(1-Amino-3-(((2-((diaminomethylene)amino)-4-thiazolyl)methyl)thio)propylidene)sulfamide
3-(((2-((Aminoiminomethyl)amino)-4-thiazolyl)methyl)thio)-N-(aminosulfonyl)propanimidamide
3-(((2-((Diaminomethylene)amino)-4-thiazolyl)methyl)thio)-N(sup 2)-sulfamoylpropionamidine
Famotidina
Famotidine
Famotidinum
N-Sulfamoyl-3-((2-guanidinothiazol-4-yl)methylthio)propionamide

External IDs

L 643341 / MK-208 / YM-11170

Product Images

Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Bci Famotidine	Tablet	20 mg	Oral	Baker Cummins Inc	Not applicable	Not applicable
Bci Famotidine	Tablet	40 mg	Oral	Baker Cummins Inc	Not applicable	Not applicable
Famotidine	Powder, for suspension	40 mg/5mL	Oral	Paddock Laboratories, Inc.	2010-05-28	2015-04-30
Famotidine 10mg	Tablet	10 mg	Oral	Laboratoire Riva Inc	Not applicable	Not applicable
Famotidine Injection	Solution	10 mg	Intravenous	Mylan Pharmaceuticals	Not applicable	Not applicable
Famotidine Injection	Solution	10 mg	Intravenous	Mylan Pharmaceuticals	Not applicable	Not applicable
Famotidine Injection	Solution	10 mg	Intravenous	Fresenius Kabi	Not applicable	Not applicable
Famotidine Injection	Solution	10 mg	Intravenous	Hospira, Inc.	Not applicable	Not applicable
Famotidine IV Injection	Solution	10 mg	Intravenous	Teva	Not applicable	Not applicable
Famotidine IV Injection	Solution	10 mg	Intravenous	Teva	Not applicable	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Apo-famotidine Injectable	Solution	10 mg	Intravenous	Apotex Corporation	2003-11-17	2013-08-02
Apo-famotidine Injectable	Solution	10 mg	Intravenous	Apotex Corporation	2004-05-27	2013-08-02
Apo-famotidine Tab 20mg USP	Tablet	20 mg	Oral	Apotex Corporation	1993-12-31	Not applicable
Apo-famotidine Tab 40mg USP	Tablet	40 mg	Oral	Apotex Corporation	1993-12-31	Not applicable
Famotidine	Tablet	20 mg/1	Oral	Unit Dose Services	2016-01-29	Not applicable
Famotidine	Tablet	40 mg/1	Oral	Mesource Pharmaceuticals	2001-04-16	2017-03-31
Famotidine	Injection, solution	10 mg/1mL	Intravenous	Baxter Laboratories	2001-04-06	2014-03-31
Famotidine	Tablet	20 mg/1	Oral	bryant ranch prepack	2001-04-16	Not applicable
Famotidine	Tablet, film coated	20 mg/1	Oral	Contract Pharmacy Services Pa	2017-09-20	Not applicable
Famotidine	Tablet	20 mg/1	Oral	Blenheim Pharmacal, Inc.	2015-03-25	Not applicable

