Hexamidine
Grundinformationen
- CAS
3811-75-4- Standard-SMILES
N=C(N)c1ccc(OCCCCCCOc2ccc(C(=N)N)cc2)cc1- InChIKey
OQLKNTOKMBVBKV-UHFFFAOYSA-N- Summenformel
- C20H26N4O2
- Durchschnittliche Molmasse
- 354,4 g/mol
- Monoisotopische Masse
- 354,20557608
Überblick
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.
Namen und Bezeichner
- Bevorzugter Name
- Hexamidine
- IUPAC
- 4-[6-(4-carbamimidoylphenoxy)hexoxy]benzenecarboximidamide
- Englischer Name
- Hexamidine
- Summenformel
- C20H26N4O2
- Molmasse
- 354.45
Namen und Synonyme
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
Weitere Namen anzeigen
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
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 2,9
- Polarare Oberfläche (TPSA)
- 118 Ų
- H-Brücken-Donoren
- 4
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 11
- Schwere Atome
- 26
- Formalladung
- 0
- Komplexität
- 388
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
Cosmetics
Cosmetic ingredients (Hexamidine) -> CIR (Cosmetic Ingredient Review)
Preservative
PesticidesBiocide
Physikochemische Eigenschaften
- Siedepunkt
- 548.6 · 548.6±60.0 °C(Predicted)
- Dichte
- 1.19 · 1.19±0.1 g/cm3(Predicted)
- pka
- 12.8 · 12.80±0.50(Predicted)
- Kosmetik-Inhaltsstoffe Funktionen
- PRESERVATIVE
- 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
- LogP
- 3 · 3.000 (est)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
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)
Gefahrenhinweise
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
Toxikologische Informationen
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
Chemie und Industrie
Pharmakologische Informationen
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.
Verwendung und Herstellung
UsesCIR ingredient: Hexamidine
Use ClassificationCosmetics -> Preservative
Anwendungen
BeschreibungHexamidine (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].
Verwendenhexamidine 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.
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