| 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 |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- Famotidina [Spanish]
- Famotidinum [Latin]
|
| Brand names |
- 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
|
| Brand name 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 |
|
| 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 |
|
| Pathways |
| Pathway |
Name |
SMPDB ID |
|
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 |
|
| Patents |
| Country |
Patent Number |
Approved |
Expires |
| 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 |
| Melting point |
163-164 oC |
| Experimental Properties |
|
| Predicted Properties |
|
| References |
|---|
| Synthesis Reference |
Not Available
|
| General Reference |
Not Available
|
| External Links |
|
| ATC Codes |
|
| AHFS Codes |
|
| PDB Entries |
Not Available |
| FDA label |
show (1.1 MB)
|
| MSDS |
show (73.8 KB)
|
| Interactions |
|---|
| Drug Interactions |
Not Available |
| 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 
Gene: HRH2
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report
References:
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
- 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
- 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
- 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
- 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
- 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
- Weydert JA, Ball TM, Davis MF: Systematic review of treatments for recurrent abdominal pain. Pediatrics. 2003 Jan;111(1):e1-11. Pubmed
- 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
- 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
- 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
- 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
|
| 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
Gene: SLC22A2
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report
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
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
Gene: SLC22A8
Protein Sequence: FASTA
SNPs: SNPJam Report
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
- 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
- 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
|
