FAMOTIDINE

Details

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

SHOW SMILES / InChI

Structure Search

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	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.drugbank.ca/drugs/DB00927
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/famotidine.html

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

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H2 receptor 46 Target ID: CHEMBL1941 Sources: http://www.drugbank.ca/drugs/DB00927	Antagonist 2849		0.3 µM [IC50]
Solute carrier family 22 member 3 6 Target ID: CHEMBL2073673 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16141367	Inhibitor 8504		6.7 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Duodenal ulcer 49 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/019462s038lbl.pdf	Curative	Approved 8583	PEPCID Approved Use PEPCID is indicated in: 1. Short-term treatment of active duodenal ulcer. 2. Maintenance therapy for duodenal ulcer patients at reduced dosage after healing of an active ulcer. 3. Short-term treatment of active benign gastric ulcer. 4. Short-term treatment of gastroesophageal reflux disease (GERD). PEPCID is indicated for shortterm treatment of patients with symptoms of GERD PEPCID is also indicated for the short-term treatment of esophagitis due to GERD including erosive or ulcerative disease diagnosed by endoscopy 5. Treatment of pathological hypersecretory conditions (e.g., Zollinger-Ellison Syndrome, multiple endocrine adenomas) Launch Date 1986
Gastric ulcer 74 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/019462s038lbl.pdf	Curative	Approved 8583	PEPCID Approved Use PEPCID is indicated in: 1. Short-term treatment of active duodenal ulcer. 2. Maintenance therapy for duodenal ulcer patients at reduced dosage after healing of an active ulcer. 3. Short-term treatment of active benign gastric ulcer. 4. Short-term treatment of gastroesophageal reflux disease (GERD). PEPCID is indicated for shortterm treatment of patients with symptoms of GERD PEPCID is also indicated for the short-term treatment of esophagitis due to GERD including erosive or ulcerative disease diagnosed by endoscopy 5. Treatment of pathological hypersecretory conditions (e.g., Zollinger-Ellison Syndrome, multiple endocrine adenomas) Launch Date 1986
Gastroesophageal reflux disease 68 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/019462s038lbl.pdf	Primary	Approved 8583	PEPCID Approved Use PEPCID is indicated in: 1. Short-term treatment of active duodenal ulcer. 2. Maintenance therapy for duodenal ulcer patients at reduced dosage after healing of an active ulcer. 3. Short-term treatment of active benign gastric ulcer. 4. Short-term treatment of gastroesophageal reflux disease (GERD). PEPCID is indicated for shortterm treatment of patients with symptoms of GERD PEPCID is also indicated for the short-term treatment of esophagitis due to GERD including erosive or ulcerative disease diagnosed by endoscopy 5. Treatment of pathological hypersecretory conditions (e.g., Zollinger-Ellison Syndrome, multiple endocrine adenomas) Launch Date 1986