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
7 Select Acid Controller	Tablet	20 mg/1	Oral	7 Eleven	2014-08-05	Not applicable
Acid Control	Tablet	20 mg	Oral	Apotex Corporation	2014-04-28	Not applicable
Acid Control	Tablet	10 mg	Oral	Vita Health Products Inc	1998-10-27	Not applicable
Acid Control	Tablet	10 mg	Oral	Pendopharm Division Of De Pharmascience Inc	1997-09-08	2015-01-19
Acid Control	Tablet	10 mg	Oral	Teva	1997-06-17	Not applicable
Acid Control	Tablet	10 mg	Oral	Apotex Corporation	2000-07-11	Not applicable
Acid Control Original Strength	Tablet	10 mg/1	Oral	Medicine Shoppe International	2009-10-19	2012-04-09
Acid Controller	Tablet	20 mg/1	Oral	International Laboratories, Llc	2016-05-27	Not applicable
Acid Controller	Tablet	20 mg/1	Oral	H.E.B.	2016-09-14	Not applicable
Acid Controller	Tablet	10 mg/1	Oral	H.E.B.	2015-10-23	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Acid Controller Complete	Famotidine (10 mg/1) + Calcium Carbonate (800 mg/1) + Magnesium hydroxide (165 mg/1)	Tablet, chewable	Oral	Shopko Stores Operating	2013-06-05	2017-01-15
Acid Controller Complete	Famotidine (10 mg/1) + Calcium Carbonate (800 mg/1) + Magnesium hydroxide (165 mg/1)	Tablet, chewable	Oral	Safeway	2008-08-06	2017-01-19
Acid Controller Complete	Famotidine (10 mg/1) + Calcium Carbonate (800 mg/1) + Magnesium hydroxide (165 mg/1)	Tablet, chewable	Oral	Shopko Stores Operating	2013-06-05	2016-11-16
Acid Controller Complete dual action	Famotidine (10 mg/1) + Calcium Carbonate (800 mg/1) + Magnesium hydroxide (165 mg/1)	Tablet, chewable	Oral	Walgreen	2008-07-30	Not applicable
Acid Controller Complete dual action	Famotidine (10 mg/1) + Calcium Carbonate (800 mg/1) + Magnesium hydroxide (165 mg/1)	Tablet, chewable	Oral	Walgreen	2008-07-30	2017-07-25
Acid Reducer Complete	Famotidine (10 mg/1) + Calcium Carbonate (800 mg/1) + Magnesium hydroxide (165 mg/1)	Tablet, chewable	Oral	Shopko Stores Operating Co., LLC	2016-01-06	Not applicable
Acid Reducer Complete	Famotidine (10 mg/1) + Calcium Carbonate (800 mg/1) + Magnesium hydroxide (165 mg/1)	Tablet, chewable	Oral	Rite Aid	2009-05-15	2017-09-08
Acid Reducer Complete	Famotidine (10 mg/1) + Calcium Carbonate (800 mg/1) + Magnesium hydroxide (165 mg/1)	Tablet, chewable	Oral	Walgreen Company	2016-01-29	Not applicable
Acid Reducer Complete	Famotidine (10 mg/1) + Calcium Carbonate (800 mg/1) + Magnesium hydroxide (165 mg/1)	Tablet, chewable	Oral	Walgreen Company	2016-01-29	Not applicable
Acid Reducer Complete	Famotidine (10 mg/1) + Calcium Carbonate (800 mg/1) + Magnesium hydroxide (165 mg/1)	Tablet, chewable	Oral	Shopko Stores Operating Co., LLC	2016-01-12	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Famotidine	Famotidine (2 mg/1mL)	Injection, solution	Intravenous	Cantrell Drug Company	2014-06-11	Not applicable

International/Other Brands

Amfamox / Antodine / Confobos / Cronol / Digervin / Dispromil / Duovel / Durater / Famocid / Famosan / Famotep / Famox / Famoxal / Famtac / Famulcer / Fanosin / Fluxid / Gaster / Lecedil / Motiax / Mylanta AR / Notidin / Nulceran / Panalba / Pepcid / Pepcid RPD / Pepcidin / Pepcidine / Pepdine / Pepfamin / Quamatel / Renapepsa / Rubacina / Sedanium-R / Supertidine / Tairal / Tipodex / Ulfagel / Ulfamid / Ulgarine / Vagostal

Categories

UNII

5QZO15J2Z8

CAS number

76824-35-6

Weight

Average: 337.445
Monoisotopic: 337.044934829

Chemical Formula

C₈H₁₅N₇O₂S₃

InChI Key

XUFQPHANEAPEMJ-UHFFFAOYSA-N

InChI

InChI=1S/C8H15N7O2S3/c9-6(15-20(12,16)17)1-2-18-3-5-4-19-8(13-5)14-7(10)11/h4H,1-3H2,(H2,9,15)(H2,12,16,17)(H4,10,11,13,14)

IUPAC Name

3-[({2-[(diaminomethylidene)amino]-1,3-thiazol-4-yl}methyl)sulfanyl]-N'-sulfamoylpropanimidamide

SMILES

NC(N)=NC1=NC(CSCCC(N)=NS(N)(=O)=O)=CS1

Pharmacology

Indication

For the treatment of peptic ulcer disease (PUD) and gastroesophageal reflux disease (GERD).

Associated Conditions

Pharmacodynamics

Famotidine, a competitive histamine H₂-receptor antagonist, is used to treat gastrointestinal disorders such as gastric or duodenal ulcer, gastroesophageal reflux disease, and pathological hypersecretory conditions. Famotidine inhibits many of the isoenzymes of the hepatic CYP450 enzyme system. Other actions of Famotidine include an increase in gastric bacterial flora such as nitrate-reducing organisms.

