RANITIDINE

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Trade Names
Synonyms
Status
Molecule Category Free-form
ATC A02BA02
UNII 884KT10YB7
EPA CompTox DTXSID8045191

Structure

InChI Key VMXUWOKSQNHOCA-UHFFFAOYSA-N
Smiles CNC(=C[N+](=O)[O-])NCCSCc1ccc(CN(C)C)o1
InChI
InChI=1S/C13H22N4O3S/c1-14-13(9-17(18)19)15-6-7-21-10-12-5-4-11(20-12)8-16(2)3/h4-5,9,14-15H,6-8,10H2,1-3H3

Physicochemical Descriptors

Property Name Value
Molecular Formula C13H22N4O3S
Molecular Weight 314.41
AlogP 1.46
Hydrogen Bond Acceptor 7.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 10.0
Polar Surface Area 83.58
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 21.0

Bioactivity

Mechanism of Action Action Reference
Histamine H2 receptor antagonist ANTAGONIST DailyMed FDA
Protein: Histamine H2 receptor
Description: Histamine H2 receptor
Organism : Homo sapiens
P25021 ENSG00000113749
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- 650-2300 - - -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Histamine receptor
- 3400 65-170 54-501 44
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - - 29
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC47 family of multidrug and toxin extrusion transporters
- 8300 - - 29
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- - - - 0
Transporter Primary active transporter P-type ATPase Hydrogen potassium ATPase
- 40 - - -
Assay Description Organism Bioactivity Reference
Inhibition of guinea pig acetylcholinesterase Cavia porcellus 650.0 nM
Evaluated against tetragastrin stimulated gastric acid secretion in conscious Hiedenhain-pouch dogs at a dose of 0.32 mg/Kg, po Canis lupus familiaris 41.0 %
Evaluated for the inhibition of H+/K+ ATPase enzyme from fundic mucosa of white rabbits at 100 uM Oryctolagus cuniculus 100.0 %
In vitro inhibition of Histamine H2 receptor by measuring its ability to block the histamine-stimulated adenylate cyclase of guinea pig hippocampal homogenate Cavia porcellus 501.19 nM
Histamine H2 receptor antagonistic activity Cavia porcellus 1.05 ug.mL-1
H2 receptor antagonistic activity against histamine stimulated chronotropic response in isolated guinea pig right atrium at 1x10E-6 g/mL. Cavia porcellus 44.0 %
Compound was evaluated in vitro inhibitory activity against histamine H2 receptor in isolated Guinea pig right atria. Cavia porcellus 64.57 nM
Histamine H2 receptor antagonistic activity on the isolated spontaneously beating guinea pig right atrium Cavia porcellus 169.82 nM
Inhibition of [125I]APT binding to histamine H2 receptor in guinea pig cerebral membranes. Cavia porcellus 53.7 nM
Inhibition of P-gp was determined using rhodamine-assay in human CaCo-2 cells None 0.0 %
Antisecretory activity evaluated by the inhibition of 14C -AP uptake in isolated rabbit parietal cells stimulated by exogenous histamine Oryctolagus cuniculus 40.0 nM
Inhibition of histamine stimulated gastric acid secretion in lumen perfused stomach of anesthetized rats Rattus norvegicus 72.0 %
Inhibition of aspirin induced gastric lesions in rats after peroral dose of 32 mg/kg Rattus norvegicus 3.0 %
In Vivo gastric Mucosal protective activity against gastric mucosal lesions induced by 0.6 N HCl in rats. (200 mg/kg, po) Rattus norvegicus -16.8 %
Evaluated against histamine stimulated gastric acid secretion in lumen perfused anaesthetized rats after 1 mg/kg intravenous dose Rattus norvegicus 72.0 %
Inhibition of histamine stimulated chronotropic response in isolated guinea pig right atrium Cavia porcellus 44.0 %
Inhibition of histamine-stimulated chronotropic response in isolated guinea pig right atrium Cavia porcellus 44.0 %
Inhibition of histamine-stimulated gastric acid secretion in lumen-perfused stomach of anesthetized rats Rattus norvegicus 72.0 %
Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells at 100 uM by confocal microscopy Homo sapiens 28.8 %
Binding affinity to histamine H2 receptor (unknown origin) Homo sapiens 63.0 nM
Inhibition of human MATE1-mediated ASP+ uptake expressed in HEK293 cells at 20 uM after 1.5 mins by fluorescence assay Homo sapiens 29.0 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 26.81 %
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 -0.26 % 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 -0.26 %

Environmental Exposure

Environmental Exposure Map
Countries
Croatia
Czech Republic
Germany
Hungary
Romania
Serbia
Slovakia
Slovenia
USA

Cross References

Resources Reference
ChEBI 92246
ChEMBL CHEMBL1790041
DrugBank DB00863
DrugCentral 2358
FDA SRS 884KT10YB7
Guide to Pharmacology 1234
KEGG D00422
PubChem 5039
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