Synonym
10Oelsaminosylelsarosylchartarin; elsamicin A; BBM 2478A; BMY2800; BRN 5214813; BMY28090 D03977
IUPAC/Chemical Name
10-(((2S,3R,4S,5S,6R)-3-(((2R,3R,4R,5S,6R)-3-amino-5-hydroxy-4-methoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4,5-dihydroxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-6-hydroxy-1-methylbenzo[h]chromeno[5,4,3-cde]chromene-5,12-dione
InChi Key
MGQRRMONVLMKJL-KWJIQSIXSA-N
InChi Code
InChI=1S/C33H35NO13/c1-11-9-10-16-19-17(11)29(38)46-25-18-14(24(36)21(20(19)25)30(39)44-16)7-6-8-15(18)45-32-28(33(4,40)27(37)13(3)43-32)47-31-22(34)26(41-5)23(35)12(2)42-31/h6-10,12-13,22-23,26-28,31-32,35-37,40H,34H2,1-5H3/t12-,13-,22-,23+,26-,27+,28+,31-,32+,33+/m1/s1
SMILES Code
O=C1OC2=C(C3=C(O4)C5=C(O[C@H]6[C@H](O[C@@H]7[C@H](N)[C@@H](OC)[C@@H](O)[C@@H](C)O7)[C@@](C)(O)[C@@H](O)[C@@H](C)O6)C=CC=C5C(O)=C31)C(C4=O)=C(C)C=C2
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, not in water
Shelf Life
>5 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
In a phase II trial, : Elsamitrucin showed modest activity in patients with relapsed or refractory non-Hodgkin's lymphoma. Toxicity was relatively mild, consisted mainly of asthenia, nausea and vomiting and did not include myelosuppression. The activity of elsamitrucin in this group of patients and its lack of myelosuppression suggest utility in this disease especially when combined with other proven agents. see http://www.ncbi.nlm.nih.gov/pubmed/8913843.
In another phase II trial to test the antitumor activity of Elsamitrucin in metastatic cancer of the breast, colon and rectum, non-small cell lung and ovary. Patients with colorectal or non-small cell lung cancer could not have received prior chemotherapy. Treatment consisted of Elsamitrucin 25 mg/m2/week given as a 5-10 min infusion for at least 3-6 weekly doses. RESULTS: One hundred and five patients entered the studies, 97 were eligible, 94 are evaluable for toxicity and 75 for response. Toxicity mainly consisted of mild nausea/vomiting, and less frequently reversible hepatotoxicity and malaise. No objective responses were seen. CONCLUSION: Elsamitrucin at this dose and schedule is not an active drug in metastatic breast cancer, colorectal cancer, non-small cell lung cancer or ovarian cancer. see http://www.ncbi.nlm.nih.gov/pubmed/8075039.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
653.63
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.
| 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: Barceló F, Portugal J. Elsamicin A binding to DNA. A comparative thermodynamic characterization. FEBS Lett. 2004 Oct 8;576(1-2):68-72. PubMed PMID: 15474012.
2: Portugal J. Chartreusin, elsamicin A and related anti-cancer antibiotics. Curr Med Chem Anticancer Agents. 2003 Nov;3(6):411-20. Review. PubMed PMID: 14529449.
3: van Acker FA, van Acker SA, Haenen GR, Bast A, van der Vijgh WJ. In vitro screening of antitumour agents for cardiotoxicity by means of isolated mouse left atria. Anticancer Res. 2000 Nov-Dec;20(6B):4483-7. PubMed PMID: 11205292.
4: Shen LL. DNA-unwinding test using eukaryotic DNA topoisomerase I. Methods Mol Biol. 2001;95:149-60. PubMed PMID: 11089228.
5: Costanza ME, Weiss RB, Henderson IC, Norton L, Berry DA, Cirrincione C, Winer E, Wood WC, Frei E 3rd, McIntyre OR, Schilsky RL. Safety and efficacy of using a single agent or a phase II agent before instituting standard combination chemotherapy in previously untreated metastatic breast cancer patients: report of a randomized study--Cancer and Leukemia Group B 8642. J Clin Oncol. 1999 May;17(5):1397-406. PubMed PMID: 10334524.
6: Vaquero A, Portugal J. Modulation of DNA-protein interactions in the P1 and P2 c-myc promoters by two intercalating drugs. Eur J Biochem. 1998 Jan 15;251(1-2):435-42. PubMed PMID: 9492315.
7: RodrÃguez-Campos A, AzorÃn F, Portugal J. Influence of elsamicin A on the activity of mammalian topoisomerase I. Biochemistry. 1996 Aug 27;35(34):11177-82. PubMed PMID: 8780522.
8: Allen SL, Schacter LP, Lichtman SM, Bukowski R, Fusco D, Hensley M, O'Dwyer P, Mittelman A, Rosenbloom B, Huybensz S. Phase II study of elsamitrucin (BMY-28090) for the treatment of patients with refractory/relapsed non-Hodgkin's lymphoma. Invest New Drugs. 1996;14(2):213-7. PubMed PMID: 8913843.
9: Portugal J. Abortive transcription of the T7 promoter induced by elsamicin A. Anticancer Drug Des. 1995 Jul;10(5):427-38. PubMed PMID: 7639931.
10: Alhambra C, Luque FJ, Portugal J, Orozco M. Molecular dynamics study of the binding of elsamicin A to DNA. Eur J Biochem. 1995 Jun 1;230(2):555-66. PubMed PMID: 7607229.
