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Also known as: Iron(iii) citrate, Iron citrate, 3522-50-7, Zerenex, 6043-74-9, 28633-45-6

Molecular Formula

C₆H₅FeO₇

Molecular Weight

244.94 g/mol

InChI Key

NPFOYSMITVOQOS-UHFFFAOYSA-K

FDA UNII

63G354M39Z

1 2D Structure

Ferric Citrate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-hydroxypropane-1,2,3-tricarboxylate;iron(3+)

2.1.2 InChI

InChI=1S/C6H8O7.Fe/c7-3(8)1-6(13,5(11)12)2-4(9)10;/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12);/q;+3/p-3

2.1.3 InChI Key

NPFOYSMITVOQOS-UHFFFAOYSA-K

2.1.4 Canonical SMILES

C(C(=O)[O-])C(CC(=O)[O-])(C(=O)[O-])O.[Fe+3]

2.2 Other Identifiers

2.2.1 UNII

63G354M39Z

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Ferric Citrate Anhydrous

2. Ferric Citrate Dihydrate

3. Ferric Citrate Hydrate

4. Ferric Citrate Iron(+3) Salt

5. Ferric Citrate Trihydrate

6. Ferric Citrate, 59fe-labeled Cpd

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

8. Ferric-citric Acid

9. Iron(iii) Citrate

10. Jtt-751

11. Zerenex

2.3.2 Depositor-Supplied Synonyms

1. Iron(iii) Citrate

2. Iron Citrate

3. 3522-50-7

4. Zerenex

5. 6043-74-9

6. 28633-45-6

7. Citric Acid, Iron(3+) Salt

8. Ferrum Citricum

9. Ferriccitrate

10. Iron(iii) Citrate Tribasic

11. 1,2,3-propanetricarboxylic Acid, 2-hydroxy-, Iron(3+) Salt (1:1)

12. Ferric Citrate Anhydrous

13. Krx-0502

14. Iron(iii)citrate

15. Iron Citrate, Fec6h5o7

16. Auryxia

17. Iron(3+) Citrate

18. 63g354m39z

19. 2338-05-8

20. Iron, (hydrogen Citrato(3-))-

21. Citric Acid, Iron(3+) Salt (1:1)

22. Ferrous Citrate

23. Iron(iii) 2-hydroxypropane-1,2,3-tricarboxylate

24. 2-hydroxy-1,2,3-propanetricarboxylic Acid Iron Salt

25. Ferric Citrate [usan]

26. Ferric Citrate Tetrahydrate

27. Jtt-751

28. Ferric Citrate (van)

29. 2-hydroxypropane-1,2,3-tricarboxylate;iron(3+)

30. Nsc-112227

31. Fexeric

32. Iron(3+) 2-hydroxypropane-1,2,3-tricarboxylate

33. Unii-63g354m39z

34. Jtt 751

35. Fe(iii)-citrate Complex (1:1)

36. Einecs 222-536-6

37. Einecs 249-117-0

38. Iron(iii)-citrate

39. Iron (iii) Citrate

40. Nsc 112227

41. Citric Acid, Iron Salt

42. 1185-57-5

43. Citric Acid,iron(3+)salt

44. Ferric Citrate [mi]

45. Schembl42945

46. Ferric Citrate [fcc]

47. 2-hydroxypropane-1,2,3-tricarboxylate; Iron(3+)

48. Ferric Citrate [inci]

49. Ferrum Citricum [hpus]

50. Ccris 6843

51. Dtxsid0037657

52. Ferric Citrate [who-dd]

53. Iron(iii) Citrate;iron Citrate

54. Hy-n1428c

55. 1,2,3-propanetricarboxylic Acid, 2-hydroxy-, Iron(3+) Salt

56. Bcp30645

57. Ferric Citrate [orange Book]

58. Akos015918266

59. Db09162

60. Db-119245

61. Cs-0030977

62. Ft-0626407

63. Ft-0627304

64. Ft-0652224

65. Iron 2-hydroxy-1,2,3-propanetricarboxylate

66. A832727

67. Iron(3+); 2-oxidanylpropane-1,2,3-tricarboxylate

68. Q15628111

69. 1,2,3-propanetricarboxylic Acid, 2-hydroxy-, Iron Salt (1:?)

