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Chemistry

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Also known as: Ferrous gluconate, Ferrousgluconate, Iron gluconate, Ferrous gluconate anhydrous, 299-29-6, Iron(ii) gluconate, anhydrous
Molecular Formula
C12H22FeO14
Molecular Weight
446.14  g/mol
InChI Key
VRIVJOXICYMTAG-IYEMJOQQSA-L
FDA UNII
781E2AXH0K

Iron, Bis(D-Gluconato-Kappao1,Kappao2)-
Ferrous Gluconate is a form of mineral iron for oral administration, Ferrous Gluconate is absorbed in the stomach and small intestine and combines with apoferritin to form ferritin, which is stored in the liver, spleen, red bone marrow, and intestinal mucosa. Important in transport of oxygen by hemoglobin to the tissues, iron is also found in myoglobin, transferrin, and ferritin, and is as a component of many enzymes such as catalase, peroxidase, and cytochromes. (NCI04)
1 2D Structure

Iron, Bis(D-Gluconato-Kappao1,Kappao2)-

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
iron(2+);(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoate
2.1.2 InChI
InChI=1S/2C6H12O7.Fe/c2*7-1-2(8)3(9)4(10)5(11)6(12)13;/h2*2-5,7-11H,1H2,(H,12,13);/q;;+2/p-2/t2*2-,3-,4+,5-;/m11./s1
2.1.3 InChI Key
VRIVJOXICYMTAG-IYEMJOQQSA-L
2.1.4 Canonical SMILES
C(C(C(C(C(C(=O)[O-])O)O)O)O)O.C(C(C(C(C(C(=O)[O-])O)O)O)O)O.[Fe+2]
2.1.5 Isomeric SMILES
C([C@H]([C@H]([C@@H]([C@H](C(=O)[O-])O)O)O)O)O.C([C@H]([C@H]([C@@H]([C@H](C(=O)[O-])O)O)O)O)O.[Fe+2]
2.2 Other Identifiers
2.2.1 UNII
781E2AXH0K
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Apo-ferrous Gluconate

