Milbemectin
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| Category | Antibiotics |
| Catalog number | BBF-04275 |
| CAS | 1799297-76-9 |
| Molecular Weight | 1071.38 |
| Molecular Formula | C31H44O7.C32H46O7 |
| Purity | >95% by HPLC |
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Description
It is a mixture of the two most abundant milbemycin analogues, A3 and A4. It is the macrolide antibiotic produced by streptomyces hydroscopicus subsp. Aureolarcrimosus. It is a highly selective and potent insecticide and acaricide used as an agri-chemical for crop protection.
Specification
| Related CAS | 51570-36-6 (Milbemycin) 122666-95-9 (Milbemycin A) 120478-39-9 (Milbemycin A) 51596-10-2 (A3) 51596-11-3 (A4) |
| Synonyms | Milbemycin A3 and Milbemycin A4 (Mixture); (6R,25R)-5-O-demethyl-28-deoxy-6,28-epoxy-25-methyl-milbemycin B and (6R,25R)-5-O-demethyl-28-deoxy-6,28-epoxy-25-ethyl-milbemycin B (Mixture); Antibiotic B 41A3 and Antibiotic B 41A4 (Mixture) |
| Storage | Store at -20°C |
| IUPAC Name | (1R,4S,5'S,6R,6'R,8R,10E,13R,14E,16E,20R,21R,24S)-21,24-dihydroxy-5',6',11,13,22-pentamethylspiro[3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6,2'-oxane]-2-one;(1R,4S,5'S,6R,6'R,8R,10E,13R,14E,16E,20R,21R,24S)-6'-ethyl-21,24-dihydroxy-5',11,13,22-tetramethylspiro[3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6,2'-oxane]-2-one |
| Canonical SMILES | CCC1C(CCC2(O1)CC3CC(O2)CC=C(CC(C=CC=C4COC5C4(C(C=C(C5O)C)C(=O)O3)O)C)C)C.CC1CCC2(CC3CC(O2)CC=C(CC(C=CC=C4COC5C4(C(C=C(C5O)C)C(=O)O3)O)C)C)OC1C |
| InChI | InChI=1S/C32H46O7.C31H44O7/c1-6-27-21(4)12-13-31(39-27)17-25-16-24(38-31)11-10-20(3)14-19(2)8-7-9-23-18-36-29-28(33)22(5)15-26(30(34)37-25)32(23,29)35;1-18-7-6-8-23-17-35-28-27(32)21(4)14-26(31(23,28)34)29(33)36-25-15-24(10-9-19(2)13-18)38-30(16-25)12-11-20(3)22(5)37-30/h7-10,15,19,21,24-29,33,35H,6,11-14,16-18H2,1-5H3;6-9,14,18,20,22,24-28,32,34H,10-13,15-17H2,1-5H3/b8-7+,20-10+,23-9+;7-6+,19-9+,23-8+/t19-,21-,24+,25-,26-,27+,28+,29+,31+,32+;18-,20-,22+,24+,25-,26-,27+,28+,30-,31+/m00/s1 |
| InChI Key | YSKQMQHQUJEAQB-YPPYQCCRSA-N |
Properties
| Appearance | White to Off-white Solid |
| Antibiotic Activity Spectrum | Parasites |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO |
Reference Reading
1. Moxidectin: an oral treatment for human onchocerciasis
María-Gloria Basáñez, Philip Milton, Jonathan I D Hamley, Martin Walker Expert Rev Anti Infect Ther . 2020 Nov;18(11):1067-1081. doi: 10.1080/14787210.2020.1792772.
Introduction:Moxidectin is a milbemycin endectocide recently approved for the treatment of human onchocerciasis. Onchocerciasis, earmarked for elimination of transmission, is a filarial infection endemic in Africa, Yemen, and the Amazonian focus straddling Venezuela and Brazil. Concerns over whether the predominant treatment strategy (yearly mass drug administration (MDA) of ivermectin) is sufficient to achieve elimination in all endemic foci have refocussed attention upon alternative treatments. Moxidectin's stronger and longer microfilarial suppression compared to ivermectin in both phase II and III clinical trials indicates its potential as a novel powerful drug for onchocerciasis elimination.Areas covered:This work summarizes the chemistry and pharmacology of moxidectin, reviews the phase II and III clinical trials evidence on tolerability, safety, and efficacy of moxidectin versus ivermectin, and discusses the implications of moxidectin's current regulatory status.Expert opinion:Moxidectin's superior clinical performance has the potential to substantially reduce times to elimination compared to ivermectin. If donated, moxidectin could mitigate the additional programmatic costs of biannual ivermectin distribution because, unlike other alternatives, it can use the existing community-directed treatment infrastructure. A pediatric indication (for children <12 years) and determination of its usefulness in onchocerciasis-loiasis co-endemic areas will greatly help fulfill the potential of moxidectin for the treatment and elimination of onchocerciasis.
2. Persistence behaviour of milbemectin in/on tea under North-East Indian climatic condition
Suparna Pal, Bappaditya Kanrar, Chiranjit Kundu, Anjan Bhattacharyya Bull Environ Contam Toxicol . 2012 Mar;88(3):377-80. doi: 10.1007/s00128-011-0471-0.
A multi-location field trial was conducted under North-East Indian climatic condition viz. Siliguri and Dooars, West Bengal, India during Monsoon 2005 to evaluate the dissipation pattern of Milbemectin formulation (Milbeknock 1% EC) in/on tea field at two application rates (5 and 10 g a.i. ha(-1)). The quantitative analysis was performed using High Performance Liquid Chromatography (HPLC) with fluorescence detection at 460 nm. Following the first order kinetics the acaricide dissipates with half-life (T(1/2)) value ranges between 4.93-5.28 days and 6.84-10.76 days in made tea samples of Siliguri and Dooars field, respectively.
3. FDA-Approved Antiparasitic Drugs in the 21st Century: A Success for Helminthiasis?
Josué de Moraes, Timothy G Geary Trends Parasitol . 2020 Jul;36(7):573-575. doi: 10.1016/j.pt.2020.04.005.
Diseases caused by helminth infections affect more than a quarter of the population of the world, but the therapeutic arsenal is limited. The approval of moxidectin in 2018 and triclabendazole in 2019 by the FDA marked an important moment in the fight against diseases of poverty, such as helminthiases.
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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 ╳
