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Ferric Derisomaltose

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Interquim Ferric Derisomaltose

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Chemistry

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Also known as: 1345510-43-1, Iron(3+);(2s,3r,4r,5r)-6-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-[[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyhexane-1,2,3,4,5-pentol, Db15617

Molecular Formula

C₁₈H₃₄FeO₁₆+₃

Molecular Weight

562.3 g/mol

InChI Key

JTQTXQSGPZRXJF-DOJSGGEQSA-N

Ferric Derisomaltose is an iron carbohydrate complex composed of ferric hydroxide and the carbohydrate derisomaltose, that may be used for the treatment of iron deficiency anemia. Upon intravenous administration of ferric derisomaltose, ferric iron is released and binds to transferrin. Transferrin-bound iron is transported to erythroid precursor cells and incorporated into hemoglobin.

1 2D Structure

Ferric Derisomaltose

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

iron(3+);(2S,3R,4R,5R)-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyhexane-1,2,3,4,5-pentol

2.1.2 InChI

InChI=1S/C18H34O16.Fe/c19-1-5(21)9(23)10(24)6(22)3-31-17-16(30)14(28)12(26)8(34-17)4-32-18-15(29)13(27)11(25)7(2-20)33-18;/h5-30H,1-4H2;/q;+3/t5-,6+,7+,8+,9+,10+,11+,12+,13-,14-,15+,16+,17-,18-;/m0./s1

2.1.3 InChI Key

JTQTXQSGPZRXJF-DOJSGGEQSA-N

2.1.4 Canonical SMILES

C(C1C(C(C(C(O1)OCC2C(C(C(C(O2)OCC(C(C(C(CO)O)O)O)O)O)O)O)O)O)O)O.[Fe+3]

2.1.5 Isomeric SMILES

C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@H](O2)OC[C@H]([C@H]([C@@H]([C@H](CO)O)O)O)O)O)O)O)O)O)O)O.[Fe+3]

2.2 Synonyms

2.2.1 Depositor-Supplied Synonyms

1. 1345510-43-1

2. Iron(3+);(2s,3r,4r,5r)-6-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-[[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyhexane-1,2,3,4,5-pentol

3. Db15617

2.3 Create Date

2014-11-22

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₃₄FeO₁₆+₃
Molecular Weight	562.3 g/mol
Hydrogen Bond Donor Count	12
Hydrogen Bond Acceptor Count	16
Rotatable Bond Count	11
Exact Mass	562.119621 g/mol
Monoisotopic Mass	562.119621 g/mol
Topological Polar Surface Area	280 Å²
Heavy Atom Count	35
Formal Charge	3
Complexity	598
Isotope Atom Count	0
Defined Atom Stereocenter Count	14
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Indication

This drug is indicated for the treatment of iron deficiency anemia in adult patients who have experienced intolerance to oral iron preparations or insufficient clinical response to orally administered iron. Ferric derisomaltase is also indicated for patients with non-hemodialysis dependent chronic kidney disease. In Australia and United Kingdom, ferric derisomaltase is indicated for cases in which rapid delivery of iron is required.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Ferric derisomaltase increases the reticulocyte count and ultimately increases hemoglobin, treating iron deficiency anemia and its various symptoms. Parenteral iron, such as ferric derisomaltose, may cause false elevations in serum bilirubin levels and falsely reduced serum calcium.

5.2 Absorption, Distribution and Excretion

Absorption

After a single 1000 mg dose, the Cmax and AUC of serum iron were 408 g/mL and 17730 g.h /mL, respectively. Serum ferritin concentrations reach their peak about 7 days after a single dose of intravenous ferric derisomaltose. A note on concomitant oral iron The absorption of oral iron is decreased when administered with intravenous iron. The administration of oral iron should be delayed until at least 5 days after the last ferric derisomaltose injection.

Route of Elimination

Renal elimination was not a significant route of elimination in single-dose pharmacokinetic studies. Iron can often accumulate in the body leading to iron overload followed by toxic effects. Small amounts of ferric derisomaltose are excreted in the urine and feces.

Volume of Distribution

Ferric derisomaltose or released iron that was released is found in cells of the reticuloendothelial system (RES). It is found to be highly concentrated in the liver and spleen. The volume of distribution of other forms of intravenous iron is 3L, on average, in a 70 kg adult. Though the specific volume of distribution of ferric derisomaltose is not readily available in the literature, it is likely similar to other intravenous forms of iron.

Clearance

Intravenous iron is cleared from the plasma. Ferric derisomaltose is not eliminated via the kidneys, as the size of the complex is large and cannot be excreted via the nephron.

5.3 Metabolism/Metabolites

Iron in the circulation is taken up by the plasma by cells of the RES. This binds proteins that form hemosiderin or ferritin, as well transferrin. Following this step, the bound iron replenishes low hemoglobin (Hb) and iron.

5.4 Biological Half-Life

The plasma-half live of intravenous iron is about 1-4 days.

5.5 Mechanism of Action

This drug is a complex made of iron (III) hydroxide and derisomaltose, which is an iron carbohydrate oligosaccharide that works to releases iron. The released iron then binds to the transport protein, transferrin, and is taken to erythroid precursor cells for incorporation into the hemoglobin molecule.

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