DEFERIPRONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C7H9NO2
Molecular Weight	139.1519
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CN1C=CC(=O)C(O)=C1C

InChI

InChIKey=TZXKOCQBRNJULO-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C7H9NO2
Molecular Weight	139.1519
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

Deferiprone (trade name Ferriprox) is an iron chelator indicated for the treatment of patients with transfusional iron overload due to thalassemia syndromes when current chelation therapy is inadequate. Deferiprone is an orally bioavailable bidentate ligand with iron chelating activity. Deferiprone binds to iron in a 3:1 (ligand:iron) molar ratio. By binding to iron, deferiprone is able to remove excess iron from the body. All the adverse effects of deferiprone are considered reversible, controllable and manageable. These include agranulocytosis with frequency of about 0.6%, neutropenia 6%, musculoskeletal and joint pains 15%, gastrointestinal complains 6% and zinc deficiency 1%.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Iron 18	Chelating Agent 139

Conditions

Condition	Modality	Targets	Highest Phase	Product
Thalassemia syndrome 1	Secondary		Approved 8,583	FERRIPROX
Iron overload 4	Primary		Approved 8,583	FERRIPROX

C_max

Value	Dose	Analyte	Population
33.4 ug/mL	33 mg/kg single, oral	DEFERIPRONE serum	Homo sapiens
43.3 ug/mL	33 mg/kg single, oral	DEFERIPRONE serum	Homo sapiens
30.6 ug/mL	33 mg/kg single, oral	DEFERIPRONE serum	Homo sapiens
60.8 ug/mL	33 mg/kg single, oral	DEFERIPRONE 3-O-BETA-D-GLUCURONIDE serum	Homo sapiens
118.8 ug/mL	33 mg/kg single, oral	DEFERIPRONE 3-O-BETA-D-GLUCURONIDE serum	Homo sapiens
150.8 ug/mL	33 mg/kg single, oral	DEFERIPRONE 3-O-BETA-D-GLUCURONIDE serum	Homo sapiens
34.1 ug/mL	33 mg/kg single, oral	DEFERIPRONE plasma	Homo sapiens
35.2 ug/mL	33 mg/kg single, oral	DEFERIPRONE 3-O-BETA-D-GLUCURONIDE plasma	Homo sapiens
54.4 ug/mL	50 mg/kg single, oral	DEFERIPRONE plasma	Homo sapiens
51.4 ug/mL	50 mg/kg single, oral	DEFERIPRONE 3-O-BETA-D-GLUCURONIDE plasma	Homo sapiens
64.8 μM	25 mg/kg single, oral	DEFERIPRONE plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
95.4 ug*h/mL	33 mg/kg single, oral	DEFERIPRONE plasma	Homo sapiens
205.5 ug*h/mL	33 mg/kg single, oral	DEFERIPRONE 3-O-BETA-D-GLUCURONIDE plasma	Homo sapiens
152.1 ug*h/mL	50 mg/kg single, oral	DEFERIPRONE plasma	Homo sapiens
331.2 ug*h/mL	50 mg/kg single, oral	DEFERIPRONE 3-O-BETA-D-GLUCURONIDE plasma	Homo sapiens
15001 μM × min	25 mg/kg single, oral	DEFERIPRONE plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
1.77 h	33 mg/kg single, oral	DEFERIPRONE serum	Homo sapiens
2.03 h	33 mg/kg single, oral	DEFERIPRONE serum	Homo sapiens
2.2 h	33 mg/kg single, oral	DEFERIPRONE serum	Homo sapiens
2.58 h	33 mg/kg single, oral	DEFERIPRONE 3-O-BETA-D-GLUCURONIDE serum	Homo sapiens
2.58 h	33 mg/kg single, oral	DEFERIPRONE 3-O-BETA-D-GLUCURONIDE serum	Homo sapiens
3.35 h	33 mg/kg single, oral	DEFERIPRONE 3-O-BETA-D-GLUCURONIDE serum	Homo sapiens
1.8 h	33 mg/kg single, oral	DEFERIPRONE plasma	Homo sapiens
2.5 h	33 mg/kg single, oral	DEFERIPRONE 3-O-BETA-D-GLUCURONIDE plasma	Homo sapiens
1.8 h	50 mg/kg single, oral	DEFERIPRONE plasma	Homo sapiens
2.6 h	50 mg/kg single, oral	DEFERIPRONE 3-O-BETA-D-GLUCURONIDE plasma	Homo sapiens
168 min	25 mg/kg single, oral	DEFERIPRONE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
30 mg/kg 2 times / day multiple, oral Recommended	unhealthy, 29–71	Disc. AE: Neutropenic sepsis, Fatigue...
100 mg/kg multiple, oral Recommended	unhealthy	Disc. AE: Arthralgia, Joint effusion...
33 mg/kg 3 times / day multiple, oral Recommended	unhealthy	Disc. AE: Agranulocytosis, Fetal damage...
33 mg/kg 3 times / day multiple, oral Recommended	unhealthy	Disc. AE: Aspartate aminotransferase increased, Alanine aminotransferase increased...
33 mg/kg 3 times / day multiple, oral Recommended	unhealthy	Disc. AE: Nausea, Vomiting...

