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    Sodium Citrate

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    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

    2D Structure

    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.