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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

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

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

Certificates of Analysis (COA)

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L G Mendelsohn et al.
Seminars in oncology, 26(2 Suppl 6), 42-47 (1999-12-22)
The pyrrolopyrimidine-based antifolate, N-¿4-[2-(2-amino-3,4-dihydro-4-oxo-7H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl ]benzoyl¿glutamic acid, LY231514 (MTA) has demonstrated antitumor activity in a broad array of human tumors, including breast cancer, colon cancer, non-small cell lung cancer, head and neck cancer, pancreatic cancer, and other solid tumors. The biochemical
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
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).
J I Borrell et al.
Journal of medicinal chemistry, 44(14), 2366-2369 (2001-06-29)
We recently described the syntheses of 12a-c, 4-amino-7-oxo substituted analogues of 5-deaza-5,6,7,8-tetrahydrofolic acid (5-DATHF), and 5,10-dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF), in six steps from commercially available p-substituted methyl benzoates in 20-27% overall yields. Such analogues were tested in vitro against CCRF-CEM leukemia
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