C_max

Value	Dose	Co-administered	Analyte	Population
73 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/019462s039lbl.pdf	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:		FAMOTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
424 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/019462s039lbl.pdf	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:		FAMOTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
3 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/019462s039lbl.pdf	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:		FAMOTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
82.5% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/019462s039lbl.pdf	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:		FAMOTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
0.5 mg/kg 2 times / day steady, oral Recommended Dose: 0.5 mg/kg, 2 times / day Route: oral Route: steady Dose: 0.5 mg/kg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7846741/	unhealthy, 11 - 15 years Health Status: unhealthy Age Group: 11 - 15 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/7846741/	Sources: https://pubmed.ncbi.nlm.nih.gov/7846741/
80 mg 3 times / day steady, oral Highest studied dose Dose: 80 mg, 3 times / day Route: oral Route: steady Dose: 80 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/32499303/	unhealthy, 20 - 70 years Health Status: unhealthy Age Group: 20 - 70 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/32499303/	Other AEs: Dizziness, Dry skin... Other AEs: Dizziness (grade 1, 2 patients) Dry skin (grade 1, 1 patient) Insomnia (grade 1, 1 patient) Gastrointestinal disorder (NOS) (grade 1, 1 patient) Forgetfulness (grade 1, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/32499303/
1 mg/kg 1 times / day steady, intravenous Recommended Dose: 1 mg/kg, 1 times / day Route: intravenous Route: steady Dose: 1 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7846741/	unhealthy, 6 - 15 years Health Status: unhealthy Age Group: 6 - 15 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/7846741/	Sources: https://pubmed.ncbi.nlm.nih.gov/7846741/
26.6 mg 3 times / day steady, oral Highest studied dose Dose: 26.6 mg, 3 times / day Route: oral Route: steady Dose: 26.6 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/23024710/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/23024710/	Other AEs: Anemia, Nausea... Other AEs: Anemia (2 patients) Nausea (6 patients) Dyspepsia (5 patients) Diarrhea (5 patients) Constipation (4 patients) Abdominal pain upper (3 patients) Gastroesophageal reflux disease (2 patients) Vomiting (2 patients) Stomach discomfort (2 patients) Abdominal pain (2 patients) Edema peripheral (2 patients) Arthralgia (1 patient) Back pain (2 patients) Headache (3 patients) Hypertension (3 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/23024710/

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252			inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2B6 926 CYP2C19 2057 OCT1 620 OCT2 779 OCT3 159 MATE1 415 MATE2 267	OCT2 434

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/019462s039lbl.pdf#page=6 Page: 6.0	weak	likely (co-administration study) Comment: may lead to substantial increases in blood concentrations of tizanidine, a CYP1A2 substrate; can't find inhibition value Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/019462s039lbl.pdf#page=6 Page: 6.0
OCT2 782	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16141367/	yes [IC50 114 uM]
OCT1 656	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16141367/	yes [IC50 28 uM]
OCT3 161	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16141367/	yes [IC50 6.7 uM]
CYP2B6 1160	inhibitor 4027 Sources: https://www.tandfonline.com/doi/abs/10.3109/00498254.2011.653655?journalCode=ixen20 Page: 1.0	yes [Inhibition 100 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://www.tandfonline.com/doi/abs/10.3109/00498254.2011.653655?journalCode=ixen20 Page: 1.0	yes [Inhibition 100 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://www.tandfonline.com/doi/abs/10.3109/00498254.2011.653655?journalCode=ixen20 Page: 1.0	yes [Inhibition 100 uM]
MATE1 416	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/19164462/	yes [Ki 0.6 uM]
MATE2 267	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/19164462/	yes [Ki 9.7 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
OCT2 434	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16006492/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubmed.ncbi.nlm.nih.gov/25253561/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:4975	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:4975
ChemicalBook	CB5706585	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5706585
eMolecules	538460	https://www.emolecules.com/cgi-bin/more?vid=538460
eMolecules	6842898	https://www.emolecules.com/cgi-bin/more?vid=6842898
eMolecules	901873	https://www.emolecules.com/cgi-bin/more?vid=901873
MolPort	MolPort-002-557-620	https://www.molport.com/shop/molecule-link/MolPort-002-557-620
MolPort	MolPort-003-666-342	https://www.molport.com/shop/molecule-link/MolPort-003-666-342
MolPort	MolPort-003-941-395	https://www.molport.com/shop/molecule-link/MolPort-003-941-395
MolPort	MolPort-006-069-255	https://www.molport.com/shop/molecule-link/MolPort-006-069-255
Selleck Chemicals	famotidine-pepcid	http://www.selleckchem.com/products/famotidine-pepcid.html
ZINC	ZINC000001530636	http://zinc15.docking.org/substances/ZINC000001530636