Mechanism of action

Famotidine binds competitively to H₂-receptors located on the basolateral membrane of the parietal cell, blocking histamine affects. This competitive inhibition results in reduced basal and nocturnal gastric acid secretion and a reduction in gastric volume, acidity, and amount of gastric acid released in response to stimuli including food, caffeine, insulin, betazole, or pentagastrin.

Target	Actions	Organism
AHistamine H2 receptor	antagonist	Human

Absorption

The bioavailability of oral doses is 40-45%.

Volume of distribution

Not Available

Protein binding

15-20%

Metabolism

Hepatic.

Route of elimination

Renal clearance is 250-450 mL/min, indicating some tubular excretion.

Half life

2.5-3.5 hours

Clearance

renal cl=250-450 mL/min

Toxicity

Intravenous, mouse: LD₅₀ = 244.4mg/kg; Oral, mouse: LD₅₀ = 4686 mg/kg. Symptoms of overdose include emesis, restlessness, pallor of mucous membranes or redness of mouth and ears, hypotension, tachycardia and collapse.

Affected organisms

Humans and other mammals

Pathways

Pathway	Category
Famotidine Action Pathway	Drug action

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Drug	Interaction
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid	Famotidine can cause a decrease in the absorption of 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.
2,5-Dimethoxy-4-ethylamphetamine	2,5-Dimethoxy-4-ethylamphetamine may decrease the sedative and stimulatory activities of Famotidine.
2,5-Dimethoxy-4-ethylthioamphetamine	2,5-Dimethoxy-4-ethylthioamphetamine may decrease the sedative and stimulatory activities of Famotidine.
3,4-Methylenedioxyamphetamine	3,4-Methylenedioxyamphetamine may decrease the sedative and stimulatory activities of Famotidine.
4-Bromo-2,5-dimethoxyamphetamine	4-Bromo-2,5-dimethoxyamphetamine may decrease the sedative and stimulatory activities of Famotidine.
Abafungin	Famotidine can cause a decrease in the absorption of Abafungin resulting in a reduced serum concentration and potentially a decrease in efficacy.
Abexinostat	The risk or severity of QTc prolongation can be increased when Famotidine is combined with Abexinostat.
Acebutolol	The risk or severity of QTc prolongation can be increased when Famotidine is combined with Acebutolol.
Aceprometazine	The risk or severity of QTc prolongation can be increased when Famotidine is combined with Aceprometazine.
Acetyldigoxin	The risk or severity of QTc prolongation can be increased when Famotidine is combined with Acetyldigoxin.

Food Interactions

Avoid alcohol.
Limit caffeine intake.
Take without regard to meals, food may slightly increase the product's bioavailability.

References

Synthesis Reference

Montserrat Ballester-Rodes, Francisco E. Palomo-Nicolau, Antonio L. Palomo-Coli, "Famotidine polymorphic forms and their preparation process." U.S. Patent US5021582, issued March, 1987.

US5021582

General References

Not Available

External Links

Human Metabolome Database: HMDB0001919
KEGG Drug: D00318
PubChem Compound: 3325
PubChem Substance: 46507397
ChemSpider: 3208
BindingDB: 50036754
ChEBI: 4975
ChEMBL: CHEMBL902
Therapeutic Targets Database: DAP000341
PharmGKB: PA449586
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
PDRhealth: PDRhealth Drug Page
Wikipedia: Famotidine

ATC Codes

A02BA53 — Famotidine, combinations

A02BA03 — Famotidine

AHFS Codes

56:28.12 — Histamine H2-antagonists

FDA label

Download (1.05 MB)

