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MedKoo Cat#: 201150 | Name: Edatrexate

Description:

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

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).

Chemical Structure

Edatrexate
Edatrexate
CAS#80576-83-6 (free base)

Theoretical Analysis

MedKoo Cat#: 201150

Name: Edatrexate

CAS#: 80576-83-6 (free base)

Chemical Formula: C22H25N7O5

Exact Mass: 467.1917

Molecular Weight: 467.48

Elemental Analysis: C, 56.52; H, 5.39; N, 20.97; O, 17.11

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
Edatrexate monohydrate 80576-83-6 (free base)
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
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).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 467.48 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
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.