Nemadectin
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| Category | Antibiotics |
| Catalog number | BBF-03709 |
| CAS | 102130-84-7 |
| Molecular Weight | 612.79 |
| Molecular Formula | C36H52O8 |
| Purity | >95% by HPLC |
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Description
The dominant member of a class of milbemycins; shows pronounced nematocidal and insecticidal activity
Specification
| Synonyms | CL-287088; S541A; LL-F28249 alpha |
| Storage | Store at -20°C |
| IUPAC Name | (6R,24S)-4',21,24-trihydroxy-5',11,13,22-tetramethyl-6'-(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 |
| Canonical SMILES | CC1CC(=CCC2CC(CC3(O2)CC(C(C(O3)C(=CC(C)C)C)C)O)OC(=O)C4C=C(C(C5C4(C(=CC=C1)CO5)O)O)C)C |
| InChI | InChI=1S/C36H52O8/c1-20(2)13-24(6)32-25(7)30(37)18-35(44-32)17-28-16-27(43-35)12-11-22(4)14-21(3)9-8-10-26-19-41-33-31(38)23(5)15-29(34(39)42-28)36(26,33)40/h8-11,13,15,20-21,25,27-33,37-38,40H,12,14,16-19H2,1-7H3/t21?,25?,27?,28?,29?,30?,31?,32?,33?,35-,36+/m0/s1 |
| InChI Key | YNFMRVVYUVPIAN-PAYOQHMGSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | White Solid |
| Antibiotic Activity Spectrum | parasites |
| Boiling Point | 789.4°C at 760 mmHg |
| Density | 1.2 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. Poor water solubility. |
Reference Reading
1.New nemadectin congener from Streptomyces microflavus neau3: fermentation, isolation, structure elucidation and biological activities.
Xiang WS1, Wang JD, Wang M, Wang XJ. J Antibiot (Tokyo). 2010 Apr;63(4):171-5. doi: 10.1038/ja.2010.12. Epub 2010 Feb 26.
Bioactivity-guided fractionation of Streptomyces microflavus neau3 fermentation broth was used to determine the chemical identity of bioactive constituents. The structure of the new compound 1 was determined on the basis of spectroscopic analysis, including 1D and 2D NMR, as well as HRESI-MS, ESI-MS, UV and IR, and compared with the data reported in the literature. The acaricidal and nematocidal activities of the isolated compound 1 and its previously reported analogs 2, 3, 4 and 5 were evaluated. The results demonstrate that compounds 1, 2, 3, 4 and 5, especially compound 1, have potential as antiparasitics with acaricidal and nematocidal activities. These lactones shed new insights into the structural diversity of nemadectin and milbemycin analog libraries that are potentially accessible by combinatorial biosynthesis.
2.Trace analysis of endectocides in milk by high performance liquid chromatography with fluorescence detection.
Cerkvenik-Flajs V1, Milcinski L, Süssinger A, Hodoscek L, Danaher M, Antonić J. Anal Chim Acta. 2010 Mar 24;663(2):165-71. doi: 10.1016/j.aca.2010.01.040. Epub 2010 Feb 6.
An analytical method has been developed for the simultaneous determination of the following endectocide drugs in milk: ivermectin, abamectin, doramectin, moxidectin, eprinomectin, emamectin and nemadectin. Samples were extracted with acetonitrile, purified with solid-phase extraction on a reversed phase C(8), derivatised with N-methylimidazole, trifluoroacetic anhydride and acetic acid to a stable fluorescent derivative, and were further analysed by gradient high performance liquid chromatography (HPLC) on an endcapped reversed phase Supelcosil LC-8-DB. The derivatisation step was mathematically optimised and the method was validated according to the requirements of Commission Decision 2002/657/EC, using fortified raw bovine milk. Mean recovery was between 78 and 98%. The repeatability (CV(r)) and within-laboratory reproducibility (CV(W)) ranged from 4.6 to 13.4% and from 6.6 to 14.5%, respectively. Decision limits (CCalpha) for analytes with MRL values, namely eprinomectin and moxidectin, were determined to be 24.
3.Isolation and characterization of degradation products of moxidectin using LC, LTQ FT-MS, H/D exchange and NMR.
Awasthi A1, Razzak M, Al-Kassas R, Greenwood DR, Harvey J, Garg S. Anal Bioanal Chem. 2012 Nov;404(8):2203-22. doi: 10.1007/s00216-012-6393-9. Epub 2012 Sep 18.
This study aimed to evaluate the degradation profile and pathways, and identify unknown impurities of moxidectin under stress conditions. During the experiments, moxidectin samples were stressed using acid, alkali, heat and oxidation, and chromatographic profiles were compared with known impurities given in European Pharmacopeia (EP) monograph. Moxidectin has shown good stability under heat, while reaction with alkali produced 2-epi and ∆2,3 isomers (impurities D and E in EP) by characteristic reactions of the oxahydrindene (hexahydrobenzofuran) portion of the macrocyclic lactone. Two new, previously unreported, unknown degradation products, i.e. impurity 1 and impurity 2, detected after acid hydrolysis of moxidectin (impurity 2 was also observed to a lesser extent after oxidation), were isolated from sample matrices and identified using liquid chromatography, NMR, high-resolution FT-ICR MS, and hydrogen/deuterium exchange studies. FTMS analysis showed accurate mass of molecular ion peaks for moxidectin at m/z 640.
4.Reversal of P-glycoprotein-mediated multidrug resistance in vitro by doramectin and nemadectin.
Gao A1, Wang X, Xiang W, Liang H, Gao J, Yan Y. J Pharm Pharmacol. 2010 Mar;62(3):393-9. doi: 10.1211/jpp.62.03.0016.
OBJECTIVES: Multidrug resistance (MDR) is a serious obstacle encountered in cancer treatment. This study was performed to explore the reversal of MDR by doramectin from the avermectin family and nemadectin belonging to the milbemycin family.
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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 ╳
