Grundinformationen
- CAS
65195-55-3- Standard-SMILES
CC[C@H](C)[C@H]1O[C@]2(C=C[C@@H]1C)C[C@@H]1C[C@@H](C/C=C(\C)[C@@H](O[C@H]3C[C@H](OC)[C@@H](O[C@H]4C[C@H](OC)[C@@H](O)[C@H](C)O4)[C@H](C)O3)[C@@H](C)/C=C/C=C3\CO[C@@H]4[C@H](O)C(C)=C[C@@H](C(=O)O1)[C@]34O)O2- InChIKey
RRZXIRBKKLTSOM-XPNPUAGNSA-N- Summenformel
- C48H72O14
- Durchschnittliche Molmasse
- 873,1 g/mol
- Monoisotopische Masse
- 872,49220697
Überblick
Avermectin B1a is an avermectin.
Namen und Bezeichner
- Bevorzugter Name
- avermectin B1a
- IUPAC
- (1'R,2R,3S,4'S,6S,8'R,10'E,12'S,13'S,14'E,16'E,20'R,21'R,24'S)-2-[(2S)-butan-2-yl]-21',24'-dihydroxy-12'-[(2R,4S,5S,6S)-5-[(2S,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-3,11',13',22'-tetramethylspiro[2,3-dihydropyran-6,6'-3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene]-2'-one
- Lokaler Name
- Abamectin
- Englischer Name
- Avermectin B1a
- Summenformel
- C48H72O14
- Molmasse
- 873.09
Namen und Synonyme
AVERMECTIN B1A65195-55-3Abamectin B1a5-O-Demethylavermectin A1aabamectin component B1aAvermectin B(1)aAvermectin A1a, 5-O-demethyl-Antibiotic C 076B1aCaswell No. 063ABAbamectin komponente B1aK54ZMM929KDTXSID9058238
Weitere Namen anzeigen
AbamectinaAvamectin B1aDoramectin ImpurityC-076B1aABERMECTINSAbamectinumAntibiotic C-076B1aAbamectine [french]
CHEBI:29534(1'R,2R,3S,4'S,6S,8'R,10'E,12'S,13'S,14'E,16'E,20'R,21'R,24'S)-2-[(2S)-butan-2-yl]-21',24'-dihydroxy-12'-[(2R,4S,5S,6S)-5-[(2S,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-3,11',13',22'-tetramethylspiro[2,3-dihydropyran-6,6'-3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene]-2'-oneC-076(1'R,2R,3S,4'S,6S,8'R,10'E,12'S,13'S,14'E,16'E,20'R,21'R,24'S)-2-((2S)-butan-2-yl)-21',24'-dihydroxy-12'-((2R,4S,5S,6S)-5-((2S,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy-4-methoxy-6-methyloxan-2-yl)oxy-3,11',13',22'-tetramethylspiro(2,3-dihydropyran-6,6'-3,7,19-trioxatetracyclo(15.6.1.14,8.020,24)pentacosa-10,14,16,22-tetraene)-2'-oneRefChem:6604DTXCID403892avermectin B1a (purity >=80 %)265-610-3
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3,8
- Polarare Oberfläche (TPSA)
- 170 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 14
- Frei drehbare Bindungen
- 8
- Schwere Atome
- 62
- Formalladung
- 0
- Komplexität
- 1.730
Experimentelle und physikochemische Eigenschaften
Pesticides
Environmental transformation -> Pesticides (parent, predecessor)
Nematicides, Transformation products, Acaricides, Insecticides
Animal DrugsPharmaceuticals -> UK Veterinary Medicines Directorate List
Collision Cross Section290.5 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physikochemische Eigenschaften
- Siedepunkt
- 940.9 · 940.9±65.0 °C(Predicted)
- Dichte
- 1.24 · 1.24±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- Löslichkeit
- 143.4 mg/mL · ≥143.4 mg/mL in DMSO; ≥11.86 mg/mL in EtOH with ultrasonic; insoluble in H2O
- Aggregatzustand
- Powder
- pka
- 12.42 · 12.42±0.70(Predicted)
- Farbe
- White to light yellow
- Stabilität
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Danger
H300: Fatal if swallowed [Danger Acute toxicity, oral]
P203, P260, P264, P270, P271, P273, P280, P284, P301+P316, P304+P340, P316, P318, P319, P320, P321, P330, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Danger
H300+H330 (37.5%): Fatal if swallowed or if inhaled [Danger Acute toxicity, oral; acute toxicity, inhalation]
P203, P260, P261, P262, P264, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P316, P317, P318, P319, P320, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Gefahrenhinweise
Regulatory InformationREACH registered substance: avermectin B1a (purity ≥80 %) (EC: 265-610-3)
Hazard Classes and Categories
Acute Tox. 2 (100%)
Acute toxicity (ingestion) - category 2
Repr. 2
Toxikologische Informationen
Health EffectsAvermectins are neurotoxic and have reproductive and developmental effects. (L1826)
Toxicity SummaryIt has low solubility in water and extensive non-specific binding. It opens GABA-insensitive chloride channels, reducing membrane resistance and increasing conductance inward. (T10)
Signs and SymptomsAvermectins cause irritation of skin and eyes, central nervous system depression (incoordination, tremors, lethargy, excitation, pupil dilation, coma), vomiting, convulsions and/or tremors, and respiratory failure at high doses. (L1826)
Chemie und Industrie
Pharmakologische Informationen
MeSH Pharmacological ClassificationAgents that kill parasitic worms. They are used therapeutically in the treatment of HELMINTHIASIS in man and animal.
Verwendung und Herstellung
UsesActive ingredient in some commercial ant bait traps. (L829)
Use Classification
Veterinary Drug -> ANTHELMINTHIC_AGENT -> JECFA Functional Classes
Environmental transformation -> Pesticides (parent, predecessor)
Nematicides, Transformation products, Acaricides, Insecticides
Anwendungen
BeschreibungAvermectin B1a is a macrocyclic lactone disaccharide anthelmintic agent that binds to high and low affinity sites on the mammalian GABAA receptor. Binding to the high affinity site activates the receptor to increase chloride influx, while binding to the low affinity site blocks the channel. Avermectin B1a inhibits binding of the glycine receptor antagonist strychnine to membranes and the solubilized receptor from rat spinal cord (Kis = 1.3 and 3.6 μM, respectively). Formulations containing avermectin B1a (>80%) and avermectin B1b (~20%; ) are used in insecticides and veterinary anthelmintic formulas as abamectin .
VerwendenAvermectin B1a is the major component (>80%) of a commercially available anthelmintic used to control parasitic nematodes in livestock. Avermectin B1a contains a secbutyl residue in the 25-position. In vitro and in vivo studies have shown that this analogue is the more potent analogue in the commercial product.
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