Sodium citrate

Identification

Summary

Sodium citrate is an ingredient used for the anticoagulation of whole blood as part of automated apheresis procedures.

Brand Names
As 3, Bss, Bss Ophthalmic Solution, Cpda-1 Blood Collection System, Dalmacol, EnLyte, Intersol, Leukotrap, Nauzene, Oracit, Tricitrasol
Generic Name
Sodium citrate
DrugBank Accession Number
DB09154
Background

Sodium citrate is the sodium salt of citric acid. It is white, crystalline powder or white, granular crystals, slightly deliquescent in moist air, freely soluble in water, practically insoluble in alcohol. Like citric acid, it has a sour taste. From the medical point of view, it is used as alkalinizing agent. It works by neutralizing excess acid in the blood and urine. It has been indicated for the treatment of metabolic acidosis.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 258.068
Monoisotopic: 257.97283534
Chemical Formula
C6H5Na3O7
Synonyms
  • Anhydrous sodium citrate
  • Anhydrous trisodium citrate
  • Citric acid, trisodium salt
  • Natrii citras
  • Natrocitral
  • Sodium citrate anhydrous
  • Sodium citrate, anhydrous
  • Sodium citrate,anhydrous
  • trisodium citrate anhydrous
  • Trisodium citrate concentration
  • Trisodium citrate, anhydrous
  • Trisodium-citrate
External IDs
  • E-331(III)
  • FEMA NO. 3026, ANHYDROUS-
  • INS NO.331(III)
  • INS-331(III)

Pharmacology

Indication

Used as an anticoagulant during plasmophoresis as well as a neutralizing agent in the treatment of upset stomach and acidic urine Label 6 7.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatAcidosisCombination Product in combination with: Citric acid (DB04272), Sodium chloride (DB09153), Potassium citrate (DB09125)••••••••••••••••••••
Used in combination to treatAllergic coughCombination Product in combination with: Diphenhydramine (DB01075), Dextromethorphan (DB00514)•••••••••••••••••
Used in combination to treatAllergiesCombination Product in combination with: Dextromethorphan (DB00514), Diphenhydramine (DB01075)•••••••••••••••••
Used in combination to treatAsthmaCombination Product in combination with: Phenylephrine (DB00388), Chlorpheniramine (DB01114), Ammonium chloride (DB06767)•••••••••••••••••
Used in combination to treatAsthma chronic, coughCombination Product in combination with: Dextromethorphan (DB00514), Diphenhydramine (DB01075)•••••••••••••••••
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Citrate prevents activation of the clotting cascade by chelating calcium ions. Citrate neutralizes acid in the stomach and urine, raising the pH 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 1 2. 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 1. 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 8. It also acts as a diuretic and increases the urinary excretion of calcium.

Absorption

Tmax of 98-130min 3.

Volume of distribution

19-39L 3.

Protein binding

Not Available

Metabolism

Citrate is metabolized to bicarbonate in the liver and plays a role as an intermediate in the citric acid cycle 5 9.

Route of elimination

Largely eliminated through hepatic metabolism with very little cleared by the kidneys 3 4.

Half-life

18-54 min 3

Clearance

Total clearance of 313-1107mL/min 3.

