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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

Essai

≥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

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Certificats d'analyse (COA)

Lot/Batch Number
0000315238
0000297561
0000297562
0000185786
0000194264

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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
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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
J Moran et al.
Journal of periodontology, 55(5), 278-282 (1984-05-01)
The phenomenon of surface adsorption appears fundamental to the antiplaque activity of the cationic antiseptics. Moreover, reaction with chromogenic material is relevant to the local side effect of staining. The purpose of this investigation was to determine how such local
W R Roberts et al.
Journal of clinical periodontology, 8(4), 295-310 (1981-08-01)
A study was carried out to compare the antibacterial properties of four cationic antiseptics, three of which are available as commercial mouthrinse preparations. Minimum inhibitory concentrations for alexidine, cetyl pyridinium chloride, chlorhexidine gluconate and hexetidine against a range of standard
M Addy et al.
Journal of clinical periodontology, 8(3), 220-230 (1981-06-01)
A blind cross-over trial was carried out to compare the tooth and tongue staining associated with the use of a 0.035% alexidine and a 0.2% chlorhexidine mouthrinse. Twenty-two volunteers were divided into two groups termed "tea drinkers" and "non-tea drinkers".
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