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
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
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| 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 |
DescriptionSources: http://www.drugbank.ca/drugs/DB00927Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/famotidine.html
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8204567
Curator's Comment: Famotidine is a potent highly selective H2 receptor antagonist which crosses the blood-brain barrier.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL1941 Sources: http://www.drugbank.ca/drugs/DB00927 |
0.3 µM [IC50] | ||
Target ID: CHEMBL2073673 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16141367 |
6.7 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | PEPCID Approved UsePEPCID 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 Date1986 |
|||
| Curative | PEPCID Approved UsePEPCID 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 Date1986 |
|||
| Primary | PEPCID Approved UsePEPCID 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 Date1986 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
73 ng/mL |
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 |
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 |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3 h |
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 |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
82.5% |
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: |
unhealthy, 11 - 15 years Health Status: unhealthy Age Group: 11 - 15 years Sex: M Sources: |
|
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: |
unhealthy, 20 - 70 years Health Status: unhealthy Age Group: 20 - 70 years Sex: M+F Sources: |
Other AEs: Dizziness, Dry skin... Other AEs: Dizziness (grade 1, 2 patients) Sources: Dry skin (grade 1, 1 patient) Insomnia (grade 1, 1 patient) Gastrointestinal disorder (NOS) (grade 1, 1 patient) Forgetfulness (grade 1, 1 patient) |
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: |
unhealthy, 6 - 15 years Health Status: unhealthy Age Group: 6 - 15 years Sex: M Sources: |
|
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: |
unhealthy, adult |
Other AEs: Anemia, Nausea... Other AEs: Anemia (2 patients) Sources: 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) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Dry skin | grade 1, 1 patient | 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: |
unhealthy, 20 - 70 years Health Status: unhealthy Age Group: 20 - 70 years Sex: M+F Sources: |
| Forgetfulness | grade 1, 1 patient | 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: |
unhealthy, 20 - 70 years Health Status: unhealthy Age Group: 20 - 70 years Sex: M+F Sources: |
| Gastrointestinal disorder (NOS) | grade 1, 1 patient | 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: |
unhealthy, 20 - 70 years Health Status: unhealthy Age Group: 20 - 70 years Sex: M+F Sources: |
| Insomnia | grade 1, 1 patient | 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: |
unhealthy, 20 - 70 years Health Status: unhealthy Age Group: 20 - 70 years Sex: M+F Sources: |
| Dizziness | grade 1, 2 patients | 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: |
unhealthy, 20 - 70 years Health Status: unhealthy Age Group: 20 - 70 years Sex: M+F Sources: |
| Arthralgia | 1 patient | 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: |
unhealthy, adult |
| Abdominal pain | 2 patients | 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: |
unhealthy, adult |
| Anemia | 2 patients | 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: |
unhealthy, adult |
| Back pain | 2 patients | 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: |
unhealthy, adult |
| Edema peripheral | 2 patients | 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: |
unhealthy, adult |
| Gastroesophageal reflux disease | 2 patients | 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: |
unhealthy, adult |
| Stomach discomfort | 2 patients | 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: |
unhealthy, adult |
| Vomiting | 2 patients | 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: |
unhealthy, adult |
| Abdominal pain upper | 3 patients | 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: |
unhealthy, adult |
| Headache | 3 patients | 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: |
unhealthy, adult |
| Hypertension | 3 patients | 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: |
unhealthy, adult |
| Constipation | 4 patients | 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: |
unhealthy, adult |
| Diarrhea | 5 patients | 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: |
unhealthy, adult |
| Dyspepsia | 5 patients | 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: |
unhealthy, adult |
| Nausea | 6 patients | 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: |
unhealthy, adult |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
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 Page: 6.0 |
||
| yes [IC50 114 uM] | ||||
| yes [IC50 28 uM] | ||||
| yes [IC50 6.7 uM] | ||||
Page: 1.0 |
yes [Inhibition 100 uM] | |||
Page: 1.0 |
yes [Inhibition 100 uM] | |||
Page: 1.0 |
yes [Inhibition 100 uM] | |||
| yes [Ki 0.6 uM] | ||||
| yes [Ki 9.7 uM] |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Hepatoprotective, antinociceptive and antioxidant activities of cimetidine, ranitidine and famotidine as histamine H2 receptor antagonists. | 2011-02 |
|
| Effect of histamine H2 receptor antagonism on levodopa-induced dyskinesia in the MPTP-macaque model of Parkinson's disease. | 2010-07-30 |
|
| Pulse infusion interleukin-2 with famotidine and cyclophosphamide has activity in previously treated metastatic melanoma. | 2010-04 |
|
| 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 |
|
| Famotidine is inferior to pantoprazole in preventing recurrence of aspirin-related peptic ulcers or erosions. | 2010-01 |
|
| Phosphodiesterase isozymes involved in regulating acid secretion in the isolated mouse stomach. | 2009-12 |
|