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AEs

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AE	Significance	Dose	Population
Fatigue	10% Disc. AE	30 mg/kg 2 times / day multiple, oral Recommended	unhealthy, 29–71
Neutropenic sepsis	30% Disc. AE	30 mg/kg 2 times / day multiple, oral Recommended	unhealthy, 29–71
Abdominal discomfort	non-serious Disc. AE	100 mg/kg multiple, oral Recommended	unhealthy
Arthralgia	non-serious Disc. AE	100 mg/kg multiple, oral Recommended	unhealthy
Epistaxis	non-serious Disc. AE	100 mg/kg multiple, oral Recommended	unhealthy

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2,252	inhibitor 2,438	inhibitor 2,507	inhibitor 2,217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A1 132 CYP1A2 2,153 CYP2E1 1,060	UGT1A6 343 UGT1A7 249 UGT1A8 323 UGT1A9 423 UGT1A10 331 UGT1A1 479 UGT1A3 470 UGT1A4 399 UGT1A5 56 UGT2B4 278 UGT2B7 456 UGT2B10 131 UGT2B15 236 UGT2B17 237 UGT2B28 65

Drug as perpetrator

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Target	Modality	Activity
CYP1A1 272	inhibitor 4,027	no
CYP1A2 2,333	inhibitor 4,027	no
CYP2C9 2,497	inhibitor 4,027	no
CYP2D6 2,546	inhibitor 4,027	no
CYP2E1 1,146	inhibitor 4,027	no

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Drug as victim

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Target	Modality	Activity
UGT1A6 343	substrate 4,014	major
UGT1A10 331	substrate 4,014	minor
UGT1A8 323	substrate 4,014	minor
UGT1A9 423	substrate 4,014	minor
UGT1A1 479	substrate 4,014	no

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2,263	inhibitor 2,237

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:68554	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:68554
ChemicalBook	CB0308124	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0308124
eMolecules	502935	https://www.emolecules.com/cgi-bin/more?vid=502935
MolPort	MolPort-001-792-505	https://www.molport.com/shop/molecule-link/MolPort-001-792-505
Selleck Chemicals	deferiprone	http://www.selleckchem.com/products/deferiprone.html

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PubMed

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Title	Date	PubMed
Molecular factors affecting the complex formation between deferiprone (L1) and Cu(II). Possible implications on efficacy and toxicity.	2001	11799848
Genotoxicity of iron chelators in L5178Y mouse lymphoma cells.	2001	11774367
Structure-function investigation of the interaction of 1- and 2-substituted 3-hydroxypyridin-4-ones with 5-lipoxygenase and ribonucleotide reductase.	2001 Dec 28	11602611
[Therapeuetic management of patients with thalassemia major].	2001 May	11475036
Determination of a new oral iron chelator, ICL670, and its iron complex in plasma by high-performance liquid chromatography and ultraviolet detection.	2001 May 5	11393706

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Patents

Sample Use Guides

In Vivo Use Guide

25 mg/kg to 33 mg/kg body weight, orally, three times per day, for a total daily dose of 75 mg/kg to 99 mg/kg body weight.

