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Sulfapyridine

Alias: A-499; A499; A 499
Cat No.:V15475 Purity: ≥98%
Sulfapyridine is the major metabolite of Sulfasalazine, a sulfonamide antibiotic.
Sulfapyridine
Sulfapyridine Chemical Structure CAS No.: 144-83-2
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5g
Other Sizes

Other Forms of Sulfapyridine:

  • N-Acetyl sulfapyridine-d4
  • Sulfapyridine D4
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
Sulfapyridine is the major metabolite of Sulfasalazine, a sulfonamide antibiotic. Sulfapyridine inhibits recombinant P. carinii dihydropterin synthase (DHPS) with IC50 of 0.18 μM. Sulfapyridine has antibacterial, anti~inflammatory and antirheumatic effects.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
In rheumatoid arthritis (RA) synoviocytes, sulfapyridine suppresses the synthesis of IL-8, chemokine (CXC motif) ligand 1 (CXCL1), and monocyte chemoattractant protein 1 (MCP-1)[1]. Sulfapyridine has a minimum inhibitory concentration (MIC) range of 3.1–25 μg/mL for Yersinia enterocolitica and 25–100 μg/mL for Salmonella. Salmonella jejuni/E. Sulfapyridine has a lower susceptibility to coli, with MIC values ranging from 200 to 800 μg/mL. Three of the five E. Coli and Shigella. Sulfapyridine at 1600 μg/mL did not affect the coli strains. For two E, 25 μg/mL inhibits. strains of Coli [2].
ln Vivo
In rats, compound 48/80 elicited a systemic allergic reaction that was greatly reduced by sulfapyridine (1 and 10 μg/kg; intraperitoneal injection) [4].
ADME/Pharmacokinetics
Absorption, Distribution and Excretion
Approximately 60-80% of the metabolism/metabolites are metabolized by the liver. Known metabolites of sulfapyridine include sulfapyridine N-acetyl. Biological Half-Life: 6-14 hours.
Toxicity/Toxicokinetics
Protein Binding
Approximately 50% is bound to plasma proteins.
References

[1]. Effects of salazosulfapyridine on the profile of cell surface proteins, revealed by biotinylation of cell surface proteins and 2-dimentional electrophoresis. Biochim Biophys Acta Proteins Proteom. 2019 Jan;1867(1):47-56.

[2]. In vitro susceptibility of diarrhoea producing gram negative enteric bacteria to sulfasalazine, 5-aminosalicylic acid, sulfapyridine and four quinolones. Brief report. APMIS. 1988 Jun;96(6):568-70.

[3]. Inhibition of recombinant Pneumocystis carinii dihydropteroate synthetase by sulfa drugs. Antimicrob Agents Chemother. 1995 Aug;39(8):1756-63.

[4]. Inhibitory effect of mast cell-mediated immediate-type allergic reactions by sulfapyridine. Immunopharmacol Immunotoxicol. 2000 May;22(2):253-66.

Additional Infomation
Sulfapyridine is an odorless or nearly odorless white or pale yellow crystalline powder with a slightly bitter taste. Its aqueous solution is neutral. (NTP, 1992)
Sulfapyridine is a sulfonamide compound consisting of a pyridine ring with a 4-aminobenzenesulfonamide group attached at the 2-position. It is used as an anti-infective agent, dermatological drug, xenobiotic, environmental pollutant, and drug allergen. It belongs to the pyridine, sulfonamide, substituted aniline, and sulfonamide antibiotic classes. Its function is related to sulfonamide compounds.
It has antibacterial activity but may be toxic; it was once used to treat certain skin diseases. It is now discontinued.
Sulfapyridine is a short-acting sulfonamide antibiotic, a byproduct of the nonsteroidal anti-inflammatory drug sulfasalazine. Its production and use were discontinued in 1990.
An antibacterial drug, possibly toxic, used to treat certain skin diseases.
See also: Sulfapyridine sodium (in salt form). Indications For the treatment of dermatitis herpetiformis, benign mucosal pemphigoid, and pyoderma gangrenosa. Mechanism of Action Sulfapyridine is a competitive inhibitor of bacterial dihydropteranoic acid synthase. Inhibition of this enzyme is crucial for these organisms to synthesize folic acid by processing the substrate para-aminobenzoic acid (PABA). The activity of dihydropteranoic acid synthase is essential for folic acid synthesis, which is necessary for the synthesis of nucleic acids such as DNA or RNA by cells. Therefore, if DNA molecules cannot be synthesized, cells cannot divide. Pharmacodynamics Sulfapyridine is a sulfonamide antibiotic. Sulfonamides are synthetic antibacterial antibiotics with broad-spectrum antibacterial activity against most Gram-positive bacteria and many Gram-negative bacteria. However, many strains of the same bacterial species may develop resistance. Sulfonamides inhibit bacterial growth by competitively inhibiting para-aminobenzoic acid in the folic acid metabolic cycle. Bacteria exhibit similar sensitivity to various sulfonamides; resistance to one sulfonamide implies resistance to all sulfonamides. Most sulfonamides are well absorbed orally. However, parenteral administration is challenging due to the strong alkalinity and tissue irritation of soluble sulfonamide salts. Sulfonamides are widely distributed in all tissues. High concentrations can be reached in pleural fluid, peritoneal fluid, synovial fluid, and ocular fluid. Although these drugs are no longer used to treat meningitis, high concentrations remain in the cerebrospinal fluid of patients with meningeal infections. Pus can inhibit their antibacterial activity.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C11H11N3O2S
Molecular Weight
249.288
Exact Mass
249.057
CAS #
144-83-2
Related CAS #
Sulfapyridine-d4;1189863-86-2
PubChem CID
5336
Appearance
White to off-white solid powder
Density
1.4±0.1 g/cm3
Boiling Point
473.5±51.0 °C at 760 mmHg
Melting Point
191-193°C
Flash Point
240.2±30.4 °C
Vapour Pressure
0.0±1.2 mmHg at 25°C
Index of Refraction
1.674
LogP
0.03
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
3
Heavy Atom Count
17
Complexity
331
Defined Atom Stereocenter Count
0
InChi Key
GECHUMIMRBOMGK-UHFFFAOYSA-N
InChi Code
InChI=1S/C11H11N3O2S/c12-9-4-6-10(7-5-9)17(15,16)14-11-3-1-2-8-13-11/h1-8H,12H2,(H,13,14)
Chemical Name
4-amino-N-pyridin-2-ylbenzenesulfonamide
Synonyms
A-499; A499; A 499
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 : ~60 mg/mL (~240.68 mM)
H2O : < 0.1 mg/mL
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 3 mg/mL (12.03 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 30.0 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: ≥ 3 mg/mL (12.03 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 30.0 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: ≥ 3 mg/mL (12.03 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 30.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.0114 mL 20.0570 mL 40.1139 mL
5 mM 0.8023 mL 4.0114 mL 8.0228 mL
10 mM 0.4011 mL 2.0057 mL 4.0114 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:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
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)
  • Click the “Calculate” button
  • 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:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • 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.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
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.

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