Basic information
- CAS
97534-21-9- Standard SMILES
O=C(Nc1ccccc1)c1c(O)[nH]c(=S)[nH]c1=O- InChIKey
GFYRZTLCYQQVHZ-UHFFFAOYSA-N- Molecular formula
- C11H9N3O3S
- Average molar mass
- 263.27 g/mol
- Monoisotopic mass
- 263.03646233
Names & identifiers
- Preferred name
- 6-hydroxy-4-oxo-N-phenyl-2-sulfanylidene-1H-pyrimidine-5-carboxamide
- IUPAC
- 6-hydroxy-4-oxo-N-phenyl-2-sulfanylidene-1H-pyrimidine-5-carboxamide
- English name
- MERBARONE
- Molecular formula
- C11H9N3O3S
- Molecular weight
- 263.27
Names & synonyms
6-hydroxy-4-oxo-N-phenyl-2-sulfanylidene-1H-pyrimidine-5-carboxamideUPDDI-002948596-Hydroxy-4-oxo-N-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamideCC-PMLSC-PW-kmcmerbaroneNCIMech_000589MLS000541751SCHEMBL5953740CHEMBL1600807SCHEMBL19236433BDBM46106cid_3000671HMS2198P18
Show more names
RLBN1001RLBN-1001MERBARONENSC-336628Merbarone - CAS 97534-21-9 - Calbiochem5-(N-PHENYLCARBAMOYL)-2-THIOBARBITURIC ACID5-(N-PHENYLCARBOXAMIDO)-2-THIOBARBITURIC ACID5-(N-Phenylcarbamoyl)-2-thiobarbituric acid, NSC-336628hexahydro-4,6-dioxo-n-phenyl-2-thioxo-5-pyrimidinecarboxamid4,6-Dioxo-N-phenyl-2-thioxohexahydropyrimidine-5-carboxamide
CCG-35687CCG-36359SB60231NCGC00247369-01NCI60_002957SMR000472460NS001224415-Pyrimidinecarboxamide,6-dioxo-N-phenyl-2-thioxo-
Properties
Computed structural properties
- XLogP
- 1.1
- Topological polar surface area
- 123 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 427
Physicochemical properties
- Density
- 1.51 · 1.51±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- 5 mg/mL · DMSO: >5mg/mL
- form
- solid
- pka
- -2.16 · -2.16±0.20(Predicted)
- color
- Pink to purple
- InChI
- 1S/C11H9N3O3S/c15-8(12-6-4-2-1-3-5-6)7-9(16)13-11(18)14-10(7)17/h1-5H,(H,12,15)(H3,13,14,16,17,18)
- InChIKey
- GFYRZTLCYQQVHZ-UHFFFAOYSA-N
- SMILES
- Sc1nc(c(c(n1)O)C(=O)Nc2ccccc2)O
- FDA UNII
- 9 IF596V · YWB9IF596V
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
- WGK Germany
- 3 · 3
- RTECS
- 7714625 · UV7714625
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- rtecs
- UV7714625
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Applications
UsesMerbarone has been used to study its effect on the occurrence of DNA lesions.
General DescriptionA cell-permeable anticancer drug that inhibits the catalytic activity of topoisomerase II (topo II) without damaging DNA or stabilizing DNA-topo II cleavable complexes (IC50 = 20 μM for purified mammalian topo II versus IC50 = ~ 200 μM for topo I). Also induces apoptosis in human leukemic CEM cells through a caspase-3-like protease-dependent mechanism.
Suppliers17 total
上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
江苏艾康生物医药研发有限公司025-5885952 15955137747 · [email protected]
銳迪國際科技有限公司18024082417 · [email protected]
学研惠（武汉）科技有限公司15727060112 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
上海奈亦斯生物科技有限公司18321139117 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
Related reactions
1 records
Compound notes
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