70. 1,2,3-propanetricarboxylic Acid, 2-hydroxy-, Iron(2+) Salt (2:3)

2.4 Create Date

2005-07-19

3 Chemical and Physical Properties

Molecular Formula	C₆H₅FeO₇
Molecular Weight	244.94 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	2
Exact Mass	244.938463 g/mol
Monoisotopic Mass	244.938463 g/mol
Topological Polar Surface Area	141 Å²
Heavy Atom Count	14
Formal Charge	0
Complexity	211
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
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 Information

1 of 2
Drug Name	Ferric citrate
PubMed Health	Ferric Citrate (Oral route)
Drug Classes	Phosphate Binder
Drug Label	Ferric Citrate is known chemically as iron (+3), x (1, 2, 3-propanetricarboxylic acid, 2 hydroxy-), y (H2O)Ferric Citrate 210 mg ferric iron tablets, equivalent to 1g ferric citrate, are film-coated, peach-colored, and oval-shaped tablets embossed wi...
Active Ingredient	Ferric citrate
Dosage Form	Tablet
Route	Oral
Strength	210mg
Market Status	Prescription
Company	Keryx Biopharma

2 of 2
Drug Name	Ferric citrate
PubMed Health	Ferric Citrate (Oral route)
Drug Classes	Phosphate Binder
Drug Label	Ferric Citrate is known chemically as iron (+3), x (1, 2, 3-propanetricarboxylic acid, 2 hydroxy-), y (H2O)Ferric Citrate 210 mg ferric iron tablets, equivalent to 1g ferric citrate, are film-coated, peach-colored, and oval-shaped tablets embossed wi...
Active Ingredient	Ferric citrate
Dosage Form	Tablet
Route	Oral
Strength	210mg
Market Status	Prescription
Company	Keryx Biopharma

4.2 Therapeutic Uses

Source of iron in treating iron-deficiency anemias. It is less constipating than inorg forms of iron. It is free from astringent & irritant properties. However, ferric ion is less well absorbed than ferrous ion, so that its supposed advantages are outweighed by its lesser efficacy, and it is considered to be an obsolete preparation. In the forms presently marketed, a unit dose provides only the recommended daily allowance of iron (15 mg). /former use/

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 777

VET: Used in prevention & treatment of anemias. Oral biololgy availabilities in rats and chicks have been reported as 107 and 115% respectively, compared to ferrous sulfate. Counteracts oral poisonous effects of gossypol (in cottonseed meal) in poultry trials. Used in wide variety of oral and parenteral hematinics.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 216

Hematinic

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 90

VET: In iron deficiency anemia.

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 90

For more Therapeutic Uses (Complete) data for FERRIC AMMONIUM CITRATE (6 total), please visit the HSDB record page.

Hematinic

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 716

The in vitro and in vivo availability of iron from total parenteral nutrition solutions to which ferrous citrate has been added was investigated. In vitro experiments showed that 74% of the added iron was available to transferrin. In 7 patients in whom in vivo availability was tested by red cell incorporation, the mean availability was 81%. It was concluded that ferrous citrate is a safe and effective means of iron supplementation in patients on TPN therapy.

Sayers MH et al. JPEN J Parenter Enteral Nutr 7 (2): 117-20 (1983)

4.3 Drug Indication

Fexeric is indicated for the control of hyperphosphataemia in adult patients with chronic kidney disease (CKD).

5 Pharmacology and Biochemistry

5.1 FDA Pharmacological Classification

5.1.1 Pharmacological Classes

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

5.2 ATC Code

V03AE

V - Various

V03 - All other therapeutic products

V03A - All other therapeutic products

V03AE - Drugs for treatment of hyperkalemia and hyperphosphatemia

V03AE08 - Ferric citrate

5.3 Absorption, Distribution and Excretion

The absorption and endogenous excretion of iron in man was studied by monitoring the fecal excretion of a stable iron isotope (58Fe). The study was carried out for 12 healthy volunteers who were divided into two groups. Group I received 58Fe-labeled ferric ammonium citrate (III) (58FeAC) equivalent to 6 mg of iron as a control, and group II received a combination of 500 mg of vitamin C and 58FeAC. A new formula was used to calculate the 58Fe absorption ratio reflecting the pool of iron in the intestinal cells, and the ratio was compared with that obtained from Janghorbani's formula, which has been used as one of the common methods. As a result, the 58Fe absorption ratio in group II was statistically significantly higher than that of group I (34.4 +/- 6.1% vs. 15.0 +/- 5.5%, M +/- SD) using Janghorbani's formula. The similar absorption ratio (34.1 +/- 6.0% vs. 14.8 +/- 5.5%) was also obtained by our new formula. Our results confirmed the previous findings that the availability of iron is stimulated by the supplementation of vitamin C. Both formulae agreed in the absorption of iron, indicating that the endogenous excretion of iron (caused by the desquamated cells) in the intestine does not disguise the iron absorption.