MSDS

Download (73.8 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
1	Completed	Not Available	Healthy Volunteers / Lupus / Psoriasis	1
1	Completed	Not Available	Human Immunodeficiency Virus (HIV) Infections	1
1	Completed	Basic Science	Drug Drug Interaction (DDI)	1
1	Completed	Basic Science	Healthy Volunteers	2
1	Completed	Health Services Research	Healthy Volunteers	1
1	Completed	Other	Healthy Volunteers	1
1	Completed	Screening	Fibrosis	1
1	Completed	Treatment	Bioavailability	2
1	Completed	Treatment	Colorectal Cancers / Lung Cancer Non-Small Cell Cancer (NSCLC) / Malignancies / Melanoma / Thyroid Papillary Carcinoma	1
1	Completed	Treatment	Healthy Volunteers	2
1	Completed	Treatment	Human Immunodeficiency Virus (HIV) Infections / Infection, Human Immunodeficiency Virus I	1
1	Completed	Treatment	Psoriasis	1
1	Recruiting	Treatment	Diseases of Oesophagus Stomach and Duodenum	1
1, 2	Recruiting	Treatment	Colorectal Cancers	1
2	Active Not Recruiting	Treatment	Malignant Neoplasm of Stomach	1
2	Completed	Treatment	Cerebrovascular Accident, Acute / Edema of the cerebrum	1
2	Completed	Treatment	Dyskinesias	1
2	Not Yet Recruiting	Treatment	Pulmonary Arterial Hypertension (PAH) / Right Heart Failure	1
2	Recruiting	Treatment	HNSCC / HPV-Related Squamous Cell Carcinoma	1
2	Recruiting	Treatment	Plasmodium Infections	1
2, 3	Completed	Treatment	Malaria caused by Plasmodium falciparum	1
2, 3	Completed	Treatment	Reflux, Gastroesophageal	1
2, 3	Recruiting	Treatment	Schizophrenic Disorders	1
3	Completed	Prevention	Ulcers	1
3	Completed	Treatment	Erosive Esophagitis(EE)	1
3	Completed	Treatment	Peptic Ulcer Bleeding / Upper Gastrointestinal Hemorrhage	1
3	Completed	Treatment	Reflux, Gastroesophageal	1
3	Not Yet Recruiting	Treatment	Fallopian Tube Cancer / Ovarian Epithelial Cancer / Primary Peritoneal Carcinoma	2
3	Not Yet Recruiting	Treatment	Malaria caused by Plasmodium falciparum	1
4	Active Not Recruiting	Prevention	Peptic Ulcers	1
4	Completed	Not Available	Human Immunodeficiency Virus (HIV)	1
4	Completed	Not Available	Human Immunodeficiency Virus (HIV) Infections	1
4	Completed	Prevention	Marginal Ulcers	1
4	Completed	Prevention	Peptic Ulcer/Erosions	1
4	Completed	Prevention	Ulcers	1
4	Completed	Treatment	Heartburn	1
4	Completed	Treatment	Juvenile Idiopathic Arthritis (JIA)	1
4	Completed	Treatment	Schizophrenic Disorders	1
4	Recruiting	Treatment	Rheumatoid Arthritis	1
4	Unknown Status	Treatment	Aspirin / Indigestion	1
Not Available	Active Not Recruiting	Treatment	Metastatic Melanoma	1
Not Available	Completed	Not Available	Anemias / Iron Deficiency / Plasmodium Infections / Schistosomiasis Infection	1
Not Available	Completed	Not Available	Community Acquired Pneumonia (CAP) / Gastro-esophageal Reflux Disease (GERD)	1
Not Available	Completed	Not Available	Healthy Volunteers	2
Not Available	Completed	Not Available	Rhytidoplasty	1
Not Available	Completed	Treatment	Plasmodium Infections	1
Not Available	Recruiting	Prevention	Peptic Ulcers	2
Not Available	Recruiting	Supportive Care	Cancer, Breast / Post-Operative Nausea and Vomiting (PONV)	1
Not Available	Recruiting	Treatment	Malignant Neoplasm of Stomach	1
Not Available	Unknown Status	Not Available	Parasitemia	1

Pharmacoeconomics

Manufacturers

Lupin ltd
Navinta llc
Salix pharmaceuticals inc
Akorn strides llc
Apotex inc richmond hill
Apothecon inc div bristol myers squibb
App pharmaceuticals llc
Baxter healthcare corp anesthesia and critical care
Baxter healthcare corp
Bedford laboratories div ben venue laboratories inc
Hospira inc
Ben venue laboratories inc
Claris lifesciences ltd
Abbott laboratories
Baxter healthcare internati0nal specialty therapies div
Merck research laboratories div merck co inc
L perrigo co
Schwarz pharma inc
Actavis elizabeth llc
Alembic ltd
Apotex inc
Carlsbad technology inc
Dr reddys laboratories ltd
Genpharm inc
Ivax pharmaceuticals inc sub teva pharmaceuticals usa
Mutual pharmaceutical co inc
Mylan pharmaceuticals inc
Perrigo co
Ranbaxy laboratories inc
Sandoz inc
Teva pharmaceuticals usa inc
Watson laboratories inc
Wockhardt ltd
Wockhardt americas inc

