Basic information
- 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- Molecular formula
- C48H72O14
- Average molar mass
- 873.1 g/mol
- Monoisotopic mass
- 872.49220697
Overview
Avermectin B1a is an avermectin.
Names & identifiers
- Preferred 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
- English name
- Avermectin B1a
- Molecular formula
- C48H72O14
- Molecular weight
- 873.09
Names & synonyms
AVERMECTIN B1A65195-55-3Abamectin B1a5-O-Demethylavermectin A1aabamectin component B1aAvermectin B(1)aAvermectin A1a, 5-O-demethyl-Antibiotic C 076B1aCaswell No. 063ABAbamectin komponente B1aK54ZMM929KDTXSID9058238
Show more names
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
Properties
Computed structural properties
- XLogP
- 3.8
- Topological polar surface area
- 170 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 14
- Rotatable bonds
- 8
- Heavy atoms
- 62
- Formal charge
- 0
- Complexity
- 1,730
Experimental & physicochemical properties
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]
Physicochemical properties
- Boiling point
- 940.9 · 940.9±65.0 °C(Predicted)
- Density
- 1.24 · 1.24±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- 143.4 mg/mL · ≥143.4 mg/mL in DMSO; ≥11.86 mg/mL in EtOH with ultrasonic; insoluble in H2O
- form
- Powder
- pka
- 12.42 · 12.42±0.70(Predicted)
- color
- White to light yellow
- Stability
- Hygroscopic
Safety & regulation
GHS classification
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)
Hazard information
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
Toxicology
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)
Carcinogen ClassificationNot listed by IARC.
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationAgents that kill parasitic worms. They are used therapeutically in the treatment of HELMINTHIASIS in man and animal.
Uses & manufacturing
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
Applications
DescriptionAvermectin 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 .
UsesAvermectin 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.
Suppliers100 total
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
Related reactions
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Compound notes
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