Please Wait
Applying Filters...
Menu
Xls
2D Structure
Also known as: Tetraferric tricitrate decahydrate, Ferric citrate hydrate, Ferric citrate [usan], Krx-0502, Db14520, Iron (as ferric citrate) [vandf]
Molecular Formula
C18H32Fe4O31
Molecular Weight
967.8  g/mol
InChI Key
UISKQNNAQKPSDO-UHFFFAOYSA-E
FDA UNII
Q91187K011

Tetraferric tricitrate decahydrate is an iron containing phosphate binder used to treat hyperphosphatemia and iron deficiency anemia in adults with chronic kidney disease. Tetraferric tricitrate decahydrate was granted FDA approval on 5 September 2014.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
iron(3+);2-oxidopropane-1,2,3-tricarboxylate;decahydrate
2.1.2 InChI
InChI=1S/3C6H7O7.4Fe.10H2O/c3*7-3(8)1-6(13,5(11)12)2-4(9)10;;;;;;;;;;;;;;/h3*1-2H2,(H,7,8)(H,9,10)(H,11,12);;;;;10*1H2/q3*-1;4*+3;;;;;;;;;;/p-9
2.1.3 InChI Key
UISKQNNAQKPSDO-UHFFFAOYSA-E
2.1.4 Canonical SMILES
C(C(=O)[O-])C(CC(=O)[O-])(C(=O)[O-])[O-].C(C(=O)[O-])C(CC(=O)[O-])(C(=O)[O-])[O-].C(C(=O)[O-])C(CC(=O)[O-])(C(=O)[O-])[O-].O.O.O.O.O.O.O.O.O.O.[Fe+3].[Fe+3].[Fe+3].[Fe+3]
2.2 Other Identifiers
2.2.1 UNII
Q91187K011
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Ferric Citrate

2. Ferric Citrate Anhydrous

3. Ferric Citrate Dihydrate

4. Ferric Citrate Hydrate

5. Ferric Citrate Iron(+3) Salt

6. Ferric Citrate Trihydrate

7. Ferric Citrate, 59fe-labeled Cpd

8. Ferric Citrate, Iron Salt, 59fe-labeled Cpd

9. Ferric-citric Acid

10. Iron(iii) Citrate

11. Jtt-751

12. Zerenex

2.3.2 Depositor-Supplied Synonyms

1. Tetraferric Tricitrate Decahydrate

2. Ferric Citrate Hydrate

3. Ferric Citrate [usan]

4. Krx-0502

5. Db14520

6. Iron (as Ferric Citrate) [vandf]

7. Q91187k011

8. Q22075864

9. 1,2,3-propanetricarboxylic Acid, 2-hydroxy-, Iron(3+) Salt, Hydrate (4:3:10)

2.4 Create Date
2015-02-20
3 Chemical and Physical Properties
Molecular Weight 967.8 g/mol
Molecular Formula C18H32Fe4O31
Hydrogen Bond Donor Count10
Hydrogen Bond Acceptor Count31
Rotatable Bond Count6
Exact Mass967.83250 g/mol
Monoisotopic Mass967.83250 g/mol
Topological Polar Surface Area440 Ų
Heavy Atom Count53
Formal Charge0
Complexity211
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count17
4 Drug and Medication Information
4.1 Drug Indication

Tetraferric tricitrate decahydrate is indicated to control serum phosphorous in adults with chronic kidney disease who require dialysis. Tetraferric tricitrate decahydrate is also indicated to treat iron deficiency anemia in adults with chronic kidney disease who are not on dialysis.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Tetraferric tricitrate decahydrate is an iron containing product indicated to treat iron deficiency anemia and hyperphosphatemia. It has a wide therapeutic index, as doses can be varied significantly between patients. Tetraferric tricitrate decahydrate has a long duration of action in the treatment of iron deficiency anemia, due to the slow loss of iron from the body, and a moderate duration of action in the treatment of hyperphosphatemia, due to its action being dependant on residence time in the gastrointestinal tract. Patients should be counselled regarding the risk of iron overload.


5.2 Absorption, Distribution and Excretion

Absorption

Ferric iron has been shown to have inferior bioavailability to ferrous iron preparations. Tetraferric tricitrate decahydrate has 19% the bioavailability of ferrous ascorbate.


Route of Elimination

Unabsorbed oral Tetraferric tricitrate decahydrate is eliminated in the feces. The absorbed iron from Tetraferric tricitrate decahydrate is generally not eliminated from the body by any route other than blood loss and exfoliation of epithelial cells.


Clearance

Data regarding the clearance of iron is not readily available. However, iron loss due to exfoliation of epithelial cells is approximately 1mg/day.


5.3 Metabolism/Metabolites

Ferric cation is converted to ferrous iron by duodenal cytochrome B reductase. The heavy chain ferritin may also convert ferric iron to ferrous iron


5.4 Mechanism of Action

Ferric (Fe3+) iron is absorbed from the gastrointestinal tract by divalent metal transporter-1, and reduced to ferrous (Fe2+) iron by ferrireductase and cytochrome b reductase 1. Ferrous iron is stored intracellularly in ferritin and transported into the blood by ferroportin 1. Transport by ferroportin 1 is coupled with oxidation to ferric iron by hephaestin or ceruloplasmin. Ferric iron in plasma is bound to transferrin, which carries iron to other cells. Iron is transported to mitochondria for the synthesis of heme or iron-sulfur clusters, which are integral parts of several metalloproteins like hemoglobin. Ferric iron can also bind to phosphate in the gastrointestinal tract, which precipitates as the insoluble ferric phosphate. Ferric phosphate remains unabsorbed and is eliminated in the feces. Decreased phosphate absorption gradually lowers phosphate levels in the blood.