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SML0040

Sigma-Aldrich

Lometrexol hydrate

≥95% (HPLC)

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Synonym(s):
LY 264618 hydrate, N-[4-[2-[(6R)-2-amino-3,4,5,6,7,8-hexahydro-4-oxopyrido[2,3-d]pyrimidin-6-yl]ethyl]benzoyl]-L-glutamic acid hydrate
Empirical Formula (Hill Notation):
C21H25N5O6 · xH2O
CAS Number:
106400-81-1
Molecular Weight:
443.45 (anhydrous basis)
UNSPSC Code:
12352200
PubChem Substance ID:
329825110
NACRES:
NA.77

Quality Level

100

Assay

≥95% (HPLC)

form

powder

color

white to light yellow

solubility

DMSO: ≥5 mg/mL

storage temp.

2-8°C

SMILES string

O.NC1=NC(=O)C2=C(NC[C@H](CCc3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)C2)N1

InChI

1S/C21H25N5O6.H2O/c22-21-25-17-14(19(30)26-21)9-12(10-23-17)2-1-11-3-5-13(6-4-11)18(29)24-15(20(31)32)7-8-16(27)28;/h3-6,12,15H,1-2,7-10H2,(H,24,29)(H,27,28)(H,31,32)(H4,22,23,25,26,30);1H2/t12-,15+;/m1./s1

InChI key

AEFQSKJUVDZANQ-YLCXCWDSSA-N

Related Categories

Application

Lometrexol hydrate was used to compare the biological activity of potent inhibitor of human GARFTase.

Biochem/physiol Actions

Glycinamide Ribonucleotide Formyltransferase (GARFTase) is a folate-dependent enzyme required for de novo purine synthesis. Lometrexate is a potent inhibitor of GARFTase, but does not interfere with enzymes involved in the synthesis of folate. Lometrexerol has been tested clinically for the treatment of various cancers as an anti-folate like agent, similar to methotrexate. Treatment with lometrexol rapidly decreases ATP and GTP levels, cell cycle arrest and induces apoptosis. Although depletion of nucleotide pools induces p53 expression, lometrexol is cytotoxic in both wild-type and mutant p53 expressing tumor cells. Lometrexol is cytotoxic in CCRF-CEm leukemia cells with an IC50 of 2.9 nM.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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New agents in cancer clinical trials.
J Adams et al.
Oncogene, 19(56), 6687-6692 (2001-06-28)
A Tse et al.
The Journal of biological chemistry, 273(40), 25944-25952 (1998-09-25)
Mouse L1210 cell variants were selected for resistance to 5, 10-dideazatetrahydrofolate, a potent inhibitor of the first folate-dependent enzyme in de novo purine synthesis, glycinamide ribonucleotide formyltransferase. The drug-resistant phenotype selected was conditional to the folate compound used to support
G Jansen et al.
The Journal of biological chemistry, 273(46), 30189-30198 (1998-11-07)
CEM/MTX is a subline of human CCRF-CEM leukemia cells which displays >200-fold resistance to methotrexate (MTX) due to defective transport via the reduced folate carrier (RFC). CEM/MTX-low folate (LF) cells, derived by a gradual deprivation of folic acid from 2.3
C Shih et al.
Advances in enzyme regulation, 38, 135-152 (1998-10-08)
Extensive biochemical and pharmacological evidence indicates that LY231514 is a novel antifolate antimetabolite. LY231514 is transported into cells mainly through the reduced folate carrier system and extensively metabolized to polyglutamated forms. The polyglutamates of LY231514 inhibit at least three key
X Lu et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 7(7), 2114-2123 (2001-07-13)
The impact of p53 status on cellular sensitivity to antifolate drugs has been examined in seven human cell lines (A549, MCF7, T-47D, CCRF-CEM, COR-L23, A2780, and HCT-116) and p53 nonfunctional counterparts of two of the cell lines (HCT-116/N7 and A2780/CP70).
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