An alkyl bis(biguanide) antiseptic
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Alexidine (hydrochloride)

Item No. 13876

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N1,N14-bis(2-ethylhexyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediimidamide, dihydrochloride
CAS Number
1715-30-6
Molecular Formula
C26H56N10 • 2HCl
Formula Weight
581.7
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 5 mg/mlDMSO: 16 mg/mlDMSO:PBS(pH7.2) (1:1): 0.50 mg/mlEthanol: 11 mg/ml
λmax
237 nm
SMILES
CCC(CCCC)CNC(NC(NCCCCCCNC(NC(NCC(CC)CCCC)=N)=N)=N)=N.Cl.Cl
InChi Code
InChI=1S/C26H56N10.2ClH/c1-5-9-15-21(7-3)19-33-25(29)35-23(27)31-17-13-11-12-14-18-32-24(28)36-26(30)34-20-22(8-4)16-10-6-2;;/h21-22H,5-20H2,1-4H3,(H5,27,29,31,33,35)(H5,28,30,32,34,36);2*1H
InChi Key
BRJJFBHTDVWTCJ-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 mg

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    Product Description

    Alexidine is an alkyl bis(biguanide) antiseptic which has been used in mouthwashes to eliminate plaque forming microorganisms.1 It binds to lipopolysaccharide and lipoteichoic acid and inhibits fungal phospholipase B (IC50 ~ 250 nM).2,3 Alexidine also inhibits the mitochondrial phosphatase PTPMT1 (IC50 = 1.08 μM, in vitro) and induces apoptosis in cancer cell lines (ED50 = 1.8-2.6 μM).4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Coburn, R.A., Baker, P.J., Evans, R.T., et al. In vitro antiplaque properties of a series of alkyl bis(biguanides). J. Med. Chem. 21(8), 828-829 (1978).

    2. Zorko, M., and Jerala, R. Alexidine and chlorhexidine bind to lipopolysaccharide and lipoteichoic acid and prevent cell activation by antibiotics. J. Antimicrob. Chemother. 62(4), 730-737 (2008).

    3. Ganendren, R., Widmer, F., Singhal, V., et al. In vitro antifungal activities of inhibitors of phospholipases from the fungal pathogen Cryptococcus neoformans. Antimicrob. Agents Chemother. 48(5), 1561-1569 (2004).

    4. Doughty-Shenton, D., Joseph, J.D., Zhang, J., et al. Pharmacological targeting of the mitochondrial phosphatase PTPMT1. J. Pharmacol. Exp. Ther. 333(2), 584-592 (2010).

    5. Yip, K.W., Ito, E., Mao, X., et al. Potential use of alexidine dihydrochloride as an apoptosis-promoting anticancer agent. Mol. Cancer Ther. 5(9), 2234-2240 (2006).