PMID:1294703 Hashimoto F et al; J Nutr Sci Vitaminol (Tokyo) 38 (5): 435-49 (1992)

The absorption of a commercial brand of small-particle reduced iron was evaluated in 10 normal subjects. For each subject, the hemoglobin incorporation method was used to measure the true absorption of 60 mg of iron from either ferrous sulfate or ferric ammonium citrate. The iron tolerance test (ITT) was also studied for these two compounds and for reduced iron. This procedure consisted of measuring the area under the curve of plasma iron elevations at specified times for 6 hours, or the peak plasma iron, corrected by the plasma iron disappearance rate obtained from measuring plasma iron at specified times for 4 hours after the slow intravenous injection of 0.4 mg of iron as ferric citrate. Only the ITT was used to measure the absorption of 60 mg of reduced iron. Reference dose iron ascorbate absorption was measured in each subject. The absorption of ferric ammonium citrate and reduced iron was expressed as percent of dose and also as absorption percent of that of ferrous sulfate. Mean % geometric "true absorptions" were 39.0 for reference dose, 10.4 for FeSO4 and 2.4 for ferric ammonium citrate. The later was 23% that of FeSO4. By ITT the mean geometric % absorptions were 7.9, 3.7 and 3.2 for FeSO4, ferric ammonium citrate and reduced iron respectively, or 47 and 41% of that of FeSO4. We propose that the true absorption of the commercial brand of reduced iron tested was 20% that of FeSO4 based on the relation between the ITT results of reduced iron and the ITT and true absorption values of ferric ammonium citrate in relation to FeSO4.

PMID:11791474 Gonzalez H et al; Arch Latinoam Nutr 51 (3): 217-24 (2001)

Gastrointestinal absorption of iron is adequate ... /yet/ ... lower from ferrous citrate ... /than ferrous sulfate, fumarate, gluconate, succinate, glutamate, and lactate/.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1315

This study demonstrated that anticholinergic agents decreased iron absorption in man and animals. Six normal males were given 10 Ci of 59Fe ferrous citrate dissolved in water containing 250 mg of ferrous sulfate after an overnight fast. Whole body counts were done 4 hours later and used as baseline studies. Sixty minutes before the administration of radioiron, the subjects received a dose of 62.5 mg of hexocyclium methosulfate (Tral). The dose was repeated 6 hours later. Four hours after ingestion of radioiron, whole body counting was done. Every 5 days thereafter, for 15 days, a plateau of body radioactivity was reached in all subjects. Percentage absorption was calculated from the final to initial counts, after correction. Similar experiments were done in rats with atropine sulfate. In both experiments, the anticholinergic agent produced a decrease in iron absorption. The effect of atropine persisted when the iron was delivered intragastrically, but not intraduodenally. Another set of experiments showed that iron absorption decreases when radioiron is intraduodenally given in deproteinized acid gastric juice, or in 0.1N HCl, but not when mixed with neutralized gastric juice.

Orrego-Matte H et al; Am J Dige Dis 16 (9): 789-795 (1971)

The uptake of ferrous citrate 59Fe was studied in pregnant rats with or without a 4-dimethylamino-stilben(DS)-induced sarcoma tumor. ... The embryo showed higher concentrations of 59Fe. ... Iron loading only affected the embryo liver. Tumors and the placenta showed a different incorporation of 59Fe.

PMID:3857177 Anghileri LJ et al; Eur J Nucl Med 10 (5-6): 288-9 (1985)

5.4 Mechanism of Action

... Iron loading by 24-hour incubation with 0.36 mmol/L ferric ammonium citrate resulted in a decrease in the activity of nicotinamide adenine dinucleotide (NADH)-cytochrome c oxidoreductase (complex I+III) to 35.3%+/-11.2% of the value in untreated controls; of succinate-cytochrome c oxidoreductase (complex II+III) to 57.4%+/-3.1%; and of succinate dehydrogenase to 63.5%+/-12.6% (p < 0.001 in all cases). The decrease in activity of other mitochondrial enzymes, including NADH-ferricyanide reductase, succinate ubiquinone oxidoreductase (complex II), cytochrome c oxidase (complex IV), and ubiquinol cytochrome c oxidoreductase (complex III), was less impressive and ranged from 71.5%+/-15.8% to 91.5%+/-14.6% of controls. That the observed loss of respiratory enzyme activity was a specific effect of iron toxicity was clearly demonstrated by the complete restoration of enzyme activities by in vitro iron chelation therapy. Sequential treatment with iron and doxorubicin caused a loss of complex I+III and complex II+III activity that was greater than that seen with either agent alone but was only partially correctable by DF treatment. Alterations in cellular adenosine triphosphate measurements paralleled very closely the changes observed in respiratory complex activity.

PMID:9605112 Link G et al; J Lab Clin Med 131 (5): 466-74 (1998)

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