(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编号: 912
• 分子式: C20H28N4O9S2
• 平均质量: 532.58772
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (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传统名: (4Z)-4-{2-[4-(diaminomethylidene)cyclohexa-2,5-dien-1-ylidene]ethylidene}-3-oxocyclohexa-1,5-diene-1-carboximidamide diisethionate
• 别名: HSB; Hydroxystilbamidine Isethionate

登记号

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

理论计算性质

• 极化性: 31.261623 Å^3
• 极化表面积: 118.98 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: false
• 质子受体: 5
• 质子供体: 4
• LogD (pH = 5.5): -2.7721922
• LogD (pH = 7.4): -2.468123
• Log P: -0.07062754
• 摩尔折射率: 110.6561 cm^3

分子性质

理化性质

• 疏水性(logP): 1.679

详细说明

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]

参考文献

• 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