Sulfaphenazole
(Synonyms: 磺胺苯吡唑) 目录号 : GC11638
Sulfaphenazole是一种磺胺类抗菌药物。它竞争性地抑制细菌二氢叶酸合酶，阻断细菌叶酸合成，从而抑制细菌生长和繁殖。
Cas No.:526-08-9
Sample solution is provided at 25 µL, 10mM.
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Sulfaphenazole is a sulfonamide antibacterial drug. It competitively inhibits bacterial dihydrofolate synthase, blocking bacterial folate synthesis and thereby inhibiting bacterial growth and reproduction [1]. Sulfaphenazole is a selective inhibitor of the human cytochrome P450 (CYP) 2C9 enzyme [2]. Sulfaphenazole is a cytoprotective agent that prevents light-induced photoreceptor cell death. Sulfaphenazole inhibits light-induced necrosis and apoptosis triggered by mitochondrial stress [3].
In yeast expressed human cytochromes P450 of the 1A, 3A, and 2C subfamilies, Sulfadilamide acts as a strong and competitive inhibitor of CYP 2C9 with the Ki value of 0.3±0.1μM. The Ki values of Sulfadilamide for CYP 2C8 and 2C18 were 63 and 29μM, respectively. Sulfaphenazole failed to inhibit CYP 1A1, 1A2, 3A4, and 2C19 [2]. Sulfaphenazole (10μM; 1h) causes the numbers of light-induced apoptotic and necrotic cells decreased by 33 and 44%, respectively[3].
In a model of Diabetic male mice (db/db strain), Sulfaphenazole(5.13mg/kg; po; 8 weeks) reduces oxidative stress (measured as plasma levels of 8-isoprostane), increases NO bioavailability (measured as NO2−), and restores endothelial function in db/db mice without affecting plasma glucose levels [4]. Sulfaphenazole (100µL; ip; 15d) exposure post-injury was found to improve tissue perfusion in mouse models of both thermal injury and I/R-induced pressure injury, leading to reduced overall severity, improved wound closure and increased scar tensile strength [5]. In a rat model of myocardial ischemia-reperfusion (I/R) injury, Sulfaphenazole (30mg/kg; iv) treatment restored cardiac function and reduced myocardial infarct size. Furthermore, Sulfaphenazole reduced superoxide anion levels and enhanced NO bioavailability in reperfused hearts [6]. In a rat model of acute myocardial infarction (MI), Sulfaphenazole (8.1mg/kg; ip; 3d) pretreatment of rats with ameliorated I=R-induced myocardial damage and improved cardiac contractile functions by decreasing superoxide production, peroxynitrite formation, and by enhancing NO bioavailability, myocardial tissue oxygenation, and iNOS expression [7].
References:
[1].Elmongy E I, Alanazi W S, Aldawsari A I, et al. Antimicrobial evaluation of sulfonamides after coupling with thienopyrimidine coplanar structure[J]. Pharmaceuticals, 2024, 17(2): 188.
[2].Rettie A E, Jones J P. Clinical and toxicological relevance of CYP2C9: drug-drug interactions and pharmacogenetics[J]. Annu. Rev. Pharmacol. Toxicol., 2005, 45(1): 477-494.
[3]. Bogaard J, Chang Q, Berdyshev E A, et al. Cytochrome P450 2C Inhibitors Protect Photoreceptors from Light Induced Cell Death[J]. Investigative Ophthalmology & Visual Science, 2014, 55(13): 4387-4387.
