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D193

Sigma-Aldrich

DL-α-Difluoromethylornithine hydrochloride hydrate

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

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C6H12F2N2O2 · xHCl · yH2O
CAS Number:
70052-12-9
Molecular Weight:
182.17 (anhydrous free base basis)
MDL number:
MFCD00242734
UNSPSC Code:
12352200
PubChem Substance ID:
24278809
NACRES:
NA.77

product name

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

Quality Level

100

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.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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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)
K V Lisitskaia et al.
Prikladnaia biokhimiia i mikrobiologiia, 49(2), 124-128 (2013-06-26)
A new biotest system was developed based on highly proliferating human cell cultures (lines LNCaP and PC-3). With the help of this system, two known synthetic polyamines--alpha-difluoromethylornithine (DFMO) and methylglioxalbis(guanylhydrason) (MGBG)--as well as four new synthetic analogues difenyl containing amines
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)
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)
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