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A8986

Sigma-Aldrich

Alexidine dihydrochloride

≥95% (HPLC)

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C26H56N10 · 2HCl
Numéro CAS:
1715-30-6
Poids moléculaire :
581.71
Numéro CE :
216-994-6
Numéro MDL:
MFCD00082369
Code UNSPSC :
12352200
ID de substance PubChem :
329771026
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥95% (HPLC)

Forme

powder

Conditions de stockage

desiccated

Couleur

white to off-white

Solubilité

DMSO: ≥10 mg/mL

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

BRJJFBHTDVWTCJ-UHFFFAOYSA-N

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Application

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

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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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
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
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
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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Articles

Phosphoprotein Phosphatases (Tyrosine)

Protein tyrosine phosphatases' catalytic mechanism involves transient phosphorylation.

Phosphoprotein Phosphatases (Tyrosine)

Protein tyrosine phosphatases' catalytic mechanism involves transient phosphorylation.

Phosphoprotein Phosphatases (Tyrosine)

Protein tyrosine phosphatases' catalytic mechanism involves transient phosphorylation.

Phosphoprotein Phosphatases (Tyrosine)

Protein tyrosine phosphatases' catalytic mechanism involves transient phosphorylation.

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