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A7019

Sigma-Aldrich

(±)Amethopterin hydrate

≥95%, powder

Synonym(s):

4-Amino-10-methylfolic acid, DL-4-Amino-N10-methylpteroylglutamic acid, MTX, Methylaminopterin

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About This Item

Empirical Formula (Hill Notation):
C20H22N8O5 · xH2O
CAS Number:
60388-53-6
Molecular Weight:
454.44 (anhydrous basis)
EC Number:
262-213-7
MDL number:
MFCD00150845
UNSPSC Code:
12352200
PubChem Substance ID:
24891167

Assay

≥95%

form

powder

color

yellow to yellow with an orange cast

solubility

H2O: insoluble

storage temp.

−20°C

SMILES string

O.CN(Cc1cnc2nc(N)nc(N)c2n1)c3ccc(cc3)C(=O)NC(CCC(O)=O)C(O)=O

Gene Information

human ... DHFRP1(573971) , FPGS(2356) , SLC19A1(6573) , TYMS(7298)
mouse ... Dhfr(13361)
rat ... Dhfr(24312)

Application

Amethopterin is a folic acid antagonist and potent anticancer agent. Amethopterin blocks DNA synthesis by preventing the production of tetrahydrofolate cofactors which are required to make thymidine. Amethopterin is actively transported into cells by the folate transporter where it is converted to a high molecular weight polyglutamate metabolite by folylpolyglutamate synthase, a dihydrofolate reductase inhibitor.

Biochem/physiol Actions

Amethopterin is a folic acid antagonist and potent anticancer agent. Blocks DNA synthesis by blocking the production of tetrahydrofolate covactors required for the synthesis of thymidine. Amethopterin 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. Amethopterin-polyglutamate is degraded intracellularly by γ-glutamyl hydrolase.

Reconstitution

Add a minimal amount of 0.1 N NaOH to solubilize, then dilute in neutral buffer or saline. Diluted stock is stable for 1 week refrigerated and for 1 month frozen at −20 °C. References: Cell & Tissue Culture: Laboratory Procedures, Chapter 27, Page 27D:3.2 (A. Doyle, et al., eds, John Wiley) and Cell Biology: A Laboratory Handbook, vol. 2, page 417 (Julio E. Celis, ed., Academic Press).

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H301,H315,H319,H360

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2

Storage Class Code

6.1B - Non-combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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