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

MedKoo CAT#: 597216

CAS#: 52454-37-2

Description: 10-Deazaaminopterin is a poly-gamma-glutamyl metabolites of the experimental anticancer drug, an antineoplastic agent, folic acid antagonist, and enzyme inhibitor.

Chemical Structure

CAS# 52454-37-2

Theoretical Analysis

MedKoo Cat#: 597216
Name: 10-Deazaaminopterin
CAS#: 52454-37-2
Chemical Formula: C20H21N7O5
Exact Mass: 439.1604
Molecular Weight: 439.43
Elemental Analysis: C, 54.67; H, 4.82; N, 22.31; O, 18.20

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.

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Synonym: 10-Deazaaminopterin; 10-Deaza-aminopterin; NSC 311469; NSC-311469; NSC311469;

IUPAC/Chemical Name: (4-(2-(2,4-diaminopteridin-6-yl)ethyl)benzoyl)-L-glutamic acid


InChi Code: InChI=1S/C20H21N7O5/c21-16-15-17(27-20(22)26-16)23-9-12(24-15)6-3-10-1-4-11(5-2-10)18(30)25-13(19(31)32)7-8-14(28)29/h1-2,4-5,9,13H,3,6-8H2,(H,25,30)(H,28,29)(H,31,32)(H4,21,22,23,26,27)/t13-/m0/s1

SMILES Code: O=C(O)CC[C@@H](C(O)=O)NC(C1=CC=C(CCC2=NC3=C(N)N=C(N)N=C3N=C2)C=C1)=O

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

Shelf Life: >3 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: 2934.99.03.00

Preparing Stock Solutions

The following data is based on the product molecular weight 439.43 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

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1: Marchi E, O'Connor OA. Safety and efficacy of pralatrexate in the treatment of patients with relapsed or refractory peripheral T-cell lymphoma. Ther Adv Hematol. 2012 Aug;3(4):227-35. doi: 10.1177/2040620712445330. PubMed PMID: 23606933; PubMed Central PMCID: PMC3627334.

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6: Krug LM, Heelan RT, Kris MG, Venkatraman E, Sirotnak FM. Phase II trial of pralatrexate (10-propargyl-10-deazaaminopterin, PDX) in patients with unresectable malignant pleural mesothelioma. J Thorac Oncol. 2007 Apr;2(4):317-20. PubMed PMID: 17409804.

7: Fury MG, Krug LM, Azzoli CG, Sharma S, Kemeny N, Wu N, Kris MG, Rizvi NA. A phase I clinical pharmacologic study of pralatrexate in combination with probenecid in adults with advanced solid tumors. Cancer Chemother Pharmacol. 2006 May;57(5):671-7. Epub 2005 Aug 31. PubMed PMID: 16136310.

8: Johansen M, Zukowski T, Hoff PM, Newman RA, Ni D, Hutto T, Abbruzzeese J, Berghorn E, Hausheer F, Madden T. Final results of a phase I and pharmacokinetic study of gamma-methylene-10-deazaaminopterin (MDAM) administered intravenously daily for five consecutive days in patients with solid tumors. Cancer Chemother Pharmacol. 2004 May;53(5):370-6. Epub 2003 Dec 18. PubMed PMID: 15060739.

9: Wang ES, O'Connor O, She Y, Zelenetz AD, Sirotnak FM, Moore MA. Activity of a novel anti-folate (PDX, 10-propargyl 10-deazaaminopterin) against human lymphoma is superior to methotrexate and correlates with tumor RFC-1 gene expression. Leuk Lymphoma. 2003 Jun;44(6):1027-35. PubMed PMID: 12854905.

10: Krug LM, Azzoli CG, Kris MG, Miller VA, Khokhar NZ, Tong W, Ginsberg MS, Venkatraman E, Tyson L, Pizzo B, Baez V, Ng KK, Sirotnak FM. 10-propargyl-10-deazaaminopterin: an antifolate with activity in patients with previously treated non-small cell lung cancer. Clin Cancer Res. 2003 Jun;9(6):2072-8. PubMed PMID: 12796370.

11: Wright JE, Yurasek GK, Chen YN, Rosowsky A. Further studies on the interaction of nonpolyglutamatable aminopterin analogs with dihydrofolate reductase and the reduced folate carrier as determinants of in vitro antitumor activity. Biochem Pharmacol. 2003 May 1;65(9):1427-33. PubMed PMID: 12732354.

12: 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.

13: Whetstine JR, Gifford AJ, Witt T, Liu XY, Flatley RM, Norris M, Haber M, Taub JW, Ravindranath Y, Matherly LH. Single nucleotide polymorphisms in the human reduced folate carrier: characterization of a high-frequency G/A variant at position 80 and transport properties of the His(27) and Arg(27) carriers. Clin Cancer Res. 2001 Nov;7(11):3416-22. PubMed PMID: 11705857.

14: Khokhar NZ, She Y, Rusch VW, Sirotnak FM. Experimental therapeutics with a new 10-deazaaminopterin in human mesothelioma: further improving efficacy through structural design, pharmacologic modulation at the level of MRP ATPases, and combined therapy with platinums. Clin Cancer Res. 2001 Oct;7(10):3199-205. PubMed PMID: 11595715.

15: Sirotnak FM, Wendel HG, Bornmann WG, Tong WP, Miller VA, Scher HI, Kris MG. Co-administration of probenecid, an inhibitor of a cMOAT/MRP-like plasma membrane ATPase, greatly enhanced the efficacy of a new 10-deazaaminopterin against human solid tumors in vivo. Clin Cancer Res. 2000 Sep;6(9):3705-12. PubMed PMID: 10999764.

16: Krug LM, Ng KK, Kris MG, Miller VA, Tong W, Heelan RT, Leon L, Leung D, Kelly J, Grant SC, Sirotnak FM. Phase I and pharmacokinetic study of 10-propargyl-10-deazaaminopterin, a new antifolate. Clin Cancer Res. 2000 Sep;6(9):3493-8. Erratum in: Clin Cancer Res 2001 Apr;7(4):1102. PubMed PMID: 10999734.

17: Pitts C, Bowen D, Southerland WM. Interaction energy analyses of folate analog binding to human dihydrofolate reductase: contribution of the antifolate substructural regions to complex stability. Drug Metabol Drug Interact. 2000;16(2):99-121. PubMed PMID: 10962643.

18: Sirotnak FM, DeGraw JI, Colwell WT, Piper JR. A new analogue of 10-deazaaminopterin with markedly enhanced curative effects against human tumor xenografts in mice. Cancer Chemother Pharmacol. 1998;42(4):313-8. PubMed PMID: 9744777.

19: Roy K, Tolner B, Chiao JH, Sirotnak FM. A single amino acid difference within the folate transporter encoded by the murine RFC-1 gene selectively alters its interaction with folate analogues. Implications for intrinsic antifolate resistance and directional orientation of the transporter within the plasma membrane of tumor cells. J Biol Chem. 1998 Jan 30;273(5):2526-31. PubMed PMID: 9446553.

20: Su H, Chen TL, Hausheer FH, Rowinsky EK. Novel high-performance liquid chromatographic assay using fluorescence detection for the quantitation of plasma gamma-methylene-10-deazaaminopterin and its major metabolite, 7-hydroxy-gamma-methylene-10-deazaaminopterin, in patients with solid cancers in a phase I trial. J Chromatogr B Biomed Sci Appl. 1997 Aug 1;695(2):401-8. PubMed PMID: 9300877.