Sulfaphenazole是一种磺胺类抗菌药物。它竞争性地抑制细菌二氢叶酸合酶，阻断细菌叶酸合成，从而抑制细菌生长和繁殖[1]。Sulfaphenazole是人类细胞色素P450 (CYP) 2C9酶的选择性抑制剂[2]。Sulfaphenazole是一种细胞保护剂，可防止光诱导的感光细胞死亡。Sulfaphenazole可抑制光诱导的坏死和线粒体应激引发的细胞凋亡[3]。
在酵母表达的1A、3A和2C亚家族人类细胞色素P450中，Sulfaphenazole是CYP 2C9的强效竞争性抑制剂，Ki值为0.3±0.1μM。Sulfaphenazole对CYP 2C8和2C18的Ki值分别为63μM和29μM。Sulfaphenazole对CYP 1A1、1A2、3A4和2C19无抑制作用[2]。Sulfaphenazole（10μM；1h）可使光诱导的凋亡细胞和坏死细胞数量分别减少33%和44%[3]。
在糖尿病雄性小鼠（db/db 品系）模型中，Sulfaphenazole（5.13mg/kg；po；8 weeks）可降低氧化应激（以血浆 8-异前列腺素水平衡量）、提高 NO 生物利用度（以 NO2− 衡量）并恢复 db/db 小鼠的内皮功能，且不影响血浆葡萄糖水平 [4]。在小鼠热损伤和 I/R 诱发的压力损伤模型中，损伤后给予Sulfaphenazole（100µL；ip；15d）可改善组织灌注，从而降低整体损伤严重程度、改善伤口闭合并增加疤痕拉伸强度 [5]。在大鼠心肌缺血再灌注 (I/R) 损伤模型中，Sulfaphenazole（30mg/kg；iv）预治疗可恢复心脏功能并减少心肌梗死面积。此外，Sulfaphenazole还可降低再灌注心脏中的超氧阴离子水平并提高 NO 生物利用度 [6]。在急性心肌梗死（MI）大鼠模型中，Sulfaphenazole（8.1mg/kg；ip；3d）预处理大鼠可改善I/R诱导的心肌损伤，并通过减少超氧化物的产生、过氧亚硝酸盐的形成，以及通过增强NO的生物利用度、心肌组织氧合和iNOS的表达来改善心脏收缩功能[7]。
| Cell experiment [1]: | |
Cell lines | 661W cells |
Preparation Method | 661W cells were seeded onto 96 well plates and given 9-cis retinal overnight to sensitize them to light. Cells were then given serum free media with/without a compound of interest. The 661W cells were pretreated with 10μM Sulfaphenazole for 1 hour.Then cells were exposed to 11,000 lux of light to inflict cell death. Media fractions and lipid extracts were obtained following light exposure to perform lipid profiling using LC/MS. |
Reaction Conditions | 10 μM; 1h |
Applications | Sulfaphenazole (10 μM; 1h) causes the numbers of light-induced apoptotic and necrotic cells decreased by 33 and 44%, respectively. |
| Animal experiment [2]: | |
Animal models | Diabetic male mice (db/db strain) |
Preparation Method | Diabetic male mice (db/db strain) and their age-matched controls received daily intraperitoneal injections of either the CYP 2C inhibitor sulfaphenazole (5.13mg/kg) or saline (vehicle control) for 8 weeks. |
Dosage form | 5.13mg/kg; po; 8 weeks |
Applications | Sulfaphenazole reduces oxidative stress (measured as plasma levels of 8-isoprostane), increases NO bioavailability (measured as NO2−), and restores endothelial function in db/db mice without affecting plasma glucose levels. |
References: | |
| Cas No. | 526-08-9 | SDF | |
| 别名 | 磺胺苯吡唑 | ||
| 化学名 | 4-amino-N-(1-phenyl-1H-pyrazol-5-yl)-benzenesulfonamide | ||
| Canonical SMILES | NC1=CC=C(S(NC2=CC=NN2C3=CC=CC=C3)(=O)=O)C=C1 | ||
| 分子式 | C15H14N4O2S | 分子量 | 314.4 |
| 溶解度 | ≥ 13.15mg/mL in DMSO | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 3.1807 mL | 15.9033 mL | 31.8066 mL |
| 5 mM | 636.1 μL | 3.1807 mL | 6.3613 mL |
| 10 mM | 318.1 μL | 1.5903 mL | 3.1807 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Quality Control & SDS
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- Purity: >98.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet