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MedKoo Cat#: 563694 | Name: Milbemycin A3 Oxime
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Milbemycin A3 Oxime is an opener of glutamate sensitive chloride channels in neurons of invertebrates, leading to paralysis by hyperpolarisation of these cells and blocking signal transfer. Milbemycin A3 Oxime is also an anthelmintic. Formulations containing milbemycin A3 oxime, in combination with milbemycin A4 oxime, have been used in the treatment of parasitic infections in dogs.

Chemical Structure

Milbemycin A3 Oxime
Milbemycin A3 Oxime
CAS#114177-14-9 (A3 Oxime)

Theoretical Analysis

MedKoo Cat#: 563694

Name: Milbemycin A3 Oxime

CAS#: 114177-14-9 (A3 Oxime)

Chemical Formula: C31H43NO7

Exact Mass: 541.3040

Molecular Weight: 541.69

Elemental Analysis: C, 68.74; H, 8.00; N, 2.59; O, 20.67

Price and Availability

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1mg USD 500.00 2 weeks
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Related CAS #
51570-36-6 (free base) 129496-10-2 (oxime) 114177-14-9 (A3 Oxime)
Synonym
Milbemycin A3 Oxime; Milbemycin A3 5-oxime; Milbemycin A3 5 oxime
IUPAC/Chemical Name
(1′R,2R,4′S,5S,6R, 8′R,10′E,13′R,14′E,16′E,20′R,21′Z,24′S)-24′-hydroxy-21′-(hydroxyimino)-5,6,11′,13′,22′-pentamethyl 3,4,5,6-tetrahydrospiro[pyran-2,6′-[3,7,19]trioxatetracyclo-[15.6.1.14,8.020,24]pentacosa[10,14,16,22]tetraen]-2′-one
InChi Key
VDBGCWFGLMXRIK-DPSDDZCLSA-N
InChi Code
InChI=1S/C31H43NO7/c1-18-7-6-8-23-17-36-28-27(32-35)21(4)14-26(31(23,28)34)29(33)37-25-15-24(10-9-19(2)13-18)39-30(16-25)12-11-20(3)22(5)38-30/h6-9,14,18,20,22,24-26,28,34-35H,10-13,15-17H2,1-5H3/b7-6+,19-9+,23-8+,32-27-/t18-,20-,22?,24+,25-,26-,28+,30+,31-/m0/s1
SMILES Code
O=C(O[C@]1([H])C[C@]2(O[C@](C1)([H])C/C=C(C)/C[C@@H](C)/C=C/C=C3CO[C@@]/4([H])[C@@]5\3O)CC[C@H](C)C(C)O2)[C@]5([H])C=C(C)C4=N\O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Milbemycin A3 Oxime is an opener of glutamate sensitive chloride channels.
In vitro activity:
The neuropharmacological mechanisms underlying the action of milbemycin oxime on the motility of Angiostrongylus cantonensis and Dirofilaria immitis were examined in vitro. In A. cantonensis, milbemycin oxime caused inhibitory effects at low concentrations of > or = 10(-9) g/ml, and paralysis was elicited at 10(-8) - 10(-6) g/ml. Reference: Parasitol Res. 1992;78(4):349-53. https://pubmed.ncbi.nlm.nih.gov/1409536/
In vivo activity:
The activities of the synthesized compounds were studied in dogs naturally infested with microfilariae of Dirofilaria immitis. The 5-keto-5-oximes of milbemycin D (7), A4 (8) and A3 (9) had quite high efficacy to control the microfilariae and more potency than their parents, while the 5-O-acyl oximes (11-15) also exhibited high activity. Reference: Agric Biol Chem. 1991 Oct;55(10):2615-21. https://pubmed.ncbi.nlm.nih.gov/1368759/
Solvent mg/mL mM
Solubility
DMF 30.0 55.38
DMSO 30.0 55.38
Ethanol 30.0 55.38
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 541.69 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Lee HH, Terada M. In vitro effects of milbemycin oxime: mechanism of action against Angiostrongylus cantonensis and Dirofilaria immitis. Parasitol Res. 1992;78(4):349-53. doi: 10.1007/BF00937095. PMID: 1409536. 2. Tsukamoto Y, Sato K, Mio S, Sugai S, Yanai T, Kitano N, Muramatsu S, Nakada Y, Ide J. Synthesis of 5-keto-5-oxime derivatives of milbemycins and their activities against microfilariae. Agric Biol Chem. 1991 Oct;55(10):2615-21. PMID: 1368759.
In vitro protocol:
