You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameFamotidine
Accession NumberDB00927  (APRD00296)
Typesmall molecule
Groupsapproved
Description

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

Structure
Thumb
Synonyms
SynonymLanguageCode
FamotidinaSpanishINN
FamotidinumLatinINN
SaltsNot Available
Brand names
NameCompany
AmfamoxNot Available
AntodineNot Available
ConfobosNot Available
CronolNot Available
DigervinNot Available
DispromilNot Available
DuovelNot Available
DuraterNot Available
FamocidNot Available
FamosanNot Available
FamotepNot Available
FamoxNot Available
FamoxalNot Available
FamtacNot Available
FamulcerNot Available
FanosinNot Available
FluxidNot Available
GasterNot Available
LecedilNot Available
MotiaxNot Available
Mylanta ARNot Available
NotidinNot Available
NulceranNot Available
PanalbaNot Available
PepcidNot Available
Pepcid ACNot Available
Pepcid RPDNot Available
PepcidinNot Available
PepcidineNot Available
PepdineNot Available
PepfaminNot Available
QuamatelNot Available
RenapepsaNot Available
RubacinaNot Available
Sedanium-RNot Available
SupertidineNot Available
TairalNot Available
TipodexNot Available
UlfagelNot Available
UlfamidNot Available
UlgarineNot Available
VagostalNot Available
Brand mixturesNot Available
Categories
CAS number76824-35-6
WeightAverage: 337.445
Monoisotopic: 337.044934829
Chemical FormulaC8H15N7O2S3
InChI KeyXUFQPHANEAPEMJ-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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassAzoles
SubclassThiazoles
Direct parent2,4-disubstituted Thiazoles
Alternative parentsAminothiazoles; Organic Sulfuric Acids and Derivatives; Guanidines; Thioethers; Polyamines; Amidines
Substituents1,3-thiazolamine; sulfuric acid derivative; guanidine; polyamine; amidine; thioether; amine; organonitrogen compound
Classification descriptionThis compound belongs to the 2,4-disubstituted thiazoles. These are compounds containing a thiazole ring substituted at positions 2 and 4 only.
Pharmacology
IndicationFor the treatment of peptic ulcer disease (PUD) and gastroesophageal reflux disease (GERD).
PharmacodynamicsFamotidine, 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 actionFamotidine 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.
AbsorptionThe bioavailability of oral doses is 40-45%.
Volume of distributionNot Available
Protein binding15-20%
Metabolism

Hepatic.

Route of eliminationRenal clearance is 250-450 mL/min, indicating some tubular excretion.
Half life2.5-3.5 hours
Clearance
  • renal cl=250-450 mL/min
ToxicityIntravenous, 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Non-inhibitor 0.9231
CYP450 2C19 substrate Non-inhibitor 0.9025
CYP450 3A4 substrate 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
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
Dosage forms
FormRouteStrength
SolutionIntravenous
TabletOral
Prices
Unit descriptionCostUnit
Pepcid 30 40 mg tablet Bottle125.5USDbottle
Pepcid 40 mg/5ml Suspension 50ml Bottle123.88USDbottle
Pepcid 30 20 mg tablet Bottle64.13USDbottle
Mylanta Double-Strength 400-400-40 mg/5ml Suspension 710ml Bottle10.15USDbottle
Mylanta 200-200-20 mg/5ml Suspension 710ml Bottle9.23USDbottle
Mylanta 200-200-20 mg/5ml Suspension 355ml Bottle7.99USDbottle
Mylanta Double-Strength 400-400-40 mg/5ml Suspension 355ml Bottle7.99USDbottle
Famotidine 40 mg tablet3.43USDtablet
Pepcid 40 mg tablet3.02USDtablet
Famotidine powder2.74USDg
Famotidine 20 mg tablet1.76USDtablet
Pepcid 20 mg tablet1.6USDtablet
Apo-Famotidine 40 mg Tablet1.11USDtablet
Mylan-Famotidine 40 mg Tablet1.11USDtablet
Novo-Famotidine 40 mg Tablet1.11USDtablet
Nu-Famotidine 40 mg Tablet1.11USDtablet
Pepcid ac 10 mg tablet0.72USDtablet
Famotidine 40 mg/4 ml vial0.71USDml
Famotidine 500 mg/50 ml vial0.71USDml
Apo-Famotidine 20 mg Tablet0.62USDtablet
Mylan-Famotidine 20 mg Tablet0.62USDtablet
Novo-Famotidine 20 mg Tablet0.62USDtablet
Nu-Famotidine 20 mg Tablet0.62USDtablet
Pepcid ac 20 mg tablet0.58USDtablet
Famotidine-ns 20 mg/10 ml syrg0.54USDml
Pepcid ac 10 mg gelcap0.48USDcapsule
Pepcid complete tablet chew0.4USDtablet
Famotidine 20 mg/2 ml vial0.36USDml
Famotidine 10 mg/ml vial0.28USDml
CVS Pharmacy acid controller 20 mg tablet0.24USDtablet
CVS Pharmacy acid controller tablet0.24USDtablet
Acid reducer 20 mg tablet0.22USDtablet
Acid controller 10 mg tablet0.21USDtablet
Mylanta gas 125 mg tablet chew0.16USDtablet
Acid reducer 10 mg tablet0.15USDtablet
Famotidine 10 mg tablet0.15USDtablet
Famotidine 20 mg piggyback0.13USDml
Mylanta gelcap0.12USDcapsule
Mylanta ultimate-strength tablet0.07USDtablet
Mylanta ultra chew tablet0.06USDtablet
Pv acid reducer 10 mg tablet0.05USDtablet
Mylanta liq0.02USDml
Mylanta supreme antacid liq0.02USDml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
United States68149782002-02-262022-02-26
United States50751141993-05-232010-05-23
Canada21782772000-11-142016-06-05
Canada20526791997-12-022011-08-21
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point163.5 °CPhysProp
water solubility1000 mg/L (at 20 °C)MERCK INDEX (1996)
logP-0.64ISLAM,MS & NARURKAR,MM (1993)
Predicted Properties
PropertyValueSource
water solubility2.71e-01 g/lALOGPS
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 area175.83ChemAxon
rotatable bond count6ChemAxon
refractivity80.46ChemAxon
polarizability32.02ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraMS/MS1D NMR2D NMR
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 ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00318
PubChem Compound5702160
PubChem Substance46507397
ChemSpider3208
ChEBI4975
ChEMBLCHEMBL902
Therapeutic Targets DatabaseDAP000341
PharmGKBPA449586
Drug Product Database2242327
RxListhttp://www.rxlist.com/cgi/generic/famot.htm
Drugs.comhttp://www.drugs.com/famotidine.html
PDRhealthhttp://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/pep1325.shtml
WikipediaFamotidine
ATC CodesA02BA03
AHFS Codes
  • 56:28.12
PDB EntriesNot Available
FDA labelshow(1.05 MB)
MSDSshow(73.8 KB)
Interactions
Drug Interactions
Drug
AtazanavirThis gastric pH modifier decreases the levels/effects of atazanavir
CefditorenH2-Antagonists such as famotidine may decrease the serum concentration of cefditoren. Cefditoren prescribing information recommends to avoid concomitant use with H2-antagonists (eg, famotidine, ranitidine) and antacids as well. Consider alternative methods to minimize/control acid reflux (eg, diet modification) or alternative antimicrobial therapy if use of H2-antagonists can not be avoided.
EnoxacinFamotidine may decrease the absorption of enoxacin.
ItraconazoleThe H2-receptor antagonist, famotidine, may decrease the absorption of itraconazole.
KetoconazoleThe H2-receptor antagonist, famotidine, may decrease the absorption of ketoconazole.
RilpivirineHistamine-2 receptor antagonists increase gastric pH which causes a decrease in the exposure of rilpivirine thus reducing efficacy.
Food Interactions
  • Avoid alcohol.
  • Limit caffeine intake.
  • Take without regard to meals, food may slightly increase the product's bioavailability.

Targets

1. Histamine H2 receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Histamine H2 receptor P25021 Details

References:

  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  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
  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
  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
  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
  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
  7. Weydert JA, Ball TM, Davis MF: Systematic review of treatments for recurrent abdominal pain. Pediatrics. 2003 Jan;111(1):e1-11. Pubmed
  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
  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
  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
  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

Enzymes

1. Cytochrome P450 2C19

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C19 P33261 Details

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. Epub 2009 Nov 24. Pubmed

Transporters

1. Solute carrier family 22 member 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 2 O15244 Details

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

2. Solute carrier family 22 member 8

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 8 Q8TCC7 Details

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
  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
  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

Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:12