Adverse Effects
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Toxicity

Overdose toxicity is mainly due to alkalosis as well as tetany or depressed heart function due to lack of free calcium 8.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbciximabThe risk or severity of bleeding can be increased when Abciximab is combined with Sodium citrate.
AceclofenacThe risk or severity of bleeding and hemorrhage can be increased when Aceclofenac is combined with Sodium citrate.
AcemetacinThe risk or severity of bleeding and hemorrhage can be increased when Sodium citrate is combined with Acemetacin.
AcenocoumarolThe risk or severity of bleeding can be increased when Acenocoumarol is combined with Sodium citrate.
AcetophenazineAcetophenazine may increase the neurotoxic activities of Sodium citrate.
Food Interactions
  • Take with or without food. Recommendations vary from product to product - consult individual product monographs for additional information.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Sodium citrate dihydrateB22547B95K6132-04-3NLJMYIDDQXHKNR-UHFFFAOYSA-K
Active Moieties
NameKindUNIICASInChI Key
Citric acidunknownXF417D3PSL77-92-9KRKNYBCHXYNGOX-UHFFFAOYSA-N
Sodium cationionicLYR4M0NH3717341-25-2FKNQFGJONOIPTF-UHFFFAOYSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Anticoagulant Sod Citrate Soltn 4gm/100mlSolution4 gExtracorporealBaxter Laboratories1990-12-31Not applicableCanada flag
Anticoagulant Sodium CitrateSolution10 g/250mLIntravenousMedsep Corporation2011-04-15Not applicableUS flag
Anticoagulant Sodium Citrate 4% W/V Solution, USPSolution4 g / 100 mLUnknownHaemonetics Corporation2012-10-01Not applicableCanada flag
Anticoagulant Sodium Citrate Sol 4% USPLiquid4 %IntravenousCutter Med & Biol, Division Of Miles Canada Ltd.1988-12-311996-09-09Canada flag
Anticoagulant Sodium Citrate Solution USPSolution4 gExtracorporealFenwal, Inc.2011-11-012021-06-30Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Anticoagulant Sodium CitrateSolution40 mg/1mLIntravenousCSL Plasma Inc.2022-07-01Not applicableUS flag
Anticoagulant Sodium CitrateSolution40 mg/1mLExtracorporealLaboratorios Grifols Sa2019-10-25Not applicableUS flag
Sodium Citrate 4% w/v AnticoagulantInjection, solution4 g/100mLIntravenousTerumo Bct, Ltd2018-06-26Not applicableUS flag
Sodium Citrate w/v AnticoagulantInjection, solution4 g/100mLIntravenousTerumo Bct, Ltd2018-06-26Not applicableUS flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Bromo SeltzerPowder3.5 g / 5.83 gOralWarner Lambert Canada Inc.1976-12-311999-08-13Canada flag
CVS Health Nausea ReliefTablet, chewable230 mg/1OralCVS Pharmacy,Inc.2019-05-22Not applicableUS flag
Emetrol ChewablesTablet, chewable230 mg/1OralWellSpring Pharmaceutical Corporation2022-03-15Not applicableUS flag
Emetrol Chewables Mixed BerryTablet, chewable230 mg/1OralWellSpring Pharmaceutical Corporation2023-07-01Not applicableUS flag
Emetrol Chewables OrangeTablet, chewable230 mg/1OralWellSpring Pharmaceutical Corporation2023-07-01Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
A-C-D SolutionSodium citrate (250 mg / 10 mL) + Citric acid (80 mg / 10 mL) + Dextrose, unspecified form (132 mg / 10 mL)LiquidIntravenousDraximage A Division Of Draxis Specialty Pharmaceuticals Inc1959-12-312003-07-08Canada flag
Acd ASodium citrate (2.2 g/100mL) + Citric acid monohydrate (0.80 g/100mL) + D-glucose monohydrate (2.45 g/100mL)Injection, solutionIntravenousTerumo BCT Ltd2002-02-25Not applicableUS flag
Acd ASodium citrate dihydrate (2.2 g/100mL) + Citric acid monohydrate (0.8 g/100mL) + D-glucose monohydrate (2.45 g/100mL)Injection, solutionIntravenousTerumo Bct, Ltd.2002-02-25Not applicableUS flag
Acd ASodium citrate dihydrate (2.2 g/100mL) + Citric acid monohydrate (0.8 g/100mL) + D-glucose monohydrate (2.45 g/100mL)Injection, solutionIntravenousTerumo Bct, Ltd.2002-02-25Not applicableUS flag
ACD Blood-Pack Units (PL 146 Plastic)Sodium citrate dihydrate (1.48 g/67.5mL) + Citric acid (493 mg/67.5mL) + D-glucose monohydrate (1.65 g/67.5mL)SolutionExtracorporealFenwal, Inc.2007-03-01Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Anticoagulant Citrate Dextrose Solution-ASodium citrate (2.20 g/100mL) + Citric acid monohydrate (0.73 g/100mL) + Dextrose, unspecified form (2.45 g/100mL)SolutionExtracorporealBiomet Biologics2010-01-012010-09-06US flag
CVS Health Nausea ReliefSodium citrate dihydrate (230 mg/1)Tablet, chewableOralCVS Pharmacy,Inc.2019-05-22Not applicableUS flag
Cytosol Ophthalmics - Balanced Salt SolutionSodium citrate dihydrate (1.70 mg/1mL) + Calcium chloride dihydrate (48 mg/1mL) + Magnesium chloride hexahydrate (30 mg/1mL) + Potassium chloride (75 mg/1mL) + Sodium acetate trihydrate (3.90 mg/1mL) + Sodium chloride (6.40 mg/1mL)SolutionIrrigationBiomet Biologics2010-01-012010-09-04US flag
Cytra 3Sodium citrate (500 mg/5mL) + Citric acid monohydrate (334 mg/5mL) + Potassium citrate monohydrate (550 mg/5mL)SyrupOralPegasus Laboratories2006-05-052009-10-17US flag
Cytra 3Sodium citrate (500 mg/5mL) + Citric acid monohydrate (334 mg/5mL) + Potassium citrate monohydrate (550 mg/5mL)SyrupOralCypress Pharmaceuticals, Inc2008-07-292014-10-11US flag

