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Calcium Citrate

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Also known as: 813-94-5, Tricalcium dicitrate, Tricalcium citrate, Acicontral, Calcitrate, Calcium citrate, tribasic

Molecular Formula

C₁₂H₁₀Ca₃O₁₄

Molecular Weight

498.4 g/mol

InChI Key

FNAQSUUGMSOBHW-UHFFFAOYSA-H

FDA UNII

86117BWO7P

A colorless crystalline or white powdery organic, tricarboxylic acid occurring in plants, especially citrus fruits, and used as a flavoring agent, as an antioxidant in foods, and as a sequestrating agent. (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)

1 2D Structure

Calcium Citrate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

tricalcium;2-hydroxypropane-1,2,3-tricarboxylate

2.1.2 InChI

InChI=1S/2C6H8O7.3Ca/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

FNAQSUUGMSOBHW-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.[Ca+2].[Ca+2].[Ca+2]

2.2 Other Identifiers

2.2.1 UNII

86117BWO7P

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Calcium Citrates

2. Citrate, Calcium

3. Citrates, Calcium

2.3.2 Depositor-Supplied Synonyms

1. 813-94-5

2. Tricalcium Dicitrate

3. Tricalcium Citrate

4. Acicontral

5. Calcitrate

6. Calcium Citrate, Tribasic

7. Calcium Citrate Anhydrous

8. Calcium 2-hydroxy-1,2,3-propanetricarboxylate (3:2)

9. Tricalcium Citrate Tetrahydrate

10. Ins No.333(iii)

11. Ins-333(iii)

12. 2-hydroxy-1,2,3-propanetricarboxylic Acid Calcium Salt (2:3)

13. 1,2,3-propanetricarboxylic Acid, 2-hydroxy-, Calcium Salt (2:3)

14. 86117bwo7p

15. E-333(iii)

16. Tricalcium;2-hydroxypropane-1,2,3-tricarboxylate

17. Calcimax

18. Citrical

19. Calcium (as Citrate)

20. Calcium 2-hydroxypropane-1,2,3-tricarboxylate (3:2)

21. Tribasic Calcium Citrate

22. Calcium Citrate [usan]

23. 7693-13-2

24. Hsdb 5756

25. Citric Acid, Calcium Salt (2:3)

26. Einecs 212-391-7

27. Calciumcitrate

28. Unii-86117bwo7p

29. Lime Citrate

30. Calcium Citrate Powder

31. Calcium Citrate Tribasic

32. Calcium Citrate, Anhydrous

33. Ec 212-391-7

34. Calcium Citrate Usp, Fcc

35. Tricalcium Bis(citric Acid)

36. Calcium Citrate [mi]

37. Calcium Citrate [hsdb]

38. Chembl2106123

39. Dtxsid7061148

40. Calcium Citrate [who-dd]

41. Citric Acid Calcium Salt (2:3)

42. Chebi:190513

43. Mfcd00078618

44. Akos015839590

45. Db11093

46. Calcium Citrate Malate Glycinate 21% 40m

47. Q420280

48. Calcium Citrate Malate Carbonate 23%, Coarse Granu

49. J-509604

50. Calcium 2-hydroxypropane-1,2,3-tricarboxylate (3/2)

51. Tricalcium Bis(2-hydroxypropane-1,2,3-tricarboxylic Acid)

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₂H₁₀Ca₃O₁₄
Molecular Weight	498.4 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	14
Rotatable Bond Count	4
Exact Mass	497.8948275 g/mol
Monoisotopic Mass	497.8948275 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 Drug Indication

For use as an over the counter calcium supplement.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Increases plasma calcium levels leading to a decrease in calcium flux and increase in calcium deposition into bone

5.2 MeSH Pharmacological Classification

Food Additives

Substances used in the processing or storage of foods or animal feed including ANTIOXIDANTS; FOOD PRESERVATIVES; FOOD COLORING AGENTS; FLAVORING AGENTS; ANTI-INFECTIVE AGENTS; EXCIPIENTS and other similarly used substances. Many of the same substances are used as PHARMACEUTIC AIDS. (See all compounds classified as Food Additives.)

5.3 ATC Code

A - Alimentary tract and metabolism

A12 - Mineral supplements

A12A - Calcium

A12AA - Calcium

A12AA13 - Calcium citrate

5.4 Absorption, Distribution and Excretion

Absorption

The percentage of calcium absorbed varies inversely with intake. Tmax of about 3.5-5h varying with formulation.

Route of Elimination

Cleared via the kidneys but largely reabsorbed (98-99%) under normal conditions.

5.5 Mechanism of Action

Calcium citrate increases plasma calcium levels. This reduces calcium flux from osteocyte activity by reducing the secretion of parathyroid hormone (PTH). Calcium does this by stimulating a G-protein coupled calcium receptor on the surface of parathyroid cells. The reduction in calcium flux increases the amount of calcium deposited in bone resulting in an increase in bone mineral density. The reduction in PTH secretion also reduces the amount of vitamin D metabolized to its active form, calcidiol. Since calcidiol increases the expression of calcium dependent ATPases and transient receptor potential cation channel subfamily V member 6 (TRPV6) both of which are involved in calcium uptake from the gut, a reduction in calcidiol results in less calcium absorption. Additionally, TRPV5, the channel responsible for calcium reabsorption in the kidney, is downregulated when PTH secretion is reduced thus increasing calcium excretion via the kidneys. Another hormone, calitonin, is likely involved in the reduction of bone resorption during periods of high plasma calcium.

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