ranitidine   Click here for help

GtoPdb Ligand ID: 1234

Synonyms: AH-19065 | Gavilast® | GR-122311X | Zantac®
Approved drug
ranitidine is an approved drug (FDA (1977))
Compound class: Synthetic organic
Comment: There is some ambiguity in the exact stereochemistry of ranitidine as represented in the literature and on other databases. The structure shown here matches that in the PubChem entry above. Other common representations include CID 657345. N.B. The structure shown in the INN document does not have a charge.
Marketed formulations may contain ranitidine hydrochloride (PubChem CID 3033332).
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: ranitidine

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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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 CDK toolkit. 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 3
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 108.88
Molecular weight 314.14
XLogP 1.28
No. Lipinski's rules broken 0
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.

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Canonical SMILES CNC(=C[N+](=O)[O-])NCCSCc1ccc(o1)CN(C)C
Isomeric SMILES CN/C(=C\[N+](=O)[O-])/NCCSCc1ccc(o1)CN(C)C
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/b13-9+
InChI Key VMXUWOKSQNHOCA-UKTHLTGXSA-N
References
1. Aschenbrenner DS. (2020)
Ranitidine Withdrawn From the Market.
Am J Nurs, 120 (8): 23. [PMID:32732474]
2. Beukers MW, Klaassen CH, De Grip WJ, Verzijl D, Timmerman H, Leurs R. (1997)
Heterologous expression of rat epitope-tagged histamine H2 receptors in insect Sf9 cells.
Br J Pharmacol, 122 (5): 867-74. [PMID:9384502]
3. Leurs R, Smit MJ, Menge WM, Timmerman H. (1994)
Pharmacological characterization of the human histamine H2 receptor stably expressed in Chinese hamster ovary cells.
Br J Pharmacol, 112 (3): 847-54. [PMID:7921611]
4. Wagner JA, Dinh JC, Lightdale JR, Gold BD, Colombo JM. (2021)
Is this the end for ranitidine? NDMA presence continues to confound.
Clin Transl Sci, 14 (4): 1197-1200. [PMID:33934515]