1. Lee HH, Terada M. In vitro effects of milbemycin oxime: mechanism of action against Angiostrongylus cantonensis and Dirofilaria immitis. Parasitol Res. 1992;78(4):349-53. doi: 10.1007/BF00937095. PMID: 1409536.
In vivo protocol:
1. Tsukamoto Y, Sato K, Mio S, Sugai S, Yanai T, Kitano N, Muramatsu S, Nakada Y, Ide J. Synthesis of 5-keto-5-oxime derivatives of milbemycins and their activities against microfilariae. Agric Biol Chem. 1991 Oct;55(10):2615-21. PMID: 1368759.
1: Becker MD, Young BC. Treatment of severe lipophilic intoxications with intravenous lipid emulsion: a case series (2011-2014). Vet Med (Auckl). 2017 Oct 30;8:77-85. doi: 10.2147/VMRR.S129576. eCollection 2017. PubMed PMID: 30050859; PubMed Central PMCID: PMC6042488. 2: Abbate JM, Napoli E, Arfuso F, Gaglio G, Giannetto S, Halos L, Beugnet F, Brianti E. Six-month field efficacy and safety of the combined treatment of dogs with Frontline Tri-Act® and NexGard Spectra®. Parasit Vectors. 2018 Jul 16;11(1):425. doi: 10.1186/s13071-018-2957-7. PubMed PMID: 30012179; PubMed Central PMCID: PMC6048810. 3: Cochrane ZN, Berger DJ, Viall AK, Schrunk D, Hans Coetzee JF. Evaluation of compounded aqueous milbemycin oxime: issues with formulation potency and reproducibility. J Small Anim Pract. 2018 Jul 11. doi: 10.1111/jsap.12907. [Epub ahead of print] PubMed PMID: 29998573. 4: Grant T, Wiseman S, Snyder DE. Effects of milbemycin oxime, combined with spinosad, when administered orally to microfilaremic dogs infected with adult heartworms (Dirofilaria immitis). J Am Vet Med Assoc. 2018 May 1;252(9):1084-1089. doi: 10.2460/javma.252.9.1084. PubMed PMID: 29641338. 5: Bowman DD, Drake J. Examination of the "susceptibility gap" in the treatment of canine heartworm infection. Parasit Vectors. 2017 Nov 9;10(Suppl 2):513. doi: 10.1186/s13071-017-2433-9. Review. PubMed PMID: 29143689; PubMed Central PMCID: PMC5688481. 6: McCall JW, Varloud M, Hodgkins E, Mansour A, DiCosty U, McCall S, Carmichael J, Carson B, Carter J. Shifting the paradigm in Dirofilaria immitis prevention: blocking transmission from mosquitoes to dogs using repellents/insecticides and macrocyclic lactone prevention as part of a multimodal approach. Parasit Vectors. 2017 Nov 9;10(Suppl 2):525. doi: 10.1186/s13071-017-2438-4. PubMed PMID: 29143678; PubMed Central PMCID: PMC5688480. 7: Heredia Cardenas R, Romero Núñez C, Miranda Contreras L. Efficacy of two anthelmintic treatments, spinosad/milbemycin oxime and ivermectin/praziquantel in dogs with natural Toxocara spp. infection. Vet Parasitol. 2017 Nov 30;247:77-79. doi: 10.1016/j.vetpar.2017.09.016. Epub 2017 Sep 22. PubMed PMID: 29080769. 8: Nagayoshi Y, Miyazaki T, Shimamura S, Nakayama H, Minematsu A, Yamauchi S, Takazono T, Nakamura S, Yanagihara K, Kohno S, Mukae H, Izumikawa K. Unexpected effects of azole transporter inhibitors on antifungal susceptibility in Candida glabrata and other pathogenic Candida species. PLoS One. 2017 Jul 11;12(7):e0180990. doi: 10.1371/journal.pone.0180990. eCollection 2017. PubMed PMID: 28700656; PubMed Central PMCID: PMC5507446. 9: Beugnet F, Meyer L, Fourie J, Larsen D. Preventive efficacy of NexGard Spectra(®) against Dipylidium caninum infection in dogs using a natural flea (Ctenocephalides felis) infestation model. Parasite. 2017;24:16. doi: 10.1051/parasite/2017017. Epub 2017 May 12. PubMed PMID: 28497745; PubMed Central PMCID: PMC5432962. 10: Tielemans E, Lebon W, Dumont P, Taweethavonsawat P, Larsen D, Rehbein S. Efficacy of afoxolaner plus milbemycin oxime chewable tablets (NexGard Spectra(®), Merial) against adult Ancylostoma ceylanicum hookworm, in dogs. Vet Parasitol. 