Packagers

Advanced Pharmaceutical Services Inc.
Akorn Inc.
Amerisource Health Services Corp.
APP Pharmaceuticals
A-S Medication Solutions LLC
Atlantic Biologicals Corporation
Baxter International Inc.
Bedford Labs
Ben Venue Laboratories Inc.
Bryant Ranch Prepack
Cardinal Health
Carlsbad Technology Inc.
Chain Drug
Corepharma LLC
CVS Pharmacy
Dispensing Solutions
Diversified Healthcare Services Inc.
Doctor Reddys Laboratories Ltd.
H.J. Harkins Co. Inc.
Heartland Repack Services LLC
Hospira Inc.
Ivax Pharmaceuticals
Johnson & Johnson Healthcare
Kaiser Foundation Hospital
Lake Erie Medical and Surgical Supply
Legacy Pharmaceuticals Packaging LLC
Lupin Pharmaceuticals Inc.
Major Pharmaceuticals
Mckesson Corp.
Medisca Inc.
Merck & Co.
Murfreesboro Pharmaceutical Nursing Supply
Mylan
Northstar Rx LLC
Nucare Pharmaceuticals Inc.
PCA LLC
PD-Rx Pharmaceuticals Inc.
Perrigo Co.
Pharmaceutical Utilization Management Program VA Inc.
Pharmedium
Physicians Total Care Inc.
Preferred Pharmaceuticals Inc.
Prepackage Specialists
Prepak Systems Inc.
Rebel Distributors Corp.
Redpharm Drug
Remedy Repack
Salix Pharmaceuticals
Sandhills Packaging Inc.
Southwood Pharmaceuticals
Strides Arcolab Limited
Teva Pharmaceutical Industries Ltd.
UDL Laboratories
Vangard Labs Inc.
Walgreen Co.
Watson Pharmaceuticals
Wockhardt Ltd.
Yung Shin Pharmaceutical Industry Ltd.
Zydus Pharmaceuticals

Dosage forms

Form	Route	Strength
Tablet, coated	Oral
For suspension	Oral	40 mg/5mL
Injection	Intravenous	10 mg/1mL
Injection, solution	Intravenous	10 mg/1mL
Injection, solution	Intravenous	2 mg/1mL
Powder, for solution	Oral	40 mg/5mL
Powder, for suspension	Oral	40 mg/5mL
Tablet	Oral	10 mg/1
Tablet	Oral	20 mg/1
Tablet	Oral	40 mg/1
Tablet, coated	Oral	20 mg/1
Tablet, coated	Oral	40 mg/1
Tablet, film coated	Oral	10 mg/1
Tablet, film coated	Oral	20 mg/1
Tablet, film coated	Oral	40 mg/1
Tablet, film coated, extended release	Oral	10 mg/1
Solution	Intravenous	10 mg
Tablet, orally disintegrating	Oral	20 mg/1
Tablet, orally disintegrating	Oral	40 mg/1
Injection, solution	Intravenous	20 mg/50mL
Injection, solution, concentrate	Intravenous	10 mg/1mL
Tablet	Oral	10 mg
Tablet, chewable	Oral	20 mg/1
Tablet, chewable	Oral
Tablet	Oral	20 mg
Tablet	Oral	40 mg
Tablet, coated	Oral	10 mg/1

