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

Stem definition	Drug id	CAS RN
	666	77-92-9

Description:

Molecule	Description
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

Molecule

Description

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:

Dose	Unit	Route
2	g	O

ADMET properties:

None

Approvals:

Date	Agency	Company	Orphan
June 22, 1982	FDA	BAXTER HLTHCARE

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Toxic epidermal necrolysis	68.43	25.22	30	1878	21616	34933407
Appendicolith	55.61	25.22	20	1888	8581	34946442
Blood phosphorus increased	53.88	25.22	19	1889	7702	34947321
Drug hypersensitivity	48.66	25.22	38	1870	80491	34874532
Appendicitis	45.08	25.22	20	1888	14787	34940236
Myasthenia gravis	40.62	25.22	15	1893	6925	34948098
Dry mouth	36.79	25.22	22	1886	30143	34924880
Ventricular fibrillation	36.75	25.22	20	1888	22934	34932089
Blood uric acid increased	35.86	25.22	15	1893	9609	34945414
Stress	34.09	25.22	21	1887	30326	34924697
Cardiogenic shock	33.99	25.22	20	1888	26598	34928425
Ascites	25.98	25.22	21	1887	46550	34908473
Abdominal distension	25.71	25.22	23	1885	58469	34896554

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Appendicolith	60.28	18.99	20	3421	8531	79732416
Toxic epidermal necrolysis	54.45	18.99	30	3411	44551	79696396
Blood phosphorus increased	49.03	18.99	18	3423	10329	79730618
Appendicitis	43.03	18.99	20	3421	20774	79720173
Myasthenia gravis	38.12	18.99	15	3426	10384	79730563
Ventricular fibrillation	34.94	18.99	20	3421	31906	79709041
Blood uric acid increased	34.49	18.99	15	3426	13345	79727602
Abdominal distension	33.49	18.99	33	3408	119617	79621330
Drug hypersensitivity	30.85	18.99	50	3391	298866	79442081
Cardiogenic shock	29.92	18.99	20	3421	41894	79699053
Stress	28.12	18.99	25	3416	79587	79661360
Analgesic therapy	23.60	18.99	6	3435	1003	79739944
Sleep disorder therapy	23.52	18.99	6	3435	1018	79739929
Thrombosis	23.15	18.99	23	3418	84077	79656870
Hyperphosphataemia	22.68	18.99	9	3432	6367	79734580
Drug therapy	22.57	18.99	6	3435	1195	79739752
Neuralgia	21.61	18.99	15	3426	33369	79707578
Dry mouth	20.49	18.99	22	3419	87997	79652950
Ascites	19.58	18.99	20	3421	75542	79665405

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Source	Code	Description
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	antibiotics
CHEBI has role	CHEBI:38161	Chelating agent
CHEBI has role	CHEBI:64049	pH control agents
CHEBI has role	CHEBI:78675	fundamental metabolites
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

Drug Use | Suggest Off label Use Form| |View source of the data|

Disease	Relation	SNOMED_ID	DOID
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

Species	Use	Relation
Cattle	Dehydration associated with diarrhea	Indication
Cattle	Early treatment of scouring	Indication
Cattle	Followup treatment following intravenous fluid therapy	Indication

🐶 Veterinary products

Product	Applicant	Ingredients
Re-Sorb, Vytrate	Zoetis Inc.	6

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (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 strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
1%;1.8%;0.4%	PHEXXI	EVOFEM INC	N208352	May 22, 2020	RX	GEL	VAGINAL	10568855	March 15, 2033	PREVENTION OF PREGNANCY
1%;1.8%;0.4%	PHEXXI	EVOFEM INC	N208352	May 22, 2020	RX	GEL	VAGINAL	11337989	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	9827231	June 26, 2034	FOR CLEANSING THE LARGE INTESTINE AS A PREPARATION FOR COLONOSCOPY

Orange Book exclusivity data (new drug applications)

Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Exclusivity date	Description
1%;1.8%;0.4%	PHEXXI	EVOFEM INC	N208352	May 22, 2020	RX	GEL	VAGINAL	May 22, 2023	NEW PRODUCT

Bioactivity Summary:

Target	Class	UniProt	Action	Type	Activity value (-log[M])	Bioact source
3-dehydroquinate dehydratase	Enzyme	AROQ_HELPY		Kd	5.60	CHEMBL
3-dehydroquinate dehydratase	Enzyme	AROQ_STRCO		Kd	5.14	CHEMBL
Transient receptor potential cation channel subfamily V member 4	Ion channel	TRPV4_MOUSE	ACTIVATOR	EC50	5.60	IUPHAR

External reference:

ID	Source
4017464	VUID
N0000145852	NUI
D00037	KEGG_DRUG
5949-29-1	SECONDARY_CAS_RN
21183	RXNORM
4017464	VANDF
4018049	VANDF
4020085	VANDF
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
XF417D3PSL	UNII

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Sodium Citrate and Citric Acid	HUMAN PRESCRIPTION DRUG LABEL	2	0121-0595	SOLUTION	334 mg	ORAL	unapproved drug other	12 sections
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
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
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
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 Heartburn	HUMAN OTC DRUG LABEL	2	0280-0047	TABLET, EFFERVESCENT	1000 mg	ORAL	OTC monograph final	17 sections
Alka-Seltzer Heartburn Relief Extra Strength	HUMAN OTC DRUG LABEL	2	0280-0079	TABLET, EFFERVESCENT	1000 mg	ORAL	OTC monograph final	16 sections
Alka-Seltzer Heartburn Relief Extra Strength	HUMAN OTC DRUG LABEL	2	0280-0079	TABLET, EFFERVESCENT	1000 mg	ORAL	OTC monograph final	16 sections
Alka-Seltzer Heartburn Relief Lemon Lime	HUMAN OTC DRUG LABEL	2	0280-0083	TABLET, EFFERVESCENT	1000 mg	ORAL	OTC monograph final	16 sections
Alka-Seltzer Heartburn Relief Lemon Lime	HUMAN OTC DRUG LABEL	2	0280-0083	TABLET, EFFERVESCENT	1000 mg	ORAL	OTC monograph final	16 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 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
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 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
Walgreens Antacid Pain Relief Extra Strength	HUMAN OTC DRUG LABEL	3	0363-0541	TABLET, EFFERVESCENT	1000 mg	ORAL	OTC monograph final	17 sections
Sodium Citrate and Citric Acid	HUMAN PRESCRIPTION DRUG LABEL	2	0904-7316	SOLUTION	334 mg	ORAL	unapproved drug other	12 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