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A8986

Sigma-Aldrich

Alexidine dihydrochloride

≥95% (HPLC)

Synonym(e):

1,1′-Hexamethylene-bis(5-[2-ethylhexyl]biguanide)

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About This Item

Empirische Formel (Hill-System):
C26H56N10 · 2HCl
CAS-Nummer:
1715-30-6
Molekulargewicht:
581.71
EG-Nummer:
216-994-6
MDL-Nummer:
MFCD00082369
UNSPSC-Code:
12352200
PubChem Substanz-ID:
329771026
NACRES:
NA.77

Assay

≥95% (HPLC)

Form

powder

Lagerbedingungen

desiccated

Farbe

white to off-white

Löslichkeit

DMSO: ≥10 mg/mL

Lagertemp.

−20°C

SMILES String

Cl.Cl.CCCCC(CC)CNC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)NCC(CC)CCCC

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

InChIKey

BRJJFBHTDVWTCJ-UHFFFAOYSA-N

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Anwendung

Alexidine dihydrochloride has been used:
  • as an antiseptic to study its antimicrobial activity in saliva-derived microcosm biofilms
  • as a protein tyrosine phosphatase localized to the mitochondrion 1 (PTPMT1)-specific inhibitor to study its effects on spare respiratory capacity and viability of CD8+ T cells
  • as a PTPMT1 inhibitor to study its antiviral effect on  human cytomegalovirus (HCMV) replication in HCMV-infected human foreskin fibroblast (HFF) cells

Biochem./physiol. Wirkung

Alexidine dihydrochloride is a bisbiguanide compound. It has been studied in the treatment of head and neck cancer. Alexidine dihydrochloride also exhibits antibiofilm and antifungal activity against several fungal species. It causes mitochondrial apoptosis in mammalian cells due to its anti-cancer activity. Alexidine dihydrochloride is a component of oral disinfectant and contact lens solution.
Alexidine dihydrochloride is a potent and selective PTPMT1 (Protein Tyrosine Phosphatase Localized to the Mitochondrion 1) inhibitor. Alexidine increases insulin secretion by isolated rat pancreatic islets.

Leistungsmerkmale und Vorteile

This compound is featured on the Phosphoprotein Phosphatases (Tyrosine) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

Gefahreneinstufungen

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

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Chlorhexidin ≥99.5%

Sigma-Aldrich

282227

Chlorhexidin

Chlorhexidin Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1421

Chlorhexidin

8-Aminochinolin 98%

Sigma-Aldrich

260789

8-Aminochinolin

Chlorhexidin -digluconat -Lösung 20% in H2O

Sigma-Aldrich

C9394

Chlorhexidin -digluconat -Lösung

J A Chawner et al.
The Journal of applied bacteriology, 66(3), 243-252 (1989-03-01)
A comparative study of the growth inhibitory and bactericidal activities of two related bisbiguanide antiseptics, alexidine and chorhexidine is reported. Whilst overall bactericidal activities and MICs were similar, alexidine was more rapid in its action and it is suggested that
Sophia R Schwarz et al.
Clinical oral investigations, 25(5), 2939-2950 (2020-10-10)
The aims of this study were to investigate the antimicrobial efficacy of antiseptics in saliva-derived microcosm biofilms, and to examine phenotypic adaption of bacteria upon repeated exposure to sub-inhibitory antiseptic concentrations. Saliva-derived biofilms were formed mimicking caries- or gingivitis-associated conditions
Zeinab Mamouei et al.
mSphere, 3(5) (2018-11-02)
Invasive fungal infections due to Candida albicans, Aspergillus fumigatus, and Cryptococcus neoformans constitute a substantial threat to hospitalized immunocompromised patients. Further, the presence of drug-recalcitrant biofilms on medical devices and emergence of drug-resistant fungi, such as Candida auris, introduce treatment
Allison Campolo et al.
Pathogens (Basel, Switzerland), 10(2) (2021-01-31)
Acanthamoeba keratitis (AK) is a serious ocular infection caused by a ubiquitous free-living amoeba, Acanthamoeba. This infection often results in extensive corneal damage and blindness, and is notoriously difficult to cure. While Acanthamoeba is an abundant organism, AK is most
Mateja Zorko et al.
The Journal of antimicrobial chemotherapy, 62(4), 730-737 (2008-07-19)
Many antibiotics used to treat infections cause release of immunostimulatory cell wall components from bacteria. Therefore, a combination of antimicrobial and endotoxin-neutralizing activity is desired to prevent inflammation induced by destroyed bacteria. Chlorhexidine and alexidine are amphipathic bisbiguanides and could
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Artikel

Phosphoprotein Phosphatases (Tyrosine)

Protein tyrosine phosphatases' catalytic mechanism involves transient phosphorylation.

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