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Details

Stereochemistry ACHIRAL
Molecular Formula C8H15N7O2S3
Molecular Weight 337.445
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FAMOTIDINE

SMILES

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

InChI

InChIKey=XUFQPHANEAPEMJ-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C8H15N7O2S3
Molecular Weight 337.445
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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. 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.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Differences in the antisecretory actions of the proton pump inhibitor AG-1749 (lansoprazole) and the histamine H2-receptor antagonist famotidine in rats and dogs.
1991 Apr
Switching of H(2)-Receptor Antagonists to Over-the-Counter Status in Finland : Implications for Consumption and Adverse Effects.
2005
[Gastroprotective effects of histamine H2-receptor blockers in Helicobacter-like gastric mucosa lesions].
2005
Synergistic action of famotidine and chlorpheniramine on acetic acid-induced chronic gastric ulcer in rats.
2005 Dec 7
Effect of preoperative short course famotidine on TILs and survival in breast cancer.
2005 Oct-Dec
[Complex evaluation of the action of inhibitors of hydrochloric acid secretion on gastric function in ulcer disease].
2006
Histamine mediates the stimulatory action of ghrelin on acid secretion in rat stomach.
2006 Aug
Cimetidine induces interleukin-18 production through H2-agonist activity in monocytes.
2006 Aug
Assessing the efficacy of famotidine and rebamipide in the treatment of gastric mucosal lesions in patients receiving long-term NSAID therapy (FORCE--famotidine or rebamipide in comparison by endoscopy).
2006 Dec
In vitro availability of metformin in presence of h(2) receptor antagonists.
2006 Jan
Coagulation-dependent gene expression and liver injury in rats given lipopolysaccharide with ranitidine but not with famotidine.
2006 May
Activity of continuous infusion plus pulse interleukin-2 with famotidine in patients with metastatic kidney cancer or melanoma previously treated with interleukin-2.
2006 Oct
Tolerance to H2 receptor antagonist correlates well with the decline in efficacy against gastroesophageal reflux in patients with gastroesophageal reflux disease.
2006 Oct
Expression of HSP72 in the gastric mucosa is regulated by gastric acid in rats-correlation of HSP72 expression with mucosal protection.
2006 Oct 20
Impact of blockade of histamine H2 receptors on chronic heart failure revealed by retrospective and prospective randomized studies.
2006 Oct 3
Omeprazole may be superior to famotidine in the management of iatrogenic ulcer after endoscopic mucosal resection: a prospective randomized controlled trial.
2006 Sep 1
Histamine stimulation of MMP-1(collagenase-1) secretion and gene expression in gastric epithelial cells: role of EGFR transactivation and the MAP kinase pathway.
2007
The efficacy of hydrotalcite compared with OTC famotidine in the on-demand treatment of gastroesophageal reflux disease: a non-inferiority trial.
2007 Jan
[Clinical study on effect of Jianwei Yuyang Granule in treating patients with gastric ulcer].
2007 Jul
Novel role of famotidine in downregulation of matrix metalloproteinase-9 during protection of ethanol-induced acute gastric ulcer.
2007 Jul 15
The role of tumor necrosis factor alpha in lipopolysaccharide/ranitidine-induced inflammatory liver injury.
2007 Nov
Gastric antisecretory drugs induce leukocyte-endothelial cell interactions through gastrin release and activation of CCK-2 receptors.
2007 Oct
Gastroprotective and antioxidant effects of montelukast on indomethacin-induced gastric ulcer in rats.
2007 Sep
A randomized, double-blind, placebo-controlled clinical study of the histamine H2-receptor antagonist famotidine in Japanese patients with nonerosive reflux disease.
2008
Can negative cardiac effect of proton pump inhibitor and high-dose H2-blocker have clinical influence on patients with stable angina?
2008 Aug
Low-dose cyclophosphamide and continuous-infusion interleukin-2 with famotidine in previously treated metastatic melanoma or kidney cancer.
2008 Feb
Antinociception induced by central administration of histamine in the formalin test in rats.
2008 Jul-Sep
Nonsurgical resolution of gallbladder mucocele in two dogs.
2008 Jun 1
Effects of mepyramine and famotidine on the physostigmine-induced antinociception in the formalin test in rats.
2008 Nov 15
High-dose intensity pulse interleukin-2 with famotidine has activity in metastatic melanoma.
2008 Oct
[Efficacy and safety of famotidine for the treatment of stress ulcers in neonates].
2008 Oct
Gastroprotective and anti-oxidative properties of ascorbic acid on indomethacin-induced gastric injuries in rats.
2008 Winter
Risk factors for the development of gastric mucosal lesions in rheumatoid arthritis patients receiving long-term nonsteroidal anti-inflammatory drug therapy and the efficacy of famotidine obtained from the FORCE study.
2009
Comparison of the effects of omeprazole and famotidine in treatment of upper abdominal symptoms in patients with reflux esophagitis.
2009
Cytokine responses of intraepithelial lymphocytes are regulated by histamine H(2) receptor.
2009
High-dose intensity pulse interleukin-2 with famotidine in metastatic kidney cancer.
2009 Apr
Phosphodiesterase isozymes involved in regulating acid secretion in the isolated mouse stomach.
2009 Dec
Activity of continuous infusion + pulse interleukin-2 with famotidine in metastatic melanoma.
2009 Feb
Hepatitis following famotidine: a case report.
2009 Jan 27
Comparative study on the gastroprotective potential of some antidepressants in indomethacin-induced ulcer in rats.
2009 Jul 15
Drug-induced torsades de pointes: data mining of the public version of the FDA Adverse Event Reporting System (AERS).
2009 Jun
Characterization of mechanisms underlying the effects of esomeprazole on the impairment of gastric ulcer healing with addition of NSAID treatment.
2009 Jun
Effects of pantoprazole on ulcer healing delay associated with NSAID treatment.
2009 Mar
[Neurological complications of acute intermittent porphyria precipitated by porphyrinogenic drugs and efficiency of heme-arginate treatment].
2009 Sep
Protective effect of mirtazapine on indomethacin-induced ulcer in rats and its relationship with oxidant and antioxidant parameters.
2009 Sep
Pulse infusion interleukin-2 with famotidine and cyclophosphamide has activity in previously treated metastatic melanoma.
2010 Apr
Rebamipide may be comparable to H2 receptor antagonist in healing iatrogenic gastric ulcers created by endoscopic mucosal resection: a prospective randomized pilot study.
2010 Apr
Famotidine is inferior to pantoprazole in preventing recurrence of aspirin-related peptic ulcers or erosions.
2010 Jan
Effect of histamine H2 receptor antagonism on levodopa-induced dyskinesia in the MPTP-macaque model of Parkinson's disease.
2010 Jul 30
Hepatoprotective, antinociceptive and antioxidant activities of cimetidine, ranitidine and famotidine as histamine H2 receptor antagonists.
2011 Feb
Patents

