Milbemycin free base

For research use only. Not for therapeutic Use.

  • CAT Number: I032284
  • CAS Number: 51570-36-6
  • Molecular Formula: C31H44O7
  • Molecular Weight: 528.69
  • Purity: 98%
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Milbemycin free base(Cat No.:I032284)is an antiparasitic compound derived from the fermentation of Streptomyces bacteria, widely used in veterinary medicine to treat a variety of parasitic infections in animals. It works by binding to glutamate-gated chloride channels in the nervous systems of parasites, leading to paralysis and death. Milbemycin is effective against roundworms, heartworms, and other internal and external parasites in dogs, cats, and livestock. The free base form of milbemycin is the active ingredient in several antiparasitic treatments, providing broad-spectrum efficacy and safety when used as directed.


Catalog Number I032284
CAS Number 51570-36-6
Synonyms

Milbemycin (free base); CL301,423; CL-301,423; CL 301,423

Molecular Formula C31H44O7
Purity 98%
Solubility Soluble in DMSO
Appearance Solid powder
Storage Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
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
InChI InChI=1S/C31H44O7/c1-18-7-6-8-23-17-35-28-27(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/h6-9,14,18,20,22,24-28,32,34H,10-13,15-17H2,1-5H3/b7-6+,19-9+,23-8+/t18-,20-,22+,24+,25-,26-,27+,28+,30-,31+/m0/s1
InChIKey ZLBGSRMUSVULIE-GSMJGMFJSA-N
SMILES C[C@H]1CC[C@]2(C[C@@H]3C[C@H](O2)C/C=C(/C[C@H](/C=C/C=C/4\CO[C@H]5[C@@]4([C@@H](C=C([C@H]5O)C)C(=O)O3)O)C)\C)O[C@@H]1C
Reference

1: Wang H, Cheng X, Liu Y, Li S, Zhang Y, Wang X, Xiang W. Improved milbemycin production by engineering two Cytochromes P450 in Streptomyces bingchenggensis. Appl Microbiol Biotechnol. 2020 Apr;104(7):2935-2946. doi: 10.1007/s00253-020-10410-8. Epub 2020 Feb 11. PMID: 32043186.
2: Gill JH, Lacey E. Avermectin/milbemycin resistance in trichostrongyloid nematodes. Int J Parasitol. 1998 Jun;28(6):863-77. doi: 10.1016/s0020-7519(98)00068-x. PMID: 9673866.
3: He H, Ye L, Li C, Wang H, Guo X, Wang X, Zhang Y, Xiang W. SbbR/SbbA, an Important ArpA/AfsA-Like System, Regulates Milbemycin Production in Streptomyces bingchenggensis. Front Microbiol. 2018 May 23;9:1064. doi: 10.3389/fmicb.2018.01064. PMID: 29875761; PMCID: PMC5974925.
4: Qi H, Zhang J, Hao ZK, Zhang SY, Li JS, Zhang LQ, Wang JD, Xiang WS. Two novel milbemycin derivatives from the genetically engineered strain Streptomyces avermitilis AVE-H39. J Antibiot (Tokyo). 2020 Sep;73(9):642-645. doi: 10.1038/s41429-020-0317-2. Epub 2020 May 29. PMID: 32472052.
5: Wang JD, Qi H, Zhang J, Li JS, Zhang SY, Hao ZK, Zhang LQ, Xiang WS. Two new 13-hydroxylated milbemycin metabolites from the genetically engineered strain Streptomyces avermitilis AVE-H39. J Asian Nat Prod Res. 2020 Aug 27:1-7. doi: 10.1080/10286020.2020.1803294. Epub ahead of print. PMID: 32851866.
6: Molento MB, Nielsen MK, Kaplan RM. Resistance to avermectin/milbemycin anthelmintics in equine cyathostomins – current situation. Vet Parasitol. 2012 Apr 19;185(1):16-24. doi: 10.1016/j.vetpar.2011.10.013. Epub 2011 Oct 18. PMID: 22047763.
7: Walker B, Izumikawa K, Tsai HF, Bennett JE. Milbemycin A4 oxime as a probe of azole transport in Candida glabrata. FEMS Yeast Res. 2014 Aug;14(5):755-61. doi: 10.1111/1567-1364.12164. Epub 2014 Jun 12. PMID: 24838041; PMCID: PMC4126866.
8: Zeltins A, Turks M, Skrastina D, Lugiņina J, Kalnciema I, Balke I, Bizdēna Ē, Skrivelis V. Synthesis and Immunological Evaluation of Virus-Like Particle- Milbemycin A₃/A₄ Conjugates. Antibiotics (Basel). 2017 Sep 11;6(3):18. doi: 10.3390/antibiotics6030018. PMID: 28892001; PMCID: PMC5617982.
9: Danaher M, Radeck W, Kolar L, Keegan J, Cerkvenik-Flajs V. Recent developments in the analysis of avermectin and milbemycin residues in food safety and the environment. Curr Pharm Biotechnol. 2012 May;13(6):936-51. doi: 10.2174/138920112800399068. PMID: 22039790.
10: Wolstenholme AJ, Rogers AT. Glutamate-gated chloride channels and the mode of action of the avermectin/milbemycin anthelmintics. Parasitology. 2005;131 Suppl:S85-95. doi: 10.1017/S0031182005008218. PMID: 16569295.

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