A derivative of milbemycin A4
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Milbemycin A4 oxime

Item No. 27938

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(6R,25R)-5-demethoxy-28-deoxy-6,28-epoxy-25-ethyl-5-(hydroxyimino)-milbemycin B
CAS Number
93074-04-5
Synonyms
  • 5-Ketomilbemycin A4 oxime
  • 5-Oxomilbemycin A4 5-oxime
Molecular Formula
C32H45NO7
Formula Weight
555.7
Purity
≥99%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: solubleDMSO: solubleEthanol: solubleMethanol: soluble
SMILES
CC[C@H]([C@@H](C)CC1)O[C@]21C[C@](OC([C@@]3([H])[C@@]4(O)[C@@]5([H])/C(C(C)=C3)=N/O)=O)([H])C[C@](C/C=C(C)/C[C@@H](C)/C=C/C=C4\CO5)([H])O2
InChi Code
InChI=1S/C32H45NO7/c1-6-27-21(4)12-13-31(40-27)17-25-16-24(39-31)11-10-20(3)14-19(2)8-7-9-23-18-37-29-28(33-36)22(5)15-26(30(34)38-25)32(23,29)35/h7-10,15,19,21,24-27,29,35-36H,6,11-14,16-18H2,1-5H3/b8-7+,20-10+,23-9+,33-28+/t19-,21-,24+,25-,26-,27+,29+,31+,32+/m0/s1
InChi Key
YCAZFHUABUMOIM-GVFHBPHBSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $296

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    5 mg

    $814

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    Cayman Chemical
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    Product Description

    Milbemycin A4 oxime is a derivative of milbemycin A4 (Item No. 17155) and a component of milbemycin oxime (Item No. 17164), compounds that both have insecticidal and nematocidal activity.1,2 Milbemycin A4 oxime (0.05 mg/kg) reduces the number of microfilariae of the heartworm D. immitis in naturally infested dogs.3 It inhibits the growth of clinical isolates of C. glabrata with MIC80 values ranging from 16 to greater than 32 μg/ml.1 Milbemycin A4 oxime (2.5 μg/ml) blocks efflux of fluconazole (Item No. 11594) from a clinical isolate of C. glabrata, but not from a strain lacking the efflux pumps CgCDR1 and PDH1, and reduces the MICs of fluconazole and 4-nitroquinoline 1-oxide in wild-type C. glabrata. It enhances adriamycin-induced inhibition of cell growth, as well as increases the intracellular accumulation of adriamycin and the P-glycoprotein substrate rhodamine 123 (Item No. 16672), in adriamycin-resistant, but not -sensitive, MCF-7 breast cancer cells in a concentration-dependent manner.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Walker, B., Izumikawa, K., Tsai, H.F., et al. Milbemycin A4 oxime as a probe of azole transport in Candida glabrata. FEMS Yeast Res. 14(5), 755-761 (2014).

    2. Xu, Q., Li, J., Shen, Z., et al. An LC-MS method for determination of milbemycin oxime in dog plasma. J. Chromatogr. Sci. 52(9), 999-1004 (2014).

    3. Tsukamoto, Y., Sato, K., Mio, S., et al. Synthesis of 5-keto-5-oxime derivatives of milbemycins and their activities against microfilariae. Agric. Biol. Chem. 55(10), 2615-2621 (1991).

    4. Xiang, W., Gao, A.H., Liang, H., et al. Reversal of P-glycoprotein-mediated multidrug resistance in vitro by milbemycin compounds in adriamycin-resistant human breast carcinoma (MCF-7/adr) cells. Toxicol. In Vitro 24(6), 1474-1481 (2010).