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Ferric Carboxymaltose

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95 US Patents
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Interquim Ferric Carboxymaltose

Synopsis

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Chemistry

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Also known as: 9007-72-1, Ex-a3450, (2s,3s,4s,5r)-4-[(2r,3r,4r,5s,6r)-5-[(2r,3r,4r,5s,6r)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,5,6-tetrahydroxyhexanoate;iron(3+);oxygen(2-);hydroxide;hydrate

Molecular Formula

C₂₄H₄₄FeO₂₅-

Molecular Weight

788.4 g/mol

InChI Key

MFBBZTDYOYZJGB-HAONTEFVSA-L

Ferric Carboxymaltose is an iron replacement product and chemically, an iron carbohydrate complex. FDA approved on July 25, 2013.

1 2D Structure

Ferric Carboxymaltose

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S,3S,4S,5R)-4-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,5,6-tetrahydroxyhexanoate;iron(3+);oxygen(2-);hydroxide;hydrate

2.1.2 InChI

InChI=1S/C24H42O22.Fe.2H2O.O/c25-1-5(29)18(11(32)14(35)21(39)40)44-23-16(37)12(33)20(7(3-27)42-23)46-24-17(38)13(34)19(8(4-28)43-24)45-22-15(36)10(31)9(30)6(2-26)41-22;;;;/h5-20,22-38H,1-4H2,(H,39,40);;2*1H2;/q;+3;;;-2/p-2/t5-,6-,7-,8-,9-,10+,11+,12-,13-,14+,15-,16-,17-,18+,19-,20-,22-,23-,24-;;;;/m1..../s1

2.1.3 InChI Key

MFBBZTDYOYZJGB-HAONTEFVSA-L

2.1.4 Canonical SMILES

C(C1C(C(C(C(O1)OC2C(OC(C(C2O)O)OC3C(OC(C(C3O)O)OC(C(CO)O)C(C(C(=O)[O-])O)O)CO)CO)O)O)O)O.O.[OH-].[O-2].[Fe+3]

2.1.5 Isomeric SMILES

C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@@H]2[C@H](O[C@@H]([C@@H]([C@H]2O)O)O[C@@H]3[C@H](O[C@@H]([C@@H]([C@H]3O)O)O[C@@H]([C@@H](CO)O)[C@H]([C@@H](C(=O)[O-])O)O)CO)CO)O)O)O)O.O.[OH-].[O-2].[Fe+3]

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Ferinject

2. Injectafer

3. Iron Carboxymaltose

4. Iron Dextri-maltose

5. Polynuclear Iron (iii)-hydroxide 4(r)-(poly-(1->4)-o-alpha-d-glucopyranosyl)-oxy-2(r),3(s),5(r), 6-tetrahydroxy-hexanoate

6. Vit 45

7. Vit-45

2.2.2 Depositor-Supplied Synonyms

1. 9007-72-1

2. Ex-a3450

3. (2s,3s,4s,5r)-4-[(2r,3r,4r,5s,6r)-5-[(2r,3r,4r,5s,6r)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,5,6-tetrahydroxyhexanoate;iron(3+);oxygen(2-);hydroxide;hydrate

2.3 Create Date

2014-11-22

3 Chemical and Physical Properties

Molecular Formula	C₂₄H₄₄FeO₂₅-
Molecular Weight	788.4 g/mol
Hydrogen Bond Donor Count	16
Hydrogen Bond Acceptor Count	25
Rotatable Bond Count	13
Exact Mass	788.152102 g/mol
Monoisotopic Mass	788.152102 g/mol
Topological Polar Surface Area	382 Å²
Heavy Atom Count	50
Formal Charge	-1
Complexity	940
Isotope Atom Count	0
Defined Atom Stereocenter Count	19
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	5

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Injectafer
PubMed Health	ferric carboxymaltose
Drug Classes	Iron Supplement
Drug Label	Ferric carboxymaltose, an iron replacement product, is an iron carbohydrate complex with the chemical name of polynuclear iron (III) hydroxide 4(R)-(poly-(14)-O--D-glucopyranosyl)-oxy-2(R),3(S),5(R),6-tetrahydroxy-hexanoate. It has a relative mo...
Active Ingredient	Ferric carboxymaltose
Dosage Form	Injectable
Route	Intravenous
Strength	750mg iron/15ml (50mg iron/ml)
Market Status	Prescription
Company	Luitpold
Patent	7612109; 7754702

2 of 2
Drug Name	Injectafer
PubMed Health	ferric carboxymaltose
Drug Classes	Iron Supplement
Drug Label	Ferric carboxymaltose, an iron replacement product, is an iron carbohydrate complex with the chemical name of polynuclear iron (III) hydroxide 4(R)-(poly-(14)-O--D-glucopyranosyl)-oxy-2(R),3(S),5(R),6-tetrahydroxy-hexanoate. It has a relative mo...
Active Ingredient	Ferric carboxymaltose
Dosage Form	Injectable
Route	Intravenous
Strength	750mg iron/15ml (50mg iron/ml)
Market Status	Prescription
Company	Luitpold
Patent	7612109; 7754702

4.2 Drug Indication

Ferric carboxymaltose is a iron replacement product indicated for the treatment of iron deficiency anemia in adult patients who have intolerance to oral iron or have had unsatisfactory response to oral iron or those who have non-dialysis dependent chronic kidney disease.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

When measured using positron emission tomography (PET), the red cell uptake of 59-Fe and 52-Fe from INJECTAFER ranged from 61% to 99%. In patients with iron deficiency, the red cell uptake ranged from 91% to 99%. In patients with renal anemia, the red cell uptake ranged from 61% to 84%.

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Parenteral Iron Replacement [EPC]; Phosphate Binder [EPC]; Phosphate Chelating Activity [MoA]; Iron [CS]

5.3 Absorption, Distribution and Excretion

Absorption

When a single dose of 100 to 1000 mg of iron was given to iron deficient patients, the maximum serum concentration (Cmax) was 37 g/mL to 333 g/mL. These levels were obtained 15 minutes to 1.21 hours post dose (Tmax).

Route of Elimination

Renal elimination of iron was negligible.

Volume of Distribution

3 L

5.4 Biological Half-Life

7 to 12 hours.

5.5 Mechanism of Action

Ferric carboxymaltose is a colloidal iron (III) hydroxide in complex with carboxymaltose, a carbohydrate polymer that release iron.

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