2. Dextriferron

3. Eisen-sandoz

4. Feg Iron

5. Fergon

6. Ferroglucon

7. Ferrogluconaat Fna

8. Ferrous Gluconate

9. Ferrum Verla

10. Loesferron

11. Losferron

12. Rulofer G

13. Simron

14. Vitaferro Brause

2.3.2 Depositor-Supplied Synonyms

1. Ferrous Gluconate

2. Ferrousgluconate

3. Iron Gluconate

4. Ferrous Gluconate Anhydrous

5. 299-29-6

6. Iron(ii) Gluconate, Anhydrous

7. 781e2axh0k

8. Iron(2+) Gluconate (1:2)

9. 18829-42-0

10. D-gluconic Acid, Iron(2+) Salt (2:1)

11. Iron(2+);(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanoate

12. Ferrous Gluconate Dihydrate

13. Ferroglyconicum

14. Biofergate

15. Ferronicum

16. Glucoferron

17. Feravol

18. Ferlucon

19. Ferrose

20. Flourish

21. Glucomax

22. Gluferate

23. Nionate

24. Entron

25. Fenton

26. Ferox

27. Irox

28. Ferro-agepha

29. Ferrum Polon

30. Gluco-ferrum

31. Ray-gluciron

32. Iromon (gador)

33. Fergon Preparations

34. Iron-ii Gluconate

35. Irox (gador)

36. Ferrin 55

37. Gluconic Acid Iron Salt

38. 6047-12-7

39. Ferrous Gluconate [usan]

40. Unii-781e2axh0k

41. Hsdb 461

42. Iron Digluconate

43. Iron, Bis(d-gluconato-o1,o2)-

44. Einecs 206-076-3

45. 699014-53-4

46. Gluconic Acid, Iron(2+) Salt (2:1), D-

47. Ec 206-076-3

48. Schembl35424

49. Ferrous Gluconate [mi]

50. Ferrous Gluconate [hsdb]

51. Akos015901488

52. Db14488

53. Gluconic Acid, Iron(2+) Salt (2:1)

54. Iron, Bis(d-gluconato-kappao1,kappao2)-

55. Q421291

2.4 Create Date
2007-12-12
3 Chemical and Physical Properties
Molecular Weight 446.14 g/mol
Molecular Formula C12H22FeO14
Hydrogen Bond Donor Count10
Hydrogen Bond Acceptor Count14
Rotatable Bond Count8
Exact Mass446.035891 g/mol
Monoisotopic Mass446.035891 g/mol
Topological Polar Surface Area283 Ų
Heavy Atom Count27
Formal Charge0
Complexity165
Isotope Atom Count0
Defined Atom Stereocenter Count8
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count3
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


...Iron absorption tests were performed on 55 patients 3.2+/-2.0 years after isolated gastric bypass to identify those at higher risk for the late development of anemia. Twenty-nine of this group agreed to a therapeutic trial of iron /gluconate/ alone or with vitamin C over a 2-month period. All 55 patients were followed up for 27.1+/-1.0 months following the study. The iron absorption test identified patients with low iron stores, as indicated by low serum ferritin, and those with sufficient absorption surface to benefit from oral iron. The addition of vitamin C appears to enhance the therapeutic effect of iron by correcting ferritin deficits (P < 0.01) and anemia (P < 0.05). Differences in intestine length bypassed by the operation (10 vs. 100 cm) did not affect late ferritin and hemoglobin values.

PMID:10065575 Rhode BM et al; Obes Surg 9 (1): 17-21 (1999)


...A study was... conducted on 40 women aged 20-35, with iron-deficiency anemia during or immediately after pregnancy all of whom presented Hb <10 gr/dL, Ht <33% and serum iron <60 ug/dL. All women with pregnancy-related pathological conditions, pre-existing on concomitant disease (Type I diabetes, heart diseases etc.) were excluded from the study. The women whose blood chemical parameters were largely homogeneous at the start of the study were divided into four treatment groups of 10 patients each and were treated as follows: Group A with oral liquid ferrous gluconate (75 mg per diem in 2 vials a day); Group B with solid ferrous gluconate (80 mg per diem in a single effervescent tablet); Group C with solid ferrous sulfate (105 mg per diem in a single tablet); and Group D with ferric protein succinylate (80 mg per diem in 2 vials a day). All were given iron treatment for 30 days. Treatment efficacy was analysed by comparing basal and final parameters using the T-test for paired dependent samples. The tolerance of the 4 treatment protocols was assessed by the analysis of any side effects such as nausea, vomiting, epigastric pain, diarrhea, constipation or other disorders reported by patients during treatment. Analysis of the therapeutic efficacy parameters (red blood cells, hemoglobin, hematocrit and serum iron) showed significant improvements but no statistically significant differences between the groups. However, the Group A patients treated with oral doses of liquid ferrous gluconate received a significantly lower cumulative dose of iron elements than the other groups: in detail 150 mg (p<0.05) less than Groups B and D; 900 mg (<0.001) less than Group C. By the end of treatment the Group A patients revealed significant increases versus basal values in red blood cells (p<0.001) 1,051,000 per cu mm or 33%, in Hb (p<0.001) 2.83 gr/dL or 32%, in Ht (p<0.001) 8.32% or 32%, in serum iron (p<0.05) 19.5 ug/dL or 61%. The same group also showed an increase in ferritin amounting to 7.8 ug/dL or 24% of the basal value. As to safety, only Group A patients reported no side effects and produced no drop-outs. Gastrointestinal and other aspecific side effects caused 1 drop-out each in Groups B and C and 2 drop-outs in Group D.

PMID:9005381 Casparis D et al; Minerva Ginecol 48 (11): 511-518 (1996)


4.2 Drug Warning

...A study was therefore conducted on 40 women aged 20-35, with iron-deficiency anemia during or immediately after pregnancy all of whom presented Hb <10 gr/dL, Ht <33% and serum iron <60 ug/dL. ...As to safety, only Group A patients reported no side effects and produced no drop-outs. Gastrointestinal and other aspecific side effects caused 1 drop-out each in Groups B and C and 2 drop-outs in Group D.

