| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| 50mg |
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| Targets |
The primary target of Sulfamethoxazole-NO is tissue proteins, to which it binds as a hapten. It is the major immunogen responsible for sulfonamide hypersensitivity reactions (allergy) [15L10-L12]. The compound modifies tissue proteins by forming covalent adducts (haptenation), which are recognized by the immune system as foreign antigens, leading to an allergic response. It produces modest ascorbic acid depletion and hemoglobin adduct formation, contributing to its immunogenicity and cytotoxicity [15L14-L17].
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| ln Vitro |
Sulfamethoxazole-NO is cytotoxic in cell-based systems, though specific IC50 values are not provided. It is immunogenic in rodents, meaning it can induce an immune response when administered to animals [15L9-L12]. The compound also produces modest ascorbic acid depletion and hemoglobin adduct formation [15L14-L17]. The immunogenicity is attributed to its ability to haptenate (covalently modify) tissue proteins, creating neoantigens that trigger an allergic response.
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| ln Vivo |
In rodents, Sulfamethoxazole-NO is immunogenic, meaning it can induce an allergic-type immune response when administered [15L9-L12]. The compound haptenates tissue proteins, leading to the formation of antibody responses against the modified proteins [15L14-L17]. This immunogenicity is relevant to understanding the mechanism of sulfonamide drug hypersensitivity reactions. Specific in vivo efficacy data is not applicable as the compound is not a therapeutic agent but rather a toxic/metabolic product associated with adverse drug reactions.
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| Enzyme Assay |
Not applicable. Sulfamethoxazole-NO is a metabolite and immunogen, not typically used in cell-free enzyme binding assays. Its characterization involves standard analytical methods including HPLC and mass spectrometry for identity and purity confirmation. The compound has a purity of 98% and is stored at 4degC, protected from light [15L7]. To study its protein haptenation, a model protein (e.g., human serum albumin, HSA) is incubated with Sulfamethoxazole-NO in PBS at 37degC for 4-24 hours, and adduct formation is analyzed by MALDI-TOF mass spectrometry or by Western blot using an anti-sulfamethoxazole antibody.
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| Cell Assay |
The immunogenicity and cytotoxicity of Sulfamethoxazole-NO can be assessed in dendritic cell activation assays. Procedure: Human peripheral blood mononuclear cells (PBMCs) are isolated from healthy donors by Ficoll density gradient centrifugation. Monocytes are enriched by positive selection using CD14 magnetic beads and cultured with GM-CSF (50 ng/mL) and IL-4 (30 ng/mL) for 7 days to generate immature dendritic cells (iDCs). iDCs are treated with varying concentrations of Sulfamethoxazole-NO (1-100 uM) for 24-48 hours. DC activation is assessed by measuring the expression of CD80, CD83, CD86, and HLA-DR by flow cytometry. Cytokine secretion (IL-6, IL-12, TNF-alpha, IL-10) in the culture supernatant is measured by ELISA. For T cell proliferation assays, autologous T cells are labeled with CFSE and co-cultured with drug-treated DCs for 5-7 days, and T cell proliferation is measured by CFSE dilution by flow cytometry.
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| Animal Protocol |
The immunogenicity of Sulfamethoxazole-NO can be evaluated in a mouse model of drug hypersensitivity. Procedure: Female BALB/c mice (6-8 weeks, n=10 per group) are immunized with Sulfamethoxazole-NO (100-200 ug) emulsified in complete Freund's adjuvant (CFA) on day 0, followed by a booster immunization with the same dose in incomplete Freund's adjuvant (IFA) on day 14. On day 21, blood is collected by retro-orbital puncture, and serum is analyzed for anti-SMX-NO antibodies by ELISA using SMX-NO-conjugated BSA as the coating antigen. For a challenge study, mice are previously sensitized with SMX-NO in CFA, then challenged intraperitoneally with SMX-NO (50-100 ug) on day 28. Anaphylactic responses (body temperature drop, clinical signs, mast cell degranulation) are monitored. Alternatively, the compound can be administered to mice without adjuvant to study non-immunogenic sensitization.
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| ADME/Pharmacokinetics |
Sulfamethoxazole-NO is a nitroso metabolite of sulfamethoxazole and is not a therapeutic agent; therefore, pharmacokinetic data is not applicable. As a small molecule with a molecular weight of 283.26 g/mol, it is expected to be absorbed and distributed if administered. It is stored at 4degC protected from light due to potential photosensitivity [15L7].
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| Toxicity/Toxicokinetics |
Specific toxicology data for Sulfamethoxazole-NO is not fully detailed in the search results. The compound is cytotoxic and immunogenic, meaning it can cause cell damage and induce immune responses [15L9-L12]. It produces modest ascorbic acid depletion and hemoglobin adduct formation [15L14-L17]. In the context of sulfonamide allergy, the compound is considered a major immunogen that causes hypersensitivity reactions including rash, fever, and organ dysfunction. The compound is for research use only and is not intended for human therapeutic use.
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| References | |
| Additional Infomation |
Sulfamethoxazole-NO (SMX-NO) is the major immunogen responsible for sulfonamide hypersensitivity reactions (sulfa allergies) [15L9-L12]. It is a nitroso metabolite of the antibiotic sulfamethoxazole, formed via metabolic activation of the parent drug through hydroxylamine intermediates. The compound haptenates (covalently modifies) tissue proteins, creating neoantigens that are recognized by the immune system as foreign, leading to allergic responses. The compound produces modest ascorbic acid depletion and hemoglobin adduct formation and is immunogenic in rodents [15L14-L17]. SMX-NO is used as a research tool to study the mechanisms of drug-induced allergic reactions and to develop predictive safety assays. This product is for research use only and is not intended for human therapeutic use.
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| Molecular Formula |
C10H9N3O5S
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| Molecular Weight |
283.26
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| Exact Mass |
283.026
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| CAS # |
29699-89-6
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| PubChem CID |
717516
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| Appearance |
Solid Powder
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| Density |
1.55g/cm3
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| Boiling Point |
497.6ºC at 760 mmHg
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| Flash Point |
254.8ºC
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| Vapour Pressure |
4.87E-10mmHg at 25°C
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| Index of Refraction |
1.628
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| LogP |
3.369
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
19
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| Complexity |
421
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC1=CC(=NO1)NS(=O)(=O)C2=CC=C(C=C2)[N+](=O)[O-]
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| InChi Key |
XHJLDAHBWWMCRZ-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C10H9N3O5S/c1-7-6-10(11-18-7)12-19(16,17)9-4-2-8(3-5-9)13(14)15/h2-6H,1H3,(H,11,12)
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| Chemical Name |
N-(5-methyl-1,2-oxazol-3-yl)-4-nitrobenzenesulfonamide
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| Synonyms |
SMX-NO
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ≥ 100 mg/mL (~353.03 mM)
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.5303 mL | 17.6516 mL | 35.3033 mL | |
| 5 mM | 0.7061 mL | 3.5303 mL | 7.0607 mL | |
| 10 mM | 0.3530 mL | 1.7652 mL | 3.5303 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.
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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