Deferiprone Chemical Properties

Melting point:

272-275 °C (lit.)

Boiling point:

255.1°C (rough estimate)

Density 

1.1997 (rough estimate)

refractive index 

1.4800 (estimate)

storage temp. 

2-8°C

solubility 

Soluble in Water (up to 5 mg/ml with warming).

form 

Crystalline Powder or Needles

pka

pKa1 3.3, pKa2 9.7(at 25℃)

color 

White to off-white

Water Solubility 

Soluble in hot water

Merck 

14,2859

Stability:

Stable for 1 year from date of purchase as supplied. Solutions are not stable and must be prepared fresh daily.

InChI

InChI=1S/C7H9NO2/c1-5-7(10)6(9)3-4-8(5)2/h3-4,10H,1-2H3

InChIKey

TZXKOCQBRNJULO-UHFFFAOYSA-N

SMILES

C1(C)N(C)C=CC(=O)C=1O

CAS DataBase Reference

30652-11-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

RTECS 

UU7785940

HS Code 

29333990

Hazardous Substances Data

30652-11-0(Hazardous Substances Data)

Toxicity

LD50 i.p. in rats, mice: 650 mg/kg, 0.8-1.0 g/kg; i.g. in rats: 2.0-3.0 g/kg (Kontoghiorghes, 1995)

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Deferiprone Usage And Synthesis

Description

Deferiprone is a lipophilic iron chelator that binds to iron at a molar ratio of 3:1 (ligand: iron). Its active form is available orally, making it the only oral iron chelator. Deferiprone is a member of the 4-pyridone family and is a pyridine 4-4 (1H) -one, with a methyl substitution at positions 1 and 2 and a hydroxyl substitution at position 3. By binding to iron, Deferiprone can remove excess iron from the body and prevent serum iron overload in patients with transfusion-dependent thalassemia. It has chelation and protective effects and is primarily used to treat thalassaemia.

Chemical Properties

White Needles

Originator

Cipla (India)

Uses

3-Hydroxy-1,2-dimethyl-4(1H)-pyridone (OH-pyridone) may be used in the bacterial killing assays. It has been employed as hydroxyketone chelating agent and its cytotoxic action against oral human normal and tumor cell lines has been evaluated.

Uses

A chelator that could replace disferrioxamine. It is orally and parenterally effective in the removal of iron in vivo from rabbits and mice and also from transferrin and ferritin in vitro

Definition

ChEBI: Deferiprone is a member of the class of 4-pyridones that is pyridin-4(1H)-one substituted at positions 1 and 2 by methyl groups and at position 3 by a hydroxy group. A lipid-soluble iron-chelator used for treatment of thalassaemia. It has a role as an iron chelator and a protective agent.

brand name

Kelfer

General Description

3-Hydroxy-1,2-dimethyl-4(1H)-pyridone (Hdpp, Deferiprone) is a hydroxy ketone derivative. It reacts with uranyl salts [UO₂(NO₃)₂] in aqueous acidic solution to afford mono nuclear complexes ([UO₂(dpp)(Hdpp)₂(H₂O)]ClO₄). X-ray studies have been conducted to examine the structure and geometry of these complexes.

Clinical Use

Orally administered chelator:
Treatment of transfusional iron overload

Metabolism

Deferiprone is hepatically metabolised to an inactive glucuronide metabolite and is excreted mainly in the urine as the metabolite and the iron-deferiprone complex, with a small amount of unchanged drug.

References

1) Hider and Hoffbrand (2018),?The Role of Deferiprone in Iron Chelation; N. Engl. J. Med.,?379?2140 2) Sripetchwandee?et al.?(2016),?A combination of an iron chelator with an antioxidant effectively diminishes the dendritic loss, tau-hyperphosphorylation, amyloid-β accumulation and brain mitochondrial dynamic disruption in rats with chronic iron-overload., Neuroscience?332?191 3) Liu?et al.?(2018),?Iron and Alzheimer’s Disease: From Pathogenesis to Therapeutic Implications;?Front. Neurosci,?12?632

Deferiprone(30652-11-0)Related Product Information

• Deferiprone
• 4-HYDROXYPYRIDINE
• 3-Hydroxypyridine
• 1-BENZYL-3-[(2,6-DICHLOROBENZYL)OXY]-2-METHYL-4(1H)-PYRIDINONE
• 1-(2-CHLORO-6-FLUOROBENZYL)-3-[(2,6-DICHLOROBENZYL)OXY]-2-METHYL-4(1H)-PYRIDINONE
• 3-[(2-CHLORO-6-FLUOROBENZYL)OXY]-1-(4-FLUOROBENZYL)-2-METHYL-4(1H)-PYRIDINONE
• 3-[(2-CHLORO-6-FLUOROBENZYL)OXY]-2-METHYL-1-(4-NITROBENZYL)-4(1H)-PYRIDINONE
• 1-(2-CHLORO-6-FLUOROBENZYL)-3-[(2-CHLORO-6-FLUOROBENZYL)OXY]-2-METHYL-4(1H)-PYRIDINONE
• 1-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]-3-([3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]OXY)-2-METHYL-4(1H)-PYRIDINONE
• 3-[(2-CHLORO-6-FLUOROBENZYL)OXY]-2-METHYL-1-(4-METHYLBENZYL)-4(1H)-PYRIDINONE
• 3-[(2,6-DICHLOROBENZYL)OXY]-2-METHYL-1-(4-METHYLBENZYL)-4(1H)-PYRIDINONE
• 1-(3,4-DICHLOROBENZYL)-3-[(2,6-DICHLOROBENZYL)OXY]-2-METHYL-4(1H)-PYRIDINONE
• 3-(BENZYLOXY)-1-(2-CHLORO-6-FLUOROBENZYL)-2-METHYL-4(1H)-PYRIDINONE
• 3-[(4-CHLOROBENZYL)OXY]-1-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]-2-METHYL-4(1H)-PYRIDINONE
• 1-BENZYL-3-[(2-CHLORO-6-FLUOROBENZYL)OXY]-2-METHYL-4(1H)-PYRIDINONE
• 1-(4-CHLOROBENZYL)-3-[(2-CHLORO-6-FLUOROBENZYL)OXY]-2-METHYL-4(1H)-PYRIDINONE
• 3-[(2,6-DICHLOROBENZYL)OXY]-1-(4-FLUOROBENZYL)-2-METHYL-4(1H)-PYRIDINONE
• 3-[(2-CHLORO-6-FLUOROBENZYL)OXY]-2-METHYL-1-(3-NITRO-2-PYRIDINYL)-4(1H)-PYRIDINONE