citric acid 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | 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
  • Status: OFP
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
2 g O

ADMET properties:

None

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
kinase-safety-class ACVR2A,ACVR2B,ACVRL1,ALK,AURKA,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK4,CDK5,CDK9,DDR1,DYRK1B,EGFR,EIF2AK3,EPHB4,ERBB2,FLT3,GRK2,GSK3B,IKBKB,ITK,JAK1,JAK2,JAK3,KDR,MAP2K6,MAP3K14,MAP3K21,MAP3K7,MAPK10,MAPK12,MAPK7,MAPKAPK2,MTOR,NTRK1,NTRK2,PDK1,PDK2,PDK4,PIK3CA,PIK3CB,PIK3CD,PIK3CG,PIM2,PRKCD,PRKDC,SIK2,SIK3,STK33,SYK,TEK,TGFBR1,TTK,ULK1,ZAP70 58
kinase-selectivity-class AXL,BRAF,CDK4,CDK9,EIF2AK3,EPHB4,ERBB2,GRK2,MAP2K6,MAP3K14,MAPK7,PRKDC,STK33,SYK,TEK,TGFBR1,ZAP70 17
pfas-class PFAS structural alert (1 = True, 0 = False) 0

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
Vaginal flatulence 82.41 38.35 21 1092 12617 90614717
Proctitis 78.48 38.35 21 1092 15238 90612096
Female genital tract fistula 75.20 38.35 21 1092 17847 90609487
Radiculopathy 74.47 38.35 21 1092 18484 90608850
Vaginal discharge 73.42 38.35 21 1092 19443 90607891
Chronic sinusitis 69.25 38.35 21 1092 23781 90603553
Paraesthesia oral 63.35 38.35 21 1092 31638 90595696
Procedural pain 62.28 38.35 21 1092 33339 90593995
Oral candidiasis 61.02 38.35 21 1092 35434 90591900
Macular degeneration 59.61 38.35 21 1092 37949 90589385
Frequent bowel movements 51.33 38.35 21 1092 56914 90570420
Colitis ulcerative 50.18 38.35 21 1092 60245 90567089
Colitis 47.17 38.35 21 1092 69921 90557413
Haematochezia 46.89 38.35 21 1092 70892 90556442
Rectal haemorrhage 46.87 38.35 22 1091 82722 90544612

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
Myasthenia gravis 142.08 76.09 54 3854 16083 42601344
Hyperphosphataemia 142.06 76.09 51 3857 12953 42604474
Analgesic therapy 124.71 76.09 39 3869 6485 42610942
Sleep disorder therapy 122.59 76.09 39 3869 6855 42610572
Hypophosphataemia 118.47 76.09 51 3857 20894 42596533
Neuralgia 117.92 76.09 54 3854 25593 42591834
Drug therapy 117.20 76.09 37 3871 6343 42611084
Incorrect route of product administration 114.34 76.09 52 3856 24253 42593174
Bacterial infection 110.57 76.09 53 3855 27826 42589601
Activated partial thromboplastin time prolonged 107.60 76.09 44 3864 15859 42601568
Congenital hiatus hernia 105.95 76.09 34 3874 6140 42611287
Drug hypersensitivity 103.55 76.09 80 3828 99309 42518118
Stress 98.09 76.09 57 3851 44155 42573272
Anticoagulant therapy 94.62 76.09 29 3879 4506 42612921
Bronchopulmonary aspergillosis allergic 94.23 76.09 29 3879 4569 42612858
Appendicolith 93.65 76.09 38 3870 13418 42604009
Antacid therapy 93.50 76.09 29 3879 4688 42612739
Blood calcium increased 91.70 76.09 33 3875 8421 42609006
End stage renal disease 82.84 76.09 37 3871 16521 42600906
Swelling 81.88 76.09 55 3853 54830 42562597
Blood test abnormal 81.49 76.09 34 3874 12872 42604555
Sleep disorder 81.01 76.09 52 3856 48043 42569384
Ulcer 79.89 76.09 36 3872 16405 42601022
Intentional product misuse 78.20 76.09 56 3852 61844 42555583
Appendicitis 78.10 76.09 38 3870 20575 42596852
Diabetes mellitus 77.37 76.09 55 3853 60032 42557395

FDA Adverse Event Reporting System (Geriatric)