| [Neurological complications of acute intermittent porphyria precipitated by porphyrinogenic drugs and efficiency of heme-arginate treatment]. | 2009-09 |
|
| Protective effect of mirtazapine on indomethacin-induced ulcer in rats and its relationship with oxidant and antioxidant parameters. | 2009-09 |
|
| Comparative study on the gastroprotective potential of some antidepressants in indomethacin-induced ulcer in rats. | 2009-07-15 |
|
| Antinociception induced by central administration of histamine in the formalin test in rats. | 2009-06-26 |
|
| Drug-induced torsades de pointes: data mining of the public version of the FDA Adverse Event Reporting System (AERS). | 2009-06 |
|
| Characterization of mechanisms underlying the effects of esomeprazole on the impairment of gastric ulcer healing with addition of NSAID treatment. | 2009-06 |
|
| High-dose intensity pulse interleukin-2 with famotidine in metastatic kidney cancer. | 2009-04 |
|
| Effects of pantoprazole on ulcer healing delay associated with NSAID treatment. | 2009-03 |
|
| Activity of continuous infusion + pulse interleukin-2 with famotidine in metastatic melanoma. | 2009-02 |
|
| Hepatitis following famotidine: a case report. | 2009-01-27 |
|
| 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 |
|
| Effects of mepyramine and famotidine on the physostigmine-induced antinociception in the formalin test in rats. | 2008-11-15 |
|
| High-dose intensity pulse interleukin-2 with famotidine has activity in metastatic melanoma. | 2008-10 |
|
| [Efficacy and safety of famotidine for the treatment of stress ulcers in neonates]. | 2008-10 |
|
| Can negative cardiac effect of proton pump inhibitor and high-dose H2-blocker have clinical influence on patients with stable angina? | 2008-08 |
|
| Nonsurgical resolution of gallbladder mucocele in two dogs. | 2008-06-01 |
|
| Low-dose cyclophosphamide and continuous-infusion interleukin-2 with famotidine in previously treated metastatic melanoma or kidney cancer. | 2008-02 |
|
| Gastroprotective and anti-oxidative properties of ascorbic acid on indomethacin-induced gastric injuries in rats. | 2008 |
|
| A randomized, double-blind, placebo-controlled clinical study of the histamine H2-receptor antagonist famotidine in Japanese patients with nonerosive reflux disease. | 2008 |
|
| The role of tumor necrosis factor alpha in lipopolysaccharide/ranitidine-induced inflammatory liver injury. | 2007-11 |
|
| Gastric antisecretory drugs induce leukocyte-endothelial cell interactions through gastrin release and activation of CCK-2 receptors. | 2007-10 |
|
| Gastroprotective and antioxidant effects of montelukast on indomethacin-induced gastric ulcer in rats. | 2007-09 |
|
| Novel role of famotidine in downregulation of matrix metalloproteinase-9 during protection of ethanol-induced acute gastric ulcer. | 2007-07-15 |
|
| [Clinical study on effect of Jianwei Yuyang Granule in treating patients with gastric ulcer]. | 2007-07 |
|
| The efficacy of hydrotalcite compared with OTC famotidine in the on-demand treatment of gastroesophageal reflux disease: a non-inferiority trial. | 2007-01 |
|
| 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 |
|
| 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 |
|
| Expression of HSP72 in the gastric mucosa is regulated by gastric acid in rats-correlation of HSP72 expression with mucosal protection. | 2006-10-20 |
|
| Impact of blockade of histamine H2 receptors on chronic heart failure revealed by retrospective and prospective randomized studies. | 2006-10-03 |
|
| 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 |
|
| Tolerance to H2 receptor antagonist correlates well with the decline in efficacy against gastroesophageal reflux in patients with gastroesophageal reflux disease. | 2006-10 |
|
| Omeprazole may be superior to famotidine in the management of iatrogenic ulcer after endoscopic mucosal resection: a prospective randomized controlled trial. | 2006-09-01 |
|
| Histamine mediates the stimulatory action of ghrelin on acid secretion in rat stomach. | 2006-08 |
|
| Cimetidine induces interleukin-18 production through H2-agonist activity in monocytes. | 2006-08 |
|
| Coagulation-dependent gene expression and liver injury in rats given lipopolysaccharide with ranitidine but not with famotidine. | 2006-05 |
|
| Effect of preoperative short course famotidine on TILs and survival in breast cancer. | 2006-01-05 |
|
| In vitro availability of metformin in presence of h(2) receptor antagonists. | 2006-01 |
|
| [Complex evaluation of the action of inhibitors of hydrochloric acid secretion on gastric function in ulcer disease]. | 2006 |
|
| Synergistic action of famotidine and chlorpheniramine on acetic acid-induced chronic gastric ulcer in rats. | 2005-12-07 |
|
| 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 |
|
| 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 |
Patents
Sample Use Guides
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23857299
Famotidine (10-1,000 µM) inhibited methadone and oxycodone cytochrome P450-dependent metabolism >50%.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 22:50:33 GMT 2025
by
admin
on
Mon Mar 31 22:50:33 GMT 2025
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| Record UNII |
36YPT1XMT2
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| Record Status |
Validated (UNII)
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| Record Version |
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Preferred Name | English | ||
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19831515
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DTXSID20910894
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108885-67-2
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300000047375
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50377
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36YPT1XMT2
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108885-67-2
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NON-SPECIFIC STOICHIOMETRY | |||
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125193-62-6
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