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Merck
CN

223948

L-Amethopterin hydrate

98%

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

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About This Item

Empirical Formula (Hill Notation):
C20H22N8O5 · xH2O
CAS Number:
133073-73-1
Molecular Weight:
454.44 (anhydrous basis)
UNSPSC Code:
12352005
PubChem Substance ID:
24853414
MDL number:
MFCD00150847

Key Documents

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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

assay

98%

form

powder

optical activity

[α]25/D +17°, c = 1 in 0.05 M Na2CO3

storage temp.

−20°C

Gene Information

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

Application

Potent inhibitor of dihydrofolate reductase and agent for antitumor studies. Use to inhibit dihydrofolate reductase in DHFR-based protein expression systems.
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.
Potent inhibitor of dihydrofolate reductase and agent for antitumor studies.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

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

Storage Class

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

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKBJ4445V
090M17193V
MKBG8227V
MKBG8157V
MKBG3072V

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S P Sasso et al.
Biochimica et biophysica acta, 1207(1), 74-79 (1994-07-20)
The thermodynamic parameters of the binding of some folate analogues (methotrexate, trimetrexate and trimethoprim) to dihydrofolate reductases from different species have been measured with a flow microcalorimetric method at 37 degrees C. In the absence of NADPH, the three inhibitors
F M Huennekens
Advances in enzyme regulation, 34, 397-419 (1994-01-01)
Methotrexate (MTX), one of the earliest cancer chemotherapy agents, continues to be used extensively in the treatment of leukemia and a variety of other tumors. The efficacy of this drug results from its facile uptake by cells, rapid polyglutamylation and
A Nagy et al.
Proceedings of the National Academy of Sciences of the United States of America, 90(13), 6373-6376 (1993-07-01)
A convenient synthetic method is described for the preparation of peptide-methotrexate (MTX) conjugates in which MTX is coupled selectively through the gamma-carboxyl group of its glutamic acid moiety to a free amino group in peptide analogs. The syntheses of a
Josef Singer et al.
Molecular cancer therapeutics, 13(7), 1777-1790 (2014-04-24)
Passive immunotherapy with monoclonal antibodies represents a cornerstone of human anticancer therapies, but has not been established in veterinary medicine yet. As the tumor-associated antigen EGFR (ErbB-1) is highly conserved between humans and dogs, and considering the effectiveness of the
Ian Joseph Cohen et al.
Pediatric blood & cancer, 61(1), 7-10 (2013-09-17)
To determine the optimal time of folinic acid rescue after methotrexate (MTX) treatment in patients with ALL, we selected and evaluated relevant studies that included doses, rescue delay, and side effects. Rescue at 42-48 hours resulted in considerable toxicity, except
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