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
Hyperphosphataemia 169.77 47.05 52 4978 16329 110567940
Myasthenia gravis 167.87 47.05 55 4975 21456 110562813
Analgesic therapy 152.23 47.05 40 4990 7244 110577025
Sleep disorder therapy 151.23 47.05 40 4990 7431 110576838
Drug therapy 142.64 47.05 38 4992 7253 110577016
Hypophosphataemia 133.83 47.05 52 4978 33130 110551139
Congenital hiatus hernia 129.01 47.05 34 4996 6225 110578044
Neuralgia 124.40 47.05 55 4975 48423 110535846
Bacterial infection 123.86 47.05 54 4976 45982 110538287
Activated partial thromboplastin time prolonged 122.95 47.05 44 4986 22324 110561945
Appendicolith 121.57 47.05 39 4991 14216 110570053
Anticoagulant therapy 109.90 47.05 29 5001 5332 110578937
Antacid therapy 109.25 47.05 29 5001 5455 110578814
Incorrect route of product administration 101.01 47.05 52 4978 64009 110520260
End stage renal disease 98.58 47.05 37 4993 21436 110562833
Thrombosis 97.55 47.05 61 4969 108601 110475668
Bronchopulmonary aspergillosis allergic 96.93 47.05 29 5001 8397 110575872
Appendicitis 95.24 47.05 39 4991 28425 110555844
Stress 94.22 47.05 59 4971 105289 110478980
Blood calcium increased 89.84 47.05 33 4997 18007 110566262
Diabetes mellitus 89.73 47.05 56 4974 99325 110484944
Blood phosphorus increased 89.24 47.05 32 4998 16308 110567961
Chronic obstructive pulmonary disease 87.35 47.05 57 4973 109101 110475168
Blood test abnormal 81.70 47.05 35 4995 28519 110555750
Ventricular fibrillation 81.30 47.05 39 4991 41274 110542995
Gout 79.57 47.05 37 4993 36529 110547740
Intentional product misuse 77.20 47.05 57 4973 132847 110451422
Troponin increased 77.06 47.05 34 4996 29732 110554537
Multiple organ dysfunction syndrome 74.78 47.05 59 4971 151651 110432618
Hyperlipidaemia 74.07 47.05 35 4995 35813 110548456
Blood uric acid increased 73.73 47.05 30 5000 21499 110562770
Benign prostatic hyperplasia 71.44 47.05 28 5002 18206 110566063
Ulcer 70.84 47.05 36 4994 43080 110541189
Respiratory symptom 65.86 47.05 25 5005 14920 110569349
Drug hypersensitivity 65.10 47.05 91 4939 453999 110130270
Pleuritic pain 63.99 47.05 25 5005 16115 110568154
Cardiogenic shock 63.86 47.05 37 4993 57301 110526968
Aspiration 63.65 47.05 30 5000 30503 110553766
Micturition urgency 63.01 47.05 26 5004 19294 110564975
Hyponatraemia 61.92 47.05 62 4968 217591 110366678
Breath sounds abnormal 59.31 47.05 27 5003 25377 110558892
Cardiovascular disorder 58.91 47.05 26 5004 22734 110561535
Vaginal flatulence 55.99 47.05 21 5009 12123 110572146
Ascites 54.30 47.05 40 4990 92768 110491501
Iron deficiency 50.71 47.05 22 5008 18454 110565815
Pulmonary embolism 50.09 47.05 55 4975 214419 110369850
Female genital tract fistula 49.73 47.05 21 5009 16498 110567771
Proctitis 49.24 47.05 21 5009 16906 110567363
Sleep disorder 48.23 47.05 52 4978 198592 110385677
Vaginal discharge 48.10 47.05 21 5009 17887 110566382

FDA Adverse Event Reporting System (Pediatric)

None

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
FDA MoA N0000175833 Acidifying Activity
FDA EPC N0000175835 Calculi Dissolution Agent
FDA EPC N0000175980 Anti-coagulant
CHEBI has role CHEBI:33281 antimicrobial agent
CHEBI has role CHEBI:38161 chelator
CHEBI has role CHEBI:64049 food acidity regulator
CHEBI has role CHEBI:66981 ophthalmology drug
CHEBI has role CHEBI:78675 fundamental metabolite
CHEBI has role CHEBI:232436 calcium chelator
MeSH PA D000925 Anticoagulants
MeSH PA D002614 Chelating Agents
MeSH PA D006401 Hematologic Agents
MeSH PA D064449 Sequestering Agents
MeSH PA D065096 Calcium Chelating Agents

Related Drugs by ATC class:

A09AB Acid preparations 3 drugs
betaineglutamic acidhydrochloric acid

Drug Use | Suggest Off label Use Form| |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




🐶 Veterinary Drug Use

SpeciesUseRelation
Cattle Dehydration associated with diarrhea Indication
Cattle Early treatment of scouring Indication
Cattle Followup treatment following intravenous fluid therapy Indication

