An internal standard for the quantification of ornidazole
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Unlabeled Version(s)
26818Ornidazole
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Ornidazole-d5

Item No. 33810

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
α-(chloro(methyl-d2))-2-methyl-5-nitro-1H-imidazole-1-ethan-α,β,β-d3-ol
CAS Number
2747915-64-4
Synonyms
  • (±)-Ornidazole-d5
Molecular Formula
C7H5D5ClN3O3
Formula Weight
224.7
Purity
≥99% deuterated forms (d1-d5)
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: solubleMethanol: soluble
SMILES
OC(C([2H])([2H])Cl)([2H])C([2H])([2H])N1C(C)=NC=C1[N+]([O-])=O
InChi Code
InChI=1S/C7H10ClN3O3/c1-5-9-3-7(11(13)14)10(5)4-6(12)2-8/h3,6,12H,2,4H2,1H3/i2D2,4D2,6D
InChi Key
IPWKIXLWTCNBKN-VLZDWVQFSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Ornidazole-d5 is intended for use as an internal standard for the quantification of ornidazole (Item No. 26818) by GC- or LC-MS. Ornidazole is an orally bioavailable 5-nitroimidazole derivative with antibacterial and antiprotozoal activities.1,2 Ornidazole inhibits the growth of clinical isolates of B. fragilis (MICs = 0.5-5 μM) and various anaerobic bacteria when used at concentrations ranging from less than 0.1 to 3.2 μg/ml.2,3 It also inhibits the growth of Giardia isolates (IC50s = 0.01-0.47 μg/ml).4 Oral administration of ornidazole reduces T. vaginalis and T. foetus infection in mice and E. histolytica infection in rats with curative dose (CD50) values of 37, 3, and 10 mg/kg, respectively.1 Ornidazole (400 mg/kg per day) induces infertility in male rats within 7 days and inhibits spermatozoa binding to rat oocyte zona pellucida.5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hoffer, M., and Grunberg, E. Synthesis and antiprotozoal activity of 1-(3-chloro-2-hydroxypropyl)-substituted nitroimidazoles. J. Med. Chem. 17(9), 1019-1020 (1974).

    2. Jokipii, L., and Jokipii, A.M. Comparative evaluation of the 2-methyl-5-nitroimidazole compounds dimetridazole, metronidazole, secnidazole, ornidazole, tinidazole, carnidazole, and panidazole against Bacteroides fragilis and other bacteria of the Bacteroides fragilis group. Antimicrob. Agents Chemother. 28(4), 561-564 (1985).

    3. Wüst, J. Susceptibility of anaerobic bacteria to metronidazole, ornidazole, and tinidazole and routine susceptibility testing by standardized methods. Antimicrob. Agents Chemother. 11(4), 631-637 (1977).

    4. Majewska, A.C., Kasprzak, W., De Jonckheere, J.F., et al. Heterogeneity in the sensitivity of stocks and clones of Giardia to metronidazole and ornidazole. Trans. R. Soc. Trop. Med. Hyg. 85(1), 67-69 (1991).

    5. Oberländer, G., Yeung, C.H., and Cooper, T.G. Induction of reversible infertility in male rats by oral ornidazole and its effects on sperm motility and epididymal secretions. J. Reprod. Fertil. 100(2), 551-559 (1994).

    6. Bone, W., Jones, N.G., Kamp, G., et al. Effect of ornidazole on fertility of male rats: Inhibition of a glycolysis-related motility pattern and zona binding required for fertilization in vitro. J. Reprod. Fertil. 118(1), 127-135 (2000).