Elsamitrucin

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

MedKoo CAT#: 201230

CAS#: 97068-30-9

Description: Elsamitrucin is a heterocyclic antineoplastic antibiotic isolated from the bacterium Actinomycete strain J907-21. Elsamitrucin intercalates into DNA at guanine-cytosine (G-C)-rich sequences and inhibits topoisomerase I and II, resulting in single-strand breaks and inhibition of DNA replication. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).


Price and Availability

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Elsamitrucin is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 201230
Name: Elsamitrucin
CAS#: 97068-30-9
Chemical Formula: C33H35NO13
Exact Mass: 653.21084
Molecular Weight: 653.63
Elemental Analysis: C, 60.64; H, 5.40; N, 2.14; O, 31.82


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


Technical Data

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, 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).

Harmonized System Code:
293490


Additional Information

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.
 
 


References

 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: Rodríguez-Campos A, Azorín 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.