Skip to Content
Merck
All Photos(1)

Documents

M2070

Sigma-Aldrich

Merbarone

≥98% (HPLC), solid

Synonym(s):

5-(N-Phenylcarbamoyl)-2-thiobarbituric acid, NSC-336628

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C11H9N3O3S
CAS Number:
97534-21-9
Molecular Weight:
263.27
MDL number:
MFCD00866337
UNSPSC Code:
12352200
PubChem Substance ID:
24724534
NACRES:
NA.77

Assay

≥98% (HPLC)

form

solid

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

solubility

DMSO: >5 mg/mL

storage temp.

2-8°C

SMILES string

O=C1NC(=S)NC(=O)C1C(=O)Nc2ccccc2

InChI

1S/C11H9N3O3S/c15-8(12-6-4-2-1-3-5-6)7-9(16)13-11(18)14-10(7)17/h1-5,7H,(H,12,15)(H2,13,14,16,17,18)

InChI key

JARCFMKMOFFIGZ-UHFFFAOYSA-N

Application

Merbarone has been used to study its effect on the occurrence of DNA lesions.

Biochem/physiol Actions

Thiobarbituric acid with aniline joined by an amide linkage forms merbarone. It is known to prolong cell cycle progression by inducing DNA double strand breaks, retarding S phase and arresting G2 phase. This delays cell entry into mitosis. Merbarone possesses cytotoxic and genotoxic action and promotes endoreduplication. Merbarone has mild antitumor action and is also found to nephrotoxic.
Selective topoisomerase II inhibitor. Blocks topo II-mediated DNA cleavage without stabilizing DNA-topo II-cleavable complexes. Induces apoptosis in CEM cells via caspase 3 dependent mechanism.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Ling Wang et al.
Mutation research, 616(1-2), 70-82 (2006-12-19)
Merbarone, a topoisomerase II (topo II) inhibitor which, in contrast to etoposide, does not stabilize topo II-DNA cleavable complexes, was previously shown to be a potent clastogen in vitro and in vivo. To investigate the possible mechanisms, we compared the
Nuria Pastor et al.
Mutation research, 738-739, 45-51 (2012-08-28)
In the last years a number of reports have shown that the so-called topoisomerase II (topo II) catalytic inhibitors are able to induce DNA and chromosome damage, an unexpected result taking into account that they do not stabilize topo II-DNA
U R Malik et al.
Medical oncology (Northwood, London, England), 14(3-4), 159-162 (1998-02-19)
The standard treatment for patients with primary malignant glioma includes surgical resection, radiotherapy, and nitrosourea. Despite this multimodality approach, adults with newly diagnosed glioblastoma multiforme (GBM) and high-grade astrocytoma have a median survival duration of 50 weeks and 150 weeks
Yoko Otake et al.
Molecular pharmacology, 69(4), 1477-1485 (2006-01-26)
Studies were carried out to address possible cellular mechanisms by which merbarone, a catalytic inhibitor of DNA topoisomerase II, can block tumor cell growth without inducing extensive DNA cleavage. Merbarone induced the release of high molecular weight DNA fragments from
Alexei Mikhailov et al.
The Journal of cell biology, 166(4), 517-526 (2004-08-11)
When early prophase PtK(1) or Indian muntjac cells are exposed to topoisomerase II (topo II) inhibitors that induce little if any DNA damage, they are delayed from entering mitosis. We show that this delay is overridden by inhibiting the p38
View All Related Papers

Articles

Caspases Inhibitors and Activators

Agents reported to activate cellular caspases include chemotherapeutic drugs, TNF receptor agonists, and other enzymes. Inhibitors of apoptosis were the first identified endogenous caspase inhibitors.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service