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Merck
CN

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

Key Documents

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Product Name

Alexidine dihydrochloride, ≥95% (HPLC)

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

SMILES string

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

assay

≥95% (HPLC)

form

powder

storage condition

desiccated

color

white to off-white

solubility

DMSO: ≥10 mg/mL

storage temp.

−20°C

Quality Level

100

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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

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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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
T E Balanyk et al.
Journal of dental research, 64(12), 1356-1360 (1985-12-01)
Two antimicrobial varnishes were developed to be applied to the teeth for the eradication of Streptococcus mutans infections. One of them contained chlorhexidine acetate as the antimicrobial agent and the other, erythromycin base. Both varnishes contained Sumatra benzoin. Each of
Xiang Zhu et al.
Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research, 31(3), 560-572 (2015-09-13)
Aseptic loosening and periprosthetic infection leading to inflammatory osteolysis is a major complication associated with total joint arthroplasty (TJA). The liberation of bacterial products and/or implant-derived wear particles activates immune cells that produce pro-osteoclastogenic cytokines that enhance osteoclast recruitment and
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Articles

Phosphoprotein Phosphatases (Tyrosine)

Protein tyrosine phosphatases' catalytic mechanism involves transient phosphorylation.

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