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Merck
CN

M2070

Merbarone

≥98% (HPLC), solid

Synonym(s):

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

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About This Item

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

Key Documents

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Product Name

Merbarone, ≥98% (HPLC), solid

InChI key

JARCFMKMOFFIGZ-UHFFFAOYSA-N

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)

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

Quality Level

200

Related Categories

Application

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

Biochem/physiol Actions

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.
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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000444198
0000444198
0000412102
0000412102
0000135487

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Y Y Mo et al.
Molecular pharmacology, 55(2), 216-222 (1999-02-03)
Many anticancer agents exert their cytotoxicity through DNA damage and induction of apoptosis. Fas ligand (FasL), a key component of T lymphocytes, has been shown to be induced by some of those agents. To address what is an early signal
B B Hasinoff et al.
Biochemical pharmacology, 53(12), 1843-1853 (1997-06-15)
A Chinese hamster ovary (CHO) cell line highly resistant to the non-cleavable complex-forming topoisomerase II inhibitor dexrazoxane (ICRF-187, Zinecard) was selected. The resistant cell line (DZR) was 1500-fold resistant (IC50 = 2800 vs 1.8 microM) to continuous dexrazoxane exposure. DZR
Novel mechanisms of resistance to inhibitors of DNA topoisomerases.
W T Beck et al.
Advances in enzyme regulation, 37, 17-26 (1997-01-01)
DNA breaks and chromatin structural changes enhance the transcription of Autoimmune Regulator target genes
Guha M, et al.
The Journal of Biological Chemistry, 292(16), 6542-6554 (2017)
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
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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.

半胱天冬酶抑制剂和活化剂

据报道可激活细胞半胱天冬酶的试剂包括化疗药物、TNF 受体激动剂和其他酶。细胞凋亡抑制剂是第一个确定的内源性半胱天冬酶抑制剂。

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