Methotrexate, (R)-

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

Structure Search

SMILES

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=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	454.4393
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
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
Dihydrofolate reductase 61 Target ID: CHEMBL202 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6713386	Inhibitor 8504		30.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

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	19595065
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	18969580
Simultaneous determination of L- and D-methotrexate using a sequential injection analysis/amperometric biosensors system.	2003-11-30	14611762
Occurrence and significance of D-methotrexate as a contaminant of commercial methotrexate.	1984-05	6713386

Patents

Sample Use Guides

In Vivo Use Guide

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 `Mon Mar 31 22:03:21 GMT 2025` Edited by `admin` on `Mon Mar 31 22:03:21 GMT 2025`
Record UNII	W12798130R
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Methotrexate, (R)-

Common Name

English

(R)-METHOTREXATE

Preferred Name

English

METHOTREXATE IMPURITY F [EP IMPURITY]

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 [USP-RS]

Common Name

English

Code System Code Type Description

RS_ITEM_NUM

1413988