An internal standard for the quantification of chlorhexidine
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Chlorhexidine-d8 (hydrochloride)

Item No. 33463

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N1,N14-bis(4-chlorophenyl-d4)-3,12-diimino-2,4,11,13-tetraazatetradecanediimidamide, dihydrochloride
CAS Number
2012598-75-1
Synonyms
  • CHX-d8
Molecular Formula
C22H22Cl2D8N10 • 2HCl
Formula Weight
586.4
Purity
≥99% deuterated forms (d1-d8)
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: solubleMethanol: soluble
SMILES
ClC(C([2H])=C1[2H])=C([2H])C([2H])=C1NC(NC(NCCCCCCNC(NC(NC2=C([2H])C([2H])=C(C([2H])=C2[2H])Cl)=N)=N)=N)=N.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/i5D,6D,7D,8D,9D,10D,11D,12D;;
InChi Key
WJLVQTJZDCGNJN-ZYNYSASXSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Chlorhexidine-d8 is intended for use as an internal standard for the quantification of chlorhexidine (Item Nos. 17343 | 26924) by GC- or LC-MS. 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).