Edotecarin

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

MedKoo CAT#: 201160

CAS#: 174402-32-5

Description: Edotecarin is a synthetic indolocarbazole with antineoplastic activity. Edotecarin inhibits the enzyme topoisomerase I through stabilization of the DNA-enzyme complex and enhanced single-strand DNA cleavage, resulting in inhibition of DNA replication and decreased tumor cell proliferation. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).


Price and Availability

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Edotecarin 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#: 201160
Name: Edotecarin
CAS#: 174402-32-5
Chemical Formula: C29H28N4O11
Exact Mass: 608.17546
Molecular Weight: 608.55
Elemental Analysis: C, 57.24; H, 4.64; N, 9.21; O, 28.92


Synonym: PHA782615. Code name: J107088; ED749.

IUPAC/Chemical Name: 6-((1,3-dihydroxypropan-2-yl)amino)-2,10-dihydroxy-12-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione

InChi Key: QMVPQBFHUJZJCS-NTKFZFFISA-N

InChi Code: InChI=1S/C29H28N4O11/c34-7-10(8-35)31-33-27(42)20-18-13-3-1-11(37)5-15(13)30-22(18)23-19(21(20)28(33)43)14-4-2-12(38)6-16(14)32(23)29-26(41)25(40)24(39)17(9-36)44-29/h1-6,10,17,24-26,29-31,34-41H,7-9H2/t17-,24-,25+,26-,29-/m1/s1

SMILES Code: O=C1N(NC(CO)CO)C(C2=C1C3=C(C4=C2C5=C(N4[C@H]6[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O6)C=C(O)C=C5)NC7=C3C=CC(O)=C7)=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: Saif MW, Sellers S, Diasio RB, Douillard JY. A phase I dose-escalation study of edotecarin (J-107088) combined with infusional 5-fluorouracil and leucovorin in patients with advanced/metastatic solid tumors. Anticancer Drugs. 2010 Aug;21(7):716-23. PubMed PMID: 20581657.

2: Sunami S, Nishimura T, Nishimura I, Ito S, Arakawa H, Ohkubo M. Synthesis and biological activities of topoisomerase I inhibitors, 6-arylmethylamino analogues of edotecarin. J Med Chem. 2009 May 28;52(10):3225-37. PubMed PMID: 19397324.

3: Norden AD, Drappatz J, Muzikansky A, David K, Gerard M, McNamara MB, Phan P, Ross A, Kesari S, Wen PY. An exploratory survival analysis of anti-angiogenic therapy for recurrent malignant glioma. J Neurooncol. 2009 Apr;92(2):149-55. Epub 2008 Nov 29. PubMed PMID: 19043778.

4: Animati F, Berettoni M, Bigioni M, Binaschi M, Felicetti P, Gontrani L, Incani O, Madami A, Monteagudo E, Olivieri L, Resta S, Rossi C, Cipollone A. Synthesis, biological evaluation, and molecular modeling studies of rebeccamycin analogues modified in the carbohydrate moiety. ChemMedChem. 2008 Feb;3(2):266-79. PubMed PMID: 18157856.

5: Teicher BA. Next generation topoisomerase I inhibitors: Rationale and biomarker strategies. Biochem Pharmacol. 2008 Mar 15;75(6):1262-71. Epub 2007 Oct 22. Review. PubMed PMID: 18061144.

6: Bayes M. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2007 Mar;29(2):153-73. PubMed PMID: 17440629.

7: Carvajal RD, Ilson DH, Noy A. Possible role of edotecarin, a novel topoisomerase I inhibitor, in therapy-related myelodysplastic syndrome. Leuk Lymphoma. 2007 Jan;48(1):192-4. PubMed PMID: 17325867.

8: Ciomei M, Croci V, Stellari F, Amboldi N, Giavarini R, Pesenti E. Antitumor activity of edotecarin in breast carcinoma models. Cancer Chemother Pharmacol. 2007 Jul;60(2):229-35. Epub 2006 Nov 7. PubMed PMID: 17089166.

9: Hurwitz HI, Cohen RB, McGovren JP, Hirawat S, Petros WP, Natsumeda Y, Yoshinari T. A phase I study of the safety and pharmacokinetics of edotecarin (J-107088), a novel topoisomerase I inhibitor, in patients with advanced solid tumors. Cancer Chemother Pharmacol. 2007 Jan;59(1):139-47. Epub 2006 Jul 4. PubMed PMID: 16819636.

10: Ciomei M, Croci V, Ciavolella A, Ballinari D, Pesenti E. Antitumor efficacy of edotecarin as a single agent and in combination with chemotherapy agents in a xenograft model. Clin Cancer Res. 2006 May 1;12(9):2856-61. PubMed PMID: 16675581.