Caracemide

Modify Date: 2024-01-02 22:24:06

Caracemide Structure
Caracemide structure
Common Name Caracemide
CAS Number 81424-67-1 Molecular Weight 189.16900
Density 1.259g/cm3 Boiling Point N/A
Molecular Formula C6H11N3O4 Melting Point N/A
MSDS N/A Flash Point N/A

 Use of Caracemide


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].

 Names

Name Caracemide
Synonym More Synonyms

 Caracemide 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
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

~%

Caracemide Structure

Caracemide

CAS#:81424-67-1

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

 Precursor & DownStream

Precursor  2

DownStream  0

 Synonyms

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