Route of Administration: Oral

In Vitro Use Guide

Proliferating CD4+ T cells from control and RRMS subjects, cultured with or without IL-2, decreased in response to 75 μM deferiprone, although the extent of decreased proliferation of CD4+ T cells from RRMS subjects was less than for control subjects. Proliferating CD8+ T cells from control subjects, cultured with or without IL-2, also decreased in response to 75 μM deferiprone, and this decrease was seen in proliferating CD8+ T cells from RRMS cultured with IL-2.

Substance Class	Chemical
Record UNII	2BTY8KH53L
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

DEFERIPRONE

Official Name

English

APO-066

Preferred Name

English

4(1H)-PYRIDINONE, 3-HYDROXY-1,2-DIMETHYL-

Systematic Name

English

DEFERIPRONE [EP MONOGRAPH]

Common Name

English

NSC-758880

Code

English

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Classification Tree

Code System

Code

Positive

EU-Orphan Drug

EU/3/10/832

Chelating Agent

NCI_THESAURUS

C62357

Designated/Withdrawn

FDA ORPHAN DRUG

340011

Designated/Withdrawn

FDA ORPHAN DRUG

581217

Designated/Withdrawn

FDA ORPHAN DRUG

264308

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Code System

Code

Type

Description

WIKIPEDIA

DEFERIPRONE

PRIMARY

CAS

30652-11-0

PRIMARY

ChEMBL

CHEMBL70927

PRIMARY

CHEBI

68554

PRIMARY

SMS_ID

100000085431

PRIMARY

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METABOLIC ENZYME -> SUBSTRATE

Interaction Type:

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					S0025AG5ZT

URIDINE DIPHOSPHATE GLUCURONOSYLTRANSFERASE 1A10

METABOLIC ENZYME -> SUBSTRATE

Interaction Type:

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					91O4LML611

FERRIC CATION

TARGET->LIGAND


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URIDINE DIPHOSPHATE GLUCURONOSYLTRANSFERASE 1A8

METABOLIC ENZYME -> SUBSTRATE

Interaction Type:

MINOR


					2BTY8KH53L

DEFERIPRONE

EXCRETED UNCHANGED

Qualification:

URINE

Amount:

95 % (average)

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					2FF8DPG57Y

3-HYDROXY-2-(HYDROXYMETHYL)-1-METHYL-4(1H)-PYRIDINONE

METABOLITE -> PARENT


					47N4BZV3Z9

(2S,3S,4S,5R,6S)-3,4,5-TRIHYDROXY-6-((2-(HYDROXYMETHYL)-1-METHYL-4-OXO-3-PYRIDYL)OXY)TETRAHYDROPYRAN-2-CARBOXYLIC ACID

METABOLITE -> PARENT


					BV1G5BFA7Z

3-METHOXY-1,2-DIMETHYL-PYRIDIN-4-ONE

METABOLITE -> PARENT


					1QOS5ADQ2R

DEFERIPRONE 3-O-.BETA.-D-GLUCURONIDE

METABOLITE -> PARENT

Interaction Type:

MAJOR

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					W0JGJ7373Y

1-METHYL-3-(METHYLAMINO)-1,5-DIHYDRO-2H-PYRROL-2-ONE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:

[<0.05] % (average)


					3A9RD92BS4

MALTOL

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:

[<0.1] % (average)

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Related Record

Type

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					2BTY8KH53L

DEFERIPRONE

ACTIVE MOIETY

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Name	Property Type	Amount	Parameters
Volume of Distribution	PHARMACOKINETIC	1.6 Liters/Kilogram (average)

Tmax	PHARMACOKINETIC	2 hours (average)	SINGLE DOSE IN THE FED STATE

Tmax	PHARMACOKINETIC	1 hours (average)	SINGLE DOSE IN FASTED HEALTHY SUBJECTS

Biological Half-life	PHARMACOKINETIC	1.9 hours (average)

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

Drug as perpetrator