI:183811
UNII
NGU5H31YO9
EC Number
635-129-7
Nikkaji
J481.172K

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
4,3
Polarare Oberfläche (TPSA)
116 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
9
Frei drehbare Bindungen
3
Schwere Atome
46

Experimentelle und physikochemische Eigenschaften

SolubilityInsoluble
Human Drugs · 4 Einträge

Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antiparasitic Agents; Anthelmintics; Antinematodal Agents; Insecticides; Macrolides

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Antifilarials

Animal Drugs · 2 Einträge

FDA approved animal drugs -> Active ingredient

Pharmaceuticals -> UK Veterinary Medicines Directorate List

Boiling PointWhen found in oily form it is expected to boil at 160 ºC
Melting Point145-154 ºC
Dissociation Constants12.8

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P203, P260, P261, P264, P264+P265, P270, P271, P273, P280, P301+P316, P304+P340, P305+P351+P338, P317, P318, P319, P321, P330, P337+P317, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 81 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory InformationMoxidectin: HSNO Approval: HSR002723 Approved with controls
Hazard Classes and CategoriesAcute Tox. 3 (100%)

Toxikologische Informationen

Hepatotoxicity · 1 Eintrag

In the large, controlled trial of moxidectin vs ivermectin in onchocerciasis, transient serum aminotransferase elevations were found in 22% of moxidectin- and 21% of ivermectin-treated participants which were above 3 times ULN in 1.2% vs 1.6%. Bilirubin levels were also frequently elevated (9.9% vs 9.5%) but were transient resolving in all patients. Thus, the liver test abnormalities were invariably transient, mild to moderate in severity, and appeared to be part of the Mazzotti reaction, resolving within days or weeks of onset. No patient developed what could be considered clinically apparent liver injury. Since approval of moxidectin as therapy of onchocerciasis in humans, there have been no reports of liver injury with symptoms or jaundice associated with its use. There have also been no reports of liver injury with use of moxidectin in other human parasitic infections [such as Strongyloides stercoralis] where liver test abnormalities were no more frequent with moxidectin than with placebo.

Drug Induced Liver Injury · 6 Einträge

Drug Induced Liver Injury Rank (DILIrank 2.0)

Moxidectin

Ambiguous-DILI-concern

4

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
EPA Human Health Benchmarks for Pharmaceuticals · 6 Einträge

Moxidectin

0.2

0.8

The recommended dosage of moxidectin is a single dose of 8 mg (four 2 mg tablets) taken orally with or without food.

Data used to generate the benchmarks include the following: Lowest Daily Dose (LDD): 8 mg/day, Lowest Therapeutic Dose (LTD): 0.1 mg/kg-day, and Screening Dose: 0.00003 mg/kg-day.

14-Jan-22

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

P - Antiparasitic products, insecticides and repellents

QP - Antiparasitic products, insecticides and repellents

Protein BindingThis pharmacokinetic property in humans is unknown.
Pharmacodynamics · 1 Eintrag

Moxidectin has been reported to be highly effective against _Onchocerca volvulus_ when compared to ivermectin. When moxidectin was administered in infected individuals, the microfilarial load in the skin was lower even when compared to the current therapy, ivermectin. The levels of microfilarial got reduced to an undetectable level while being safe to be used in mass drug administration.

Mechanism of Action · 1 Eintrag

Moxidectin selectively binds to the parasite's GABA-A and glutamate-gated chloride ion channels which are vital for the function of invertebrate nerve and muscle cells. It presents activity against the parasite but it does not kill him. Once moxidectin is bound, there is an increased permeability leading to an influx of chloride ions and flaccid paralysis of the parasite.

Biological Half-LifeMoxidectin reporter terminal half-life is 20.2 days.
Metabolism/Metabolites · 1 Eintrag

Reports have registered enzymatic modification in humans and in nematodes. In the case of moxidectin, there has been registered C29-30- and C14-mono-hydroxymethyl derivatives mainly by the cytochrome CYP3A and CYP2B. The metabolism of moxidectin is considered to contribute to a small extent to the elimination. Some other metabolites formed are O-demethyl-dihydroxy metabolites. The metabolism of the of moxidectin is not major as the major residue in fat, liver, kidney and muscle is the unchanged moxidectin.

Verwendung und Herstellung

Household ProductsInformation on 2 consumer products that contain Moxidectin in the following categories is provided:
Use ClassificationVeterinary Drug -> ANTHELMINTHIC_AGENT -> JECFA Functional Classes

Zugehörige Reaktionen

2

Notizen zur Verbindung

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