Hexamidine diisethionate
[CAS# 659-40-5]

Identification

• Classification: Analytical chemistry >> Standard >> Pharmacopoeia standards and magazine standards
• Name: Hexamidine diisethionate
• Synonyms: Hexamidine 2-hydroxyethansulfonate; 4-[6-(4-Carbamimidoylphenoxy)hexoxy]benzenecarboximidamide 2-hydroxyethanesulfonnate (1:2)
• Molecular Formula: C₂₀H₂₆N₄O₂.2(C₂H₆O₄S)
• Molecular Weight: 606.71
• CAS Registry Number: 659-40-5
• EC Number: 211-533-5
• SMILES: C1=CC(=CC=C1C(=N)N)OCCCCCCOC2=CC=C(C=C2)C(=N)N.C(CS(=O)(=O)O)O.C(CS(=O)(=O)O)O

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Risk Statements: H302-H319-H410-H411
• Safety Statements: P264-P264+P265-P270-P273-P280-P301+P317-P305+P351+P338-P330-P337+P317-P391-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Eye irritation	Eye Irrit.	2	H319
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Acute toxicity	Acute Tox.	4	H332

Discovery and Applications

Hexamidine diisethionate, also known as hexamidine, is a synthetic compound derived from imidazolines, a class of organic compounds containing a five-membered ring containing two nitrogen atoms. First synthesized in the mid-20th century, it exhibits potent antimicrobial properties against a wide range of bacteria, fungi, and protozoa and is of great value in various fields including medicine, personal care, and veterinary science.

Hexamidine diisethionate is widely used as an active ingredient in topical formulations such as antibacterial solutions, wound care products and skin antiseptics due to its broad spectrum antimicrobial activity. Its function is to disrupt the cell membrane of microorganisms, causing their destruction or growth inhibition. Hexamidine diisethionate is effective against both Gram-positive and Gram-negative bacteria as well as fungi and certain protozoa, making it a versatile antibacterial agent for the prevention and treatment of a variety of infections. Hexamidine diisethionate is commonly incorporated into topical antibacterial preparations used to clean and disinfect the skin and mucous membranes. It is used in wound care products, surgical scrubs and pre-operative skin preparation to reduce the risk of bacterial contamination and hospital infections. Hexamidine diisethionate is used as a preservative in cosmetics and personal care products to prevent microbial growth and spoilage. It helps maintain the stability and integrity of the formula, extending its shelf life and ensuring product safety. Hexamidine diisethionate is used in the treatment of various skin diseases characterized by microbial infection, inflammation or irritation of the skin and mucous membranes. It is incorporated into creams, ointments and lotions to treat conditions such as acne, seborrheic dermatitis, rosacea and fungal skin infections. Hexamidine diisethionate is also used in hair care products such as shampoos, conditioners, and scalp treatments for its antibacterial and anti-inflammatory properties. It helps fight scalp conditions associated with microbial overgrowth such as dandruff, seborrheic dermatitis and scalp acne, relieving itching, flaking and irritation. Hexamidine diisethionate is used in veterinary medicine to treat skin infections and wounds in animals. Veterinary prescription medicated shampoos, sprays, and topical solutions containing hexamidine diisethionate are used to treat bacterial and fungal skin infections in pets such as dogs, cats, and horses.

References

2023. Hexamidine and Hexamidine Diisethionate. International Journal of Toxicology, 42(3).
DOI: 10.1177/10915818231204273

2020. In Vitro Antimicrobial Activity of a New Ophthalmic Solution Containing Hexamidine Diisethionate 0.05% (Keratosept). Cornea, 39(11).
DOI: 10.1097/ico.0000000000002375

2009. p-Guanidinoethyl calixarene and parent phenol derivatives exhibiting antibacterial activities. Synthesis and biological evaluation. Bioorganic & Medicinal Chemistry, 17(15).
DOI: 10.1016/j.bmc.2009.06.040