Identification

Name
Famotidine
Accession Number
DB00927  (APRD00296)
Type
Small Molecule
Groups
Approved
Description

A competitive histamine H2-receptor antagonist. Its main pharmacodynamic effect is the inhibition of gastric secretion. [PubChem]

Structure
Thumb
Synonyms
  • (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
  • Famotidinum
  • N-Sulfamoyl-3-((2-guanidinothiazol-4-yl)methylthio)propionamide
External IDs
L 643341 / MK-208 / YM-11170
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Bci FamotidineTablet40 mgOralBaker Cummins IncNot applicableNot applicableCanada
Bci FamotidineTablet20 mgOralBaker Cummins IncNot applicableNot applicableCanada
FamotidinePowder, for suspension40 mg/5mLOralPaddock Laboratories, Inc.2010-05-282015-04-30Us
Famotidine 10mgTablet10 mgOralLaboratoire Riva IncNot applicableNot applicableCanada
Famotidine InjectionSolution10 mgIntravenousHospira, Inc.Not applicableNot applicableCanada
Famotidine InjectionSolution10 mgIntravenousMylan PharmaceuticalsNot applicableNot applicableCanada
Famotidine InjectionSolution10 mgIntravenousFresenius KabiNot applicableNot applicableCanada
Famotidine InjectionSolution10 mgIntravenousMylan PharmaceuticalsNot applicableNot applicableCanada
Famotidine IV InjectionSolution10 mgIntravenousTevaNot applicableNot applicableCanada
Famotidine IV InjectionSolution10 mgIntravenousTevaNot applicableNot applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-famotidine InjectableSolution10 mgIntravenousApotex Corporation2004-05-272013-08-02Canada
Apo-famotidine InjectableSolution10 mgIntravenousApotex Corporation2003-11-172013-08-02Canada
Apo-famotidine Tab 20mg USPTablet20 mgOralApotex Corporation1993-12-31Not applicableCanada
Apo-famotidine Tab 40mg USPTablet40 mgOralApotex Corporation1993-12-31Not applicableCanada
FamotidineTablet, film coated20 mg/1OralClinical Solutions Wholsesale2017-07-06Not applicableUs
FamotidineTablet40 mg/1OralUnit Dose Services2016-01-29Not applicableUs
FamotidineTablet20 mg/1OralRemedy Repack2017-04-25Not applicableUs
FamotidineTablet, film coated20 mg/1OralNucare Pharmaceuticals,inc.2001-04-16Not applicableUs
FamotidineInjection, solution10 mg/1mLIntravenousPfizer Laboratories Div Pfizer Inc.2011-05-102017-12-31Us
FamotidineTablet, film coated40 mg/1OralRemedy Repack2010-09-172013-02-15Us
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
7 Select Acid ControllerTablet20 mg/1Oral7 Eleven2014-08-05Not applicableUs
Acid ControlTablet10 mgOralApotex Corporation2000-07-11Not applicableCanada
Acid ControlTablet10 mgOralVita Health Products Inc1998-10-27Not applicableCanada
Acid ControlTablet10 mgOralPendopharm Division Of De Pharmascience Inc1997-09-082015-01-19Canada
Acid ControlTablet10 mgOralTeva1997-06-17Not applicableCanada
Acid ControlTablet20 mgOralApotex Corporation2014-04-28Not applicableCanada
Acid Control Original StrengthTablet10 mg/1OralMedicine Shoppe International2009-10-192012-04-09Us
Acid ControllerTablet20 mg/1OralCVS Health2006-09-28Not applicableUs
Acid ControllerTablet20 mg/1OralShopko Stores Operating2013-07-17Not applicableUs
Acid ControllerTablet20 mg/1OralWalgreen2006-09-26Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Acid Controller CompleteFamotidine (10 mg/1) + Calcium Carbonate (800 mg/1) + Magnesium hydroxide (165 mg/1)Tablet, chewableOralShopko Stores Operating2013-06-052017-01-15Us
Acid Controller CompleteFamotidine (10 mg/1) + Calcium Carbonate (800 mg/1) + Magnesium hydroxide (165 mg/1)Tablet, chewableOralShopko Stores Operating2013-06-052016-11-16Us
Acid Controller CompleteFamotidine (10 mg/1) + Calcium Carbonate (800 mg/1) + Magnesium hydroxide (165 mg/1)Tablet, chewableOralSafeway2008-08-062017-01-19Us
Acid Controller Complete dual actionFamotidine (10 mg/1) + Calcium Carbonate (800 mg/1) + Magnesium hydroxide (165 mg/1)Tablet, chewableOralWalgreen2008-07-302017-07-25Us
Acid Controller Complete dual actionFamotidine (10 mg/1) + Calcium Carbonate (800 mg/1) + Magnesium hydroxide (165 mg/1)Tablet, chewableOralWalgreen2008-07-30Not applicableUs
Acid Reducer CompleteFamotidine (10 mg/1) + Calcium Carbonate (800 mg/1) + Magnesium hydroxide (165 mg/1)Tablet, chewableOralShopko Stores Operating Co., LLC2016-01-06Not applicableUs
Acid Reducer CompleteFamotidine (10 mg/1) + Calcium Carbonate (800 mg/1) + Magnesium hydroxide (165 mg/1)Tablet, chewableOralShopko Stores Operating Co., LLC2016-01-12Not applicableUs
Acid Reducer CompleteFamotidine (10 mg/1) + Calcium Carbonate (800 mg/1) + Magnesium hydroxide (165 mg/1)Tablet, chewableOralWalgreen Company2016-01-29Not applicableUs
Acid Reducer CompleteFamotidine (10 mg/1) + Calcium Carbonate (800 mg/1) + Magnesium hydroxide (165 mg/1)Tablet, chewableOralRite Aid2009-05-152017-09-08Us
Acid Reducer CompleteFamotidine (10 mg/1) + Calcium Carbonate (800 mg/1) + Magnesium hydroxide (165 mg/1)Tablet, chewableOralWalgreen Company2016-01-29Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
FamotidineFamotidine (2 mg/1mL)Injection, solutionIntravenousCantrell Drug Company2014-06-11Not applicableUs
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.

TargetActionsOrganism
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
PathwayCategory
Famotidine Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may decrease the sedative and stimulatory activities of Famotidine.
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may decrease the sedative and stimulatory activities of Famotidine.
3,4-Methylenedioxyamphetamine3,4-Methylenedioxyamphetamine may decrease the sedative and stimulatory activities of Famotidine.
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may decrease the sedative and stimulatory activities of Famotidine.
AbexinostatThe risk or severity of QTc prolongation can be increased when Famotidine is combined with Abexinostat.
AcebutololThe risk or severity of QTc prolongation can be increased when Famotidine is combined with Acebutolol.
AceprometazineThe risk or severity of QTc prolongation can be increased when Famotidine is combined with Aceprometazine.
AcetyldigoxinThe risk or severity of QTc prolongation can be increased when Famotidine is combined with Acetyldigoxin.
AcrivastineThe risk or severity of QTc prolongation can be increased when Famotidine is combined with Acrivastine.
AcyclovirThe excretion of Famotidine can be decreased when combined with Acyclovir.
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, combinationsA02BA03 — Famotidine
AHFS Codes
  • 56:28.12 — Histamine H2-antagonists
FDA label
Download (1.05 MB)
MSDS
Download (73.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableHealthy Volunteers / Lupus / Psoriasis1
1CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
1CompletedBasic ScienceDrug-Drug Interaction (DDI)1
1CompletedBasic ScienceHealthy Volunteers2
1CompletedHealth Services ResearchHealthy Volunteers1
1CompletedOtherHealthy Volunteers1
1CompletedScreeningFibrosis1
1CompletedTreatmentBioavailability2
1CompletedTreatmentCancers / Colorectal Cancers / Lung Cancer Non-Small Cell Cancer (NSCLC) / Melanoma / Thyroid Papillary Carcinoma1
1CompletedTreatmentHealthy Volunteers2
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Human Immunodeficiency Virus I1
1CompletedTreatmentPsoriasis1
1RecruitingTreatmentDiseases of Oesophagus Stomach and Duodenum1
1, 2RecruitingTreatmentColorectal Cancers1
2Active Not RecruitingTreatmentMalignant Neoplasm of Stomach1
2CompletedTreatmentCerebrovascular Accident, Acute / Edema of the cerebrum1
2CompletedTreatmentDyskinesias1
2Not Yet RecruitingTreatmentPlasmodium Infections1
2Not Yet RecruitingTreatmentPulmonary Arterial Hypertension (PAH) / Right Heart Failure1
2RecruitingTreatmentHNSCC / HPV-Related Squamous Cell Carcinoma1
2RecruitingTreatmentPlasma Cell Myeloma1
2, 3CompletedTreatmentMalaria caused by Plasmodium falciparum1
2, 3CompletedTreatmentReflux, Gastroesophageal1
2, 3RecruitingTreatmentSchizophrenic Disorders1
3CompletedPreventionUlcers1
3CompletedTreatmentErosive Esophagitis(EE)1
3CompletedTreatmentPeptic Ulcer Bleeding / Upper Gastrointestinal Hemorrhage1
3CompletedTreatmentReflux, Gastroesophageal1
3Not Yet RecruitingTreatmentFallopian Tube Cancer / Ovarian Epithelial Cancer / Primary Peritoneal Carcinoma2
3Not Yet RecruitingTreatmentMalaria caused by Plasmodium falciparum1
4Active Not RecruitingPreventionPeptic Ulcers1
4CompletedNot AvailableHuman Immunodeficiency Virus (HIV)1
4CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
4CompletedPreventionMarginal Ulcers1
4CompletedPreventionPeptic Ulcer/Erosions1
4CompletedPreventionUlcers1
4CompletedTreatmentHeartburn1
4CompletedTreatmentJuvenile Idiopathic Arthritis (JIA)1
4CompletedTreatmentSchizophrenic Disorders1
4RecruitingTreatmentRheumatoid Arthritis1
4Unknown StatusTreatmentAspirin / Indigestion1
Not AvailableActive Not RecruitingTreatmentMetastatic Melanoma1
Not AvailableCompletedNot AvailableAnemias / Iron Deficiency / Plasmodium Infections / Schistosomiasis Infection1
Not AvailableCompletedNot AvailableCommunity Acquired Pneumonia (CAP) / Gastro-esophageal Reflux Disease (GERD)1
Not AvailableCompletedNot AvailableHealthy Volunteers2
Not AvailableCompletedNot AvailableRhytidoplasty1
Not AvailableCompletedTreatmentPlasmodium Infections1
Not AvailableRecruitingPreventionPeptic Ulcers2
Not AvailableRecruitingSupportive CareCancer, Breast / Post-Operative Nausea and Vomiting (PONV)1
Not AvailableRecruitingTreatmentMalignant Neoplasm of Stomach1
Not AvailableUnknown StatusNot AvailableParasitemia1

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
FormRouteStrength
TabletOral10 mg/1
Tablet, coatedOral
For suspensionOral40 mg/5mL
InjectionIntravenous10 mg/1mL
Injection, solutionIntravenous10 mg/1mL
Injection, solutionIntravenous2 mg/1mL
Powder, for solutionOral40 mg/5mL
Powder, for suspensionOral40 mg/5mL
TabletOral20 mg/1
TabletOral40 mg/1
Tablet, coatedOral20 mg/1
Tablet, coatedOral40 mg/1
Tablet, film coatedOral10 mg/1
Tablet, film coatedOral20 mg/1
Tablet, film coatedOral40 mg/1
Tablet, film coated, extended releaseOral10 mg/1
SolutionIntravenous10 mg
Tablet, orally disintegratingOral20 mg/1
Tablet, orally disintegratingOral40 mg/1
Injection, solutionIntravenous20 mg/50mL
Injection, solution, concentrateIntravenous10 mg/1mL
TabletOral10 mg
Tablet, chewableOral20 mg/1
Tablet, chewableOral
TabletOral20 mg
TabletOral40 mg
Tablet, coatedOral10 mg/1
Prices
Unit descriptionCostUnit
Pepcid 30 40 mg tablet Bottle125.5USD bottle
Pepcid 40 mg/5ml Suspension 50ml Bottle123.88USD bottle
Pepcid 30 20 mg tablet Bottle64.13USD bottle
Mylanta Double-Strength 400-400-40 mg/5ml Suspension 710ml Bottle10.15USD bottle
Mylanta 200-200-20 mg/5ml Suspension 710ml Bottle9.23USD bottle
Mylanta 200-200-20 mg/5ml Suspension 355ml Bottle7.99USD bottle
Mylanta Double-Strength 400-400-40 mg/5ml Suspension 355ml Bottle7.99USD bottle
Famotidine 40 mg tablet3.43USD tablet
Pepcid 40 mg tablet3.02USD tablet
Famotidine powder2.74USD g
Famotidine 20 mg tablet1.76USD tablet
Pepcid 20 mg tablet1.6USD tablet
Apo-Famotidine 40 mg Tablet1.11USD tablet
Mylan-Famotidine 40 mg Tablet1.11USD tablet
Novo-Famotidine 40 mg Tablet1.11USD tablet
Nu-Famotidine 40 mg Tablet1.11USD tablet
Pepcid ac 10 mg tablet0.72USD tablet
Famotidine 40 mg/4 ml vial0.71USD ml
Famotidine 500 mg/50 ml vial0.71USD ml
Apo-Famotidine 20 mg Tablet0.62USD tablet
Mylan-Famotidine 20 mg Tablet0.62USD tablet
Novo-Famotidine 20 mg Tablet0.62USD tablet
Nu-Famotidine 20 mg Tablet0.62USD tablet
Pepcid ac 20 mg tablet0.58USD tablet
Famotidine-ns 20 mg/10 ml syrg0.54USD ml
Pepcid ac 10 mg gelcap0.48USD capsule
Pepcid complete tablet chew0.4USD tablet
Famotidine 20 mg/2 ml vial0.36USD ml
Famotidine 10 mg/ml vial0.28USD ml
CVS Pharmacy acid controller 20 mg tablet0.24USD tablet
CVS Pharmacy acid controller tablet0.24USD tablet
Acid reducer 20 mg tablet0.22USD tablet
Acid controller 10 mg tablet0.21USD tablet
Mylanta gas 125 mg tablet chew0.16USD tablet
Acid reducer 10 mg tablet0.15USD tablet
Famotidine 10 mg tablet0.15USD tablet
Famotidine 20 mg piggyback0.13USD ml
Mylanta gelcap0.12USD capsule
Mylanta ultimate-strength tablet0.07USD tablet
Mylanta ultra chew tablet0.06USD tablet
Pv acid reducer 10 mg tablet0.05USD tablet
Mylanta liq0.02USD ml
Mylanta supreme antacid liq0.02USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5075114No1993-05-232010-05-23Us
CA2178277No2000-11-142016-06-05Canada
CA2052679No1997-12-022011-08-21Canada
US6221392No1998-04-092018-04-09Us
US6024981No1998-04-092018-04-09Us
US5854267Yes1996-06-292016-06-29Us
US6814978Yes2002-02-262022-02-26Us
US5989588Yes1998-03-302018-03-30Us
US8067451No2006-07-182026-07-18Us
US8501228No2006-07-182026-07-18Us
US8318202No2006-07-182026-07-18Us
US8449910No2006-07-182026-07-18Us
US8309127No2006-07-182026-07-18Us
US8067033No2006-07-182026-07-18Us
US5667794Yes1995-11-022015-11-02Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)163.5 °CPhysProp
water solubility1000 mg/L (at 20 °C)MERCK INDEX (1996)
logP-0.64ISLAM,MS & NARURKAR,MM (1993)
Predicted Properties
PropertyValueSource
Water Solubility0.271 mg/mLALOGPS
logP-0.2ALOGPS
logP-2ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)9.29ChemAxon
pKa (Strongest Basic)8.38ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area175.83 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity80.46 m3·mol-1ChemAxon
Polarizability32.02 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9156
Blood Brain Barrier+0.9382
Caco-2 permeable-0.8957
P-glycoprotein substrateNon-substrate0.5839
P-glycoprotein inhibitor INon-inhibitor0.9044
P-glycoprotein inhibitor IINon-inhibitor0.8701
Renal organic cation transporterNon-inhibitor0.6802
CYP450 2C9 substrateNon-substrate0.7898
CYP450 2D6 substrateNon-substrate0.9115
CYP450 3A4 substrateNon-substrate0.7558
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9297
Ames testNon AMES toxic0.5827
CarcinogenicityNon-carcinogens0.9182
BiodegradationNot ready biodegradable0.9324
Rat acute toxicity1.9523 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8366
hERG inhibition (predictor II)Inhibitor0.6481
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
MS/MS Spectrum - Quattro_QQQ 10V, N/ALC-MS/MSsplash10-000i-0029000000-087ab7a1109f0568738d
MS/MS Spectrum - Quattro_QQQ 25V, N/ALC-MS/MSsplash10-0udi-0900000000-d8a9ef8fc58c0c705232
MS/MS Spectrum - Quattro_QQQ 40V, N/ALC-MS/MSsplash10-000i-0900000000-e245f325e8c6f31a5fd0
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0005-0940000000-a2bd7381011d29592cea
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0a4i-0090000000-10306158f008021f19a5
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-014i-0090000000-90a70a7303c968311864
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-001i-0090000000-ac0250ad61059e58f431
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0002-0090000000-235724a37e50732fdf94
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4r-0950000000-0c16a77af1ba782fa15a
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4r-0950000000-02af106b93d1423b1342
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot 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 oxides
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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
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Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
sulfonamide, guanidines, 1,3-thiazole (CHEBI:4975)

Targets

Details
1. 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
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. 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]
  3. 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]
  4. 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]
  5. 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]
  6. 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]
  7. Weydert JA, Ball TM, Davis MF: Systematic review of treatments for recurrent abdominal pain. Pediatrics. 2003 Jan;111(1):e1-11. [PubMed:12509588]
  8. 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]
  9. 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]
  10. 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]
  11. 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

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
  1. 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

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
  1. 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]
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
  1. 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]
  2. 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]
  3. 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 October 21, 2018 20:27