A DNA alkylating agent
Related Products
Pro-drug Form(s)
14163Temozolomide
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MTIC

Item No. 18863

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-[2-(methylimino)hydrazinyl]-1H-imidazole-4-carboxamide
CAS Number
3413-72-7
Synonyms
  • NSC 407347
Molecular Formula
C5H8N6O
Formula Weight
168.2
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: slightlyMethanol: slightly (heated)
λmax
230, 315 nm
SMILES
NC(C1=C(/N=N/NC)NC=N1)=O
InChi Code
InChI=1S/C5H8N6O/c1-7-11-10-5-3(4(6)12)8-2-9-5/h2H,1H3,(H2,6,12)(H,7,10)(H,8,9)
InChi Key
MVBPAIHFZZKRGD-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 mg

    $94

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    5 mg

    $374

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    10 mg

    $702

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    25 mg

    $1,520

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    Cayman Chemical
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    Product Description

    MTIC is a DNA alkylating agent, an active metabolite of dacarbazine (DTIC; Item No. 21877), and an active degradation product of temozolomide (Item No. 14163).1,2,3 MTIC is cytotoxic to L-cells and decreases thymidine and uridine uptake by 55 and 65%, respectively, when used at a concentration of 1 mM.2 It is also cytotoxic to TLX5 murine lymphoma cells in a concentration-dependent manner.3 In vivo, MTIC induces formation of mammary adenofibromas in rats when administered at a cumulative dose of 890 mg per animal over 14 weeks.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Nagasawa, H.T., Shirota, F.N., and Mizuno, N.S. The mechanism of alkylation of DNA by 5-(3-methyl-1-triazeno)imidazole-4-carboxamide (MIC), a metabolite of DIC (NSC-45388). Non-involvement of diazomethane. Chem. Biol. Interact. 8(6), 403-413 (1974).

    2. Beal, D.D., Skibba, J.L., Whitnable, K.K., et al. Effects of 5-(3,3-dimethyl-1-triazeno)imidazole-4-carboxamide and its metabolites on Novikoff hepatoma cells. Cancer Res. 36(8), 2827-2831 (1976).

    3. Tsang, L.L.H., Quarterman, C.P., Gescher, A., et al. Comparison of the cytotoxicity in vitro of temozolomide and dacarbazine, prodrugs of 3-methyl-(triazen-1-yl)imidazole-4-carboxamide. Cancer Chemother. Pharmacol. 27(5), 342-346 (1991).

    4. Beal, D.D., Skibba, J.L., Croft, W.A., et al. Carcinogenicity of the antineoplastic agent, 5-(3,3-dimethyl-1-triazeno)-imidazole-4-carboxamide, and its metabolites in rats. J. Natl. Cancer Inst. 54(4), 951-957 (1975).