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2D Structure
Also known as: 33725-54-1, Iron (iii) maltol, Ferric maltol [inn], Ferric maltol [usan], St10, Ma10qyf1z0
Molecular Formula
C18H15FeO9
Molecular Weight
431.2  g/mol
InChI Key
AHPWLYJHTFAWKI-UHFFFAOYSA-K
FDA UNII
MA10QYF1Z0

Ferric maltol is an iron(III) atom complexed with 3 maltol molecules to increase the bioavailability compared to iron(II), without depositing it in the duodenum as insoluble ferric hydroxide and phosphate. Ferric maltol has been described in literature since at least the late 1980s as a potential treatment for iron deficiency. Ferric maltol was granted FDA Approval on 25 July 2019.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
iron(3+);2-methyl-4-oxopyran-3-olate
2.1.2 InChI
InChI=1S/3C6H6O3.Fe/c3*1-4-6(8)5(7)2-3-9-4;/h3*2-3,8H,1H3;/q;;;+3/p-3
2.1.3 InChI Key
AHPWLYJHTFAWKI-UHFFFAOYSA-K
2.1.4 Canonical SMILES
CC1=C(C(=O)C=CO1)[O-].CC1=C(C(=O)C=CO1)[O-].CC1=C(C(=O)C=CO1)[O-].[Fe+3]
2.2 Other Identifiers
2.2.1 UNII
MA10QYF1Z0
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Accrufer

2. Iron (iii) Maltol

3. Iron(3+) Tris(2-methyl-4-oxo-4h-pyran-3-olate)

2.3.2 Depositor-Supplied Synonyms

1. 33725-54-1

2. Iron (iii) Maltol

3. Ferric Maltol [inn]

4. Ferric Maltol [usan]

5. St10

6. Ma10qyf1z0

7. Iron(3+);2-methyl-4-oxopyran-3-olate

8. Iron(iii) 2-methyl-4-oxo-4h-pyran-3-olate

9. St10-021

10. Iron Maltol

11. Feraccru (tn)

12. Unii-ma10qyf1z0

13. Ferric Maltol [mi]

14. Ferric Maltol (usan/inn)

15. Ferric Maltol [usan:inn]

16. Ferric Maltol [who-dd]

17. St-10

18. Ferric Maltol [orange Book]

19. Who 9974

20. Db15598

21. Iron(iii)2-methyl-4-oxo-4h-pyran-3-olate

22. D10833

23. E83926

24. Q27283748

25. Iron, Tris(3-hydroxy-2-methyl-4h-pyran-4-onato-o3,o4)-

26. Iron, Tris(3-(hydroxy-.kappa.o)-2-methyl-4h-pyran-4-onato-.kappa.o4)-

27. Tris(3-(hydroxy-.kappa.o)-2-methyl-4h-pyran-4-onato-.kappa.o4)iron(iii)

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 431.2 g/mol
Molecular Formula C18H15FeO9
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count9
Rotatable Bond Count0
Exact Mass431.006543 g/mol
Monoisotopic Mass431.006543 g/mol
Topological Polar Surface Area148 Ų
Heavy Atom Count28
Formal Charge0
Complexity200
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count4
4 Drug and Medication Information
4.1 Drug Indication

Ferric maltol is indicated to treat iron deficiency in adults.


Feraccru is indicated in adults for the treatment of iron deficiency.


Treatment of iron deficiency


5 Pharmacology and Biochemistry
5.1 Pharmacology

Ferric maltol is used to provide supplemental iron to patients with an iron deficiency. It has a wide therapeutic index as patients generally take 30mg twice daily, while concentrations of 20mg/kg may produce toxicity. Patients should be counselled regarding the risk of inflammatory bowel disease flares, iron overload, and accidental ingestion in children.


5.2 MeSH Pharmacological Classification

Hematinics

Agents which improve the quality of the blood, increasing the hemoglobin level and the number of erythrocytes. They are used in the treatment of anemias. (See all compounds classified as Hematinics.)


5.3 FDA Pharmacological Classification
5.3.1 Pharmacological Classes
Parenteral Iron Replacement [EPC]; Phosphate Binder [EPC]; Phosphate Chelating Activity [MoA]; Iron [CS]
5.4 ATC Code

B03AB


B - Blood and blood forming organs

B03 - Antianemic preparations

B03A - Iron preparations

B03AB - Iron trivalent, oral preparations

B03AB10 - Ferric maltol


5.5 Absorption, Distribution and Excretion

Absorption

Ferric maltol dissociates in the gastrointestinal tract, leading to a Tmax of 1.5-3.0 hours for iron concentrations. Mean serum iron increases by 146mol/L in iron deficient patients following a single dose. a 60mg dose is approximately 14% bioavailable. 60 minutes after injection of radiolabelled ferric maltol, 11+2% of the dose is present in the bone marrow, 181% is present in the liver, and 2.61% is in the urine. Maltol has an AUC of 0.022-0.205h\*g/mL and maltol glucuronide has an AUC of 9.83-30.9h\*g/mL.


Route of Elimination

39.8-60% of an oral dose of ferric maltol is excreted in the urine as a glucuronide conjugate. Iron and ferric maltol are not excreted in the urine and unabsorbed ferric maltol is eliminated in the feces.


Volume of Distribution

Data regarding the volume of distribution of ferric maltol is not readily available.


Clearance

Data regarding the clearance of ferric maltol is not readily available.


5.6 Metabolism/Metabolites

_In vitro_, ferric maltol metabolism is predominantly glucuronidation of maltol by UGT1A6 and sulfation.


5.7 Biological Half-Life

Maltol has a half life of 0.7h.


5.8 Mechanism of Action

Ferric maltol dissociates as the iron atom is donated to unknown iron uptake mechanisms, possibly beta 3 integrin or divalent metal transporter 1, in the ileum and duodenum. Once the iron is in circulation, it then associates with transferrin and ferritin.