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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)

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)
Julie L Bronder et al.
Cancer research, 62(18), 5236-5241 (2002-09-18)
The class of folate antimetabolites typified by (6R)-dideazatetrahydrofolate (lometrexol, DDATHF) are specific inhibitors of de novo purine synthesis because of potent inhibition of glycinamide ribonucleotide formyltransferase (GART) but do not induce detectable levels of DNA strand breaks. As such, they
D R Newell
Seminars in oncology, 26(2 Suppl 6), 74-81 (1999-12-22)
Antifolate drugs, as a class, have broad-spectrum activity against both hematologic and solid human malignancies. The pharmacokinetics of the classical antifolate methotrexate have been well-defined and pharmacokinetic data can be exploited to reduce the toxicity and enhance the activity of
Robert Mauritz et al.
Biochemical pharmacology, 63(2), 105-115 (2002-02-14)
We determined the mechanisms of resistance of human CCRF-CEM leukemia cells to methotrexate (MTX) vs. those to six novel antifolates: the polyglutamatable thymidylate synthase (TS) inhibitors ZD1694, multitargeted antifolate, pemetrexed, ALIMTA (MTA) and GW1843U89, the non-polyglutamatable inhibitors of TS, ZD9331
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
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