FAMOTIDINE HYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H15N7O2S3.ClH
Molecular Weight	373.906
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=OONJNILIBCMSNC-UHFFFAOYSA-N

InChI=1S/C8H15N7O2S3.ClH/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);1H

HIDE SMILES / InChI

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 2778		0.3 µM [IC50]
Solute carrier family 22 member 3 6 Target ID: CHEMBL2073673 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16141367	Inhibitor 8297		6.7 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Duodenal ulcer 42 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/019462s038lbl.pdf	Curative	Approved 8429	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 67 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/019462s038lbl.pdf	Curative	Approved 8429	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 59 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/019462s038lbl.pdf	Primary	Approved 8429	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 n = 8 Health Status: unhealthy Condition: gastric or duodenal ulcers Age Group: 11 - 15 years Sex: M Population Size: 8 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 n = 10 Health Status: unhealthy Condition: COVID-19 Age Group: 20 - 70 years Sex: M+F Population Size: 10 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 n = 6 Health Status: unhealthy Condition: gastric or duodenal ulcers Age Group: 6 - 15 years Sex: M Population Size: 6 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 Co-administed with:: ibuprofen(800 mg) Sources: https://pubmed.ncbi.nlm.nih.gov/23024710/	unhealthy, adult n = 1022 Health Status: unhealthy Condition: chronic pain and inflammation of stomach Age Group: adult Sex: M+F Population Size: 1022 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 1587			inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2B6 810 CYP2C19 1478 OCT1 512 OCT2 647 OCT3 150 MATE1 306 MATE2 263	OCT2 355

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP1A2 1692	inhibitor 3277 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 648	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/16141367/	yes [IC50 114 uM]
OCT1 543	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/16141367/	yes [IC50 28 uM]
OCT3 150	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/16141367/	yes [IC50 6.7 uM]
CYP2B6 1001	inhibitor 3277 Sources: https://www.tandfonline.com/doi/abs/10.3109/00498254.2011.653655?journalCode=ixen20 Page: 1.0	yes [Inhibition 100 uM]
CYP2C19 1553	inhibitor 3277 Sources: https://www.tandfonline.com/doi/abs/10.3109/00498254.2011.653655?journalCode=ixen20 Page: 1.0	yes [Inhibition 100 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://www.tandfonline.com/doi/abs/10.3109/00498254.2011.653655?journalCode=ixen20 Page: 1.0	yes [Inhibition 100 uM]
MATE1 308	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/19164462/	yes [Ki 0.6 uM]
MATE2 263	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/19164462/	yes [Ki 9.7 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
OCT2 355	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/16006492/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 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
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
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

