Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H22N8O5.H2O |
| Molecular Weight | 472.4546 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.CN(CC1=CN=C2N=C(N)N=C(N)C2=N1)C3=CC=C(C=C3)C(=O)N[C@H](CCC(O)=O)C(O)=O
InChI
InChIKey=FPJYMUQSRFJSEW-BTQNPOSSSA-N
InChI=1S/C20H22N8O5.H2O/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);1H2/t13-;/m1./s1
| Molecular Formula | C20H22N8O5 |
| Molecular Weight | 454.4393 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|---|---|---|
| [Chiral selectivity in differentiation of lung cancer A549 cell to vascular endothelial cells after drug resistance induced by D-or L-methotrexate enantiomers]. | 2009-03-17 |
|
| Macrocyclic antibiotics as chiral selectors in the design of enantioselective, potentiometric membrane electrodes for the determination of l- and d-enantiomers of methotrexate. | 2004-09-08 |
|
| Simultaneous determination of L- and D-methotrexate using a sequential injection analysis/amperometric biosensors system. | 2003-11-30 |
|
| Occurrence and significance of D-methotrexate as a contaminant of commercial methotrexate. | 1984-05 |
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Apr 02 10:54:59 GMT 2025
by
admin
on
Wed Apr 02 10:54:59 GMT 2025
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| Record UNII |
3UKI40B4O6
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| Record Status |
Validated (UNII)
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| Record Version |
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331717-43-2
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NON-SPECIFIC STOICHIOMETRY | |||
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71623008
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3UKI40B4O6
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206557-07-5
Created by
admin on Wed Apr 02 10:54:59 GMT 2025 , Edited by admin on Wed Apr 02 10:54:59 GMT 2025
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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ANHYDROUS->SOLVATE |
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