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1,2,3-Propanetricarboxylic acid, 2-hydroxy-, trisodium salt
Also known as: Trisodium citrate, 68-04-2, Citrosodine, Natrocitral, Sodium citrate anhydrous, Sodium citrate, anhydrous
Molecular Formula
C6H5Na3O7
Molecular Weight
258.07  g/mol
InChI Key
HRXKRNGNAMMEHJ-UHFFFAOYSA-K
FDA UNII
RS7A450LGA

Sodium salts of citric acid that are used as buffers and food preservatives. They are used medically as anticoagulants in stored blood, and for urine alkalization in the prevention of KIDNEY STONES.
1 2D Structure

1,2,3-Propanetricarboxylic acid, 2-hydroxy-, trisodium salt

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
trisodium;2-hydroxypropane-1,2,3-tricarboxylate
2.1.2 InChI
InChI=1S/C6H8O7.3Na/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*+1/p-3
2.1.3 InChI Key
HRXKRNGNAMMEHJ-UHFFFAOYSA-K
2.1.4 Canonical SMILES
C(C(=O)[O-])C(CC(=O)[O-])(C(=O)[O-])O.[Na+].[Na+].[Na+]
2.2 Other Identifiers
2.2.1 UNII
RS7A450LGA
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Anhydrous Sodium Citrate

2. Citra Ph

3. Monosodium Citrate

4. Sodium Citrate Dihydrate

5. Sodium Citrate Monobasic

6. Sodium Citrate, Anhydrous

7. Trisodium Citrate Dihydrate

2.3.2 Depositor-Supplied Synonyms

1. Trisodium Citrate

2. 68-04-2

3. Citrosodine

4. Natrocitral

5. Sodium Citrate Anhydrous

6. Sodium Citrate, Anhydrous

7. Citric Acid, Trisodium Salt

8. Trisodium Citrate, Anhydrous

9. 1,2,3-propanetricarboxylic Acid, 2-hydroxy-, Trisodium Salt

10. Anhydrous Sodium Citrate

11. Citric Acid Trisodium Salt

12. Sodium 2-hydroxypropane-1,2,3-tricarboxylate

13. Trisodium Citrate Anhydrous

14. Fema No. 3026

15. Trisodium-citrate

16. Anhydrous Trisodium Citrate

17. 994-36-5

18. Sodium Citrate,anhydrous

19. Rs7a450lga

20. Ins No.331(iii)

21. Ins-331(iii)

22. Chebi:53258

23. E-331(iii)

24. Trisodium 2-hydroxypropane-1,2,3-tricarboxylate

25. Trisodium;2-hydroxypropane-1,2,3-tricarboxylate

26. Mfcd00012462

27. Fema No. 3026, Anhydrous-

28. Citric Acid, Sodium Salt

29. Citrosodina

30. Citnatin

31. Citreme

32. Citrosodna

33. Sodium Citrate Hydrous

34. 1,2,3-propanetricarboxylic Acid, 2-hydroxy-, Sodium Salt

35. Ccris 3293

36. Sodium Citrate (na3c6h5o7)

37. Hsdb 5201

38. Einecs 200-675-3

39. Unii-rs7a450lga

40. N-1560

41. Natrii Citras

42. Tri-sodium Citrate

43. Trisodium 2-hydroxy-1,2,3-propanetricarboxylate

44. Sodium Citrate Salt

45. 1,2,3-propanetricarboxylic Acid, 2-hydroxy-, Sodium Salt (1:3)

