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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
116M4752V
076M4723V
125M4718V
015M4713V
070M4702

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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), 253-258 (1989-03-01)
Strains of Providencia stuartii with demonstrated resistance towards chlorhexidine did not show such resistance towards either of the related biguanide antiseptics, alexidine or vantocil. Alexidine promoted a significantly faster alteration in the permeability of Escherichia coli cell membranes towards various
Hyun-Shik Kim et al.
International journal of oral science, 5(1), 26-31 (2013-03-16)
A previous study demonstrated that alexidine has greater affinity for the major virulence factors of bacteria than chlorhexidine. The aim of this study was to compare the antimicrobial activity of 1% alexidine with that of 2% chlorhexidine using Enterococcus faecalis-infected
Kenneth W Yip et al.
Molecular cancer therapeutics, 5(9), 2234-2240 (2006-09-21)
Despite advances in surgery, radiation, and chemotherapy, novel therapeutics are needed for head and neck cancer treatment. The objective of this current study was to evaluate alexidine dihydrochloride as a novel compound lead for head and neck cancers. Using a
View All Related Papers

Global Trade Item Number

SKUGTIN
A8986-10MG04061833217474
A8986-50MG04061833401088