Sample Use Guides

In Vivo Use Guide
The recommended adult oral dosage for active duodenal ulcer is 40 mg once a day at bedtime. Most patients heal within 4 weeks.
Route of Administration: Oral
In Vitro Use Guide
Famotidine (10-1,000 µM) inhibited methadone and oxycodone cytochrome P450-dependent metabolism >50%.
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:23:08 UTC 2019
Edited
by admin
on Tue Oct 22 00:23:08 UTC 2019
Record UNII
5QZO15J2Z8
Record Status Validated (UNII)
Record Version
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Name Type Language
FAMOTIDINE
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
FLUXID
Brand Name English
FAMOTIDINE COMPONENT OF PEPCID COMPLETE
Common Name English
GASTER
Brand Name English
MUCLOX
Brand Name English
AMFAMOX
Brand Name English
FAMOXAL
Brand Name English
PEPDUL
Brand Name English
(1-AMINO-3-(((2-((DIAMINOMETHYLENE)AMINO)-4-THIAZOLYL)METHYL)THIO)PROPYLIDENE)SULFAMIDE
Systematic Name English
FAMOTIDINE [MART.]
Common Name English
FAMOTIDINE [EP]
Common Name English
PEPCIDINE
Brand Name English
LECEDIL
Brand Name English
MOTIAX
Brand Name English
L 643341
Code English
GANOR
Brand Name English
FAMOTIDINE [WHO-DD]
Common Name English
FAMOTIDINE [MI]
Common Name English
FAMOTIDINE [INN]
Common Name English
PEPCID COMPLETE COMPONENT FAMOTIDINE
Common Name English
GASTRIDIN
Brand Name English
FAMODIL
Brand Name English
FAMOTIDINE [VANDF]
Common Name English
YM-11170
Code English
GASTROPEN
Brand Name English
PROPANIMIDAMIDE, N'-(AMINOSULFONYL)-3-(((2-((DIAMINOMETHYLENE)AMINO)-4-THIAZOLYL)METHYL)THIO)-
Systematic Name English
FAMOTIDINE [HSDB]
Common Name English
PEPCIDAC
Brand Name English
PEPDINE
Brand Name English
FADUL
Brand Name English
FAMOTIDINE [USP-RS]
Common Name English
FAMOTIDINE [USAN]
Common Name English
FAMOTIDINE [ORANGE BOOK]
Common Name English
FAMOSAN
Brand Name English
PEPTAN
Brand Name English
PEPCID
Brand Name English
FAMOTIDINE [USP]
Common Name English
MK-208
Code English
3-((((2-(DIAMINOMETHYLENE)AMINO)-4-THIAZOLYL)METHYL)THIO)-N-SULFAMOYLPROPIONAMIDINE
Common Name English
Classification Tree Code System Code
WHO-ATC A02BA03
Created by admin on Tue Oct 22 00:23:08 UTC 2019 , Edited by admin on Tue Oct 22 00:23:08 UTC 2019
NDF-RT N0000175784
Created by admin on Tue Oct 22 00:23:08 UTC 2019 , Edited by admin on Tue Oct 22 00:23:08 UTC 2019
WHO-VATC QA02BA03
Created by admin on Tue Oct 22 00:23:08 UTC 2019 , Edited by admin on Tue Oct 22 00:23:08 UTC 2019
NCI_THESAURUS C29702
Created by admin on Tue Oct 22 00:23:08 UTC 2019 , Edited by admin on Tue Oct 22 00:23:08 UTC 2019
WHO-ATC A02BA53
Created by admin on Tue Oct 22 00:23:08 UTC 2019 , Edited by admin on Tue Oct 22 00:23:08 UTC 2019
LIVERTOX 399