46. Sodium (iii) Citrate

47. Sodium Citrate (usp)

48. Natrii Citras, Dehydrate

49. Ec 200-675-3

50. Anticoagulant Sodium Citrate

51. Chembl1355

52. Sodium Citrate [mi]

53. Citrate Concentrated Solution

54. Dtxsid2026363

55. Sodium Citrate [who-ip]

56. 2-hydroxy-1,2,3-propanetricarboxylic Acid, Trisodium Salt

57. Citric Acid Trisodium Salt, 99%

58. Natrii Citras [who-ip Latin]

59. Akos015915009

60. Citrate Solution, Ph ~3.0, 30 Mm

61. Db09154

62. Sodium Citrate Anhydrous [hsdb]

63. Anhydrous Trisodium Citrate [ii]

64. Sodium Citrate,anhydrous [vandf]

65. Ac-15008

66. E331

67. Sodium Citrate Dihydrate Usp Fine Granular

68. Sodium Citrate, Anhydrous [who-ip]

69. B7298

70. Ft-0623960

71. D05855

72. D77308

73. Sodium Citrate, 0.5m Buffer Solution, Ph 5.0

74. Sodium Citrate, 0.5m Buffer Solution, Ph 5.5

75. Sodium Citrate, 0.5m Buffer Solution, Ph 6.0

76. Sodium Citrate, 0.5m Buffer Solution, Ph 6.5

77. Anhydrous Trisodium Citrate [usp Monograph]

78. Q409728

79. J-520101

80. Citric Acid Trisodium Salt, Anhydrous, >=98% (gc)

81. Citrate Solution, Ph 3.6+/-0.1 (25 C), 27 Mm

82. Citric Acid Trisodium Salt, Vetec(tm) Reagent Grade, 98%

83. 2-hydroxy-1,2,3-propanenetricarboxylic Acid Trisodium Salt Dihydrate

84. Citrate Concentrated Solution, Bioultra, For Molecular Biology, 1 M In H2o

85. Buffer Solution Ph 5.0 (20 C), Citric Acid ~0.096 M, Sodium Hydroxide ~0.20 M

86. Citrate Concentrated Solution, Bioreagent, Suitable For Coagulation Assays, 4 % (w/v)

87. 8055-55-8

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 258.07 g/mol
Molecular Formula C6H5Na3O7
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count7
Rotatable Bond Count2
Exact Mass257.97283534 g/mol
Monoisotopic Mass257.97283534 g/mol
Topological Polar Surface Area141 Ų
Heavy Atom Count16
Formal Charge0
Complexity211
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count4
4 Drug and Medication Information
4.1 Therapeutic Uses

...USED AS AN EXPECTORANT...& SYSTEMIC ALKALIZER. SALINE EXPECTORANTS ARE ESPECIALLY USEFUL WHEN IT IS DESIRED TO LIQUEFY THICK, TENACIOUS SPUTUM. IN THE BODY, SODIUM CITRATE IS OXIDIZED TO BICARBONATE & EXCRETED IN THE URINE; THUS, WHEN GIVEN ORALLY IT IS USEFUL IN ACIDOSIS & TO OVERCOME EXCESSIVE URINARY ACIDITY.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 802


SODIUM CITRATE ALSO HAS A DIURETIC...ACTION.

American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 40:08


SODIUM CITRATE ALSO INCREASES THE URINARY EXCRETION OF CALCIUM. THEREFORE, IT HAS BEEN EMPLOYED IN HYPERCALCEMIA & TO FACILITATE ELIMINATION OF LEAD IN POISONING DUE TO THE LATTER AGENT. /SRP: FORMER USE/

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 802


MEDICATION (VET): ANTICOAGULANT FOR COLLECTION OF BLOOD /SRP: FORMER USE/

The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 1112


4.2 Drug Warning

WHEN GIVEN IN EXCESS AMT SODIUM CITRATE MAY PRODUCE ALKALOSIS & MAY CAUSE TETANY OR DEPRESS THE HEART BY DECREASING THE IONIZED CALCIUM LEVEL OF THE BLOOD.

American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 40:08


4.3 Drug Indication

Used as an anticoagulant during plasmophoresis as well as a neutralizing agent in the treatment of upset stomach and acidic urine.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Citrate prevents activation of the clotting cascade by chelating calcium ions. Citrate neutralizes acid in the stomach and urine, raising the pH.


5.2 MeSH Pharmacological Classification

Buffers

A chemical system that functions to control the levels of specific ions in solution. When the level of hydrogen ion in solution is controlled the system is called a pH buffer. (See all compounds classified as Buffers.)


Food Preservatives

Substances capable of inhibiting, retarding or arresting the process of fermentation, acidification or other deterioration of foods. (See all compounds classified as Food Preservatives.)


Anticoagulants

Agents that prevent BLOOD CLOTTING. (See all compounds classified as Anticoagulants.)


5.3 FDA Pharmacological Classification
5.3.1 Pharmacological Classes
Anti-coagulant [EPC]; Calcium Chelating Activity [MoA]; Calculi Dissolution Agent [EPC]; Decreased Coagulation Factor Activity [PE]; Acidifying Activity [MoA]
5.4 ATC Code

B - Blood and blood forming organs

B05 - Blood substitutes and perfusion solutions

B05C - Irrigating solutions

B05CB - Salt solutions

B05CB02 - Sodium citrate


5.5 Absorption, Distribution and Excretion

Absorption

Tmax of 98-130min.


Route of Elimination

Largely eliminated through hepatic metabolism with very little cleared by the kidneys.


Volume of Distribution

19-39L.


Clearance

Total clearance of 313-1107mL/min.


IN THE BODY, SODIUM CITRATE IS OXIDIZED TO BICARBONATE & EXCRETED IN THE URINE...

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 802


5.6 Metabolism/Metabolites

Citrate is metabolized to bicarbonate in the liver and plays a role as an intermediate in the citric acid cycle.


IN THE BODY, SODIUM CITRATE IS OXIDIZED TO BICARBONATE...

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 802


5.7 Biological Half-Life

18-54 min


5.8 Mechanism of Action

Citrate chelates free calcium ions preventing them from forming a complex with tissue factor and coagulation factor VIIa to promote the activation of coagulation factor X. This inhibits the extrinsic initiation of the coagulation cascade. Citrate may also exert an anticoagulant effect via a so far unknown mechanism as restoration of calcium concentration does not fully reverse the effect of citrate. Citrate is a weak base and so reacts with hydrochloric acid in the stomach to raise the pH. It it further metabolized to bicarbonate which then acts as a systemic alkalizing agent, raising the pH of the blood and urine. It also acts as a diuretic and increases the urinary excretion of calcium.


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