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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

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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)

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

Sigma-Aldrich

D193

DL-α-Difluoromethylornithine hydrochloride hydrate

Hydroxyfasudil hydrochloride hydrate ≥98% (HPLC), solid

Sigma-Aldrich

H4413

Hydroxyfasudil hydrochloride hydrate

Naftopidil hydrochloride hydrate solid

Sigma-Aldrich

N158

Naftopidil hydrochloride hydrate

(E/Z)-Endoxifen Hydrochloride Hydrate ≥98% (HPLC)

Sigma-Aldrich

E8284

(E/Z)-Endoxifen Hydrochloride Hydrate

assay

≥97% (NMR)

assay

≥98% (HPLC)

assay

-

assay

≥98% (HPLC)

form

solid

form

solid

form

solid

form

solid

Quality Level

100

Quality Level

100

Quality Level

200

Quality Level

100

solubility

DMSO: >10 mg/mL, H2O: >10 mg/mL

solubility

H2O: >5 mg/mL

solubility

methanol: >10 mg/mL, H2O: insoluble

solubility

DMSO: >10 mg/mL

color

white

color

white

color

white

color

white to beige

Gene Information

human ... ODC1(4953)

Gene Information

-

Gene Information

human ... ADRA1A(148), ADRA1B(147), ADRA1D(146)

Gene Information

-

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.[1] It exhibits cytostatic effects on mammalian cells and tissues.[2]

Application

DL-α-Difluoromethylornithine hydrochloride hydrate has been used to reduce the effects of arginine on cell proliferation.[3] It has also been used to investigate the effect of bisphenol A (BPA) on the migration of an established ovine trophectoderm (oTr1) cell line.[4]

Biochem/physiol Actions

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000289611
0000289611
0000445024
0000445019
0000445024

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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
Development of difluoromethylornithine (DFMO) as a chemoprevention agent
Meyskens FL and Gerner EW
Clinical Cancer Research, 5(5), 945-951 (1999)
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
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)
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)
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