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Monoferrous Acid Citrate

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Chemistry

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Also known as: 23383-11-1

Molecular Formula

C₁₂H₁₀Fe₃O₁₄

Molecular Weight

545.73 g/mol

InChI Key

PFKAKHILNWLJRT-UHFFFAOYSA-H

1 2D Structure

Monoferrous Acid Citrate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 InChI

InChI=1S/2C6H8O7.3Fe/c2*7-3(8)1-6(13,5(11)12)2-4(9)10;;;/h2*13H,1-2H2,(H,7,8)(H,9,10)(H,11,12);;;/q;;3*+2/p-6

2.1.3 InChI Key

PFKAKHILNWLJRT-UHFFFAOYSA-H

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.[Fe+2].[Fe+2].[Fe+2]

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Citric Acid, Iron(2+) Salt

2. Fe(ii) Citrate

3. Fenelmin

4. Fenilene

5. Feredaim

6. Ferromia

7. Ferrostec

8. Ferrous Citrate

9. Ferrous Citrate Fe 58

10. Ferrous Citrate Fe 59

11. Ferrous Citrate Fe-58

12. Ferrous Citrate Fe-59

13. Ferrous-58 Citrate

14. Ferrous-59 Citrate

15. Ferrutope

16. Iromia

17. Monoferrous Acid Citrate

18. Sodium Ferrous Citrate

19. Tetrasodium Ferrous Dicitrate

2.2.2 Depositor-Supplied Synonyms

1. 23383-11-1

2.3 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₁₂H₁₀Fe₃O₁₄
Molecular Weight	545.73 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	14
Rotatable Bond Count	4
Exact Mass	545.811862 g/mol
Monoisotopic Mass	545.811862 g/mol
Topological Polar Surface Area	281 Å²
Heavy Atom Count	29
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	5

4 Drug and Medication Information

4.1 Therapeutic Uses

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)

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Trace Elements

A group of chemical elements that are needed in minute quantities for the proper growth, development, and physiology of an organism. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed) (See all compounds classified as Trace Elements.)

5.2 Absorption, Distribution and Excretion

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)

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