Moxidectin
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
Weitere Namen anzeigen
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
- Formalladung
- 0
- Komplexität
- 1.340
Experimentelle und physikochemische Eigenschaften
Human Drugs
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
FDA approved animal drugs -> Active ingredient
Pharmaceuticals -> UK Veterinary Medicines Directorate List
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
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
Toxikologische Informationen
Hepatotoxicity
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
Drug Induced Liver Injury Rank (DILIrank 2.0)
Moxidectin
Ambiguous-DILI-concern
4
Adverse reactions
DOI:10.1016/j.drudis.2016.02.015
EPA Human Health Benchmarks for Pharmaceuticals
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
P - Antiparasitic products, insecticides and repellents
QP - Antiparasitic products, insecticides and repellents
Pharmacodynamics
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
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.
Metabolism/Metabolites
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.
MeSH Pharmacological Classification
Agents that kill parasitic worms. They are used therapeutically in the treatment of HELMINTHIASIS in man and animal.
Substances used in the treatment or control of nematode infestations. They are used also in veterinary practice.
Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics.
Absorption, Distribution and Excretion
The penetration of moxidectin in the parasite is not restricted as this compound is a very poor substrate of p-glycoprotein, which is vital for the reduction of the uptake of lipophilic compounds from the GI tract and for the increase in biliary, intestinal and renal secretion. After oral administration of moxidectin, the plasma maximal concentration of 70.4 mg/kg was reached after 0.37 day with a reported AUC of 363.6 mcg/day/ml. It is also important to mention that oral bioavailability is enhanced with the co-administration with lipids.
When moxidectin is orally administered, 2% of the dose is eliminated unchanged in the feces within 72 hours. Renal elimination is negligible.
Moxidectin presents a larger volume of distribution and mean residence time when compared to ivermectin. The reported volume of distribution is of 1.2 l/kg.
The apparent clearance of moxidectin is 3.5 L/hour.
Verwendung und Herstellung
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