4-{[6-(4-carbamimidoylphenoxy)hexyl]oxy}benzene-1-carboximidamide

• ChemBase ID: 3454
• Molecular Formular: C20H26N4O2
• Molecular Mass: 354.44604
• Monoisotopic Mass: 354.20557609
• SMILES: c1(ccc(cc1)OCCCCCCOc1ccc(cc1)C(=N)N)C(=N)N
• Canonical SMILES: NC(=N)c1ccc(cc1)OCCCCCCOc1ccc(cc1)C(=N)N
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[6-(4-carbamimidoylphenoxy)hexyl]oxy}benzene-1-carboximidamide
• IUPAC Traditional name: hexamidine
• Synonyms: 4,4'[1,6-Hexanediylbis(Oxy)]Bisbenzenecarboximidamide; 4,4'-[1,6-Hexanediylbis(oxy)]bisbenzenecarboximidamide Hydrochloride; 1,6-Bis(4-amidinophenoxy)hexane; 4,4-Diamidino-1,6-diphenoxyhexane Hydrochloride; 4,4'-(Hexamethylenedioxy)dibenzamidine Hydrochloride; Desmodine Hydrochloride; Hexamidine Dihydrochloride; 4-[6-(4-carbamimidoylphenoxy)hexoxy]benzamidine; Hexamidine

Database IDs

• CAS Number: 50357-46-5; 3811-75-4
• PubChem SID: 46505102; 160966893
• PubChem CID: 65130
• ATC CODE: R01AX07; D08AC04; S03AA05; S01AX08; R02AA18
• CHEMBL: 25105
• Chemspider ID: 58639
• DrugBank ID: DB03808
• Wikipedia Title: Hexamidine

CALCULATED PROPERTIES

JChem

• LogD (pH = 7.4): -2.0555024
• Log P: 2.767021
• Molar Refractivity: 125.1304 cm^3
• Polarizability: 39.707184 Å^3
• Polar Surface Area: 118.2 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -2.0637906

ALOGPS 2.1

• Log P: 1.77
• LOG S: -4.4
• Solubility (Water): 1.42e-02 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 250-254°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

DrugBank - DB03808

Drug information: experimental

Toronto Research Chemicals - H294205

An amidine compound use in the treatment of amyloid-related diseases; also use as preservative in cosmetics. Antiseptic.

REFERENCES

• Taylor, P., et al.: J. Pharmaceut. Sci., 72, 1477 (1983)
• Granel, F., et al.: Clin. Infect. Diseases, 23, 839 (1983)
• Bailly, C., et al.: Biochem. J., 323, 23 (1983)
• Enyedy, I., et al.: J. Med. Chem., 44, 1349 (1983)