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chlorhexidine   Click here for help

GtoPdb Ligand ID: 14052

Approved drug PDB Ligand
chlorhexidine is an approved drug (FDA (1976), UK)
Compound class: Synthetic organic
Comment: Chlorhexidine is a bisbiguanide compound with broad-spectrum antimicrobial activity, including against Gram-negative and Gram-positive bacteria [1]. It is exploited for its topical antiseptic utility and is included in the World Health Organization's Model List of Essential Medicines (link provided in the Classification table, under the Summary tab below) for use as an antiseptic.
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 10
Hydrogen bond donors 6
Rotatable bonds 13
Topological polar surface area 177.58
Molecular weight 505.45
XLogP 1.15
No. Lipinski's rules broken 3

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 C(CCCN=C(N)/N=C(\N)/NC1=CC=C(C=C1)Cl)CCN=C(N)/N=C(\N)/NC2=CC=C(C=C2)Cl
Isomeric SMILES C1=CC(=CC=C1N/C(=N/C(=NCCCCCCN=C(/N=C(/NC2=CC=C(C=C2)Cl)\N)N)N)/N)Cl
InChI InChI=1S/C22H30Cl2N10/c23-15-5-9-17(10-6-15)31-21(27)33-19(25)29-13-3-1-2-4-14-30-20(26)34-22(28)32-18-11-7-16(24)8-12-18/h5-12H,1-4,13-14H2,(H5,25,27,29,31,33)(H5,26,28,30,32,34)
InChI Key GHXZTYHSJHQHIJ-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.
WHO Essential Medicine WHO Essential Medicines List (EML) (24th List, 2025). Download PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
(1E)-2-[6-[[amino-[(E)-[amino-(4-chloroanilino)methylidene]amino]methylidene]amino]hexyl]-1-[amino-(4-chloroanilino)methylidene]guanidine
International Nonproprietary Names Click here for help
INN number INN
500 chlorhexidine
Database Links Click here for help
CAS Registry No. 55-56-1 (source: PubChem)
ChEBI CHEBI:3614
ChEMBL Ligand CHEMBL790
DrugBank Ligand DB00878
DrugCentral Ligand 597
GtoPdb PubChem SID 518520679
PubChem CID 9552079
RCSB PDB Ligand XC9
Search Google for chemical match using the InChIKey GHXZTYHSJHQHIJ-UHFFFAOYSA-N
Search Google for chemicals with the same backbone GHXZTYHSJHQHIJ
Search PubMed clinical trials chlorhexidine
Search PubMed titles chlorhexidine
Search PubMed titles/abstracts chlorhexidine
UniChem Compound Search for chemical match using the InChIKey GHXZTYHSJHQHIJ-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey GHXZTYHSJHQHIJ-UHFFFAOYSA-N