Basic information
- CAS
3811-75-4- Standard SMILES
N=C(N)c1ccc(OCCCCCCOc2ccc(C(=N)N)cc2)cc1- InChIKey
OQLKNTOKMBVBKV-UHFFFAOYSA-N- Molecular formula
- C20H26N4O2
- Average molar mass
- 354.4 g/mol
- Monoisotopic mass
- 354.20557608
Overview
Hexamidine is a polyether that is the bis(4-guanidinophenyl) ether of hexane-1,6-diol. It has a role as an antimicrobial agent and an antiseptic drug. It is a member of guanidines, an aromatic ether and a polyether. It is functionally related to a hexane-1,6-diol.
Names & identifiers
- Preferred name
- Hexamidine
- IUPAC
- 4-[6-(4-carbamimidoylphenoxy)hexoxy]benzenecarboximidamide
- English name
- Hexamidine
- Molecular formula
- C20H26N4O2
- Molecular weight
- 354.45
Names & synonyms
Hexamidine3811-75-4HexamidinaHexamidinum4,4'-(1,6-Hexanediylbis(oxy))bis-benzenecarboximidamide3483C2H13HCHEBI:87184DTXSID60191524Benzenecarboximidamide, 4,4'-(1,6-hexanediylbis(oxy))bis-1,6-di(para-amidinophenoxy)hexane4-{[6-(4-carbamimidoylphenoxy)hexyl]oxy}benzene-1-carboximidamide4-((6-(4-carbamimidoylphenoxy)hexyl)oxy)benzene-1-carboximidamide
Show more names
Hexamidine【antipeptic】Hexcarbacholine bromide4-[6-(4-amidinophenoxy)hexoxy]benzamidine4,4'-(Hexamethylenedioxy)bis(benzamidine)4,4'-(Hexamethylenebisoxy)bis(benzamidine)4,4'-(1,6-Hexanediyl)bis(oxy)bisbenzamidine4,4'-[1,6-Hexanediylbis(oxy)]bisbenzamidine4,4'-[1,6-Hexanediylbis(oxy)]bis[benzamidine]Benzenecarboximidamide, 4,4'-[1,6-hexanediylbis(oxy)]bis-
1,6-di-(4-amidinophenoxy)hexaneRefChem:786246D08AC04DTXCID00114015R01AX07R02AA18S01AX08S03AA05
Properties
Computed structural properties
- XLogP
- 2.9
- Topological polar surface area
- 118 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 11
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 388
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Cosmetics
Cosmetic ingredients (Hexamidine) -> CIR (Cosmetic Ingredient Review)
Preservative
PesticidesBiocide
Physicochemical properties
- Boiling point
- 548.6 · 548.6±60.0 °C(Predicted)
- Density
- 1.19 · 1.19±0.1 g/cm3(Predicted)
- pka
- 12.8 · 12.80±0.50(Predicted)
- Cosmetics Ingredients Functions
- PRESERVATIVE
- Cosmetic Ingredient Review (CIR)
- Hexamidine (3811-75-4)
- InChI
- InChI=1S/C20H26N4O2/c21-19(22)15-5-9-17(10-6-15)25-13-3-1-2-4-14-26-18-11-7-16(8-12-18)20(23)24/h5-12H,1-4,13-14H2,(H3,21,22)(H3,23,24)
- InChIKey
- OQLKNTOKMBVBKV-UHFFFAOYSA-N
- SMILES
- C(OC1=CC=C(C(N)=N)C=C1)CCCCCOC1=CC=C(C(N)=N)C=C1
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302: Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Hazard information
Regulatory InformationChemical: Benzenecarboximidamide, 4,4'-[1,6-hexanediylbis(oxy)bis-
Other Safety InformationIMAP assessments - Hexamidine and its diisethionate salt: Human health tier II assessment
Hazard Classes and CategoriesAcute toxicity - category 4
Toxicology
Toxicity Summary
Hexamidine and Hexamidine Diisethionate are safe for the use in cosmetic products in the practices and concentrations of use as described in this safety assessment if used at concentrations less than or equal to 0.10%.
Safe for use in cosmetics, with qualifications
Chemistry & industry
Pharmacology
ATC Code
S01AX08
S - Sensory organs
R - Respiratory system
R - Respiratory system
D - Dermatologicals
S - Sensory organs
MeSH Pharmacological ClassificationSubstances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.
Uses & manufacturing
UsesCIR ingredient: Hexamidine
Use ClassificationCosmetics -> Preservative
Applications
DescriptionHexamidine (HEX) is a strong organic base and aromatic diamidine. Although hexamidine is primarily used as the diisethionate salt (HEX D), it was first synthesized as the dihydrochloride salt (HEX H) and patented for May & Baker Limited (U.K.) by Ewins et al. In the 1990s, the efficacy of HEX as an amoebicidal agent was demonstrated in several studies. In addition to biocidal activity, HEX, and other diamidines have demonstrated enzyme inhibition properties. Upregulation of the major cholesterol and fatty acid uptake pathways has also been demonstrated in a skin-equivalent tissue culture model following treatment with HEX[1].
Useshexamidine is generally used as a biocide and preservative. Some initial studies are indicating a potential to increase production of skin lipids, such as cholesterol, sphingolipids, and fatty acids. In turn this would help improve skin moisture content. Further evidence of this may be required.
Upstream & downstream products
Downstream products
Related reactions
2 records
Compound notes
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