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Chlorhexidine

Catalog Number
ACM55561-2
CAS
55-56-1
Structure
IUPAC Name
(1E)-2-[6-[[amino-[(E)-[amino-(4-chloroanilino)methylidene]amino]methylidene]amino]hexyl]-1-[amino-(4-chloroanilino)methylidene]guanidine
Synonyms
1,1'-Hexamethylenebis(5-(p-chlorophenyl)-biguanid;1,6-bis(5-(p-chlorophenyl)biguandino)hexane; 1,6-bis(p-chlorophenyldiguanido)hexane
Molecular Weight
505.45
Molecular Formula
C22H30Cl2N10
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
Melting Point
134-136 °C (lit.)
Purity
99+%
Density
1.39 g/cm³
Solubility
Soluble in water (0.08%) at 20 °C
Appearance
White powder
Active Content
95%
Physical State
Solid
Typical Applications
Use as antimicrobial agent, preservative.
Spec Sheet
Case Study

Chlorhexidine as an ATP-Aided Inhibitor of Bacterial Methionyl-tRNA Synthetase

Chlorhexidine as an ATP-Aided Inhibitor of Bacterial Methionyl-tRNA Synthetase Lu, Feihu, et al. European Journal of Medicinal Chemistry 268 (2024): 116303.

Chlorhexidine (CHX), a widely used antiseptic, has been identified as a selective inhibitor of bacterial methionyl-tRNA synthetase (MetRS), a key enzyme in protein biosynthesis. Through ATP-aided affinity screening, CHX exhibited strong binding to Staphylococcus aureus MetRS (SaMetRS), with an ATP-dependent enhancement of binding affinity from 10.2 μM to 0.45 μM.
Crystallographic studies revealed that CHX occupies both the enlarged l-Met pocket (EMP) and the auxiliary pocket (AP) of SaMetRS, with its chlorophenyl groups anchoring the active site. ATP adopts alternative conformations to form ionic and hydrogen bonds with CHX, stabilizing its interaction with the enzyme. Notably, CHX selectively inhibits type 1 MetRS from S. aureus and Enterococcus faecalis, while showing minimal interaction with type 2 MetRS, including the human counterpart.
These findings highlight CHX as a potential scaffold for MetRS-targeted antimicrobial development, with structural modifications focused on expanding its chlorophenyl groups and optimizing its central linker for improved potency and selectivity.

Preparation of Chlorhexidine-Loaded Chitosan Gels for Antimicrobial Wound Dressings

Preparation of Chlorhexidine-Loaded Chitosan Gels for Antimicrobial Wound Dressings Ferreira, Maria Onaira Gonçalves, et al. Journal of Drug Delivery Science and Technology 49 (2019): 375-382.

Chlorhexidine (CHX), a broad-spectrum antimicrobial agent, has been incorporated into chitosan gels to develop an advanced wound dressing with enhanced biocompatibility and antibacterial properties. Chitosan, known for its gel-forming ability in acidic media, serves as an ideal matrix for sustained CHX release.
In this study, CHX was incorporated into chitosan gels at concentrations of 2% (CHC2) and 4% (CHC4) by adding 2 mL or 4 mL of CHX to 50 mL of chitosan gel. The solutions were mixed for 10 minutes to ensure uniform CHX dispersion. The resulting gels exhibited strong antimicrobial activity, making them suitable for infection control in wound care.
The combination of CHX and chitosan provides a dual-function dressing, offering both antimicrobial protection and a favorable environment for tissue regeneration. These CHX-loaded chitosan gels hold promise for biomedical applications, including wound healing and post-surgical infection prevention.

Chlorhexidine as a Template and Antiseptic Agent in Mesoporous Organosilica Nanoparticles

Chlorhexidine as a Template and Antiseptic Agent in Mesoporous Organosilica Nanoparticles He, Yan, et al. Colloids and Surfaces B: Biointerfaces 187 (2020): 110653.

Chlorhexidine (CHX), a widely used antiseptic, has demonstrated dual functionality in the synthesis of biodegradable mesoporous organosilica nanoparticles (CHX@MONs). In this study, CHX served both as a cationic template for mesopore formation and as an active antimicrobial agent.
The CHX@MONs were synthesized using a modified sol-gel method. A mixture of CHX and TEAH3 was stirred at 80 °C before the dropwise addition of TEOS and BTES, allowing for mesopore formation. The final nanoparticles were obtained through centrifugation, followed by vacuum drying. UV-vis spectrophotometry confirmed CHX loading efficiency, with the remaining CHX in the supernatant quantified at 259 nm.
This study highlights the innovative role of CHX in nanoparticle synthesis, enabling the development of self-antiseptic nanomaterials. CHX@MONs offer potential applications in infection control, wound healing, and biomedical coatings, providing sustained antimicrobial activity while ensuring biodegradability.

Custom Q&A

What is the CAS number for Chlorhexidine?

The CAS number for Chlorhexidine is 55-56-1.

What are some synonyms for Chlorhexidine?

Some synonyms for Chlorhexidine include 1,1'-Hexamethylenebis(5-(p-chlorophenyl)-biguanid and 1,6-bis(5-(p-chlorophenyl)biguandino)hexane.

What is the molecular weight of Chlorhexidine?

The molecular weight of Chlorhexidine is 505.45.

What is the molecular formula of Chlorhexidine?

The molecular formula of Chlorhexidine is C22H30Cl2N10.

What is the InChI key for Chlorhexidine?

The InChI key for Chlorhexidine is GHXZTYHSJHQHIJ-UHFFFAOYSA-N.

What is the melting point of Chlorhexidine?

The melting point of Chlorhexidine is 134-136 °C (lit.).

What is the purity of Chlorhexidine?

The purity of Chlorhexidine is 99+%.

What is the density of Chlorhexidine?

The density of Chlorhexidine is 1.39 g/cm³.

What are the typical applications of Chlorhexidine?

Chlorhexidine is commonly used as an antimicrobial agent and preservative.

What is the physical state of Chlorhexidine?

The physical state of Chlorhexidine is a solid in the form of white powder.

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