PubMed

Title	Date	PubMed
Hepatoprotective, antinociceptive and antioxidant activities of cimetidine, ranitidine and famotidine as histamine H2 receptor antagonists.	2011-02	20070855
Effect of histamine H2 receptor antagonism on levodopa-induced dyskinesia in the MPTP-macaque model of Parkinson's disease.	2010-07-30	20310030
Pulse infusion interleukin-2 with famotidine and cyclophosphamide has activity in previously treated metastatic melanoma.	2010-04	20423231
Rebamipide may be comparable to H2 receptor antagonist in healing iatrogenic gastric ulcers created by endoscopic mucosal resection: a prospective randomized pilot study.	2010-04	20358002
Famotidine is inferior to pantoprazole in preventing recurrence of aspirin-related peptic ulcers or erosions.	2010-01	19837071
Phosphodiesterase isozymes involved in regulating acid secretion in the isolated mouse stomach.	2009-12	20388963
[Neurological complications of acute intermittent porphyria precipitated by porphyrinogenic drugs and efficiency of heme-arginate treatment].	2009-09	20180386
Protective effect of mirtazapine on indomethacin-induced ulcer in rats and its relationship with oxidant and antioxidant parameters.	2009-09	19034656
Comparative study on the gastroprotective potential of some antidepressants in indomethacin-induced ulcer in rats.	2009-07-15	19497431
Antinociception induced by central administration of histamine in the formalin test in rats.	2009-06-26	19552055
Drug-induced torsades de pointes: data mining of the public version of the FDA Adverse Event Reporting System (AERS).	2009-06	19358226
Characterization of mechanisms underlying the effects of esomeprazole on the impairment of gastric ulcer healing with addition of NSAID treatment.	2009-06	19251492
High-dose intensity pulse interleukin-2 with famotidine in metastatic kidney cancer.	2009-04	19409039
Effects of pantoprazole on ulcer healing delay associated with NSAID treatment.	2009-03	18853145
Activity of continuous infusion + pulse interleukin-2 with famotidine in metastatic melanoma.	2009-02	19243244
Hepatitis following famotidine: a case report.	2009-01-27	19173722
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	19728013
Comparison of the effects of omeprazole and famotidine in treatment of upper abdominal symptoms in patients with reflux esophagitis.	2009	19280112
Cytokine responses of intraepithelial lymphocytes are regulated by histamine H(2) receptor.	2009	19277450
Effects of mepyramine and famotidine on the physostigmine-induced antinociception in the formalin test in rats.	2008-11-15	19260335
High-dose intensity pulse interleukin-2 with famotidine has activity in metastatic melanoma.	2008-10	18999936
[Efficacy and safety of famotidine for the treatment of stress ulcers in neonates].	2008-10	18947477
Can negative cardiac effect of proton pump inhibitor and high-dose H2-blocker have clinical influence on patients with stable angina?	2008-08	18639776
Nonsurgical resolution of gallbladder mucocele in two dogs.	2008-06-01	18518811
Low-dose cyclophosphamide and continuous-infusion interleukin-2 with famotidine in previously treated metastatic melanoma or kidney cancer.	2008-02	18298334
Gastroprotective and anti-oxidative properties of ascorbic acid on indomethacin-induced gastric injuries in rats.	2008	18726076
A randomized, double-blind, placebo-controlled clinical study of the histamine H2-receptor antagonist famotidine in Japanese patients with nonerosive reflux disease.	2008	18600389
The role of tumor necrosis factor alpha in lipopolysaccharide/ranitidine-induced inflammatory liver injury.	2007-11	17698507
Gastric antisecretory drugs induce leukocyte-endothelial cell interactions through gastrin release and activation of CCK-2 receptors.	2007-10	17652263
Gastroprotective and antioxidant effects of montelukast on indomethacin-induced gastric ulcer in rats.	2007-09	17895592
Novel role of famotidine in downregulation of matrix metalloproteinase-9 during protection of ethanol-induced acute gastric ulcer.	2007-07-15	17603938
[Clinical study on effect of Jianwei Yuyang Granule in treating patients with gastric ulcer].	2007-07	17717918
The efficacy of hydrotalcite compared with OTC famotidine in the on-demand treatment of gastroesophageal reflux disease: a non-inferiority trial.	2007-01	17179910
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	17656145
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).	2006-12	17287897
Expression of HSP72 in the gastric mucosa is regulated by gastric acid in rats-correlation of HSP72 expression with mucosal protection.	2006-10-20	16945336
Impact of blockade of histamine H2 receptors on chronic heart failure revealed by retrospective and prospective randomized studies.	2006-10-03	17010798
Activity of continuous infusion plus pulse interleukin-2 with famotidine in patients with metastatic kidney cancer or melanoma previously treated with interleukin-2.	2006-10	17105418
Tolerance to H2 receptor antagonist correlates well with the decline in efficacy against gastroesophageal reflux in patients with gastroesophageal reflux disease.	2006-10	16928220
Omeprazole may be superior to famotidine in the management of iatrogenic ulcer after endoscopic mucosal resection: a prospective randomized controlled trial.	2006-09-01	16918888
Histamine mediates the stimulatory action of ghrelin on acid secretion in rat stomach.	2006-08	16838121
Cimetidine induces interleukin-18 production through H2-agonist activity in monocytes.	2006-08	16723495
Coagulation-dependent gene expression and liver injury in rats given lipopolysaccharide with ranitidine but not with famotidine.	2006-05	16401727
Effect of preoperative short course famotidine on TILs and survival in breast cancer.	2006-01-05	16391436
In vitro availability of metformin in presence of h(2) receptor antagonists.	2006-01	16632449
[Complex evaluation of the action of inhibitors of hydrochloric acid secretion on gastric function in ulcer disease].	2006	16613094
Synergistic action of famotidine and chlorpheniramine on acetic acid-induced chronic gastric ulcer in rats.	2005-12-07	16437673
Switching of H(2)-Receptor Antagonists to Over-the-Counter Status in Finland : Implications for Consumption and Adverse Effects.	2005	17523774
[Gastroprotective effects of histamine H2-receptor blockers in Helicobacter-like gastric mucosa lesions].	2005	17378382
Differences in the antisecretory actions of the proton pump inhibitor AG-1749 (lansoprazole) and the histamine H2-receptor antagonist famotidine in rats and dogs.	1991-04	1886288

