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A8986

Alexidine dihydrochloride

≥95% (HPLC), PTPMT1 inhibitor, powder

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C26H56N10 · 2HCl
CAS Number:
1715-30-6
Molecular Weight:
581.71
NACRES:
NA.77
PubChem Substance ID:
329771026
UNSPSC Code:
12352200
EC Number:
216-994-6
MDL number:
MFCD00082369
Assay:
≥95% (HPLC)
Form:
powder
Quality level:
100
Storage condition:
desiccated
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Product Name

Alexidine dihydrochloride, ≥95% (HPLC)

Quality Level

100

assay

≥95% (HPLC)

form

powder

storage condition

desiccated

color

white to off-white

solubility

DMSO: ≥10 mg/mL

storage temp.

−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

InChI key

BRJJFBHTDVWTCJ-UHFFFAOYSA-N

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

Biochem/physiol Actions

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.

Features and Benefits

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000524789
0000524789
0000478294
0000478294
0000297562

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Articles

Phosphoprotein Phosphatases (Tyrosine)

Protein tyrosine phosphatases' catalytic mechanism involves transient phosphorylation.

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
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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