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).

Chemical Structure

img
Elsamitrucin
CAS# 97068-30-9
Instruction

Theoretical Analysis

MedKoo Cat#: 201230
Name: Elsamitrucin
CAS#: 97068-30-9
Chemical Formula: C33H35NO13
Exact Mass: 653.21
Molecular Weight: 653.630
Elemental Analysis: C, 60.64; H, 5.40; N, 2.14; O, 31.82

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

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

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).

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.    

Biological target:
In vitro activity:
In vivo activity:

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.

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
Formulation protocol:
In vitro protocol:
In vivo protocol:

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

 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.