MilliporeSigma
All Photos(4)

M9929

Sigma-Aldrich

Methotrexate

meets USP testing specifications

Synonym(s):
Methotrexate hydrate, 4-Amino-10-methylfolic acid hydrate, L-4-Amino-N10-methylpteroylglutamic acid hydrate, L-Amethopterin hydrate, Antifolan hydrate, MTX hydrate, Methylaminopterin hydrate
Empirical Formula (Hill Notation):
C20H22N8O5 · xH2O
CAS Number:
Molecular Weight:
454.44 (anhydrous basis)
MDL number:
PubChem Substance ID:
NACRES:
NA.21

Agency

USP/NF
meets USP testing specifications

Quality Level

form

powder

storage temp.

−20°C

SMILES string

[H]O[H].CN(Cc1cnc2nc(N)nc(N)c2n1)c3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O

InChI

1S/C20H22N8O5.H2O/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);1H2/t13-;/m0./s1

InChI key

FPJYMUQSRFJSEW-ZOWNYOTGSA-N

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This Item
PHR13961414003M1000000
Methotrexate meets USP testing specifications

Sigma-Aldrich

M9929

Methotrexate

Methotrexate Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1396

Methotrexate

Methotrexate United States Pharmacopeia (USP) Reference Standard

USP

1414003

Methotrexate

Methotrexate European Pharmacopoeia (EP) Reference Standard

M1000000

Methotrexate

form

powder

form

-

form

-

form

-

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

Quality Level

200

Quality Level

300

Quality Level

-

Quality Level

-

Gene Information

human ... DHFR(1719), DHFRP1(573971), FPGS(2356), SLC19A1(6573), TYMS(7298)
mouse ... Dhfr(13361)
rat ... Dhfr(24312)

Gene Information

human ... DHFR(1719)

Gene Information

human ... DHFR(1719)

Gene Information

human ... DHFR(1719)

agency

USP/NF

agency

traceable to Ph. Eur. M1000000, traceable to USP 1414003

agency

-

agency

-

folic acid analogue, DHFR inhibitor, antifolate, cell transformation selection agent

-

-

-

Application

Potent inhibitor of dihydrofolate reductase and agent for antitumor studies. Use to inhibit dihydrofolate reductase in DHFR-based protein expression systems. Also effective in treatment of pyrimethamine-resistant Plasmodium vivax malaria parasites.
Potent inhibitor of dihydrofolate reductase and agent for antitumor studies. Use to inhibit dihydrofolate reductase in DHFR-based protein expression systems. Also shows immunosuppressive effects in, e.g., rheumatoid arthritis.

Biochem/physiol Actions

Methotrexate is an allosteric inhibititor of dihydrofolate reductase (DHFR), the enzyme that catalyzes the conversion of dihydrofolate to tetrahydrofolate. Since tetrahydrolfolate is required for purine and pyrimidine synthesis, methotrexate treatment results in the inhibition of DNA and RNA synthesis.

Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

Hazard Classifications

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

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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