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MedKoo Cat#: 206756 | Name: Merbarone

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Merbarone, also known as NSC-336628; RLBN-1001, is a Type II DNA topoisomerase inhibitor potentially for the treatment of solid tumors. Merbarone induces activation of caspase-activated DNase and excision of chromosomal DNA loops from the nuclear matrix. Merbarone induces apoptosis in CEM cells through activation of ICE/CED-3-like protease. Merbarone inhibits the catalytic activity of human topoisomerase IIalpha by blocking DNA cleavage.

Chemical Structure

Merbarone
Merbarone
CAS#97534-21-9

Theoretical Analysis

MedKoo Cat#: 206756

Name: Merbarone

CAS#: 97534-21-9

Chemical Formula: C11H9N3O3S

Exact Mass: 263.0365

Molecular Weight: 263.27

Elemental Analysis: C, 50.18; H, 3.45; N, 15.96; O, 18.23; S, 12.18

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Merbarone; NSC-336628; RLBN-1001; NSC336628; RLBN1001.
IUPAC/Chemical Name
5-(N-Phenylcarboxamido)-2-thiobarbituric acid
InChi Key
KIHGHKYNPNVMLM-UHFFFAOYSA-N
InChi Code
InChI=1S/C11H9N3O3S/c15-6-14(7-4-2-1-3-5-7)8-9(16)12-11(18)13-10(8)17/h1-6,8H,(H2,12,13,16,17,18)
SMILES Code
S=C(NC(C1N(C2=CC=CC=C2)C=O)=O)NC1=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 263.27 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Spallarossa A, Rotolo C, Sissi C, Marson G, Greco ML, Ranise A, La Colla P, Busonera B, Loddo R. Further SAR studies on bicyclic basic merbarone analogues as potent antiproliferative agents. Bioorg Med Chem. 2013 Nov 1;21(21):6328-36. doi: 10.1016/j.bmc.2013.08.056. PubMed PMID: 24063907. 2: Pastor N, Domínguez I, Orta ML, Campanella C, Mateos S, Cortés F. The DNA topoisomerase II catalytic inhibitor merbarone is genotoxic and induces endoreduplication. Mutat Res. 2012 Oct-Nov;738-739:45-51. doi: 10.1016/j.mrfmmm.2012.07.005. PubMed PMID: 22921906. 3: Attia SM. Dominant lethal mutations of topoisomerase II inhibitors etoposide and merbarone in male mice: a mechanistic study. Arch Toxicol. 2012 May;86(5):725-31. doi: 10.1007/s00204-011-0799-6. PubMed PMID: 22207148. 4: Wang L, Roy SK, Eastmond DA. Differential cell cycle-specificity for chromosomal damage induced by merbarone and etoposide in V79 cells. Mutat Res. 2007 Mar 1;616(1-2):70-82. PubMed PMID: 17174356. 5: Otake Y, Mims A, Fernandes DJ. Merbarone induces activation of caspase-activated DNase and excision of chromosomal DNA loops from the nuclear matrix. Mol Pharmacol. 2006 Apr;69(4):1477-85. PubMed PMID: 16434617. 6: Ranise A, Spallarossa A, Schenone S, Bruno O, Bondavalli F, Pani A, Marongiu ME, Mascia V, La Colla P, Loddo R. Synthesis and antiproliferative activity of basic thioanalogues of merbarone. Bioorg Med Chem. 2003 Jun 12;11(12):2575-89. PubMed PMID: 12757725. 7: Snyder RD. Evidence from studies with intact mammalian cells that merbarone and bis(dioxopiperazine)s are topoisomerase II poisons. Drug Chem Toxicol. 2003 Feb;26(1):15-22. PubMed PMID: 12643037. 8: Attia SM, Kliesch U, Schriever-Schwemmer G, Badary OA, Hamada FM, Adler ID. Etoposide and merbarone are clastogenic and aneugenic in the mouse bone marrow micronucleus test complemented by fluorescence in situ hybridization with the mouse minor satellite DNA probe. Environ Mol Mutagen. 2003;41(2):99-103. PubMed PMID: 12605378. 9: Wang L, Eastmond DA. Catalytic inhibitors of topoisomerase II are DNA-damaging agents: induction of chromosomal damage by merbarone and ICRF-187. Environ Mol Mutagen. 2002;39(4):348-56. PubMed PMID: 12112387. 10: Khélifa T, Beck WT. Merbarone, a catalytic inhibitor of DNA topoisomerase II, induces apoptosis in CEM cells through activation of ICE/CED-3-like protease. Mol Pharmacol. 1999 Mar;55(3):548-56. PubMed PMID: 10051540. 11: Fortune JM, Osheroff N. Merbarone inhibits the catalytic activity of human topoisomerase IIalpha by blocking DNA cleavage. J Biol Chem. 1998 Jul 10;273(28):17643-50. PubMed PMID: 9651360. 12: Malik UR, Dutcher JP, Caliendo G, Lasala P, Mitnick R, Wiernik PH. Phase II trial of merbarone in patients with malignant brain tumors. Med Oncol. 1997 Sep-Dec;14(3-4):159-62. PubMed PMID: 9468039. 13: Mo YY, Wang Q, Beck WT. Down-regulation of topoisomerase IIalpha in CEM cells selected for merbarone resistance is associated with reduced expression of Sp3. Cancer Res. 1997 Nov 15;57(22):5004-8. PubMed PMID: 9371492. 14: Kallio M, Lähdetie J. Effects of the DNA topoisomerase II inhibitor merbarone in male mouse meiotic divisions in vivo: cell cycle arrest and induction of aneuploidy. Environ Mol Mutagen. 1997;29(1):16-27. PubMed PMID: 9020303. 15: Kusumoto H, Rodgers QE, Boege F, Raimondi SC, Beck WT. Characterization of novel human leukemic cell lines selected for resistance to merbarone, a catalytic inhibitor of DNA topoisomerase II. Cancer Res. 1996 Jun 1;56(11):2573-83. PubMed PMID: 8653700. 16: Look KY, Blessing JA, Adelson MD, Morris M, Bookman MA. A phase II trial of merbarone (NSC 336628) in the treatment of recurrent epithelial ovarian carcinoma. A Gynecologic Oncology Group Study. Am J Clin Oncol. 1996 Feb;19(1):7-9. PubMed PMID: 8554040. 17: Look KY, Blessing JA, Williams L, Morris M. A phase II trial of merbarone (NSC 336628) as salvage therapy for squamous cell carcinoma of the cervix. A Gynecologic Oncology Group Study. Am J Clin Oncol. 1995 Oct;18(5):441-3. PubMed PMID: 7572765. 18: Chen M, Beck WT. Differences in inhibition of chromosome separation and G2 arrest by DNA topoisomerase II inhibitors merbarone and VM-26. Cancer Res. 1995 Apr 1;55(7):1509-16. PubMed PMID: 7882360. 19: Slavik M, Liu PY, Kraut EH, Natale RB, Flaherty LE, Sondak VK. Evaluation of merbarone (NSC 336628) in disseminated malignant melanoma. A Southwest Oncology Group study. Invest New Drugs. 1995;13(2):143-7. PubMed PMID: 8617577. 20: Ajani JA, Winn R, Baez L, Pollock T, Maher T, Hallinan-Fueger B, Newman J. Phase II study of merbarone (NSC 336628) in patients with advanced gastric carcinoma. Cancer Invest. 1994;12(5):488-90. PubMed PMID: 7922705.