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SML0040

Sigma-Aldrich

Lometrexol hydrate

≥95% (HPLC), powder, GARFTase inhibitor

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

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About This Item

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

product name

Lometrexol hydrate, ≥95% (HPLC)

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

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

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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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
J D Roberts et al.
Cancer chemotherapy and pharmacology, 45(2), 103-110 (2000-02-09)
Lometrexol [(6R)-5,10-dideaza-5,6,7,8-tetrahydrofolate] is the prototype folate antimetabolite that targets the de novo purine synthesis pathway. Early phase I trials were confounded by cumulative myelosuppression that prevented repetitive administration. Subsequent preclinical and clinical studies suggested that coadministration of folic acid might
T W Synold et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 4(10), 2349-2355 (1998-10-31)
Lometrexol inhibits the first folate-dependent enzyme in de novo purine biosynthesis and is avidly polyglutamated and retained in tissues expressing folylpolyglutamate synthetase. Although clinical studies have been limited by cumulative toxicity, preclinical studies show that pretreatment with folic acid can
Huiling Qi et al.
Cancer research, 66(11), 5875-5882 (2006-06-03)
The folate receptor (FR) type beta is a promising target for therapeutic intervention in acute myelogenous leukemia (AML), owing particularly to its selective up-regulation in the leukemic cells by all-trans retinoic acid (ATRA). Here we show, using KG-1 and MV4-11
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