🐶 Veterinary products

ProductApplicantIngredients
Re-Sorb, Vytrate Zoetis Inc. 6

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)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
1%;1.8%;0.4% PHEXX EVOFEM INC N208352 May 22, 2020 RX GEL VAGINAL 10568855 March 15, 2033 PREVENTION OF PREGNANCY
1%;1.8%;0.4% PHEXX EVOFEM INC N208352 May 22, 2020 RX GEL VAGINAL 11337989 March 15, 2033 PREVENTION OF PREGNANCY
1%;1.8%;0.4% PHEXX EVOFEM INC N208352 May 22, 2020 RX GEL VAGINAL 11992472 March 15, 2033 PREVENTION OF PREGNANCY
12GM/BOT;3.5GM/BOT;10MG/BOT CLENPIQ FERRING PHARMS INC N209589 Nov. 28, 2017 RX SOLUTION ORAL 11191753 June 23, 2034 FOR CLEANSING OF THE COLON AS A PREPARATION FOR COLONOSCOPY
12GM/BOT;3.5GM/BOT;10MG/BOT CLENPIQ FERRING PHARMS INC N209589 Nov. 28, 2017 RX SOLUTION ORAL 12576072 June 23, 2034 FOR CLEANSING OF THE COLON AS A PREPARATION FOR COLONOSCOPY
12GM/BOT;3.5GM/BOT;10MG/BOT CLENPIQ FERRING PHARMS INC N209589 Nov. 28, 2017 RX SOLUTION ORAL 9827231 June 26, 2034 FOR CLEANSING THE LARGE INTESTINE AS A PREPARATION FOR COLONOSCOPY

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])		Mechanism
action		Bioact sourceMoA source
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 Ion channel ACTIVATOR EC50 5.60 IUPHAR

External reference:

IDSource
4017464 VUID
N0000145852 NUI
D00037 KEGG_DRUG
5949-29-1 SECONDARY_CAS_RN
21183 RXNORM
C0055819 UMLSCUI
CHEBI:30769 CHEBI
CIT PDB_CHEM_ID
CHEMBL1261 ChEMBL_ID
DB04272 DRUGBANK_ID
CHEMBL2107737 ChEMBL_ID
D019343 MESH_DESCRIPTOR_UI
311 PUBCHEM_CID
2478 IUPHAR_LIGAND_ID
4458 MMSL
4459 MMSL
4460 MMSL
4933 MMSL
NOCODE MMSL
d03066 MMSL
002329 NDDF
002487 NDDF
006406 NDDF
116545009 SNOMEDCT_US
75399008 SNOMEDCT_US
4017464 VANDF
4018049 VANDF
4020085 VANDF
XF417D3PSL UNII

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 Drug 17 sections
Alka-Seltzer Heartburn Relief Extra Strength HUMAN OTC DRUG LABEL 2 0280-0079 TABLET, EFFERVESCENT 1000 mg ORAL OTC Monograph Drug 16 sections
Alka-Seltzer Heartburn Relief Lemon Lime HUMAN OTC DRUG LABEL 2 0280-0083 TABLET, EFFERVESCENT 1000 mg ORAL OTC Monograph Drug 16 sections
Alka-Seltzer Heartburn and Pain HUMAN OTC DRUG LABEL 3 0280-0160 TABLET, EFFERVESCENT 1000 mg ORAL OTC Monograph Drug 17 sections
Alka-Seltzer Extra Strength HUMAN OTC DRUG LABEL 3 0280-0211 GRANULE, EFFERVESCENT 1000 mg ORAL OTC Monograph Drug 17 sections
Alka-Seltzer Original HUMAN OTC DRUG LABEL 3 0280-4000 TABLET, EFFERVESCENT 1000 mg ORAL OTC Monograph Drug 17 sections
Alka-Seltzer Gold HUMAN OTC DRUG LABEL 3 0280-4100 TABLET, EFFERVESCENT 1000 mg ORAL OTC Monograph Drug 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 Drug 17 sections
Walgreens Antacid Pain Relief Extra Strength HUMAN OTC DRUG LABEL 3 0363-0541 TABLET, EFFERVESCENT 1000 mg ORAL OTC Monograph Drug 17 sections
Walgreens Antacid Pain Relief Extra Strength HUMAN OTC DRUG LABEL 3 0363-0541 TABLET, EFFERVESCENT 1000 mg ORAL OTC Monograph Drug 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 0942-6305 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 0942-6312 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 0942-6320 SOLUTION 209 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
ACD Blood-Pack Units (PL 146 PLASTIC) HUMAN PRESCRIPTION DRUG LABEL 3 0942-9001 SOLUTION 493 mg INTRAVENOUS NDA 2 sections
Anticoagulant Citrate Phosphate Dextrose (CPD) Blood-Pack Units in PL 146 Plastic HUMAN PRESCRIPTION DRUG LABEL 4 0942-9201 SOLUTION 105 mg INTRAVENOUS NDA 2 sections
Anticoagulant Citrate Phosphate Dextrose (CPD) Blood-Pack Units in PL 146 Plastic HUMAN PRESCRIPTION DRUG LABEL 4 0942-9202 SOLUTION 188 mg INTRAVENOUS NDA 2 sections
CPDA-1 HUMAN PRESCRIPTION DRUG LABEL 5 0942-9393 SOLUTION 209 mg INTRAVENOUS NDA 2 sections
CPDA-1 HUMAN PRESCRIPTION DRUG LABEL 5 0942-9394 SOLUTION 188 mg INTRAVENOUS NDA 2 sections