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 `Mon Mar 31 18:11:48 GMT 2025` Edited by `admin` on `Mon Mar 31 18:11:48 GMT 2025`
Record UNII	5QZO15J2Z8
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FAMOTIDINE

Official Name

English

PEPCID COMPLETE COMPONENT FAMOTIDINE

Preferred Name

English

FLUXID

Brand Name

English

GASTER

Brand Name

English

MUCLOX

Brand Name

English

AMFAMOX

Brand Name

English

FAMOXAL

Brand Name

English

PEPDUL

Brand Name

English

Famotidine [WHO-DD]

Common Name

English

[1-Amino-3-[[[2-[(diaminomethylene)amino]-4-thiazolyl]methyl]thio]propylidene]sulfamide

Systematic Name

English

FAMOTIDINE [MART.]

Common Name

English

PEPCIDINE

Brand Name

English

FAMOTIDINE [JAN]

Common Name

English

LECEDIL

Brand Name

English

MOTIAX

Brand Name

English

L 643341

Code

English

GANOR

Brand Name

English

FAMOTIDINE [MI]

Common Name

English

famotidine [INN]

Common Name

English

GASTRIDIN

Brand Name

English

FAMODIL

Brand Name

English

FAMOTIDINE [VANDF]

Common Name

English

FAMOTIDINE [USP MONOGRAPH]

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 [USP IMPURITY]

Common 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

PEPCID

Brand Name

English

FAMOTIDINE [EP MONOGRAPH]

Common Name

English

NSC-757810

Code

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