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Merck
CN

1414025

USP

Methotrexate Related Compound B

United States Pharmacopeia (USP) Reference Standard

Synonym(s):

Aminopterin, (S)-2-{4-[(2,4-Diaminopteridin-6-yl)methylamino]benzamido}pentanedioic acid, 4-Amino-PGA, 4-Aminofolic acid, 4-Aminopteroyl-L-glutamic acid

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About This Item

Empirical Formula (Hill Notation):
C19H20N8O5
CAS Number:
54-62-6
Molecular Weight:
440.41
MDL number:
MFCD00036692
UNSPSC Code:
41116107
PubChem Substance ID:
329750411
NACRES:
NA.24
Beilstein/REAXYS Number:
69045

Key Documents

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Product Name

Methotrexate Related Compound B, United States Pharmacopeia (USP) Reference Standard

SMILES string

Nc1nc(N)c2nc(CNc3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)cnc2n1

InChI

1S/C19H20N8O5/c20-15-14-16(27-19(21)26-15)23-8-11(24-14)7-22-10-3-1-9(2-4-10)17(30)25-12(18(31)32)5-6-13(28)29/h1-4,8,12,22H,5-7H2,(H,25,30)(H,28,29)(H,31,32)(H4,20,21,23,26,27)/t12-/m0/s1

InChI key

TVZGACDUOSZQKY-LBPRGKRZSA-N

grade

pharmaceutical primary standard

API family

methotrexate

manufacturer/tradename

USP

ε (extinction coefficient)

24,500 at 282 nm in 0.1 M NaOH at 1 M
25,700 at 261 nm in 0.1 M NaOH at 1 M
8,100 at 373 nm in 0.1 M NaOH at 1 M

application(s)

pharmaceutical (small molecule)

format

neat

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Related Categories

Other Notes

Sales restrictions may apply.
More potent, but more toxic, than methotrexate.

General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.
For further information and support please go to the website of the issuing Pharmacopoeia.

Analysis Note

These products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.  ​

Application

Methotrexate Related Compound B USP reference standard for use in specified quality tests and assays.

Additionally used to prepare standard, standard stock, system suitability, and system suitability stock solutions for impurity analysis in the given below monographs according to United States Pharmacopeia (USP):
  • Methotrexate
  • Methotrexate Injection
  • Methotrexate for Injection

Biochem/physiol Actions

Folic acid antagonist that binds to dihydrofolate reductase and inhibits its activity.
Folic acid antagonist. Aminopterin is actively transported into cells by the folate transporter. In the cell, it is converted to a high molecular weight polyglutamate metabolite by folylpolyglutamate synthase that, in turn, binds to dihydrofolate reductase and inhibits its activity. Aminopterin-polyglutamate is degraded intracellularly by γ-glutamyl hydrolase.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 1 Oral - Eye Irrit. 2 - Muta. 2 - Repr. 1B - Skin Irrit. 2

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

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Methotrexate Injection
United States Pharmacopeia and National Formulary
United States Pharmacopeia, 41(4), 2857-2857 (2020)
Methotrexate
United States Pharmacopeia and National Formulary
United States Pharmacopeia, 47(5), 2854-2854 (2022)
Methotrexate for Injection
United States Pharmacopeia and National Formulary
United States Pharmacopeia, 44(3), 2858-2858 (2020)

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