2-hydroxyethane-1-sulfonic acid; 4-{[5-(4-carbamimidoylphenoxy)pentyl]oxy}benzene-1-carboximidamide

• ChemBase ID: 176314
• Molecular Formular: C21H30N4O6S
• Molecular Mass: 466.5511
• Monoisotopic Mass: 466.1886057
• SMILES: c1c(ccc(c1)OCCCCCOc1ccc(cc1)C(=N)N)C(=N)N.OCCS(=O)(=O)O
• Canonical SMILES: NC(=N)c1ccc(cc1)OCCCCCOc1ccc(cc1)C(=N)N.OCCS(=O)(=O)O
• InChI: InChI=1S/C19H24N4O2.C2H6O4S/c20-18(21)14-4-8-16(9-5-14)24-12-2-1-3-13-25-17-10-6-15(7-11-17)19(22)23;3-1-2-7(4,5)6/h4-11H,1-3,12-13H2,(H3,20,21)(H3,22,23);3H,1-2H2,(H,4,5,6)
• InChIKey: NYRHYBFMOOPIRI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxyethane-1-sulfonic acid; 4-{[5-(4-carbamimidoylphenoxy)pentyl]oxy}benzene-1-carboximidamide
• IUPAC Traditional name: pentamidine sodium isethionate
• Synonyms: 4,4'-(Pentamethylenedioxy)di-benzamidine Diisethionate; 4,4'-[1,5-Pentanediylbis(oxy)]bis-benzenecarboximidamide Bis(2-hydroxyethanesulfonate); 1,5-Bis(4-amidinophenoxy)pentane Diisethionate; 4,4'-Diamidinodiphenoxypentane di(β-hydroxyethanesulfonate); Aeropent; Banambax; Diamidine; Lomidin; Lomidine; M & B 800; NebuPent; Pentacarinat; Pentam; Pentam 300; Pentamidine Isethionate

Database IDs

• PubChem SID: 164232224
• PubChem CID: 359323

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -2.5083592
• LogD (pH = 7.4): -2.500071
• Log P: 2.322452
• Molar Refractivity: 120.5294 cm^3
• Polarizability: 37.864697 Å^3
• Polar Surface Area: 118.2 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P272501

Has been widely used as a drug to treat protozoal diseases, such as malaria, amoebic dysentery and trypanosomiasis. It has also been shown to be effective for both prophylaxis of pneumocystic carinii pneumonia (PCC).

REFERENCES

• Goa, K.L., et al.: Drugs, 33, 242 (1987)
• Debs, R.J., et al.: Antimicrob. Agents Chemother., 31, 37 (1987)
• Walzer, P.D., et al.: Antimicrob. Agents Chemother., 32, 896 (1987)
• Hesk, D., et al.: J. Lab. Comp. Radiopharm., 28, 11, 1309 (1990)