97534-21-9

97534-21-9 structure

Name: Merbarone
Chemical Name: 6-hydroxy-4-oxo-N-phenyl-2-sulfanylidene-1H-pyrimidine-5-carboxamide
CAS Number: 97534-21-9
Molecular Formula: C₁₁H₉N₃O₃S
Molecular Weight: 263.27200
Catalog: Signaling Pathways Cell Cycle/DNA Damage Topoisomerase
Create Date: 2016-11-03 16:20:21
Modify Date: 2025-08-26 19:57:20
Merbarone (NSC 336628) is an orally active inhibitor of topoisomerase II. Merbarone acts primarily by blocking topoisomerase II-mediated DNA cleavage. Merbarone is an anticancer agent[1][2].

Name	6-hydroxy-4-oxo-N-phenyl-2-sulfanylidene-1H-pyrimidine-5-carboxamide
Synonyms	CC-PMLSC-PW-kmcmerbarone HMS2198P18

Description	Merbarone (NSC 336628) is an orally active inhibitor of topoisomerase II. Merbarone acts primarily by blocking topoisomerase II-mediated DNA cleavage. Merbarone is an anticancer agent[1][2].
Related Catalog	Research Areas >> Cancer Signaling Pathways >> Cell Cycle/DNA Damage >> Topoisomerase
Target	topoisomerase II[1]
In Vitro	Merbarone (1-100 μM) inhibits L1210 cells proliferation in a concentration-dependent manner, with an IC50 of 10 μM[3]. Merbarone (10-200 μM; 10 min) inhibits DNA relaxation catalyzed by human topoisomerase IIα, with an IC50 of ∼40 μM[1]. Merbarone (25-200 μM; 6 min) blocks tyopoisomerase II-mediated DNA cleavage, with an IC50 of ∼50 μM[1]. Merbarone (100 μM; 6 min) inhibits topoisomerase II-mediated DNA cleavage in a global manner[1]. Merbarone (100 μM; 6 min) does not impair topoisomerase II•DNA binding[1]. Merbarone (200 μM; 4-16 min) does not inhibit topoisomerase II-catalyzed ATP hydrolysis[1].
In Vivo	Merbarone (50 mg/kg; daily i.p. for 5 d) achieves a maximum increased life span (ILS) of 101% in P388 murine leukemia[2]. Merbarone (124 mg/kg; daily p.o. for 9 d) has anti-tumor activity in mice[2].
References	[1]. Fortune JM, et, al. Merbarone inhibits the catalytic activity of human topoisomerase IIalpha by blocking DNA cleavage. J Biol Chem. 1998 Jul 10;273(28):17643-50. [2]. Brewer AD, et, al. 5-(N-phenylcarboxamido)-2-thiobarbituric acid (NSC 336628), a novel potential antitumor agent. Biochem Pharmacol. 1985 Jun 1;34(11):2047-50. [3]. Cooney DA, et, al. Initial mechanistic studies with merbarone (NSC 336628). Biochem Pharmacol. 1985 Sep 15;34(18):3395-8.

Density	1.51g/cm3
Molecular Formula	C₁₁H₉N₃O₃S
Molecular Weight	263.27200
Exact Mass	263.03600
PSA	119.39000
LogP	0.50280
Index of Refraction	1.688

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UV7714625

CHEMICAL NAME :: 5-Pyrimidinecarboxamide, hexahydro-4,6-dioxo-N-phenyl-2-thioxo-

CAS REGISTRY NUMBER :: 97534-21-9

LAST UPDATED :: 199206

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C11-H9-N3-O3-S

MOLECULAR WEIGHT :: 263.29

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human

DOSE/DURATION :: 135 mg/kg/5D-I

TOXIC EFFECTS :: Blood - agranulocytosis Blood - thrombocytopenia Blood - changes in bone marrow (not otherwise specified)

REFERENCE :: PAACA3 Proceedings of the American Association for Cancer Research. (Waverly Press, 428 E. Preston St., Baltimore, MD 21202) V.1- 1954- Volume(issue)/page/year: 29,189,1988

Personal Protective Equipment	Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
RIDADR	NONH for all modes of transport
RTECS	UV7714625

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