Caracemide
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Caracemide
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CAS No:
81424-67-1
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Formula:
C6H11N3O4
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Chemical Name:
Caracemide
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Synonyms:
Acetamide,N-[(methylamino)carbonyl]-N-[[(methylamino)carbonyl]oxy]-;N-[(Methylamino)carbonyl]-N-[[(methylamino)carbonyl]oxy]acetamide;Caracemide;NSC 253272;N-Acetyl-N,O-di(methylcarbamoyl)hydroxylamine;(Acetyl-(methylcarbamoyl)amino) N-methylcarbamate;93051-18-4
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CAS No:
Description
Caracemide (NSC-253272) is a novel anticancer agent derived from a hydroxamic acid. Caracemide inactivates R1 by covalent modification at the substrate-binding site and inhibits the enzyme ribonucleotide reductase of Escherichia coli. Caracemide has demonstrated to produce severe central nervous system (CNS) toxicity. Caracemide has a toxic metabolite, methylisocyanate (MIC), in vivo[1][2].
Caracemide is an agent derived from acetohydroxamic acid with potential antineoplastic activity. Caracemide inhibits ribonuclease reductase, resulting in decreased DNA synthesis and tumor growth; it also inhibits acetylcholinesterase. In vivo, caracemide contributes to the formation of the neurotoxin methyl isocyanate; this effect, along with the agent's acetylcholinesterase activity, may be responsible for the severe central nervous system toxicity observed in clinical trials. (NCI04)
Safety Information
Bulk: The half life at 45 °C is estimated at 8 weeks and the time for 10% decomposition is 2 weeks. The compound is stable at room temperature for 4 weeks (HPLC). Solution: A 50 mg/mL solution in water at room temperature showed 5% decomposition after 4 hours and 17% decomposition after 24 hours (HPLC).
Computed Properties
Molecular Weight:189.17
XLogP3:-0.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:189.07495584
Monoisotopic Mass:189.07495584
Topological Polar Surface Area:87.7
Heavy Atom Count:13
Complexity:228
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes