citric acid Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
666 77-92-9

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • citric acid
  • anhydrous citric acid
  • citric acid monohydrate
A key intermediate in metabolism. It is an acid compound found in citrus fruits. The salts of citric acid (citrates) can be used as anticoagulants due to their calcium chelating ability.
  • Molecular weight: 192.12
  • Formula: C6H8O7
  • CLOGP: -2
  • LIPINSKI: 0
  • HAC: 7
  • HDO: 4
  • TPSA: 132.13
  • ALOGS: -0.26
  • ROTB: 5

Drug dosage:

DoseUnitRoute
2 g O

ADMET properties:

None

Approvals:

DateAgencyCompanyOrphan
June 22, 1982 FDA BAXTER HLTHCARE

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Gastrointestinal toxicity 75.35 18.91 24 4177 4307 46677554
Pulmonary toxicity 65.45 18.91 22 4179 4671 46677190
Neoplasm malignant 43.96 18.91 27 4174 23472 46658389
Joint injury 38.31 18.91 23 4178 19186 46662675
Hepatotoxicity 37.51 18.91 25 4176 24984 46656877
C-reactive protein abnormal 36.15 18.91 23 4178 21247 46660614
Anaesthetic complication pulmonary 35.70 18.91 6 4195 58 46681803
Therapy non-responder 34.47 18.91 29 4172 41123 46640738
Chronic kidney disease 32.59 18.91 28 4173 40843 46641018
Hyponatraemia 29.88 18.91 41 4160 101291 46580570
Joint stiffness 28.87 18.91 22 4179 27086 46654775
Upper airway obstruction 27.85 18.91 7 4194 533 46681328
Defaecation disorder 26.51 18.91 6 4195 291 46681570
Musculoskeletal stiffness 23.55 18.91 36 4165 97957 46583904
Musculoskeletal pain 23.15 18.91 30 4171 70098 46611763

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Hyponatraemic coma 70.19 20.85 10 2138 36 29950294
Lethargy 28.09 20.85 23 2125 39496 29910834
Chronic kidney disease 26.84 20.85 22 2126 37816 29912514
Hyporesponsive to stimuli 25.42 20.85 7 2141 955 29949375

Pharmacologic Action:

SourceCodeDescription
ATC A09AB04 ALIMENTARY TRACT AND METABOLISM
DIGESTIVES, INCL. ENZYMES
DIGESTIVES, INCL. ENZYMES
Acid preparations
FDA PE N0000008556 Decreased Coagulation Factor Activity
FDA MoA N0000175089 Calcium Chelating Activity
MeSH PA D000925 Anticoagulants
MeSH PA D065096 Calcium Chelating Agents
MeSH PA D002614 Chelating Agents
MeSH PA D006401 Hematologic Agents
MeSH PA D064449 Sequestering Agents
FDA MoA N0000175833 Acidifying Activity
FDA EPC N0000175835 Calculi Dissolution Agent
FDA EPC N0000175980 Anti-coagulant
CHEBI has role CHEBI:33281 antibiotics
CHEBI has role CHEBI:38161 chelating agent
CHEBI has role CHEBI:64049 acidity regulators
CHEBI has role CHEBI:78675 essential metabolite

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Pain indication 22253000
Indigestion indication 162031009
Headache disorder indication 230461009
Struvite Renal Calculi indication
Calcium Phosphate Renal Calculi indication
Renal tubular acidosis off-label use 1776003 DOID:14219
Cystinuria off-label use 85020001 DOID:9266
Calcium renal calculus off-label use 427649000
Calcium Oxalate Renal Calculi off-label use
Cystine Renal Calculi off-label use
Metabolic alkalosis contraindication 1388004
Anuria contraindication 2472002 DOID:2983
Hypocalcemia contraindication 5291005
Alcoholism contraindication 7200002
Peptic ulcer contraindication 13200003 DOID:750
Hyperkalemia contraindication 14140009
Pulmonary edema contraindication 19242006 DOID:11396
Complete atrioventricular block contraindication 27885002
Dehydration contraindication 34095006
Hypertensive disorder contraindication 38341003 DOID:10763
Hypernatremia contraindication 39355002
Gastrointestinal ulcer contraindication 40845000
Chronic heart failure contraindication 48447003
Vitamin K deficiency contraindication 52675005 DOID:11249
Nasal polyp contraindication 52756005
Congenital myotonia, autosomal dominant form contraindication 57938005
Acute nephropathy contraindication 58574008
Factor II deficiency contraindication 73975000
Reye's syndrome contraindication 74351001 DOID:14525
Gastrointestinal hemorrhage contraindication 74474003
Thrombotic thrombocytopenic purpura contraindication 78129009 DOID:10772
Oliguria contraindication 83128009
Gout contraindication 90560007 DOID:13189
Kidney disease contraindication 90708001 DOID:557
Hemophilia contraindication 90935002
Anemia due to enzyme deficiency contraindication 111577008
Gastrointestinal obstruction contraindication 126765001
von Willebrand disorder contraindication 128105004 DOID:12531
Impaired renal function disorder contraindication 197663003
Myocardial dysfunction contraindication 233928007
Gastroparesis contraindication 235675006
Disease of liver contraindication 235856003 DOID:409
Chronic diarrhea contraindication 236071009
Hyporeninemic hypoaldosteronism contraindication 236464008
Edema contraindication 267038008
Anemia contraindication 271737000 DOID:2355
Peripheral edema contraindication 271809000
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Familial hyperkalemic periodic paralysis contraindication 304737009 DOID:14451
Primary adrenocortical insufficiency contraindication 373662000
Adrenal cortical hypofunction contraindication 386584007 DOID:10493
Breastfeeding (mother) contraindication 413712001
Acute erosive gastritis contraindication 444926003
Azotemia contraindication 445009001
Severe dehydration contraindication 450316000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 2.49 acidic
pKa2 4.55 acidic
pKa3 5.74 acidic
pKa4 13.14 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
12GM/PACKET;3.5GM/PACKET;10MG/PACKET **Federal Register determination that product was not discontinued or withdrawn for safety or efficacy reasons** PREPOPIK FERRING PHARMS INC N202535 July 16, 2012 DISCN FOR SOLUTION ORAL Aug. 15, 2021 NEW PATIENT POPULATION
12GM/BOT;3.5GM/BOT;10MG/BOT CLENPIQ FERRING PHARMS INC N209589 Nov. 28, 2017 RX SOLUTION ORAL Aug. 15, 2021 NEW PATIENT POPULATION
1%;1.8%;0.4% PHEXXI EVOFEM INC N208352 May 22, 2020 RX GEL VAGINULLL May 22, 2023 NEW PRODUCT

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
pH (H+ ion activity) Unclassified OTHER DRUG LABEL DRUG LABEL
3-dehydroquinate dehydratase Enzyme Kd 5.60 CHEMBL
3-dehydroquinate dehydratase Enzyme Kd 5.14 CHEMBL
Transient receptor potential cation channel subfamily V member 4 Unclassified ACTIVATOR EC50 5.60 IUPHAR

External reference:

IDSource
XF417D3PSL UNII
4017464 VUID
N0000145852 NUI
D00037 KEGG_DRUG
5949-29-1 SECONDARY_CAS_RN
4017464 VANDF
4018049 VANDF
4020085 VANDF
C0725616 UMLSCUI
CHEBI:30769 CHEBI
CIT PDB_CHEM_ID
CHEMBL1261 ChEMBL_ID
CHEMBL2107737 ChEMBL_ID
DB04272 DRUGBANK_ID
311 PUBCHEM_CID
D019343 MESH_DESCRIPTOR_UI
2478 IUPHAR_LIGAND_ID
21183 RXNORM
4458 MMSL
4459 MMSL
4460 MMSL
4933 MMSL
NOCODE MMSL
d03066 MMSL
002329 NDDF
002487 NDDF
006406 NDDF
116545009 SNOMEDCT_US
75399008 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Sodium Citrate and Citric Acid HUMAN PRESCRIPTION DRUG LABEL 2 0121-0595 SOLUTION 334 mg ORAL unapproved drug other 12 sections
Potassium Citrate and Citric Acid HUMAN PRESCRIPTION DRUG LABEL 2 0121-0676 SOLUTION 334 mg ORAL unapproved drug other 12 sections
TRICITRATES HUMAN PRESCRIPTION DRUG LABEL 3 0121-0677 SOLUTION 334 mg ORAL unapproved drug other 12 sections
Sodium Citrate and Citric Acid HUMAN PRESCRIPTION DRUG LABEL 2 0121-1190 SOLUTION 334 mg ORAL unapproved drug other 12 sections
Alka-Seltzer Heartburn HUMAN OTC DRUG LABEL 2 0280-0047 TABLET, EFFERVESCENT 1000 mg ORAL OTC monograph final 17 sections
Alka-Seltzer Extra Strength HUMAN OTC DRUG LABEL 3 0280-0211 GRANULE, EFFERVESCENT 1000 mg ORAL OTC monograph not final 17 sections
Alka-Seltzer Original HUMAN OTC DRUG LABEL 3 0280-4000 TABLET, EFFERVESCENT 1000 mg ORAL OTC monograph not final 17 sections
Alka-Seltzer Lemon Lime HUMAN OTC DRUG LABEL 3 0280-4020 TABLET, EFFERVESCENT 1000 mg ORAL OTC monograph not final 16 sections
Alka-Seltzer Gold HUMAN OTC DRUG LABEL 3 0280-4100 TABLET, EFFERVESCENT 1000 mg ORAL OTC monograph final 16 sections
Renacidin HUMAN PRESCRIPTION DRUG LABEL 3 0327-0012 SOLUTION 6.60 g IRRIGATION NDA 14 sections
Walgreens Effervescent Pain Relief HUMAN OTC DRUG LABEL 3 0363-0421 TABLET, EFFERVESCENT 1000 mg ORAL OTC monograph final 17 sections
Walgreens Antacid Pain Relief Extra Strength HUMAN OTC DRUG LABEL 3 0363-0541 TABLET, EFFERVESCENT 1000 mg ORAL OTC monograph final 17 sections
ACD-A Human Prescription Drug Label 3 0942-0641 SOLUTION 7.30 g INTRAVENOUS NDA 2 sections
ACD-A Human Prescription Drug Label 3 0942-0641 SOLUTION 3.65 g INTRAVENOUS NDA 2 sections
CPDA-1 Human Prescription Drug Label 5 0942-6301 SOLUTION 209 mg INTRAVENOUS NDA 2 sections
CPDA-1 HUMAN PRESCRIPTION DRUG LABEL 5 0942-6305 SOLUTION 188 mg INTRAVENOUS NDA 2 sections
CPDA-1 HUMAN PRESCRIPTION DRUG LABEL 5 0942-6307 SOLUTION 209 mg INTRAVENOUS NDA 2 sections
CPDA-1 HUMAN PRESCRIPTION DRUG LABEL 5 0942-6308 SOLUTION 209 mg INTRAVENOUS NDA 2 sections
CPDA-1 Human Prescription Drug Label 5 0942-6309 SOLUTION 188 mg INTRAVENOUS NDA 2 sections
CPDA-1 HUMAN PRESCRIPTION DRUG LABEL 5 0942-6312 SOLUTION 209 mg INTRAVENOUS NDA 2 sections
CPDA-1 Human Prescription Drug Label 5 0942-6316 SOLUTION 209 mg INTRAVENOUS NDA 2 sections
CPDA-1 Human Prescription Drug Label 5 0942-6317 SOLUTION 188 mg INTRAVENOUS NDA 2 sections
CPDA-1 Human Prescription Drug Label 5 0942-6319 SOLUTION 188 mg INTRAVENOUS NDA 2 sections
CPDA-1 HUMAN PRESCRIPTION DRUG LABEL 5 0942-6320 SOLUTION 209 mg INTRAVENOUS NDA 2 sections
CPDA-1 Human Prescription Drug Label 5 0942-6321 SOLUTION 105 mg INTRAVENOUS NDA 2 sections
CPDA-1 HUMAN PRESCRIPTION DRUG LABEL 5 0942-6322 SOLUTION 188 mg INTRAVENOUS NDA 2 sections
CPDA-1 HUMAN PRESCRIPTION DRUG LABEL 5 0942-6326 SOLUTION 209 mg INTRAVENOUS NDA 2 sections
CPDA-1 Human Prescription Drug Label 5 0942-6327 SOLUTION 188 mg INTRAVENOUS NDA 2 sections
CPDA-1 Human Prescription Drug Label 5 0942-6328 SOLUTION 147 mg INTRAVENOUS NDA 2 sections
CPDA-1 Human Prescription Drug Label 5 0942-6329 SOLUTION 147 mg INTRAVENOUS NDA 2 sections