Created by admin on Tue Oct 22 00:23:08 UTC 2019 , Edited by admin on Tue Oct 22 00:23:08 UTC 2019
WHO-VATC QA02BA53
Created by admin on Tue Oct 22 00:23:08 UTC 2019 , Edited by admin on Tue Oct 22 00:23:08 UTC 2019
NDF-RT N0000000151
Created by admin on Tue Oct 22 00:23:08 UTC 2019 , Edited by admin on Tue Oct 22 00:23:08 UTC 2019
Code System Code Type Description
EPA CompTox
76824-35-6
Created by admin on Tue Oct 22 00:23:08 UTC 2019 , Edited by admin on Tue Oct 22 00:23:08 UTC 2019
PRIMARY
DRUG BANK
DB00927
Created by admin on Tue Oct 22 00:23:08 UTC 2019 , Edited by admin on Tue Oct 22 00:23:08 UTC 2019
PRIMARY
LactMed
76824-35-6
Created by admin on Tue Oct 22 00:23:08 UTC 2019 , Edited by admin on Tue Oct 22 00:23:08 UTC 2019
PRIMARY
MESH
D015738
Created by admin on Tue Oct 22 00:23:08 UTC 2019 , Edited by admin on Tue Oct 22 00:23:08 UTC 2019
PRIMARY
EVMPD
SUB07503MIG
Created by admin on Tue Oct 22 00:23:08 UTC 2019 , Edited by admin on Tue Oct 22 00:23:08 UTC 2019
PRIMARY
INN
5217
Created by admin on Tue Oct 22 00:23:08 UTC 2019 , Edited by admin on Tue Oct 22 00:23:08 UTC 2019
PRIMARY
IUPHAR
7074
Created by admin on Tue Oct 22 00:23:08 UTC 2019 , Edited by admin on Tue Oct 22 00:23:08 UTC 2019
PRIMARY
MERCK INDEX
M5241
Created by admin on Tue Oct 22 00:23:08 UTC 2019 , Edited by admin on Tue Oct 22 00:23:08 UTC 2019
PRIMARY Merck Index
ChEMBL
CHEMBL902
Created by admin on Tue Oct 22 00:23:08 UTC 2019 , Edited by admin on Tue Oct 22 00:23:08 UTC 2019
PRIMARY
RXCUI
4278
Created by admin on Tue Oct 22 00:23:08 UTC 2019 , Edited by admin on Tue Oct 22 00:23:08 UTC 2019
PRIMARY RxNorm
WIKIPEDIA
FAMOTIDINE
Created by admin on Tue Oct 22 00:23:08 UTC 2019 , Edited by admin on Tue Oct 22 00:23:08 UTC 2019
PRIMARY
HSDB
76824-35-6
Created by admin on Tue Oct 22 00:23:08 UTC 2019 , Edited by admin on Tue Oct 22 00:23:08 UTC 2019
PRIMARY
NCI_THESAURUS
C29045
Created by admin on Tue Oct 22 00:23:08 UTC 2019 , Edited by admin on Tue Oct 22 00:23:08 UTC 2019
PRIMARY
CAS
76824-35-6
Created by admin on Tue Oct 22 00:23:08 UTC 2019 , Edited by admin on Tue Oct 22 00:23:08 UTC 2019
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
USP
TRANSPORTER -> INHIBITOR
IC50
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TARGET -> INHIBITOR
TRANSPORTER -> INHIBITOR
IC50
BINDER->LIGAND
BINDING
TRANSPORTER -> NON-INHIBITOR
IC50
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
TRANSPORTER -> INHIBITOR
Related Record Type Details
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 1.4
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 2.5
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 1.9
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 1.7
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 0.19
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC