FAMOTIDINE

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Synonyms
Status
ATC A02BA03
UNII 5QZO15J2Z8
EPA CompTox DTXSID5023039

Structure

InChI Key XUFQPHANEAPEMJ-UHFFFAOYSA-N
Smiles NC(N)=Nc1nc(CSCC/C(N)=N/S(N)(=O)=O)cs1
InChI
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)

Physicochemical Descriptors

Property Name Value
Molecular Formula C8H15N7O2S3
Molecular Weight 337.46
AlogP -0.77
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 4.0
Number of Rotational Bond 7.0
Polar Surface Area 175.83
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 20.0

Bioactivity

Mechanism of Action Action Reference
Histamine H2 receptor antagonist ANTAGONIST DailyMed
Protein: Histamine H2 receptor
Description: Histamine H2 receptor
Organism : Homo sapiens
P25021 ENSG00000113749
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Lyase
- - - 126 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Histamine receptor
- 300 18-100 - 87
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 87
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- 10700 - - 14
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC47 family of multidrug and toxin extrusion transporters
- 36200 - - -
Assay Description Organism Bioactivity Reference
Evaluated against tetragastrin stimulated gastric acid secretion in conscious Hiedenhain-pouch dogs at a dose of 0.32 mg/kg, po Canis lupus familiaris 96.0 %
Compound was tested for H2 receptor antagonistic activity against histamine stimulated chronotropic response in isolated guinea pig right atrium Cavia porcellus 300.0 nM
H2 receptor antagonistic activity against histamine stimulated chronotropic response in isolated guinea pig right atrium at 1x10E-6 g/mL. Cavia porcellus 87.0 %
In vitro inhibitory activity against histamine H2-receptor in isolated Guinea pig right atria. Cavia porcellus 100.0 nM
Histamine H2 receptor antagonistic activity on the isolated spontaneously beating guinea pig right atrium Cavia porcellus 18.2 nM
Inhibition against HIV-1 integrase at 1 mM Human immunodeficiency virus 1 50.0 %
Inhibition against HIV-1 integrase at 200 uM Human immunodeficiency virus 1 50.0 %
In vivo gastric antisecretory activity in acute fistula rats (5 mg/kg, id) Rattus norvegicus 90.7 %
Inhibition of aspirin induced gastric lesions in rats after peroral dose of 32 mg/kg Rattus norvegicus 22.0 %
Inhibition of histamine stimulated gastric acid secretion in lumen perfused anaesthetized rats after 1 mg/kg intravenous dose Rattus norvegicus 96.0 %
In Vivo gastric Mucosal protective activity against gastric mucosal lesions induced by 0.6 N HCl in rats. (200 mg/kg, po) Rattus norvegicus 7.9 %
Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells at 100 uM by confocal microscopy Homo sapiens 13.9 %
Inhibition of water-immersion stress-induced ulcer formation in rat at 3 mg/kg Rattus norvegicus 59.0 %
DRUGMATRIX: Histamine H2 radioligand binding (ligand: [125I] Aminopotentidine) None 42.0 nM DRUGMATRIX: Histamine H2 radioligand binding (ligand: [125I] Aminopotentidine) None 41.0 nM
Inhibition of human MATE1-mediated ASP+ uptake expressed in HEK293 cells after 1.5 mins by fluorescence assay Homo sapiens 760.0 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 97.53 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 86.68 %
Inhibition of recombinant human CA1 preincubated for 15 mins prior to testing measured for 10 to 100 secs by phenol red based stopped-flow CO2 hydration assay Homo sapiens 922.4 nM
Inhibition of recombinant human CA2 preincubated for 15 mins prior to testing measured for 10 to 100 secs by phenol red based stopped-flow CO2 hydration assay Homo sapiens 57.9 nM
Inhibition of recombinant human CA4 preincubated for 15 mins prior to testing measured for 10 to 100 secs by phenol red based stopped-flow CO2 hydration assay Homo sapiens 938.8 nM
Inhibition of recombinant human CA6 preincubated for 15 mins prior to testing measured for 10 to 100 secs by phenol red based stopped-flow CO2 hydration assay Homo sapiens 98.2 nM
Inhibition of recombinant human CA7 preincubated for 15 mins prior to testing measured for 10 to 100 secs by phenol red based stopped-flow CO2 hydration assay Homo sapiens 3.0 nM
Inhibition of recombinant human CA9 preincubated for 15 mins prior to testing measured for 10 to 100 secs by phenol red based stopped-flow CO2 hydration assay Homo sapiens 126.3 nM
Inhibition of recombinant human CA12 preincubated for 15 mins prior to testing measured for 10 to 100 secs by phenol red based stopped-flow CO2 hydration assay Homo sapiens 45.3 nM
Inhibition of recombinant human CA13 preincubated for 15 mins prior to testing measured for 10 to 100 secs by phenol red based stopped-flow CO2 hydration assay Homo sapiens 171.5 nM
Inhibition of recombinant human CA14 preincubated for 15 mins prior to testing measured for 10 to 100 secs by phenol red based stopped-flow CO2 hydration assay Homo sapiens 677.2 nM
Inhibition of recombinant Helicobacter pylori alpha carbonic anhydrase preincubated for 15 mins prior to testing measured for 10 to 100 secs by phenol red based stopped-flow CO2 hydration assay Helicobacter pylori 20.7 nM
Inhibition of recombinant Helicobacter pylori beta carbonic anhydrase preincubated for 15 mins prior to testing measured for 10 to 100 secs by phenol red based stopped-flow CO2 hydration assay Helicobacter pylori 49.8 nM
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus 6.96 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 3.55 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 2.4 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 4.47 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 2.64 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 3.01 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans -2.8 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 12.2 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 11.54 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.04 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.04 %

Environmental Exposure

Environmental Exposure Map
Countries
Hungary
Romania
Serbia
USA

Cross References

Resources Reference
ChEBI 4975
ChEMBL CHEMBL902
DrugBank DB00927
DrugCentral 1129
FDA SRS 5QZO15J2Z8
Human Metabolome Database HMDB0001919
Guide to Pharmacology 7074
PharmGKB PA449586
SureChEMBL SCHEMBL972
ZINC ZINC000001530636
CONTENTS