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Stilbamidine (Ba 2652) Sale

(Synonyms: 司替巴脒; Ba 2652; Stilbamidin) 目录号 : GC32268

Stilbamidine (Ba 2652) 是一种衍生自芪的二脒化合物,主要以其结晶羟乙基磺酸盐的形式用于治疗各种真菌感染。

Stilbamidine (Ba 2652) Chemical Structure

Cas No.:122-06-5

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产品描述

Stilbamidine is a diamidine compound derived from Stilbene and used chiefly in the form of its crystalline isethionate salt in treating various fungal infections.

The high-affinity pentamidine transporter (HAPT1) is inhibited by Propamidine but displays only low affinity to Stilbamidine. adenosine-sensitive pentamidine transporter (ASPT1), in contrast, is strongly inhibited by Stilbamidine, and Propamidine. [3H]pentamidine uptake is determined in the presence of various concentrations of adenosine (IC50=1.2 μM) or melarsen oxide (IC50=0.7 μM), as well as in the presence of 250 μM adenosine and increasing concentrations of hypoxanthine, Propamidine (IC50=6.1 μM) and Stilbamidine (IC50=110 μM)[1]. The two diamidine compounds, Stilbamidine and Pentamidine are used to treat in multiple myeloma, a disease in which increase of the globulin content of the serum is of frequent occurrence[2].

[1]. De Koning HP. Uptake of pentamidine in Trypanosoma brucei brucei is mediated by three distinct transporters: implications for cross-resistance with arsenicals. Mol Pharmacol. 2001 Mar;59(3):586-92. [2]. BREWER AE.et al. Multiple myeloma treated with stilbamidine and pentamidine. Br Med J. 1948 Dec 4;2(4587):978-82.

Chemical Properties

Cas No. 122-06-5 SDF
别名 司替巴脒; Ba 2652; Stilbamidin
Canonical SMILES N=C(C1=CC=C(/C=C/C2=CC=C(C(N)=N)C=C2)C=C1)N
分子式 C16H16N4 分子量 264.33
溶解度 Soluble in DMSO 储存条件 Store at -20°C
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1 mg 5 mg 10 mg
1 mM 3.7831 mL 18.9157 mL 37.8315 mL
5 mM 0.7566 mL 3.7831 mL 7.5663 mL
10 mM 0.3783 mL 1.8916 mL 3.7831 mL
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Research Update

A theoretical study of the nonintercalative binding of berenil and Stilbamidine to double-stranded (dA-dT)n oligomers

Mol Pharmacol 1984 May;25(3):452-8.PMID:6727867doi

The nonintercalative binding of two diarylamidines , berenil and Stilbamidine , to the minor groove of double-stranded (dA-dT)n oligomers in the B-DNA conformation was investigated by performing theoretical computations of their intermolecular interaction energies with the groove. The method consists of an additive procedure developed previously in this laboratory using empirical formulae based on ab initio computations. The objective was to assess the extent to which the particular structure of each diarylamidine bears on its binding mode and affinity to the minor groove. The results show that the intrinsically preferred configurations of the two compounds are markedly different. Owing to its slightly curved shape, berenil interacts with the groove predominantly through its concave side, the binding occurring principally with sites (O2, O1) belonging to two thymidines on the opposite strands. The binding of Stilbamidine involves a more limited number of hydrogen-bonding interactions, although an appreciably large number of interatomic distances between its hydrogens and sites on the groove (O2, N3, O1) falls in the range 2.7-3.1 A. Each side of Stilbamidine with respect to its long axis faces a distinct strand of DNA. The importance of the electrostatic contribution of the binding energy of the two diarylamidines is underlined. Preferential binding of berenil rather than of Stilbamidine occurs only at the level of a complete helical turn of phosphates in (dA-dT)n. The energy difference increases significantly upon further buildup of phosphates. These results can be interpreted in terms of the molecular electrostatic potential in the grooves.

Tracer studies of the distribution and trypanocidal action of Stilbamidine in rats

Br J Pharmacol Chemother 1959 Mar;14(1):137-41.PMID:13651591DOI:10.1111/j.1476-5381.1959.tb00940.x.

[(14)C]Stilbamidine was used to study the distribution of the drug in the organs and tissues of rats following intravenous injection. The prophylactic action of Stilbamidine was shown to depend upon the unchanged drug retained in tissues, especially the liver. Only the parent drug was extracted from trypanosomes when an infection was treated during the acute phase, as shown by the use of the fluorescent properties of Stilbamidine in conjunction with scanning and chromatographic techniques. The action of Stilbamidine on trypanosomes is therefore a direct one. A method for the synthesis of [(14)C]Stilbamidine in much improved yield is also described.