Hexamidine Diisethionate

Synonyme: Hexamidine diisethionate, 4,4′-(hexane-1,6-diylbis(oxy))dibenzamidine diisethionate, hexamidine di(2-hydroxyethanesulfonate), hexamidine diisethionate salt

Hexamidine diisethionate is a synthetic antimicrobial agent belonging to the diamidine class, characterized by two benzamidine moieties linked via a flexible hexamethylene chain. This structure, reminiscent of propamidine and pentamidine, confers a high affinity for the minor groove of DNA, where it disrupts essential microbial processes. Its diisethionate salt form enhances water solubility, making it suitable for aqueous formulations across pharmaceutical and personal care applications.

First synthesized in the mid-20th century, hexamidine diisethionate has established itself as a well-tolerated preservative and antiseptic, particularly in ophthalmic solutions and cosmetic products. It is effective against a broad spectrum of microorganisms, including bacteria, fungi, and protozoa, and is often used in concentrations ranging from 0.05% to 0.1%. Its compatibility with other ingredients and stability over a wide pH range contribute to its popularity in multi-component formulations.

In the pharmaceutical industry, hexamidine diisethionate is employed as a preservative in eye drops and contact lens solutions, where its broad-spectrum activity ensures product sterility. In cosmetics, it serves as an antimicrobial agent in creams, lotions, and wet wipes, often in combination with other preservatives to achieve broad protection. Ongoing research explores its potential in treating protozoal infections, such as Acanthamoeba keratitis, further expanding its therapeutic relevance.

Chemical Structure & Properties

Hexamidine diisethionate features a symmetrical molecular architecture with two 4-amidinophenoxy groups connected by a hexamethylene spacer. The amidine groups are protonated under physiological conditions, facilitating electrostatic interactions with negatively charged microbial membranes and nucleic acids. The diisethionate counterions (2-hydroxyethanesulfonate) improve aqueous solubility without compromising antimicrobial activity. The compound is stable under normal storage conditions, though it should be protected from excessive heat and moisture to prevent degradation.

Mechanism of Action

• DNA minor groove binding: The diamidine structure binds to the minor groove of double-stranded DNA, interfering with transcription and replication processes in microbial cells.
• Membrane disruption: Positively charged amidine groups interact with phospholipid bilayers, increasing membrane permeability and causing leakage of intracellular components.
• Enzyme inhibition: Hexamidine inhibits key enzymes such as trypanothione reductase in protozoa, disrupting redox balance and leading to cell death.
• Broad-spectrum activity: Effective against Gram-positive and Gram-negative bacteria, yeasts, and molds, making it a versatile preservative.

Quality Specifications

Supply & Documentation

• Capacity: Annual production capacity of 50 metric tons, with scalable manufacturing to meet large-volume orders.
• Lieferzeit: 3–5 Werktage (Lagerware)
• Dokumentation: COA, MSDS, TDS, and regulatory support (e.g., REACH, FDA) provided with each shipment.
• Verpackung: 25 kg fiber drums with double polyethylene liners; custom packaging available for small-scale trials.

Angebotsanfrage

• LyvBio GmbH. — E-Mail: info@lyvbio.com