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
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)
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 |
|---|---|---|
| Hemodynamic effects of quinidine and famotidine in patients with congestive heart failure. | 1992 Mar |
|
| Prostacyclin analog prevents stress-induced expression of immediate early genes and gastric mucosal lesions in the rat stomach. | 1999 |
|
| [A case of rheumatoid arthritis associated with autoimmune hemolytic anemia due to weekly low-dose methotrexate therapy]. | 2000 Aug |
|
| Effect of polyunsaturated fatty acids on dexamethasone-induced gastric mucosal damage. | 2000 Feb |
|
| Ultrasonographic evaluation of lansoprazole-induced improvement of submucosal injury in patients with gastroesophageal reflux. | 2000 Feb |
|
| Developing a dynamic pharmacophore model for HIV-1 integrase. | 2000 Jun 1 |
|
| Delirium following a switch from cimetidine to famotidine. | 2001 Sep |
|
| Effects of H(2)-receptor antagonists on dapsone-induced methaemoglobinaemia in rats. | 2002 Apr |
|
| [A successfully treated case of intraoperative latex anaphylaxis during abdominal aorta aneurysm resection]. | 2003 Jan |
|
| Effect of exogenous administration of transforming growth factor-beta and famotidine on the healing of duodenal ulcer under the impact of indomethacin. | 2003 Jun |
|
| On the mechanisms underlying histamine induction of gastric mucosal lesions in rats with partial gastric vascular occlusion. | 2003 Jun |
|
| Famotidine for infant gastro-oesophageal reflux: a multi-centre, randomized, placebo-controlled, withdrawal trial. | 2003 May 1 |
|
| Different transport properties between famotidine and cimetidine by human renal organic ion transporters (SLC22A). | 2004 Oct 25 |
|
| Switching of H(2)-Receptor Antagonists to Over-the-Counter Status in Finland : Implications for Consumption and Adverse Effects. | 2005 |
|
| Comparison of an increased dosage regimen of rabeprazole versus a concomitant dosage regimen of famotidine with rabeprazole for nocturnal gastric acid inhibition in relation to cytochrome P450 2C19 genotypes. | 2005 Apr |
|
| Effect of pre-operative short course famotidine on tumor infiltrating lymphocytes in colorectal cancer: a double blind, placebo controlled, prospective randomized study. | 2005 Dec |
|
| Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
| Randomized, double-blind, placebo-controlled crossover trial of famotidine in patients with functional dyspepsia. | 2005 Jun |
|
| Alteration of intracellular histamine H2 receptor cycling precedes antagonist-induced upregulation. | 2005 Nov |
|
| A species difference in the transport activities of H2 receptor antagonists by rat and human renal organic anion and cation transporters. | 2005 Oct |
|
| 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 |
|
| In vitro availability of metformin in presence of h(2) receptor antagonists. | 2006 Jan |
|
| 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. | 2006 Mar |
|
| 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 |
|
| 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 |
|
| 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 |
|
| [Clinical study on effect of Jianwei Yuyang Granule in treating patients with gastric ulcer]. | 2007 Jul |
|
| Can negative cardiac effect of proton pump inhibitor and high-dose H2-blocker have clinical influence on patients with stable angina? | 2008 Aug |
|
| Phosphodiesterase isozymes involved in regulating acid secretion in the isolated mouse stomach. | 2009 Dec |
|
| Effects of pantoprazole on ulcer healing delay associated with NSAID treatment. | 2009 Mar |
|
| 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 |
|
| 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
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%.
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| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
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WHO-ATC |
A02BA03
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NDF-RT |
N0000175784
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WHO-VATC |
QA02BA03
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NCI_THESAURUS |
C29702
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WHO-ATC |
A02BA53
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LIVERTOX |
NBK548228
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WHO-VATC |
QA02BA53
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NDF-RT |
N0000000151
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| Code System | Code | Type | Description | ||
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Famotidine
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PRIMARY | |||
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DTXSID5023039
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DB00927
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757810
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D015738
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SUB07503MIG
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5QZO15J2Z8
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5217
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100000092363
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7074
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3325
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m5241
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CHEMBL902
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4278
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FAMOTIDINE
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1269200
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4975
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1129
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W-33
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3572
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C29045
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5QZO15J2Z8
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76824-35-6
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ACTIVE MOIETY
METABOLITE (PARENT)