Edatrexate

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

MedKoo CAT#: 201150

CAS#: 80576-83-6

Description: Edatrexate is a polyglutamatable folate antagonist analogue of methotrexate with antineoplastic activity. Edatrexate inhibits dihydrofolate reductase, thereby increasing cellular levels of polyglutamates, inhibiting thymidylate synthase and glycinamide ribonucleotide formyl transferase, impairing synthesis of purine nucleotides and amino acids, and resulting in tumor cell death. Edatrexate may overcome tumor resistance to methotrexate, which loses its activity after it is polyglutamated. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).


Price and Availability

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Edatrexate 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#: 201150
Name: Edatrexate
CAS#: 80576-83-6
Chemical Formula: C22H25N7O5
Exact Mass: 467.19172
Molecular Weight: 467.4778
Elemental Analysis: C, 56.52; H, 5.39; N, 20.97; O, 17.11


Synonym: 10-ethyldeazaaminopterin; 10-EDAM; CGP30694; CGP 30694; Edatrexate.

IUPAC/Chemical Name: (2S)-2-[[4-[1-(2,4-diaminopteridin-6-yl)butan-2-yl]benzoyl]amino]pentanedioic acid

InChi Key: FSIRXIHZBIXHKT-MHTVFEQDSA-N

InChi Code: InChI=1S/C22H25N7O5/c1-2-11(9-14-10-25-19-17(26-14)18(23)28-22(24)29-19)12-3-5-13(6-4-12)20(32)27-15(21(33)34)7-8-16(30)31/h3-6,10-11,15H,2,7-9H2,1H3,(H,27,32)(H,30,31)(H,33,34)(H4,23,24,25,28,29)/t11?,15-/m0/s1

SMILES Code: O=C(O)[C@@H](NC(C1=CC=C(C(CC)CC2=NC3=C(N)N=C(N)N=C3N=C2)C=C1)=O)CCC(O)=O


Technical Data

Appearance:
white 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:
>2 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


References

1: Casper ES, Schwartz GM, Leung D, Sugarman A, Bertino JR. Evaluation of dose-intense Ifosfamide, with and without edatrexate, in adults with sarcoma. Sarcoma. 1999;3(2):121-7. PubMed PMID: 18521274; PubMed Central PMCID: PMC2395414.

2: Kuriakose P, Gandara DR, Perez EA. Phase I trial of edatrexate in advanced breast and other cancers. Cancer Invest. 2002;20(4):473-9. PubMed PMID: 12094542.

3: Colon-Otero G, Niedringhaus RD, Hillman SH, Geyer S, Sloan J, Krook JE, Windschitl HE, Marks RS, Wiesenfeld M, Tschetter LK, Jett JJ; North Central Cancer Treatment Group. A phase II trial of edatrexate, vinblastine, adriamycin, cisplastin, and filgrastim (EVAC/G-CSF) in patients with non-small-cell carcinoma of the lungs: a North Central Cancer Treatment Group Trial. Am J Clin Oncol. 2001 Dec;24(6):551-5. PubMed PMID: 11801752.

4: Laurie SA, Pfister DG, Kris MG, Tong WP, Chronowski G, Pisters KM, Heelan RT, Sirotnak FM. Phase I and pharmacological study of two schedules of the antifolate edatrexate in combination with cisplatin. Clin Cancer Res. 2001 Mar;7(3):501-9. PubMed PMID: 11297240.

5: Kindler HL, Belani CP, Herndon JE 2nd, Vogelzang NJ, Suzuki Y, Green MR. Edatrexate (10-ethyl-deaza-aminopterin) (NSC #626715) with or without leucovorin rescue for malignant mesothelioma. Sequential phase II trials by the cancer and leukemia group B. Cancer. 1999 Nov 15;86(10):1985-91. PubMed PMID: 10570422.

6: Meyers FJ, Lew D, Lara PN Jr, Williamson S, Marshall E, Balcerzak SP, Rivkin SE, Samlowski W, Crawford ED. Phase II trial of edatrexate in relapsed or refractory germ cell tumors: a Southwest Oncology Group study (SWOG 9124). Invest New Drugs. 1998-1999;16(4):347-51. PubMed PMID: 10426670.

7: Rigas JR, Kris MG, Miller VA, Pisters KM, Heelan RT, Grant SC, Fennelly DW, Chou TC, Sirotnak FM. Phase I study of the sequential administration of edatrexate and paclitaxel in patients with advanced solid tumors. Ann Oncol. 1999 May;10(5):601-3. PubMed PMID: 10416013.

8: D'Andrea G, Fennelly D, Norton L, Baselga J, Gilewski T, Hudis C, Moynahan ME, Raptis G, Sklarin N, Surbone A, Theodoulou M, Templeton MA, Yao TJ, Seidman AD. Phase I study of escalating doses of edatrexate in combination with paclitaxel in patients with metastatic breast cancer. Clin Cancer Res. 1999 Feb;5(2):275-9. PubMed PMID: 10037175.

9: Edelman MJ, Gandara DR, Perez EA, Lau D, Lauder I, Turrell C, Uhrich M, Meyers F. Phase I trial of edatrexate plus carboplatin in advanced solid tumors: amelioration of dose-limiting mucositis by ice chip cryotherapy. Invest New Drugs. 1998;16(1):69-75. PubMed PMID: 9740546.