Synonym
5,10-Dideazaaminopterin;
IUPAC/Chemical Name
(4-(2-(2,4-diaminopyrido[2,3-d]pyrimidin-6-yl)ethyl)benzoyl)-L-glutamic acid
InChi Key
RGUQKUKRLMXLCM-HNNXBMFYSA-N
InChi Code
InChI=1S/C21H22N6O5/c22-17-14-9-12(10-24-18(14)27-21(23)26-17)2-1-11-3-5-13(6-4-11)19(30)25-15(20(31)32)7-8-16(28)29/h3-6,9-10,15H,1-2,7-8H2,(H,25,30)(H,28,29)(H,31,32)(H4,22,23,24,26,27)/t15-/m0/s1
SMILES Code
Nc1c2cc(CCc3ccc(C(N[C@H](C(O)=O)CCC(O)=O)=O)cc3)cnc2nc(N)n1
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
438.44
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.
| 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: 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.
2: Piper JR, DeGraw JI, Colwell WT, Johnson CA, Smith RL, Waud WR, Sirotnak FM. Analogues of methotrexate in rheumatoid arthritis. 2. Effects of 5-deazaaminopterin, 5,10-dideazaaminopterin, and analogues on type II collagen-induced arthritis in mice. J Med Chem. 1997 Jan 31;40(3):377-84. PubMed PMID: 9022805.
3: Piper JR, Ramamurthy B, Johnson CA, Otter GM, Sirotnak FM. Analogues of 10-deazaaminopterin and 5-alkyl-5,10-dideazaaminopterin with the 4-substituted 1-naphthoyl group in the place of 4-substituted benzoyl. J Med Chem. 1996 Jan 19;39(2):614-8. PubMed PMID: 8558535.
4: Piper JR, Johnson CA, Otter GM, Sirotnak FM. Synthesis and antifolate evaluation of 10-ethyl-5-methyl-5,10- dideazaaminopterin and an alternative synthesis of 10-ethyl-10- deazaaminopterin (edatrexate). J Med Chem. 1992 Aug 7;35(16):3002-6. PubMed PMID: 1501226.
5: DeGraw JI, Christie PH, Colwell WT, Sirotnak FM. Synthesis and antifolate properties of 5,10-ethano-5,10-dideazaaminopterin. J Med Chem. 1992 Jan 24;35(2):320-4. PubMed PMID: 1732549.
6: Piper JR, McCaleb GS, Montgomery JA, Kisliuk RL, Gaumont Y, Thorndike J, Sirotnak FM. Synthesis and antifolate activity of 5-methyl-5,10-dideaza analogues of aminopterin and folic acid and an alternative synthesis of 5,10-dideazatetrahydrofolic acid, a potent inhibitor of glycinamide ribonucleotide formyltransferase. J Med Chem. 1988 Nov;31(11):2164-9. PubMed PMID: 3184124.
7: Taylor EC, Harrington PJ, Fletcher SR, Beardsley GP, Moran RG. Synthesis of the antileukemic agents 5,10-dideazaaminopterin and 5,10-dideaza-5,6,7,8-tetrahydroaminopterin. J Med Chem. 1985 Jul;28(7):914-21. PubMed PMID: 4009615.
