Caracemide - CAS 81424-67-1
Catalog number: 81424-67-1
Category: Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
Molecular Weight:
DNA/RNA Synthesis
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.
Publictions citing BOC Sciences Products
  • >> More
NSC 253272;N-(methylcarbamoyl)-N-((methylcarbamoyl)oxy)acetamide
Soluble in DMSO
-20℃ Freezer
Quality Standard:
In-house standard
Shelf Life:
2 month in rt, long time
Canonical SMILES:
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.
Molecular Weight Calculator Molarity Calculator Solution Dilution Calculator

Related DNA/RNA Synthesis Products

BAY 56-3722
(CAS: 215604-74-3)

BAY 56-3722, a water-soluble camptothecin derivative, is a DNA-Intercalating drug that stabilizes the topoisomerase I-DNA covalent complex and forms an enzyme-d...

(CAS: 1338225-97-0)

Doravirine is a non-nucleoside reverse transcriptase inhibitor under development of Merck & Co. IC 50 value is 12 nM against the wild type, 21nM against K103N, ...

CAS 129716-45-6 MS-073

(CAS: 129716-45-6)

MS-073 is a Type II DNA topoisomerase inhibitor under the development of Nihon Schering. MS-073 can overcome MDR in vitro and in vivo compare to verapamil. MS-0...

CP 115953
(CAS: 136440-70-5)

CP 115953 is a Type II DNA topoisomerase inhibitor originated by Pfizer. CP 115953 inhibits topoisomerase II activity via an interaction with the enzyme and not...

CAS 1609960-31-7 TH588

(CAS: 1609960-31-7)

TH588 selectively kill U2OS and other cancer cell lines with less toxic to several primary or immortalized cells.

CAS 896705-16-1 BMH-21

(CAS: 896705-16-1)

BMH-21 is a potent small molecule DNA intercalator. BMH-21 binds ribosomal DNA and inhibits RNA polymerase I (Pol I) transcription.

CAS 841301-32-4 Amenamevir

(CAS: 841301-32-4)

Amenamevir is a DNA helicase-primase inhibitors. It has anti-HSV activity against herpes simplex keratitis. In Mar 2016, Mahuro completed a phase III trial in H...

(CAS: 124265-89-0)

This active molecular is a DNA-directed DNA polymerase inhibitor potentially originated by Medivir AB. Omaciclovir can be selectively phosphorylated by viral th...

(CAS: 1562338-42-4)

LMI070, also called as NVS-SM1, is a selective, high plasma exposure and orally active modulator of SMN2 splicing which demonstrates robust activity across dise...

Tinostamustine Hydrochloride
(CAS: 1793059-58-1)

The hydrochloride salt form of Tinostamustine, a benzimidazol derivative, has been found to be a HDAC inhibitor and could probably be effective against sorts of...

(CAS: 329059-55-4)

BRD7116, a bis-aryl sufone with cell-non-autonomous anti-leukemia activity, competitively binds to bacterial DNA gyrase and is an inhibitor of leukemia stem cel...

CAS 81424-67-1 Caracemide

(CAS: 81424-67-1)

Caracemide is an agent derived from acetohydroxamic acid. It has potential antineoplastic activity. Caracemide can inhibit ribonuclease reductase, resulting in ...

CP-74667 mesylate
(CAS: 138808-71-6)

CP-74667 is a Type II DNA topoisomerase inhibitor originated by Pfizer. No development was reported for Bacterial infections in USA.

(CAS: 840506-29-8)

Acelarin is a DNA synthesis inhibitor with EC50 of 0.2 nM. Acelarin is a prodrug based on an aryloxy phosphoramidate derivative of gemcitabine. It is converted ...

CAS 14698-29-4 Oxolinic acid

Oxolinic acid
(CAS: 14698-29-4)

Oxolinic acid, a potent inhibitor of DNA gyrase and DNA synthesis, can examined Gyrase-chromosome interactions.

CAS 127759-89-1 Lobucavir

(CAS: 127759-89-1)

Lobucavir is a RNA-directed DNA polymerase inhibitor originated by Bristol-Myers Squibb as a nucleoside analog. Treatment for Cytomegalovirus infections, Hepati...

(CAS: 325970-71-6)

L67 is a DNA Ligase Inhibitor. L67 inhibited DNA ligases I and III. L67 is a simple competitive inhibitor with respect to nicked DNA. L67 inhibits DNA ligases I...

CAS 127-07-1 Hydroxyurea

(CAS: 127-07-1)

Hydroxyurea is an antineoplastic agent that inhibits DNA synthesis through the inhibition of ribonucleoside diphosphate reductase.

CAS 64232-83-3 L189

(CAS: 64232-83-3)

L189 is a DNA ligase I, III and IV inhibitor (IC50 values are 5, 9 and 5 μM respectively) that blocks DNA binding. L189 inhibits base excision repair (BER) and ...

TH588 hydrochloride
(CAS: 1640282-30-9)

TH588 hydrochloride, with potent anti-cancer property, is a novel inhibitor that highly selectively targets MTH1 protein (IC50= 5 nM) which is required for canc...

Chemical Structure

CAS 81424-67-1 Caracemide

Quick Inquiry

Verification code

Featured Items