Categories

ATC Codes
B05CB02 — Sodium citrate
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Tricarboxylic acids and derivatives
Direct Parent
Tricarboxylic acids and derivatives
Alternative Parents
Tertiary alcohols / Carboxylic acid salts / Carboxylic acids / Organic sodium salts / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Alcohol / Aliphatic acyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid salt / Hydrocarbon derivative / Organic alkali metal salt / Organic oxide / Organic oxygen compound / Organic salt
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
organic sodium salt (CHEBI:53258)
Affected organisms
Not Available

Chemical Identifiers

UNII
RS7A450LGA
CAS number
68-04-2
InChI Key
HRXKRNGNAMMEHJ-UHFFFAOYSA-K
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
IUPAC Name
trisodium 2-hydroxypropane-1,2,3-tricarboxylate
SMILES
[Na+].[Na+].[Na+].OC(CC([O-])=O)(CC([O-])=O)C([O-])=O

References

General References
  1. Mann KG, Whelihan MF, Butenas S, Orfeo T: Citrate anticoagulation and the dynamics of thrombin generation. J Thromb Haemost. 2007 Oct;5(10):2055-61. [Article]
  2. Palta S, Saroa R, Palta A: Overview of the coagulation system. Indian J Anaesth. 2014 Sep;58(5):515-23. doi: 10.4103/0019-5049.144643. [Article]
  3. Kramer L, Bauer E, Joukhadar C, Strobl W, Gendo A, Madl C, Gangl A: Citrate pharmacokinetics and metabolism in cirrhotic and noncirrhotic critically ill patients. Crit Care Med. 2003 Oct;31(10):2450-5. [Article]
  4. Zheng Y, Xu Z, Zhu Q, Liu J, Qian J, You H, Gu Y, Hao C, Jiao Z, Ding F: Citrate Pharmacokinetics in Critically Ill Patients with Acute Kidney Injury. PLoS One. 2013 Jun 18;8(6):e65992. doi: 10.1371/journal.pone.0065992. Print 2013. [Article]
  5. Li K, Xu Y: Citrate metabolism in blood transfusions and its relationship due to metabolic alkalosis and respiratory acidosis. Int J Clin Exp Med. 2015 Apr 15;8(4):6578-84. eCollection 2015. [Article]
  6. FDA Monograph: Sodium Citrate Tablet [Link]
  7. FDA Monograph: Sodium Citrate Liquid [Link]
  8. TOXNET: Trisodium Citrate [Link]
  9. SMPDB: Citric Acid Cycle [Link]
KEGG Drug
D05855
PubChem Compound
6224
PubChem Substance
310265067
ChemSpider
5989
RxNav
56466
ChEBI
53258
ChEMBL
CHEMBL1355
Wikipedia
Sodium_citrate
FDA label
Download (124 KB)
MSDS
Download (77.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedNot AvailableCorneal Staining1
4CompletedOtherEnd Stage Renal Disease (ESRD) / End-Stage Renal Disease (ESRD)1
4CompletedPreventionCatheter Related Infections1
4CompletedPreventionCentral Line Associated Blood Stream Infections (CLABSI)1
4CompletedScreeningColonoscopy1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
LiquidIntravenous
Kit; solutionIntravenous
SolutionIrrigation; Parenteral
SolutionIntraocular
Injection, solutionExtracorporeal
SolutionUnknown
SolutionExtracorporeal
SolutionExtracorporeal4 g
SolutionExtracorporeal40 mg/1mL
SolutionIntravenous10 g/250mL
SolutionIntravenous40 mg/1mL
SolutionUnknown4 g / 100 mL
LiquidIntravenous4 %
SolutionExtracorporeal0.8 g/100ml
SolutionOther
SolutionOphthalmic
Injection, powder, for solutionIntramuscular
Injection, solutionIntramuscular
SuppositoryRectal
Tablet, effervescentOral
PowderOral3.5 g / 5.83 g
SolutionParenteral136 mmol/l
Powder, for solutionOral
KitIntravenous
SolutionRectal0.63 g
SolutionRectal630 mg
Tablet, chewableOral230 mg/1
SolutionIrrigation
LiquidOral
SolutionOral
SolutionOral334 mg/5ml
SolutionOral62.5 mg/5ml
SolutionIntravenous4.21 g/1000ml
Granule, for solutionOral
SolutionOral0.2600 g
Powder, for solutionOral460 mg/1
Capsule, liquid filledOral
Capsule, delayed release pelletsOral
Injection, suspensionIntramuscular
SyrupOral135 mg/5ml
Drug delivery systemOral20.000 g
LiquidIntraocular
Syrup
PowderOral2.65 g / pck
Drug delivery systemOral
EnemaRectal
Enema; liquidRectal
LiquidRectal
EnemaRectal12.5 % w/w
SyrupOral5 mg/5ml
SyrupOral
SyrupOral0.921 g/15mL
EmulsionRectal
Solution, concentrateOral
SolutionIntraocular; Ophthalmic
PowderOral2.645 g / pck
SolutionOral1.188 g
PowderOral
KitOral
Tablet, chewableOral
SolutionIntravenous5.03 g/l
EnemaRectal0.35 g
SyrupOral100 mg/5ml
Injection, solutionExtracorporeal
SolutionExtracorporeal
SolutionIntravenous10.0 g/250mL
Injection, solutionIntravenous4 g/100mL
SolutionIntravenous4 g/100mL
SolutionIntravenous2 g/50mL
Powder, for solutionOral2.9 g
SolutionIntraocular; Irrigation
SyrupOral102 mg/5ml
SolutionIntravenous
Injection, solutionIntravenous
GranuleOral
SuspensionOral62.5 mg/5ml
SolutionExtracorporeal14 g/30mL
Granule, effervescentOral0.72 g
Powder, for solutionOral
Granule, effervescentOral
PowderOral20.00 g
SuspensionOral135 mg/5ml
LiquidOphthalmic
Tablet
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)300MSDS
water solubility29.4g/LMSDS
Predicted Properties
PropertyValueSource
Water Solubility73.7 mg/mLALOGPS
logP-0.55ALOGPS
logP-1.3Chemaxon
logS-0.54ALOGPS
pKa (Strongest Acidic)3.05Chemaxon
pKa (Strongest Basic)-4.2Chemaxon
Physiological Charge-3Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area140.62 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity68.14 m3·mol-1Chemaxon
Polarizability14.23 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0a4i-0090000000-159e2fe9d3ea097b6f77
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-125.66848
predicted
DeepCCS 1.0 (2019)
[M+H]+127.655396
predicted
DeepCCS 1.0 (2019)
[M+Na]+133.56429
predicted
DeepCCS 1.0 (2019)