2017 Apr 30;238:87-89. doi: 10.1016/j.vetpar.2017.03.028. Epub 2017 Apr 1. PubMed PMID: 28408213. 11: Christie BL, Raines JA. Effect of an Otic Milbemycin Oxime Formulation on Tegastes acroporanus Infesting Corals. J Aquat Anim Health. 2016 Dec;28(4):235-239. doi: 10.1080/08997659.2016.1206636. PubMed PMID: 28005491. 12: Jang HY, Parent JM, Hagen C, Colwell E, Rist PM, Murphy N, Burton S, Conboy G. Paradoxical vestibular syndrome in a dog from western Newfoundland infected with French heartworm (Angiostrongylus vasorum). Can Vet J. 2016 Dec;57(12):1251-1255. PubMed PMID: 27928171; PubMed Central PMCID: PMC5109626. 13: Drag M, Saik J, Harriman J, Letendre L, Yoon S, Larsen D. Safety evaluation of orally administered afoxolaner and milbemycin oxime in eight-week-old dogs. J Vet Pharmacol Ther. 2017 Oct;40(5):447-453. doi: 10.1111/jvp.12375. Epub 2016 Nov 27. PubMed PMID: 27891622. 14: Rehbein S, Knaus M, Mallouk Y, Breiltgens T, Brianti E, Capári B, Dantas-Torres F, Gau M, Joachim A, Kaulfuß KH, Kirkova Z, Lechner J, Mihalca AD, Mirabito R, Petkevičius S, Rapti D, Shukullari E, Sedeilhan M, Dollhofer D, Kley K, Lebon W, Visser M, Jeannin P. Efficacy against nematode infections and safety of afoxolaner plus milbemycin oxime chewable tablets in domestic dogs under field conditions in Europe. Parasitol Res. 2017 Jan;116(1):259-269. Epub 2016 Oct 22. PubMed PMID: 27771803. 15: Zhang Y, He H, Liu H, Wang H, Wang X, Xiang W. Characterization of a pathway-specific activator of milbemycin biosynthesis and improved milbemycin production by its overexpression in Streptomyces bingchenggensis. Microb Cell Fact. 2016 Sep 7;15(1):152. doi: 10.1186/s12934-016-0552-1. PubMed PMID: 27604457; PubMed Central PMCID: PMC5015266. 16: Letendre L, Harriman J, Drag M, Mullins A, Malinski T, Rehbein S. The intravenous and oral pharmacokinetics of afoxolaner and milbemycin oxime when used as a combination chewable parasiticide for dogs. J Vet Pharmacol Ther. 2017 Jan;40(1):35-43. doi: 10.1111/jvp.12332. Epub 2016 Sep 7. PubMed PMID: 27604405. 17: Lebon W, Tielemans E, Rehbein S, Dumont P, Yoon S, Beugnet F, Jeannin P, Larsen D, Halos L. Monthly administrations of milbemycin oxime plus afoxolaner chewable tablets to prevent Angiostrongylus vasorum infection in dogs. Parasit Vectors. 2016 Sep 2;9(1):485. doi: 10.1186/s13071-016-1773-1. PubMed PMID: 27589951; PubMed Central PMCID: PMC5010729. 18: Otranto D, Colella V, Crescenzo G, Solari Basano F, Nazzari R, Capelli G, Petry G, Schaper R, Pollmeier M, Mallia E, Dantas-Torres F, Lia RP. Efficacy of moxidectin 2.5% and imidacloprid 10% in the treatment of ocular thelaziosis by Thelazia callipaeda in naturally infected dogs. Vet Parasitol. 2016 Aug 30;227:118-21. doi: 10.1016/j.vetpar.2016.07.035. Epub 2016 Aug 1. PubMed PMID: 27523947. 19: Beugnet F, Crafford D, de Vos C, Kok D, Larsen D, Fourie J. Evaluation of the efficacy of monthly oral administration of afoxolaner plus milbemycin oxime (NexGard Spectra(®), Merial) in the prevention of adult Spirocerca lupi establishment in experimentally infected dogs. Vet Parasitol. 2016 Aug 15;226:150-61. doi: 10.1016/j.vetpar.2016.07.002. Epub 2016 Jul 2. PubMed PMID: 27514901. 20: Fankhauser R, Hamel D, Dorr P, Reinemeyer CR, Crafford D, Bowman DD, Ulrich M, Yoon S, Larsen DL. Efficacy of oral afoxolaner plus milbemycin oxime chewables against induced gastrointestinal nematode infections in dogs. Vet Parasitol. 2016 Jul 30;225:117-22. doi: 10.1016/j.vetpar.2016.06.003. Epub 2016 Jun 3. PubMed PMID: 27369586.