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Sulfaphenazole

Alias: BRN-0308518; BRN0308518; BRN 0308518; Sulfaphenazole; Firmazolo; Inamil
Cat No.:V4047 Purity: ≥98%
Sulfaphenazole (RN-0308518; Firmazolo; Inamil;BRN 0308518), an antibiotic of the sulfonamide class, is a potent and specific inhibitor of CYP2C9 that can block atherogenic and pro-inflammatory effects of linoleic acid (increase in oxidative stress and activation of AP-1) mediated by CYP2C9.
Sulfaphenazole
Sulfaphenazole Chemical Structure CAS No.: 526-08-9
Product category: Bacterial
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Sulfaphenazole (RN-0308518; Firmazolo; Inamil; BRN 0308518), an antibiotic of the sulfonamide class, is a potent and specific inhibitor of CYP2C9 that can block atherogenic and pro-inflammatory effects of linoleic acid (increase in oxidative stress and activation of AP-1) mediated by CYP2C9. Treatment of intracerebral hemorrhage is often pointless, although considerable effort has been devoted to developing treatments for ischemic stroke. Sulfaphenazole (SPZ) has a different mechanism such as reactive oxygen species scavenging, in addition to the inhibition of superoxide production by cytochrome P450. Systemic SPZ treatment after intracerebral hemorrhage reduces striatal dysfunction, the elevation of lipid peroxidation, and brain edema in the rat. These results suggest that SPZ is a potentially effective therapeutic approach for intracerebral hemorrhage as the effect of SPZ was initiated for either 1 h or 3 d post-intracerebral hemorrhage.

Biological Activity I Assay Protocols (From Reference)
Targets
CYP2C9
ln Vitro
Sulfaphenazole (10 μM) reduces the number of light-induced necrotic and apoptotic cells by 44% and 33%, respectively, over the course of one hour[1].
ln Vivo
In diabetic mice, sulfaphenazole (5.13 mg/kg) administered intraperitoneally once a day for eight weeks restores endothelium-mediated relaxation[2].
Animal Protocol
Animal Model: Diabetic male mice (db/db strain)[2]
Dosage: 5.13 mg/kg
Administration: Intraperitoneal injections; daily; for 8 weeks
Result: In diabetic mice, sulfaphenazole (5.13 mg/kg) administered intraperitoneally once a day for eight weeks restores endothelium-mediated relaxation[2].
References

[1]. Cytochrome P450 2C epoxygenases mediate photochemical stress-induced death of photoreceptors. J Biol Chem. 2014 Mar 21;289(12):8337-52.

[2]. Sulfaphenazole treatment restores endothelium-dependent vasodilation in diabetic mice. Vascul Pharmacol. 2008 Jan;48(1):1-8.

[3]. Sulfaphenazole reduces thermal and pressure injury severity through rapid restoration of tissue perfusion. Sci Rep. 2022 Jul 23;12(1):12622.

[4]. Biol Pharm Bull.2012;35(10):1849-53.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C15H14N4O2S
Molecular Weight
314.36
Exact Mass
314.08
Elemental Analysis
C, 57.31; H, 4.49; N, 17.82; O, 10.18; S, 10.20
CAS #
526-08-9
Related CAS #
526-08-9
Appearance
Solid powder
SMILES
O=S(NC1=CC=NN1C2=CC=CC=C2)(C3=CC=C(N)C=C3)=O
InChi Key
QWCJHSGMANYXCW-UHFFFAOYSA-N
InChi Code
InChI=1S/C15H14N4O2S/c16-12-6-8-14(9-7-12)22(20,21)18-15-10-11-17-19(15)13-4-2-1-3-5-13/h1-11,18H,16H2
Chemical Name
4-amino-N-(1-phenyl-1H-pyrazol-5-yl)benzenesulfonamide
Synonyms
BRN-0308518; BRN0308518; BRN 0308518; Sulfaphenazole; Firmazolo; Inamil
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : 63~100 mg/mL ( 200.4~318.11 mM )
Ethanol : ~20 mg/mL
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (6.62 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (6.62 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (6.62 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


Solubility in Formulation 4: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.08 mg/mL (6.62 mM)

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.1811 mL 15.9053 mL 31.8107 mL
5 mM 0.6362 mL 3.1811 mL 6.3621 mL
10 mM 0.3181 mL 1.5905 mL 3.1811 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Biological Data
  • Ranking and enrichment analysis of cytoprotective hit compounds.[1].J Biol Chem. 2014 Mar 21;289(12):8337-52
  • Sulfaphenazole confers better cytoprotection than minocycline and l-sulforaphane.[1].J Biol Chem. 2014 Mar 21;289(12):8337-52
  • Expression of CYP2C is inducible by light and targeted knockdown of CYP2C55 rescues light-induced cell death.[1].J Biol Chem. 2014 Mar 21;289(12):8337-52
  • Stable expression of functional human CYP2C9-GFP fusion protein enhances cellular sensitivity to light.[1].J Biol Chem. 2014 Mar 21;289(12):8337-52
  • Sulfaphenazole inhibits light-induced necrosis and apoptosis. [1].J Biol Chem. 2014 Mar 21;289(12):8337-52
  • Sulfaphenazole inhibits light-induced calcium influx. [1].J Biol Chem. 2014 Mar 21;289(12):8337-52
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