Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H22N8O5 |
Molecular Weight | 454.4401 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(Cc1cnc2c(c(N)[nH]c(=N)n2)n1)c3ccc(cc3)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
Molecular Formula | C20H22N8O5 |
Molecular Weight | 454.4401 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/6713386
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6713386
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
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL202 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6713386 |
30.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Occurrence and significance of D-methotrexate as a contaminant of commercial methotrexate. | 1984 May |
|
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
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6713386
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6713386
The IC50 values determined with
DHFR from L5178Y were 0.7 and 9.1 nM for L-MTX and D-MTX,
respectively. On the other hand, for DHFR from the human
leukemic spleen the respective IC50 values obtained with the L and
D isomers were 0.9 and 30 nM.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 13:44:19 UTC 2021
by
admin
on
Sat Jun 26 13:44:19 UTC 2021
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Record UNII |
W12798130R
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Record Status |
Validated (UNII)
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Record Version |
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1413988
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51865-79-3
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257-482-2
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72440
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