Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H22N8O5 |
| Molecular Weight | 454.4393 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(CC1=NC2=C(N)N=C(N)N=C2N=C1)C3=CC=C(C=C3)C(=O)N[C@H](CCC(O)=O)C(O)=O
InChI
InChIKey=FBOZXECLQNJBKD-CYBMUJFWSA-N
InChI=1S/C20H22N8O5/c1-28(9-11-8-23-17-15(24-11)16(21)26-20(22)27-17)12-4-2-10(3-5-12)18(31)25-13(19(32)33)6-7-14(29)30/h2-5,8,13H,6-7,9H2,1H3,(H,25,31)(H,29,30)(H,32,33)(H4,21,22,23,26,27)/t13-/m1/s1
METHOTREXATE, (R)- (D-methotrexate) as a contaminant of commercial methotrexate, a chemotherapy agent and immune system suppressant. Methotrexate from various commercial sources has been found to contain 0.5 to 48% (w/w) of the enantiomer D-methotrexate. D-Methotrexate was found to be a good inhibitor of dihydrofolate reductase from both murine and human tumor cells, but was a poor inhibitor of L1210 and CCRF-CEM cell growth. In animal experiments with dogs and mice, D-methotrexate was rapidly absorbed from the intestine and excreted by the kidneys.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Simultaneous determination of L- and D-methotrexate using a sequential injection analysis/amperometric biosensors system. | 2003 Nov 30 |
|
| Macrocyclic antibiotics as chiral selectors in the design of enantioselective, potentiometric membrane electrodes for the determination of l- and d-enantiomers of methotrexate. | 2004 Sep 8 |
|
| [Chiral selectivity in differentiation of lung cancer A549 cell to vascular endothelial cells after drug resistance induced by D-or L-methotrexate enantiomers]. | 2009 Mar 17 |
Patents
Sample Use Guides
Dogs: Following p.o. administration of D-methotrexate (1 mg/kg) to the dog, plasma samples were taken at 30, 60, 120, 360 min, and after 24 hr and were analyzed by DHFR inhibition assay.
Route of Administration:
Oral
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SUBSTANCE RECORD
