nizatidine   Click here for help

GtoPdb Ligand ID: 7248

Synonyms: Axid® | LY-139037
Approved drug
nizatidine is an approved drug (FDA (1988))
Compound class: Synthetic organic
Comment: Nizatidine is a histamine H2 receptor antagonist. It is structurally related to ranitidine but has a thiazole ring substitution in place of the furan ring in ranitidine. Nizatidine was the last new histamine H2 receptor antagonist to be approved prior to proton pump inhibitors reaching the clinic.

nizatidine is commercially available from our sponsors

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 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 4
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 139.55
Molecular weight 331.11
XLogP 1.41
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 CNC(=CN(=O)=O)NCCSCc1csc(n1)CN(C)C
Isomeric SMILES CN/C(=C\N(=O)=O)/NCCSCc1csc(n1)CN(C)C
InChI InChI=1S/C12H21N5O2S2/c1-13-11(6-17(18)19)14-4-5-20-8-10-9-21-12(15-10)7-16(2)3/h6,9,13-14H,4-5,7-8H2,1-3H3/b11-6+
InChI Key SGXXNSQHWDMGGP-IZZDOVSWSA-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 (1988))
Approved drug? Yes. FDA (1988)
IUPAC Name Click here for help
dimethyl[(4-{[(2-{[(E)-1-(methylamino)-2-nitroethenyl]amino}ethyl)sulfanyl]methyl}-1,3-thiazol-2-yl)methyl]amine
International Nonproprietary Names Click here for help
INN number INN
5194 nizatidine
Synonyms Click here for help
Axid® | LY-139037
Database Links Click here for help
CAS Registry No. 76963-41-2
ChEMBL Ligand CHEMBL653
DrugBank Ligand DB00585
GtoPdb PubChem SID 178103822
PubChem CID 3033637
Search Google for chemical match using the InChIKey SGXXNSQHWDMGGP-IZZDOVSWSA-N
Search Google for chemicals with the same backbone SGXXNSQHWDMGGP
Search PubMed clinical trials nizatidine
Search PubMed titles nizatidine
Search PubMed titles/abstracts nizatidine
UniChem Compound Search for chemical match using the InChIKey SGXXNSQHWDMGGP-IZZDOVSWSA-N
UniChem Connectivity Search for chemical match using the InChIKey SGXXNSQHWDMGGP-IZZDOVSWSA-N
Wikipedia Nizatidine

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MedChemExpress
Nizatidine (links to external site)
Cat. No. HY-B0310