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Merck

D193

Sigma-Aldrich

DL-α-Difluoromethylornithine hydrochloride hydrate

≥97% (NMR), solid, polyamine biosynthesis inhibitor

Sinónimos:

2-(Difluoromethyl)ornithine hydrochloride hydrate, DFMO hydrochloride hydrate, Eflornithine hydrochloride hydrate

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About This Item

Fórmula empírica (notación de Hill):
C6H12F2N2O2 · xHCl · yH2O
Número de CAS:
Peso molecular:
182.17 (anhydrous free base basis)
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

product name

DL-α-Difluoromethylornithine hydrochloride hydrate, solid, ≥97% (NMR)

Quality Level

assay

≥97% (NMR)

form

solid

color

white

solubility

DMSO: >10 mg/mL
H2O: >10 mg/mL

SMILES string

O.Cl.NCCCC(N)(C(F)F)C(O)=O

InChI

1S/C6H12F2N2O2.ClH.H2O/c7-4(8)6(10,5(11)12)2-1-3-9;;/h4H,1-3,9-10H2,(H,11,12);1H;1H2

InChI key

FJPAMFNRCFEGSD-UHFFFAOYSA-N

Gene Information

human ... ODC1(4953)

General description

Difluoromethylornithine is a fluorinated ornithine analog, which acts as a rate-limiting enzyme of polyamine biosynthesis. It is used to treat female facial hirsutism and human African trypanosomiasis. Difluoromethylornithine functions as a chemopreventive and chemotherapeutic agent against neuroblastoma and colorectal cancer. It exhibits cytostatic effects on mammalian cells and tissues.

Application

DL-α-Difluoromethylornithine hydrochloride hydrate has been used to reduce the effects of arginine on cell proliferation. It has also been used to investigate the effect of bisphenol A (BPA) on the migration of an established ovine trophectoderm (oTr1) cell line.

Biochem/physiol Actions

Difluoromethylornithine (Eflornithine) inhibits polyamine biosynthesis by the selective, irreversible inhibition of ornithine decarboxylase (ODC). A chemoprotective agent that blocks angiogenesis.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


Certificados de análisis (COA)

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Functional roles of arginine during the peri-implantation period of pregnancy. III. Arginine stimulates proliferation and interferon tau production by ovine trophectoderm cells via nitric oxide and polyamine-TSC2-MTOR signaling pathways
Wang X, et al.
Biology of Reproduction, 92(3), 75-71 (2015)
Development of difluoromethylornithine (DFMO) as a chemoprevention agent
Meyskens FL and Gerner EW
Clinical Cancer Research, 5(5), 945-951 (1999)
Kerstin Dörner et al.
Nucleic acids research, 50(5), 2872-2888 (2022-02-13)
Ribosome assembly is an essential process that is linked to human congenital diseases and tumorigenesis. While great progress has been made in deciphering mechanisms governing ribosome biogenesis in eukaryotes, an inventory of factors that support ribosome synthesis in human cells
Alpha-difluoromethylornithine, an irreversible inhibitor of polyamine biosynthesis, as a therapeutic strategy against hyperproliferative and infectious diseases
LoGiudice N, et al.
Medical sciences (Basel, Switzerland), 6(1), 12-12 (2018)
Effects of BPA on expression of apoptotic genes and migration of ovine trophectoderm (oTr1) cells during the peri-implantation period of pregnancy
Elmetwally MA, et al.
Reproductive Toxicology, 83, 73-79 (2019)

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