PubMed

Title	Date	PubMed
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	1886288
[A case of rheumatoid arthritis associated with autoimmune hemolytic anemia due to weekly low-dose methotrexate therapy].	2000 Aug	11021173
[A case of famotidine-induced aseptic meningitis].	2000 Jan	10825801
Amantadine-induced cortical myoclonus.	2001 Jan 23	11160978
Effects of three H2-receptor antagonists (cimetidine, famotidine, ranitidine) on serum gastrin level.	2002	12503773
Ranitidine reduces ischemia/reperfusion-induced liver injury in rats by inhibiting neutrophil activation.	2002 Jun	12023551
Histamine inhibits lipopolysaccharide-induced tumor necrosis factor-alpha production in an intercellular adhesion molecule-1- and B7.1-dependent manner.	2003 Feb	12538815
Radioprotective properties of histamine H2 receptor antagonists: present and future prospects.	2003 Jun	13678344
Effect of exogenous administration of transforming growth factor-beta and famotidine on the healing of duodenal ulcer under the impact of indomethacin.	2003 Jun	12868675
The effect of rabeprazole alone or in combination with H2 receptor blocker on intragastric pH: a pilot study.	2004 Dec	16249975
Renal transport of organic compounds mediated by mouse organic anion transporter 3 (mOat3): further substrate specificity of mOat3.	2004 May	15100168
[Gastroprotective effects of histamine H2-receptor blockers in Helicobacter-like gastric mucosa lesions].	2005	17378382
Differential substrate and inhibitory activities of ranitidine and famotidine toward human organic cation transporter 1 (hOCT1; SLC22A1), hOCT2 (SLC22A2), and hOCT3 (SLC22A3).	2005 Dec	16141367
Effect of pre-operative short course famotidine on tumor infiltrating lymphocytes in colorectal cancer: a double blind, placebo controlled, prospective randomized study.	2005 Dec	15882879
Comparative study of the speed of acid-suppressing effects of oral administration of cimetidine and famotidine.	2005 Jul	15955208
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
A prospective randomized trial of either famotidine or omeprazole for the prevention of bleeding after endoscopic mucosal resection and the healing of endoscopic mucosal resection-induced ulceration.	2005 Jun	15943857
[Complex evaluation of the action of inhibitors of hydrochloric acid secretion on gastric function in ulcer disease].	2006	16613094
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	17287897
Coagulation-dependent gene expression and liver injury in rats given lipopolysaccharide with ranitidine but not with famotidine.	2006 May	16401727
Expression of HSP72 in the gastric mucosa is regulated by gastric acid in rats-correlation of HSP72 expression with mucosal protection.	2006 Oct 20	16945336
Novel role of famotidine in downregulation of matrix metalloproteinase-9 during protection of ethanol-induced acute gastric ulcer.	2007 Jul 15	17603938
The role of tumor necrosis factor alpha in lipopolysaccharide/ranitidine-induced inflammatory liver injury.	2007 Nov	17698507
Can negative cardiac effect of proton pump inhibitor and high-dose H2-blocker have clinical influence on patients with stable angina?	2008 Aug	18639776
High-dose intensity pulse interleukin-2 with famotidine has activity in metastatic melanoma.	2008 Oct	18999936
[Efficacy and safety of famotidine for the treatment of stress ulcers in neonates].	2008 Oct	18947477
Gastroprotective and anti-oxidative properties of ascorbic acid on indomethacin-induced gastric injuries in rats.	2008 Winter	18726076
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
Phosphodiesterase isozymes involved in regulating acid secretion in the isolated mouse stomach.	2009 Dec	20388963
Activity of continuous infusion + pulse interleukin-2 with famotidine in metastatic melanoma.	2009 Feb	19243244
Hepatitis following famotidine: a case report.	2009 Jan 27	19173722
Comparative study on the gastroprotective potential of some antidepressants in indomethacin-induced ulcer in rats.	2009 Jul 15	19497431
Characterization of mechanisms underlying the effects of esomeprazole on the impairment of gastric ulcer healing with addition of NSAID treatment.	2009 Jun	19251492
Effects of pantoprazole on ulcer healing delay associated with NSAID treatment.	2009 Mar	18853145
[Neurological complications of acute intermittent porphyria precipitated by porphyrinogenic drugs and efficiency of heme-arginate treatment].	2009 Sep	20180386
Protective effect of mirtazapine on indomethacin-induced ulcer in rats and its relationship with oxidant and antioxidant parameters.	2009 Sep	19034656
Pulse infusion interleukin-2 with famotidine and cyclophosphamide has activity in previously treated metastatic melanoma.	2010 Apr	20423231
Effect of histamine H2 receptor antagonism on levodopa-induced dyskinesia in the MPTP-macaque model of Parkinson's disease.	2010 Jul 30	20310030

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%.

Name

Type

Language

FAMOTIDINE HYDROCHLORIDE

Common Name

English

FAMOTIDINE HCL

Common Name

English

PROPANIMIDAMIDE, 3-(((2-((AMINOIMINOMETHYL)AMINO)-4-THIAZOLYL)METHYL)THIO)-N-(AMINOSULFONYL)-, HYDROCHLORIDE (1:1)

Systematic Name

English

PROPANIMIDAMIDE, 3-(((2-((AMINOIMINOMETHYL)AMINO)-4-THIAZOLYL)METHYL)THIO)-N-(AMINOSULFONYL)-, HYDROCHLORIDE

Systematic Name

English

PROPANIMIDAMIDE, 3-(((2-((AMINOIMINOMETHYL)AMINO)-4-THIAZOLYL)METHYL)THIO)-N-(AMINOSULFONYL)-, MONOHYDROCHLORIDE

Systematic Name

English

Code System Code Type Description

PUBCHEM

19831515