Elomotecan

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

MedKoo CAT#: 205828

CAS#: 220997-99-9 (Elomotecan HCl salt), 220998-10-7 (Elomotecan free base).

Description: Elomotecan (BN-80927) belongs to a novel family of camptothecin analogs, the homocamptothecins, developed on the concept of topoisomerase I (Topo I) inhibition and characterized by a stable seven-membered beta-hydroxylactone ring. Preclinical data reported here show that BN80927 retains Topo I poisoning activity in cell-free assay (DNA relaxation) as well as in living cells, in which in vivo complexes of topoisomerase experiments and quantification of DNA-protein-complexes stabilization, have confirmed the higher potency of BN80927 as compared with the Topo I inhibitor SN38. In addition, BN80927 inhibits Topo II-mediated DNA relaxation in vitro but without cleavable-complex stabilization, thus indicating catalytic inhibition. Moreover, a Topo I-altered cell line (KBSTP2), resistant to SN38, remains sensitive to BN80927, suggesting that a part of the antiproliferative effects of BN80927 are mediated by a Topo I-independent pathway. This hypothesis is also supported by in vitro data showing an antiproliferative activity of BN80927 on a model of resistance related to the noncycling state of cells (G(0)-G(1) synchronized). In cell growth assays, BN80927 is a very potent antiproliferative agent as shown by IC(50) values consistently lower than those of SN38 in tumor cell lines as well as in their related drug-resistant lines. BN80927 shows high efficiency in vivo in tumor xenograft studies using human androgen-independent prostate tumors PC3 and DU145. Altogether, these data strongly support the clinical development of BN80927. (Source: Cancer Res. 2004 Jul 15;64(14):4942-9).


Price and Availability

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Elomotecan 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#: 205828
Name: Elomotecan
CAS#: 220997-99-9 (Elomotecan HCl salt), 220998-10-7 (Elomotecan free base).
Chemical Formula: C29H32ClN3O4
Exact Mass: 521.20813
Molecular Weight: 522.03508
Elemental Analysis: C, 66.72; H, 6.18; Cl, 6.79; N, 8.05; O, 12.26


Synonym: Elomotecan; BN80927. R1559

IUPAC/Chemical Name: (R)-9-chloro-5-ethyl-5-hydroxy-10-methyl-12-((4-methylpiperidin-1-yl)methyl)-4,5-dihydrooxepino[3',4':6,7]indolizino[1,2-b]quinoline-3,15(1H,13H)-dione

InChi Key: KAQREZSTQZWNAG-GDLZYMKVSA-N

InChi Code: InChI=1S/C29H32ClN3O4/c1-4-29(36)12-26(34)37-15-21-22(29)10-25-27-20(14-33(25)28(21)35)19(13-32-7-5-16(2)6-8-32)18-9-17(3)23(30)11-24(18)31-27/h9-11,16,36H,4-8,12-15H2,1-3H3/t29-/m1/s1

SMILES Code: O=C(OC1)C[C@](O)(CC)C2=C1C(N3CC4=C(CN5CCC(C)CC5)C6=CC(C)=C(Cl)C=C6N=C4C3=C2)=O


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

  
 
 
 


References

1: Yang S, Zhang WN. [Homocamptothecins--novel promising anticancer drugs as inhibitors of topoisomerase I]. Yao Xue Xue Bao. 2004 May;39(5):396-400. Review. Chinese. PubMed PMID: 15338888.

2: Demarquay D, Huchet M, Coulomb H, Lesueur-Ginot L, Lavergne O, Camara J, Kasprzyk PG, Prévost G, Bigg DC. BN80927: a novel homocamptothecin that inhibits proliferation of human tumor cells in vitro and in vivo. Cancer Res. 2004 Jul 15;64(14):4942-9. PubMed PMID: 15256467.

3: Denny WA, Baguley BC. Dual topoisomerase I/II inhibitors in cancer therapy. Curr Top Med Chem. 2003;3(3):339-53. Review. PubMed PMID: 12570767.

4: Ulukan H, Swaan PW. Camptothecins: a review of their chemotherapeutic potential. Drugs. 2002;62(14):2039-57. Review. PubMed PMID: 12269849.

5: Huchet M, Demarquay D, Coulomb H, Kasprzyk P, Carlson M, Lauer J, Lavergne O, Bigg D. The dual topoisomerase inhibitor, BN 80927, is highly potent against cell proliferation and tumor growth. Ann N Y Acad Sci. 2000;922:303-5. PubMed PMID: 11193907.

6: Demarquay D, Coulomb H, Huchet M, Lesueur-Ginot L, Camara J, Lavergne O, Bigg D. The homocamptothecin, BN 80927, is a potent topoisomerase I poison and topoisomerase II catalytic inhibitor. Ann N Y Acad Sci. 2000;922:301-2. PubMed PMID: 11193906.

7: Lavergne O, Harnett J, Rolland A, Lanco C, Lesueur-Ginot L, Demarquay D, Huchet M, Coulomb H, Bigg DC. BN 80927: a novel homocamptothecin with inhibitory activities on both topoisomerase I and topoisomerase II. Bioorg Med Chem Lett. 1999 Sep 6;9(17):2599-602. PubMed PMID: 10498216.