Prices

Unit description	Cost	Unit
Pepcid 30 40 mg tablet Bottle	125.5USD	bottle
Pepcid 40 mg/5ml Suspension 50ml Bottle	123.88USD	bottle
Pepcid 30 20 mg tablet Bottle	64.13USD	bottle
Mylanta Double-Strength 400-400-40 mg/5ml Suspension 710ml Bottle	10.15USD	bottle
Mylanta 200-200-20 mg/5ml Suspension 710ml Bottle	9.23USD	bottle
Mylanta 200-200-20 mg/5ml Suspension 355ml Bottle	7.99USD	bottle
Mylanta Double-Strength 400-400-40 mg/5ml Suspension 355ml Bottle	7.99USD	bottle
Famotidine 40 mg tablet	3.43USD	tablet
Pepcid 40 mg tablet	3.02USD	tablet
Famotidine powder	2.74USD	g
Famotidine 20 mg tablet	1.76USD	tablet
Pepcid 20 mg tablet	1.6USD	tablet
Apo-Famotidine 40 mg Tablet	1.11USD	tablet
Mylan-Famotidine 40 mg Tablet	1.11USD	tablet
Novo-Famotidine 40 mg Tablet	1.11USD	tablet
Nu-Famotidine 40 mg Tablet	1.11USD	tablet
Pepcid ac 10 mg tablet	0.72USD	tablet
Famotidine 40 mg/4 ml vial	0.71USD	ml
Famotidine 500 mg/50 ml vial	0.71USD	ml
Apo-Famotidine 20 mg Tablet	0.62USD	tablet
Mylan-Famotidine 20 mg Tablet	0.62USD	tablet
Novo-Famotidine 20 mg Tablet	0.62USD	tablet
Nu-Famotidine 20 mg Tablet	0.62USD	tablet
Pepcid ac 20 mg tablet	0.58USD	tablet
Famotidine-ns 20 mg/10 ml syrg	0.54USD	ml
Pepcid ac 10 mg gelcap	0.48USD	capsule
Pepcid complete tablet chew	0.4USD	tablet
Famotidine 20 mg/2 ml vial	0.36USD	ml
Famotidine 10 mg/ml vial	0.28USD	ml
CVS Pharmacy acid controller 20 mg tablet	0.24USD	tablet
CVS Pharmacy acid controller tablet	0.24USD	tablet
Acid reducer 20 mg tablet	0.22USD	tablet
Acid controller 10 mg tablet	0.21USD	tablet
Mylanta gas 125 mg tablet chew	0.16USD	tablet
Acid reducer 10 mg tablet	0.15USD	tablet
Famotidine 10 mg tablet	0.15USD	tablet
Famotidine 20 mg piggyback	0.13USD	ml
Mylanta gelcap	0.12USD	capsule
Mylanta ultimate-strength tablet	0.07USD	tablet
Mylanta ultra chew tablet	0.06USD	tablet
Pv acid reducer 10 mg tablet	0.05USD	tablet
Mylanta liq	0.02USD	ml
Mylanta supreme antacid liq	0.02USD	ml

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US5075114	No	1991-12-24	2010-05-23
CA2178277	No	2000-11-14	2016-06-05
CA2052679	No	1997-12-02	2011-08-21
US6221392	No	2001-04-24	2018-04-09
US6024981	No	2000-02-15	2018-04-09
US5854267	Yes	1998-12-29	2016-06-29
US6814978	Yes	2004-11-09	2022-02-26
US5989588	Yes	1999-11-23	2018-03-30
US8067451	No	2011-11-29	2026-07-18
US8501228	No	2013-08-06	2026-07-18
US8318202	No	2012-11-27	2026-07-18
US8449910	No	2013-05-28	2026-07-18
US8309127	No	2012-11-13	2026-07-18
US8067033	No	2011-11-29	2026-07-18
US5667794	Yes	1997-09-16	2015-11-02

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	163.5 °C	PhysProp
water solubility	1000 mg/L (at 20 °C)	MERCK INDEX (1996)
logP	-0.64	ISLAM,MS & NARURKAR,MM (1993)

Predicted Properties

Property	Value	Source
Water Solubility	0.271 mg/mL	ALOGPS
logP	-0.2	ALOGPS
logP	-2	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	9.29	ChemAxon
pKa (Strongest Basic)	8.38	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	175.83 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	80.46 m³·mol^-1	ChemAxon
Polarizability	32.02 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	0.9156
Blood Brain Barrier	+	0.9382
Caco-2 permeable	-	0.8957
P-glycoprotein substrate	Non-substrate	0.5839
P-glycoprotein inhibitor I	Non-inhibitor	0.9044
P-glycoprotein inhibitor II	Non-inhibitor	0.8701
Renal organic cation transporter	Non-inhibitor	0.6802
CYP450 2C9 substrate	Non-substrate	0.7898
CYP450 2D6 substrate	Non-substrate	0.9115
CYP450 3A4 substrate	Non-substrate	0.7558
CYP450 1A2 substrate	Non-inhibitor	0.9045
CYP450 2C9 inhibitor	Non-inhibitor	0.9071
CYP450 2D6 inhibitor	Non-inhibitor	0.9231
CYP450 2C19 inhibitor	Non-inhibitor	0.9025
CYP450 3A4 inhibitor	Non-inhibitor	0.8309
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9297
Ames test	Non AMES toxic	0.5827
Carcinogenicity	Non-carcinogens	0.9182
Biodegradation	Not ready biodegradable	0.9324
Rat acute toxicity	1.9523 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.8366
hERG inhibition (predictor II)	Inhibitor	0.6481

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
MS/MS Spectrum - Quattro_QQQ 10V, N/A	LC-MS/MS	splash10-000i-0029000000-087ab7a1109f0568738d
MS/MS Spectrum - Quattro_QQQ 25V, N/A	LC-MS/MS	splash10-0udi-0900000000-d8a9ef8fc58c0c705232
MS/MS Spectrum - Quattro_QQQ 40V, N/A	LC-MS/MS	splash10-000i-0900000000-e245f325e8c6f31a5fd0
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	Not Available
MS/MS Spectrum - Linear Ion Trap , negative	LC-MS/MS	splash10-0005-0940000000-a2bd7381011d29592cea
MS/MS Spectrum - Linear Ion Trap , positive	LC-MS/MS	splash10-0a4i-0090000000-10306158f008021f19a5
MS/MS Spectrum - Linear Ion Trap , positive	LC-MS/MS	splash10-014i-0090000000-90a70a7303c968311864
MS/MS Spectrum - Linear Ion Trap , positive	LC-MS/MS	splash10-001i-0090000000-ac0250ad61059e58f431
MS/MS Spectrum - Linear Ion Trap , positive	LC-MS/MS	splash10-0002-0090000000-235724a37e50732fdf94
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0a4r-0950000000-0c16a77af1ba782fa15a
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0a4r-0950000000-02af106b93d1423b1342
1H NMR Spectrum	1D NMR	Not Applicable
[1H,13C] 2D NMR Spectrum	2D NMR	Not Applicable

Taxonomy

Description: This compound belongs to the class of organic compounds known as 2,4-disubstituted thiazoles. These are compounds containing a thiazole ring substituted at the positions 2 and 3.
Kingdom: Organic compounds
Super Class: Organoheterocyclic compounds
Class: Azoles
Sub Class: Thiazoles
Direct Parent: 2,4-disubstituted thiazoles
Alternative Parents: Organic sulfuric acids and derivatives / Heteroaromatic compounds / Guanidines / Sulfenyl compounds / Propargyl-type 1,3-dipolar organic compounds / Dialkylthioethers / Azacyclic compounds / Amidines / Organopnictogen compounds / Organic oxidesHydrocarbon derivatives
show 1 more
Substituents: 2,4-disubstituted 1,3-thiazole / Organic sulfuric acid or derivatives / Heteroaromatic compound / Guanidine / Amidine / Azacycle / Dialkylthioether / Organic 1,3-dipolar compound / Propargyl-type 1,3-dipolar organic compound / Sulfenyl compound
show 9 more
Molecular Framework: Aromatic heteromonocyclic compounds
External Descriptors: sulfonamide, guanidines, 1,3-thiazole (CHEBI:4975)

Targets

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	300	N/A	N/A	7904648

Details1. Histamine H2 receptor

Kind: Protein
Organism: Human
Pharmacological action: Yes
Actions: Antagonist

General Function: Histamine receptor activity
Specific Function: The H2 subclass of histamine receptors mediates gastric acid secretion. Also appears to regulate gastrointestinal motility and intestinal secretion. Possible role in regulating cell growth and diff...
Gene Name: HRH2
Uniprot ID: P25021
Uniprot Name: Histamine H2 receptor
Molecular Weight: 40097.65 Da

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Fukuda M, Tanaka S, Suzuki S, Kusama K, Kaneko T, Sakashita H: Cimetidine induces apoptosis of human salivary gland tumor cells. Oncol Rep. 2007 Mar;17(3):673-8. [PubMed:17273750]
Takahashi HK, Watanabe T, Yokoyama A, Iwagaki H, Yoshino T, Tanaka N, Nishibori M: Cimetidine induces interleukin-18 production through H2-agonist activity in monocytes. Mol Pharmacol. 2006 Aug;70(2):450-3. Epub 2006 May 24. [PubMed:16723495]
Kesiova M, Alexandrova A, Yordanova N, Kirkova M, Todorov S: Effects of diphenhydramine and famotidine on lipid peroxidation and activities of antioxidant enzymes in different rat tissues. Pharmacol Rep. 2006 Mar-Apr;58(2):221-8. [PubMed:16702624]
Lesclous P, Schramm F, Gallina S, Baroukh B, Guez D, Saffar JL: Histamine mediates osteoclastic resorption only during the acute phase of bone loss in ovariectomized rats. Exp Physiol. 2006 May;91(3):561-70. Epub 2006 Mar 2. [PubMed:16513821]
Amagase K, Okabe S: On the mechanisms underlying histamine induction of gastric mucosal lesions in rats with partial gastric vascular occlusion. J Pharmacol Sci. 2003 Jun;92(2):124-36. [PubMed:12832840]
Weydert JA, Ball TM, Davis MF: Systematic review of treatments for recurrent abdominal pain. Pediatrics. 2003 Jan;111(1):e1-11. [PubMed:12509588]
Miyata K, Kamato T, Nishida A, Honda K: Studies on the mechanism for the gastric mucosal protection by famotidine in rats. Jpn J Pharmacol. 1991 Feb;55(2):211-22. [PubMed:2067140]
Leurs R, Brozius MM, Smit MJ, Bast A, Timmerman H: Effects of histamine H1-, H2- and H3-receptor selective drugs on the mechanical activity of guinea-pig small and large intestine. Br J Pharmacol. 1991 Jan;102(1):179-85. [PubMed:1646056]
Inan A, Sen M, Surgit O, Ergin M, Bozer M: Effects of the histamine H2 receptor antagonist famotidine on the healing of colonic anastomosis in rats. Clinics (Sao Paulo). 2009;64(6):567-70. [PubMed:19578661]
Ojiako K, Shingala H, Schorr C, Gerber DR: Famotidine versus pantoprazole for preventing bleeding in the upper gastrointestinal tract of critically ill patients receiving mechanical ventilation. Am J Crit Care. 2008 Mar;17(2):142-7. [PubMed:18310651]

Enzymes

Details1. Cytochrome P450 2C19

Kind: Protein
Organism: Human
Pharmacological action: Unknown
Actions: Substrate

General Function: Steroid hydroxylase activity
Specific Function: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name: CYP2C19
Uniprot ID: P33261
Uniprot Name: Cytochrome P450 2C19
Molecular Weight: 55930.545 Da

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Transporters

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	36100	N/A	N/A	23241029
Ki (nM)	1800000	N/A	N/A	15496291

Details1. Solute carrier family 22 member 2

Kind: Protein
Organism: Human
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Quaternary ammonium group transmembrane transporter activity
Specific Function: Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name: SLC22A2
Uniprot ID: O15244
Uniprot Name: Solute carrier family 22 member 2
Molecular Weight: 62579.99 Da

References

Motohashi H, Uwai Y, Hiramoto K, Okuda M, Inui K: Different transport properties between famotidine and cimetidine by human renal organic ion transporters (SLC22A). Eur J Pharmacol. 2004 Oct 25;503(1-3):25-30. [PubMed:15496291]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	300000	N/A	N/A	15496291

Details2. Solute carrier family 22 member 8

Kind: Protein
Organism: Human
Pharmacological action: Unknown
Actions: Substrate
Inhibitor

General Function: Sodium-independent organic anion transmembrane transporter activity
Specific Function: Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name: SLC22A8
Uniprot ID: Q8TCC7
Uniprot Name: Solute carrier family 22 member 8
Molecular Weight: 59855.585 Da

References

Motohashi H, Uwai Y, Hiramoto K, Okuda M, Inui K: Different transport properties between famotidine and cimetidine by human renal organic ion transporters (SLC22A). Eur J Pharmacol. 2004 Oct 25;503(1-3):25-30. [PubMed:15496291]
Kobayashi Y, Ohshiro N, Tsuchiya A, Kohyama N, Ohbayashi M, Yamamoto T: Renal transport of organic compounds mediated by mouse organic anion transporter 3 (mOat3): further substrate specificity of mOat3. Drug Metab Dispos. 2004 May;32(5):479-83. [PubMed:15100168]
Tahara H, Kusuhara H, Chida M, Fuse E, Sugiyama Y: Is the monkey an appropriate animal model to examine drug-drug interactions involving renal clearance? Effect of probenecid on the renal elimination of H2 receptor antagonists. J Pharmacol Exp Ther. 2006 Mar;316(3):1187-94. Epub 2005 Nov 16. [PubMed:16291876]

Drug created on June 13, 2005 07:24 / Updated on December 18, 2018 05:46

Famotidine

Identification

Structure for Famotidine (DB00927)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

References

Enzymes

References

Transporters

References

References