Doramectin aglycone
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04236 |
| CAS | 1987883-26-0 |
| Molecular Weight | 610.78 |
| Molecular Formula | C36H50O8 |
| Purity | >95% by HPLC |
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Description
It is an acid degradation product produced by hydrolysis of the disaccharide unit of doramectin. It is an inhibitor of nematode larval development and an anthelmintic in animal health. It has no paralytic activity.
Specification
| Synonyms | 25R-cyclohexyl-22,23-didehydro-5-O-demethyl-28-deoxy-6R,28-epoxy-13S-hydroxy-milbemycin B |
| Storage | Store at -20°C |
| IUPAC Name | (1'R,2R,3S,4'S,6S,8'R,10'Z,12'S,13'S,14'Z,20'R,21'R,24'S)-2-cyclohexyl-12',21',24'-trihydroxy-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 |
| Canonical SMILES | CC1C=CC=C2COC3C2(C(C=C(C3O)C)C(=O)OC4CC(CC=C(C1O)C)OC5(C4)C=CC(C(O5)C6CCCCC6)C)O |
| InChI | InChI=1S/C36H50O8/c1-21-9-8-12-26-20-41-33-31(38)24(4)17-29(36(26,33)40)34(39)42-28-18-27(14-13-22(2)30(21)37)43-35(19-28)16-15-23(3)32(44-35)25-10-6-5-7-11-25/h8-9,12-13,15-17,21,23,25,27-33,37-38,40H,5-7,10-11,14,18-20H2,1-4H3/b9-8-,22-13-,26-12?/t21-,23-,27+,28-,29-,30-,31+,32-,33+,35+,36+/m0/s1 |
| InChI Key | SHRUSRJMZSPNGG-KUOHORTNSA-N |
Properties
| Appearance | White Solid |
| Antibiotic Activity Spectrum | Parasites |
| Boiling Point | 809.2±65.0°C at 760 mmHg |
| Density | 1.3±0.1 g/cm3 |
Reference Reading
1. Transgenic Expression of Haemonchus contortus Cytochrome P450 Hco-cyp-13A11 Decreases Susceptibility to Particular but Not All Macrocyclic Lactones in the Model Organism Caenorhabditis elegans
Jürgen Krücken, Esra Yilmaz, Natalie Jakobs Int J Mol Sci . 2022 Aug 15;23(16):9155. doi: 10.3390/ijms23169155.
The number of reported macrocyclic lactones (ML) resistance cases across all livestock hosts is steadily increasing. Different studies in the parasitic nematodeHaemonchus contortusassume the participation of cytochrome P450s (Cyps) enzymes in ML resistance. Still, functional data about their individual contribution to resistance or substrate specificity is missing. Via microinjection, transgenicCaenorhabditis elegansexpressing HCON_00141052 (transgene-Hco-cyp-13A11) from extrachromosomal arrays were generated. After 24 h of exposure to different concentrations of ivermectin (IVM), ivermectin aglycone (IVMa), selamectin (SEL), doramectin (DRM), eprinomectin (EPR), and moxidectin (MOX), motility assays were performed to determine the impact of theH. contortusCyp to the susceptibility of the worms against each ML. Whiletransgene-Hco-cyp-13A11significantly decreased susceptibility to IVM (four-fold), IVMa (2-fold), and SEL (3-fold), a slight effect for DRM and no effect for MOX, and EPR was observed. This substrate specificity ofHco-cyp-13A11could not be explained by molecular modeling and docking studies. Hco-Cyp-13A11 molecular models were obtained for alleles from isolates with different resistance statuses. Although 14 amino acid polymorphisms were detected, none was resistance specific. In conclusion, Hco-cyp-13A11 decreased IVM, IVMa, and SEL susceptibility to a different extent, but its potential impact on ML resistance is not driven by polymorphisms.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
