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Caracemide

Names

[ CAS No. ]:
81424-67-1

[ Name ]:
Caracemide

[Synonym ]:
N-Acetyl-N-(methylcarbamoyloxy)-N'-methylurea
N-((methylamino)carbonyl)-N-(((methylamino)carbonyl)oxy)acetamide

Biological Activity

[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 & Physical Properties

[ Density]:
1.259g/cm3

[ Molecular Formula ]:
C6H11N3O4

[ Molecular Weight ]:
189.16900

[ Exact Mass ]:
189.07500

[ PSA ]:
87.74000

[ LogP ]:
0.22710

[ Index of Refraction ]:
1.479

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
AC5961200
CHEMICAL NAME :
Acetamide, N-((methylamino)carbonyl)-N-(((methylamino)carbonyl)o xy)-
CAS REGISTRY NUMBER :
81424-67-1
LAST UPDATED :
199612
DATA ITEMS CITED :
7
MOLECULAR FORMULA :
C6-H11-N3-O4
MOLECULAR WEIGHT :
189.20

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
388 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
167 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
238 mg/kg
TOXIC EFFECTS :
Behavioral - tremor Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea

MUTATION DATA

TYPE OF TEST :
DNA inhibition
TEST SYSTEM :
Rodent - mouse Ascites tumor
DOSE/DURATION :
50 umol/L
REFERENCE :
NEOLA4 Neoplasma. (Karger-Libri, P.O. Box, CH-4009 Basel, Switzerland) V.4- 1957- Volume(issue)/page/year: 35,27,1988

Synthetic Route

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Precursor & DownStream

Precursor

DownStream