(4Z)-4-{2-[4-(diaminomethylidene)cyclohexa-2,5-dien-1-ylidene]ethylidene}-3-oxocyclohexa-1,5-diene-1-carboximidamide; bis(2-hydroxyethane-1-sulfonic acid)

• ChemBase ID: 912
• Molecular Formular: C20H28N4O9S2
• Molecular Mass: 532.58772
• Monoisotopic Mass: 532.1297705
• SMILES: S(=O)(=O)(O)CCO.S(=O)(=O)(O)CCO.O=C1/C(=C\C=c/2\ccc(=C(N)N)cc2)/C=CC(=C1)C(=N)N
• Canonical SMILES: NC(=N)C1=CC(=O)/C(=C\C=c\2/ccc(=C(N)N)cc2)/C=C1.OCCS(=O)(=O)O.OCCS(=O)(=O)O
• InChI: InChI=1S/C16H16N4O.2C2H6O4S/c17-15(18)12-5-2-10(3-6-12)1-4-11-7-8-13(16(19)20)9-14(11)21;2*3-1-2-7(4,5)6/h1-9H,17-18H2,(H3,19,20);2*3H,1-2H2,(H,4,5,6)/b11-4-
• InChIKey: VIDDZUWWPMDEHU-LTTFOTGMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4Z)-4-{2-[4-(diaminomethylidene)cyclohexa-2,5-dien-1-ylidene]ethylidene}-3-oxocyclohexa-1,5-diene-1-carboximidamide; bis(2-hydroxyethane-1-sulfonic acid)
• IUPAC Traditional name: (4Z)-4-{2-[4-(diaminomethylidene)cyclohexa-2,5-dien-1-ylidene]ethylidene}-3-oxocyclohexa-1,5-diene-1-carboximidamide diisethionate
• Synonyms: HSB; Hydroxystilbamidine Isethionate

Database IDs

• CAS Number: 533-22-2
• PubChem SID: 160964375; 46508302
• PubChem CID: 16051924

CALCULATED PROPERTIES

• Polarizability: 31.261623 Å^3
• Polar Surface Area: 118.98 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -2.7721922
• LogD (pH = 7.4): -2.468123
• Log P: -0.07062754
• Molar Refractivity: 110.6561 cm^3

PROPERTIES

Physical Property

• Hydrophobicity(logP): 1.679

DETAILS

DrugBank - DB01040

• Drug Groups: approved
• Description: Hydroxystilbamidine Isethionate is used in the therapy of some patients with nonprogressive blastomycosis of the skin, and pulmonary or systemic blastomycosis in children, with fewer side effects than amphotericin B. Hydroxystilbamidine Isethionate is also used in pathology for diagnostic purposes.
• Indication: Used in the treatment of nonprogressive blastomycosis of the skin and other mycoses.
• Pharmacology: Hydroxystilbamidine isethionate is a member of the diamidines, a large family of biochemially and pharmacologically interesting compounds. It has a rather unusual combination of properties, exhibiting antitrypanosomal, antimaliarial, antifungal and carcinostatic activities. It also appears to act as an immunosuppressant. This drug may be used in the treatment of blastomycosis, a disease cased by the dimorphic fungus or mold called Blastomyces dermatitids. Blastomycosis is a pulmonary infection that can lead to fever, cough and (rarely) symptoms similar to tuberculosis. Hydroxystilbamidine has largely been replaced with amphotericin B.
• Affected Organisms: Yeast, Molds, Trypanosomes
• References: [Link] ; Murgatroyd LB: 2-hydroxystilbamidine isethionate: a new fluorochrome for use in general pathology. II. The selective demonstration of fungi. Diagn Histopathol. 1982 Jul-Sep;5(3):219-22. [Pubmed] ; Folds JD, Orlando G, Spitznagel JK: Immunosuppression by hydroxystilbamidine isethionate, a lysosome-stabilizing, anti-proteolytic, antifungal drug. Infect Immun. 1975 Mar;11(3):441-4. [Pubmed]

REFERENCES

• Link
• Murgatroyd LB: 2-hydroxystilbamidine isethionate: a new fluorochrome for use in general pathology. II. The selective demonstration of fungi. Diagn Histopathol. 1982 Jul-Sep;5(3):219-22. Pubmed
• Folds JD, Orlando G, Spitznagel JK: Immunosuppression by hydroxystilbamidine isethionate, a lysosome-stabilizing, anti-proteolytic, antifungal drug. Infect Immun. 1975 Mar;11(3):441-4. Pubmed