A bis(biguanide) antimicrobial agent
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Chlorhexidine (hydrochloride)

Item No. 17343

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N1,N14-bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediimidamide, dihydrochloride
CAS Number
3697-42-5
Synonyms
  • CHX
Molecular Formula
C22H30Cl2N10 • 2HCl
Formula Weight
578.4
Purity
≥80%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 10 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/mlEthanol: 10 mg/ml
λmax
258 nm
SMILES
ClC1=CC=C(NC(NC(NCCCCCCNC(NC(NC2=CC=C(Cl)C=C2)=N)=N)=N)=N)C=C1.Cl.Cl
InChi Code
InChI=1S/C22H30Cl2N10.2ClH/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);2*1H
InChi Key
WJLVQTJZDCGNJN-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Chlorhexidine is a bis(biguanide) antimicrobial disinfectant and antiseptic agent.1 It inhibits growth of clinical methicillin-resistant S. aureus (MRSA) isolates (MIC90 = 4 μg/ml).2 It is also active against canine isolates of MRSA, methicillin-susceptible S. aureus (MSSA), methicillin-resistant S. pseudintermedius (MRSP), and methicillin-susceptible S. pseudintermedius (MSSP; MIC90s = 4, 2, 2, and 1 mg/L, respectively).3 Chlorhexidine inhibits growth of E. faecium strains (MICs = 1.2-19.6 μg/ml) and C. albicans (MIC = 5.15 μg/ml).4,5 It generates cations that bind to and destabilize the bacterial cell wall to induce death.6 Chlorhexidine also completely inhibits matrix metalloproteinase-2 (MMP-2) and MMP-9 when used at concentrations of 0.0001 and 0.002%, respectively, in a gelatin degradation assay.7 Formulations containing chlorhexidine have been used in antiseptic wound dressings, mouthwash, and toothpaste.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Karpiński, T.M., and Szkaradkiewicz, A.K. Chlorhexidine--Pharmaco-biological activity and application. Eur. Rev. Med. Pharmacol. Sci. 19(7), 1321-1326 (2015).

    2. McDanel, J.S., Murphy, C.R., Diekema, D.J., et al. Chlorhexidine and mupirocin susceptibilities of methicillin-resistant Staphylococcus aureus from colonized nursing home residents. Antimicrob. Agents Chemother. 57(1), 552-558 (2013).

    3. Clark, S.M., Loeffler, A., and Bond, R. Susceptibility in vitro of canine methicillin-resistant and -susceptible staphylococcal isolates to fusidic acid, chlorhexidine and miconazole: Opportunities for topical therapy of canine superficial pyoderma. J. Antimicrob. Chemother. 70(7), 2048-2052 (2015).

    4. Bhardwaj, P., Hans, A., Ruikar, K., et al. Reduced chlorhexidine and daptomycin susceptibility in vancomycin-resistant enterococcus faecium after serial chlorhexidine exposure. Antimicrob. Agents Chemother. 62(1), e01235-01217 (2017).

    5. Scheibler, E., da Silva, R.M., Leite, C.E., et al. Stability and efficacy of combined nystatin and chlorhexidine against suspensions and biofilms of Candida albicans. Arch. Oral Biol. 89, 70-76 (2018).

    6. Barrett-Bee, K., Newboult, L., and Edwards, S. The membrane destabilising action of the antibacterial agent chlorhexidine. FEMS Microbiol. Lett. 119(1-2), 249-253 (1994).

    7. Gendron, R., Grenier, D., Sorsa, T., et al. Inhibition of the activities of matrix metalloproteinases 2, 8, and 9 by chlorhexidine. Clin. Diag. Lab. Immun. 6(3), 437-439 (1999).

    Product Citations

    Liu, F., Zuo, X., Liu, Y., et al. Suppression of membranous LRP5 recyling, Wnt/β-catenin signaling, and colon carcinogenesis by 15-LOX-1 peroxidation of linoleic acid in PI3P. Cell Rep. 32(7), 108049 (2020).

    Khurana, N., Kim, H., Chandra, P.K., et al. Multimodal actions of the phytochemical sulforaphane suppress both AR and AR-V7 in 22Rv1 cells: Advocating a potent pharmaceutical combination against castration-resistant prostate cancer. Oncol. Rep. 38(5), 2774-2786 (2017).