PMID:9005381 Casparis D et al; Minerva Ginecol 48 (11): 511-518 (1996)


The effect of long-term oral iron supplementation on morbidity due to diarrhea, dysentery and respiratory infections in 349 children, aged 2-48 months, living in a poor community of Bangladesh, was evaluated in this double-blind study. The treatment group received 125 mg of ferrous gluconate (15 mg elemental iron) plus multivitamins and the controls received only multivitamins, daily for 15 months. House-to-house visits were made on alternate days by trained community health workers for recording symptoms and duration of illnesses and for monitoring medicine intake. Seventy-six percent of the children continued the syrup for over 1 yr. No untoward effects were noticed in either treatment group. The attack rates for diarrhea, dysentery and acute respiratory tract infections (ARI) were 3, 3 and 5 episodes per child per year, respectively. Each episode of diarrhea lasted a mean of 3 days, and those of dysentery and ARI, 5 days. The two treatment groups did not differ in the number of episodes, mean duration of each episode, or total days of illnesses due to diarrhea, dysentery and ARI. However, a 49% greater number of episodes of dysentery was observed with iron supplementation in a subset of the study children who were less than 12 months old (P=0.03).

PMID:9237937 Mitra AK et al; J Nutr 127 (8): 1451-5 (1997)


4.3 Drug Indication

Used in preventing and treating iron-deficiency anemia.


5 Pharmacology and Biochemistry
5.1 Pharmacology

The major activity of supplemental iron is in the prevention and treatment of iron deficiency anemia. Iron has putative immune-enhancing, anticarcinogenic and cognition-enhancing activities.


5.2 MeSH Pharmacological Classification

Hematinics

Agents which improve the quality of the blood, increasing the hemoglobin level and the number of erythrocytes. They are used in the treatment of anemias. (See all compounds classified as Hematinics.)


5.3 ATC Code

B - Blood and blood forming organs

B03 - Antianemic preparations

B03A - Iron preparations

B03AA - Iron bivalent, oral preparations

B03AA03 - Ferrous gluconate


B - Blood and blood forming organs

B03 - Antianemic preparations

B03A - Iron preparations

B03AD - Iron in combination with folic acid

B03AD05 - Ferrous gluconate


5.4 Absorption, Distribution and Excretion

Absorption

The efficiency of absorption depends on the salt form, the amount administered, the dosing regimen and the size of iron stores. Subjects with normal iron stores absorb 10% to 35% of an iron dose. Those who are iron deficient may absorb up to 95% of an iron dose.


The iron bioavailability and acute oral toxicity in rats of a ferrous gluconate compound stabilized with glycine (SFG), designed for food fortification, was studied in this work by means of the prophylactic method and the Wilcoxon method, respectively. For the former studies, SFG was homogeneously added to a basal diet of low iron content, reaching a final iron concentration of 20.1 +/- 2.4 mg Fe/kg diet. A reference standard diet using ferrous sulfate as an iron-fortifying source (19.0 +/- 2.1 mg Fe/kg diet) and a control diet without iron additions (9.3 +/- 1.4 mg Fe/kg diet) were prepared in the laboratory in a similar way. These diets were administered to three different groups of weaning rats during 23 d as the only type of solid nourishment. The iron bioavailability of SFG was calculated as the relationship between the mass of iron incorporated into hemoglobin during the treatment and the total iron intake per animal. This parameter resulted in 36.6 +/- 6.2% for SFG, whereas a value of 35.4 +/- 8.0% was obtained for ferrous sulfate.

PMID:12907829 Lysionek AE et al; Biol Trace Elem Res 94 (1): 73-8 (2003)


Gastrointestinal absorption of iron is adequate and essentially equal from...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


5.5 Mechanism of Action

Iron is necessary for the production of hemoglobin. Iron-deficiency can lead to decreased production of hemoglobin and a microcytic, hypochromic anemia.


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