Caracemide - CAS 81424-67-1
Catalog number: 81424-67-1
Category: Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C6H11N3O4
Molecular Weight:
189.17
COA:
Inquire
Targets:
DNA/RNA Synthesis
Description:
Caracemide is an agent derived from acetohydroxamic acid. It has potential antineoplastic activity. Caracemide can inhibit ribonuclease reductase, resulting in decreased DNA synthesis and tumor growth. But in Feb 1995, Phase II for Cancer in USA was discontinued.
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Purity:
98%
Appearance:
Powder
Synonyms:
NSC 253272;N-(methylcarbamoyl)-N-((methylcarbamoyl)oxy)acetamide
Solubility:
Soluble in DMSO
Storage:
-20℃ Freezer
MSDS:
Inquire
Application:
Cancer
Quality Standard:
In-house standard
Shelf Life:
2 month in rt, long time
Quantity:
Milligrams-Grams
InChIKey:
JURAJLFHWXNPHG-UHFFFAOYSA-N
InChI:
1S/C6H11N3O4/c1-4(10)9(5(11)7-2)13-6(12)8-3/h1-3H3,(H,7,11)(H,8,12)
Canonical SMILES:
N(OC(NC)=O)(C(NC)=O)C(C)=O
Current Developer:
Originator Aventis
1.Caracemide, a site-specific irreversible inhibitor of protein R1 of Escherichia coli ribonucleotide reductase.
Larsen IK1, Cornett C, Karlsson M, Sahlin M, Sjöberg BM. J Biol Chem. 1992 Jun 25;267(18):12627-31.
The anticancer drug caracemide, N-acetyl-N,O- di(methylcarbamoyl)hydroxylamine, and one of its degradation products, N-acetyl-O-methylcarbamoyl-hydroxylamine, were found to inhibit the enzyme ribonucleotide reductase of Escherichia coli by specific interaction with its larger component protein R1. No effect on the smaller protein R2 was observed. The effect of the degradation product was about 30 times lower than that of caracemide itself. The caracemide inactivation of R1 is irreversible, with an apparent second-order rate constant of 150 M-1 s-1. The R1R2 holoenzyme was approximately 30 times more sensitive to caracemide inactivation than the isolated R1 protein. The ribonucleotide reductase substrates were potent competitors of the caracemide inhibition, with a Kdiss for GDP binding to R1 of 80 microM. The reducing agent dithiothreitol was also found to be a potent competitor of caracemide inactivation. These results indicate that caracemide inactivates R1 by covalent modification at the substrate-binding site.
2.Differential effect of collaterally sensitive antimetabolites on P388 murine leukemia sensitive and resistant to adriamycin in vitro.
Satyamoorthy K1, Deshpande SS, Chitnis MP. Neoplasma. 1989;36(6):673-83.
Experiments were carried out in vitro using DNA polymerase and ribonucleotide reductase inhibitors to investigate their cytotoxicity to P388 murine leukemia sensitive (P388/S) and resistant (P388/R) to adriamycin (ADR). DNA polymerase inhibitors such as cytosine arabinoside (ara-C) and aphidicolin elicited comparative inhibition of DNA biosynthesis in both parental and ADR-resistant tumor cells. However, ribonucleotide reductase inhibitors such as hydroxyurea (HU) and caracemide were collaterally more sensitive to P388/R cells. Inosine diglycolaldehyde (Inox) was ineffective in showing such a response. Pretreatment with HU significantly increased intracellular ADR levels and inhibition of RNA biosynthesis by ADR in P388/R cells while, in P388/S cells, sequential or concurrent treatment with HU did not enhance intracellular ADR levels. Mechanisms underlying such an effect, implications due to reduced intracellular ATP levels in drug-resistant cells, and the possible utility of using ribonucleotide reductase as a target in drug-resistant tumors for the therapeutic benefit are discussed.
3.Studies on the metabolic fate of caracemide, an experimental antitumor agent, in the rat. Evidence for the release of methyl isocyanate in vivo.
Slatter JG1, Davis MR, Han DH, Pearson PG, Baillie TA. Chem Res Toxicol. 1993 May-Jun;6(3):335-40.
Following administration to rats of a single ip dose (6.6 mg kg-1) of the investigational antitumor agent caracemide (N-acetyl-N,O-bis[methylcarbamoyl]hydroxylamine), the mercapturic acid derivative N-acetyl-S-(N-methylcarbamoyl)cysteine (AMCC) was identified in urine by thermospray LC-MS. Quantification of this conjugate was carried out by stable isotope dilution thermospray LC-MS, which indicated that the fraction of the caracemide dose recovered as AMCC in 24-h urine collections was 54.0 +/- 5.5% (n = 4). Since AMCC is known to represent a major urinary metabolite of methyl isocyanate (MIC) in the rat, the results of this study support the contention that caracemide yields MIC as a toxic intermediate in vivo. Furthermore, with the aid of a specifically deuterium-labeled analog of caracemide ([carbamoyloxy-C2H3]caracemide), it was shown that the methylcarbamoyl group of AMCC derived from both the O-methylcarbamoyl (72%) and N-methylcarbamoyl (28%) side chains of the drug.
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CAS 81424-67-1 Caracemide

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