81424-67-1

81424-67-1 structure

Name: Caracemide
Chemical Name: Caracemide
CAS Number: 81424-67-1
Molecular Formula: C₆H₁₁N₃O₄
Molecular Weight: 189.16900
Catalog: Signaling Pathways Anti-infection Bacterial
Create Date: 2018-09-13 21:37:27
Modify Date: 2024-01-02 22:24:06
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].

Name	Caracemide
Synonyms	N-Acetyl-N-(methylcarbamoyloxy)-N'-methylurea N-((methylamino)carbonyl)-N-(((methylamino)carbonyl)oxy)acetamide

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].
Related Catalog	Research Areas >> Cancer Research Areas >> Infection Signaling Pathways >> Cell Cycle/DNA Damage >> DNA/RNA Synthesis Signaling Pathways >> Anti-infection >> Bacterial
In Vivo	The mercapturic acid derivative AMCC was identified in urine rats following administration to rats of a single i.p. dose (6.6 mg/kg) of caracemide (NSC-253272)[1]. .
References	[1]. Slatter JG, et al. Studies on the metabolic fate of caracemide, an experimental antitumor agent, in the rat. Evidence for the release of methyl isocyanate in vivo. Chem Res Toxicol. 1993 May-Jun;6(3):335-40. [2]. Larsen IK, et al. Caracemide, a site-specific irreversible inhibitor of protein R1 of Escherichia coli ribonucleotide reductase. J Biol Chem. 1992 Jun 25;267(18):12627-31.

CHEMICAL NAME :: Acetamide, N-((methylamino)carbonyl)-N-(((methylamino)carbonyl)o xy)-

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TOXIC EFFECTS :: Behavioral - tremor Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: NEOLA4 Neoplasma. (Karger-Libri, P.O. Box, CH-4009 Basel, Switzerland) V.4- 1957- Volume(issue)/page/year: 35,27,1988

546-88-3

624-83-9

81424-67-1

Literature: The Dow Chemical Company Patent: US4413009 A1, 1983 ;

Precursor 2
546-88-3 624-83-9
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