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Dicarboxylic acid transmembrane transporter activity
Specific Function
Transports C5-C7 oxodicarboxylates across the inner membranes of mitochondria. Can transport 2-oxoadipate, 2-oxoglutarate, adipate, glutarate, and to a lesser extent, pimelate, 2-oxopimelate, 2-ami...
Gene Name
SLC25A21
Uniprot ID
Q9BQT8
Uniprot Name
Mitochondrial 2-oxodicarboxylate carrier
Molecular Weight
33302.88 Da
References
  1. UniProt: Mitochondrial 2-oxodicarboxylate carrier [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Low-affinity sodium:dicarboxylate symporter activity
Specific Function
Cotransport of sodium ions and dicarboxylates such as succinate and citrate.
Gene Name
SLC13A2
Uniprot ID
Q13183
Uniprot Name
Solute carrier family 13 member 2
Molecular Weight
64409.495 Da
References
  1. UniProt: Solute carrier family 13 member 2 [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Succinate transmembrane transporter activity
Specific Function
High-affinity sodium/citrate cotransporter that mediates citrate entry into cells. The transport process is electrogenic; it is the trivalent form of citrate rather than the divalent form that is r...
Gene Name
SLC13A5
Uniprot ID
Q86YT5
Uniprot Name
Solute carrier family 13 member 5
Molecular Weight
63061.605 Da
References
  1. Inoue K, Zhuang L, Maddox DM, Smith SB, Ganapathy V: Structure, function, and expression pattern of a novel sodium-coupled citrate transporter (NaCT) cloned from mammalian brain. J Biol Chem. 2002 Oct 18;277(42):39469-76. Epub 2002 Aug 11. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Tricarboxylic acid transmembrane transporter activity
Specific Function
Involved in citrate-H(+)/malate exchange. Important for the bioenergetics of hepatic cells as it provides a carbon source for fatty acid and sterol biosyntheses, and NAD(+) for the glycolytic pathway.
Gene Name
SLC25A1
Uniprot ID
P53007
Uniprot Name
Tricarboxylate transport protein, mitochondrial
Molecular Weight
34012.46 Da
References
  1. Sun J, Aluvila S, Kotaria R, Mayor JA, Walters DE, Kaplan RS: Mitochondrial and Plasma Membrane Citrate Transporters: Discovery of Selective Inhibitors and Application to Structure/Function Analysis. Mol Cell Pharmacol. 2010;2(3):101-110. [Article]

Drug created at October 01, 2015 20:41 / Updated at March 19, 2024 11:06