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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
Structure of METHOTREXATE, (R)-

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

HIDE SMILES / InChI

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

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

Targets

Primary TargetPharmacologyConditionPotency
30.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
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

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
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 Sat Jun 26 13:44:19 UTC 2021
Edited
by admin
on Sat Jun 26 13:44:19 UTC 2021
Record UNII
W12798130R
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METHOTREXATE, (R)-
Common Name English
R-METHOTREXATE
Common Name English
METHOTREXATE, D-
Common Name English
(2R)-2-((4-(((2,4-DIAMINOPTERIDIN-6-YL)METHYL)METHYLAMINO)BENZOYL)AMINO)PENTANEDIOIC ACID
Systematic Name English
D-AMETHOPTERIN
Common Name English
D-GLUTAMIC ACID, N-(4-(((2,4-DIAMINO-6-PTERIDINYL)METHYL)METHYLAMINO)BENZOYL)-
Systematic Name English
D-METHOTREXATE
Common Name English
(R)-METHOTREXATE
Common Name English
METHOTREXATE SPECIFIED IMPURITY F [EP]
Common Name English
R-METHOTREXATE [USP-RS]
Common Name English
Code System Code Type Description
USP_CATALOG
1413988
Created by admin on Sat Jun 26 13:44:19 UTC 2021 , Edited by admin on Sat Jun 26 13:44:19 UTC 2021
PRIMARY USP-RS
CAS
51865-79-3
Created by admin on Sat Jun 26 13:44:19 UTC 2021 , Edited by admin on Sat Jun 26 13:44:19 UTC 2021
PRIMARY
FDA UNII
W12798130R
Created by admin on Sat Jun 26 13:44:19 UTC 2021 , Edited by admin on Sat Jun 26 13:44:19 UTC 2021
PRIMARY
ECHA (EC/EINECS)
257-482-2
Created by admin on Sat Jun 26 13:44:19 UTC 2021 , Edited by admin on Sat Jun 26 13:44:19 UTC 2021
PRIMARY
PUBCHEM
72440
Created by admin on Sat Jun 26 13:44:19 UTC 2021 , Edited by admin on Sat Jun 26 13:44:19 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP