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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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Famotidina [Spanish]
Famotidinum [Latin]
Salts Not Available
Brand names
Name Company
Amfamox
Antodine
Apo-Famotidine
Apogastine
Bestidine
Blocacid
Brolin
Cepal
Confobos
Cronol
Cuantin
Dibrit 40
Digervin
Dinul
Dipsin
Dispromil
Dispronil
Duovel
Durater
Evatin
Fadin
Fadine
Fadyn
Fagastine
Famo
Famocid
Famodar
Famodil
Famodin
Famodine
Famogard
Famonit
Famopsin
Famos
Famosan
Famotal
Famotep
Famotin
Famovane
Famowal
Famox
Famoxal
Famtac
Famulcer
Fanobel
Fanosin
Fanox
Farmotex
Ferotine
Fibonel
Fluxid
Fudone
Ganor
Gaster
Gastridan
Gastridin
Gastrion
Gastro
Gastrodomina
Gastrofam
Gastropen
Gastrosidin
H2 Bloc
Hacip
Huberdina
Ingastri
Invigan
Lecedil
Logos
Mensoma
Midefam
Mosul
Motiax
Muclox
Mylanta AR
Neocidine
Nevofam
Notidin
Novo-Famotidine
Nu-Famotidine
Nulceran
Nulcerin
Panalba
Pepcid
Pepcid AC
Pepcid RPD
Pepcidin
Pepcidin Rapitab
Pepcidina
Pepcidine
Pepdif
Pepdine
Pepdul
Pepfamin
Peptan
Peptidin
Peptifam
Pepzan
Purifam
Quamatel
Quamtel
Renapepsa
Restadin
Rogasti
Rubacina
Sedanium-R
Sigafam
Supertidine
Tairal
Tamin
Tipodex
Topcid
Ulcatif
Ulceprax
Ulcofam
Ulfagel
Ulfam
Ulfamid
Ulfinol
Ulgarine
Vagostal
Weimok
Whitidin
Yamarin
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Brand mixtures Not Available
Categories
  • Anti-Ulcer Agents
  • Histamine H2 Antagonists
CAS number 76824-35-6
Weight Average: 337.445
Monoisotopic: 337.044934829
Chemical Formula C8H15N7O2S3
InChI Key InChIKey=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)
Plain Text
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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Sulfonyls
  • Sulfuric Acids and Derivatives
  • Thiazoles
Substructures
  • Ethers
  • Sulfonyls
  • Sulfuric Acids and Derivatives
  • Thiazoles
  • Heterocyclic compounds
  • Guanidines
  • Aromatic compounds
  • Carboxamidines
  • Imines
Pharmacology
Indication For the treatment of peptic ulcer disease (PUD) and gastroesophageal reflux disease (GERD).
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.
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 Name SMPDB ID
Smp00231 Famotidine Pathway SMP00231
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
Form Route Strength
Solution Intravenous
Tablet Oral
Prices
Unit description Cost Unit
Pepcid 30 40 mg tablet Bottle 125.5 USD bottle
Pepcid 40 mg/5ml Suspension 50ml Bottle 123.88 USD bottle
Pepcid 30 20 mg tablet Bottle 64.13 USD bottle
Mylanta Double-Strength 400-400-40 mg/5ml Suspension 710ml Bottle 10.15 USD bottle
Mylanta 200-200-20 mg/5ml Suspension 710ml Bottle 9.23 USD bottle
Mylanta 200-200-20 mg/5ml Suspension 355ml Bottle 7.99 USD bottle
Mylanta Double-Strength 400-400-40 mg/5ml Suspension 355ml Bottle 7.99 USD bottle
Famotidine 40 mg tablet 3.43 USD tablet
Pepcid 40 mg tablet 3.02 USD tablet
Famotidine powder 2.74 USD g
Famotidine 20 mg tablet 1.76 USD tablet
Pepcid 20 mg tablet 1.6 USD tablet
Apo-Famotidine 40 mg Tablet 1.11 USD tablet
Mylan-Famotidine 40 mg Tablet 1.11 USD tablet
Novo-Famotidine 40 mg Tablet 1.11 USD tablet
Nu-Famotidine 40 mg Tablet 1.11 USD tablet
Pepcid ac 10 mg tablet 0.72 USD tablet
Famotidine 40 mg/4 ml vial 0.71 USD ml
Famotidine 500 mg/50 ml vial 0.71 USD ml
Apo-Famotidine 20 mg Tablet 0.62 USD tablet
Mylan-Famotidine 20 mg Tablet 0.62 USD tablet
Novo-Famotidine 20 mg Tablet 0.62 USD tablet
Nu-Famotidine 20 mg Tablet 0.62 USD tablet
Pepcid ac 20 mg tablet 0.58 USD tablet
Famotidine-ns 20 mg/10 ml syrg 0.54 USD ml
Pepcid ac 10 mg gelcap 0.48 USD capsule
Pepcid complete tablet chew 0.4 USD tablet
Famotidine 20 mg/2 ml vial 0.36 USD ml
Famotidine 10 mg/ml vial 0.28 USD ml
CVS Pharmacy acid controller 20 mg tablet 0.24 USD tablet
CVS Pharmacy acid controller tablet 0.24 USD tablet
Acid reducer 20 mg tablet 0.22 USD tablet
Acid controller 10 mg tablet 0.21 USD tablet
Mylanta gas 125 mg tablet chew 0.16 USD tablet
Acid reducer 10 mg tablet 0.15 USD tablet
Famotidine 10 mg tablet 0.15 USD tablet
Famotidine 20 mg piggyback 0.13 USD ml
Mylanta gelcap 0.12 USD capsule
Mylanta ultimate-strength tablet 0.07 USD tablet
Mylanta ultra chew tablet 0.06 USD tablet
Pv acid reducer 10 mg tablet 0.05 USD tablet
Mylanta liq 0.02 USD ml
Mylanta supreme antacid liq 0.02 USD ml
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DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Country Patent Number Approved Expires (estimated)
United States 6814978 2002-02-26 2022-02-26
United States 5075114 1993-05-23 2010-05-23
Canada 2178277 2000-11-14 2016-06-05
Canada 2052679 1997-12-02 2011-08-21
Properties
State solid
Experimental Properties
Property Value Source
melting point 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 2.71e-01 g/l 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 ChemAxon
rotatable bond count 6 ChemAxon
refractivity 80.46 ChemAxon
polarizability 32.02 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00318 Link_out
PubChem Compound 5702160 Link_out
PubChem Substance 46507397 Link_out
ChemSpider 3208 Link_out
ChEBI 4975 Link_out
ChEMBL 4975 Link_out
Therapeutic Targets Database DAP000341 Link_out
PharmGKB PA449586 Link_out
Drug Product Database 2242327 Link_out
RxList http://www.rxlist.com/cgi/generic/famot.htm Link_out
Drugs.com http://www.drugs.com/famotidine.html Link_out
PDRhealth http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/pep1325.shtml Link_out
Wikipedia http://en.wikipedia.org/wiki/Famotidine Link_out
ATC Codes
  • A02BA03
AHFS Codes
  • 56:28.12
PDB Entries Not Available
FDA label show (1.05 MB)
MSDS show (73.8 KB)
Interactions
Drug Interactions
Drug Interaction
Atazanavir This gastric pH modifier decreases the levels/effects of atazanavir
Cefditoren H2-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.
Enoxacin Famotidine may decrease the absorption of enoxacin.
Itraconazole The H2-receptor antagonist, famotidine, may decrease the absorption of itraconazole.
Ketoconazole The H2-receptor antagonist, famotidine, may decrease the absorption of ketoconazole.
Rilpivirine Histamine-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

Pharmacological action: yes
Actions: antagonist

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 differentiation. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase and, through a separate G protein-dependent mechanism, the phosphoinositide/protein kinase (PKC) signaling pathway

Organism class: human
UniProt ID: P25021 Link_out
Gene: HRH2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: substrate

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 imipramine

UniProt ID: P33261 Link_out
Gene: CYP2C19 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: inhibitor

Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, cisplatin and oxaliplatin. Cisplatin may develop a nephrotoxic action. Transport of creatinine is inhibited by fluoroquinolones such as DX-619 and LVFX. This transporter is a major determinant of the anticancer activity of oxaliplatin and may contribute to antitumor specificity

UniProt ID: O15244 Link_out
Gene: SLC22A2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: substrate, inhibitor

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, fexofenadine. Transports benzylpenicillin (PCG), estrone- 3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA)

UniProt ID: Q8TCC7 Link_out
Gene: SLC22A8 Link_out
Protein Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19