famotidine   Click here for help

GtoPdb Ligand ID: 7074

Synonyms: Gaster® | MK-208 | Pepcid®
Approved drug
famotidine is an approved drug (FDA (1986))
Compound class: Synthetic organic
Comment: Famotidine is a histamine H2 receptor antagonist. The drug is poorly soluble in the low pH of the stomach so suffers from poor bioavailability. Low dose (10-20 mg) famotidine is available over-the-counter in some countries. Marketing of a combination of famotidine with antacids magnesium hydroxide and calcium carbonate (Pepcidtwo®) has been officially discontinued in the UK (2015).
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View more information in the IUPHAR Pharmacology Education Project: famotidine

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 9
Hydrogen bond donors 4
Rotatable bonds 7
Topological polar surface area 237.75
Molecular weight 337.04
XLogP -1.79
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES NC(=Nc1scc(n1)CSCCC(=NS(=O)(=O)N)N)N
Isomeric SMILES NC(=Nc1scc(n1)CSCC/C(=N/S(=O)(=O)N)/N)N
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)
InChI Key XUFQPHANEAPEMJ-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1986))
IUPAC Name Click here for help
3-[[2-(diaminomethylideneamino)-1,3-thiazol-4-yl]methylsulfanyl]-N'-sulfamoylpropanimidamide
International Nonproprietary Names Click here for help
INN number INN
5217 famotidine
Synonyms Click here for help
Gaster® | MK-208 | Pepcid®
Database Links Click here for help
Specialist databases
GPCRdb Ligand famotidine
Other databases
BitterDB Ligand 101
CAS Registry No. 76824-35-6
ChEBI CHEBI:4975
ChEMBL Ligand CHEMBL902
DrugBank Ligand DB00927
DrugCentral Ligand 1129
GtoPdb PubChem SID 178103653
PubChem CID 5702160
Search Google for chemical match using the InChIKey XUFQPHANEAPEMJ-UHFFFAOYSA-N
Search Google for chemicals with the same backbone XUFQPHANEAPEMJ
Search PubMed clinical trials famotidine
Search PubMed titles famotidine
Search PubMed titles/abstracts famotidine
UniChem Compound Search for chemical match using the InChIKey XUFQPHANEAPEMJ-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey XUFQPHANEAPEMJ-UHFFFAOYSA-N
Wikipedia Famotidine