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| Other Sizes |
Purity: ≥98%
| Targets |
Sulfameter targets bacterial dihydropteroate synthase (DHPS). It is designed to competitively inhibit this enzyme, thereby interfering with the bacterial folate synthesis pathway. By blocking DHPS, Sulfameter prevents the production of dihydrofolic acid, a precursor essential for bacterial nucleic acid synthesis and growth. This inhibition is bacteriostatic rather than bactericidal, meaning it stops bacterial proliferation but does not directly kill the bacteria. Its primary target is the bacterial folate synthesis pathway, which is a well-established mechanism for sulfonamide antibiotics.
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| ln Vitro |
Sulfameter(Bayrena) is a long-acting sulfonamide antibacterial. It is used as a leprostatic agent in the treatment of urinary tract infections. Six physically healthy patients each were given 2 g of sulfameter simultaneously with a high lipid, high protein and high carbohydrate test meal. This experiment was designed as a threefold crossover study, and there was a randomized assignment of patients to the different conditions. The results show that sulfameter is significantly better absorbed when administered with a high lipid meal than when given with a high protein or high carbohydrate meal, demonstrated by the areas under the serum concentration curves (AUC), by the peak serum concentration and by the cumulative renal excretion.
Sulfameter demonstrates a range of bioactivities in vitro with notable potencies across various assays. It is a potent inducer of genomic imprint erasure (3162.3 nM) and DNA re-replication in MCF 10a breast cells (20.6 nM). It exhibits inhibitory effects against AmpC Beta-Lactamase (354.8 nM), Hepatitis C Virus (35481.3 nM), Plasmodium falciparum proliferation (0.9 nM), and Ebola virus entry (AC50 of 8912.5 nM). It also impacts sodium fluorescein uptake in OATP1B3 (112.86%) and OATP1B1 (233.46%) transfected CHO cells at 10 µM. Against SARS-CoV-2, it shows limited efficacy, inhibiting the 3CL-Pro protease by 24.24% at 20 µM. |
| ln Vivo |
In vivo, Sulfameter has been studied in human subjects for its pharmacokinetic properties. Six physically healthy patients each were given 2 g of Sulfameter simultaneously with a high lipid, high protein, and high carbohydrate test meal to assess its absorption and distribution. As a long-acting sulfonamide, it is designed for sustained antibacterial activity in the body. It is used in research models for urinary tract infections and leprosy, indicating its in vivo efficacy against these conditions. Its long-acting nature allows for less frequent dosing compared to shorter-acting sulfonamides.
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| Enzyme Assay |
Non-cellular enzyme/receptor binding assays for Sulfameter typically involve measuring its inhibitory activity against dihydropteroate synthase (DHPS). These assays use purified DHPS enzyme and a radiolabeled or spectrophotometric substrate to quantify the rate of enzymatic reaction in the presence of varying concentrations of Sulfameter. The compound's ability to competitively inhibit DHPS is assessed by determining the half-maximal inhibitory concentration (IC50) or inhibition constant (Ki). Such assays are essential for confirming the compound's mechanism of action as a sulfonamide antibiotic and for characterizing its potency against the target enzyme.
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| Cell Assay |
In vitro cell-based assays for Sulfameter are conducted using bacterial cultures to assess its antibacterial activity. Standard antimicrobial susceptibility testing, such as broth microdilution or agar dilution methods, is performed to determine the minimum inhibitory concentration (MIC) against various bacterial strains. These assays involve culturing bacteria in the presence of increasing concentrations of Sulfameter and measuring the optical density to determine the lowest concentration that inhibits visible bacterial growth. Additionally, cell-based assays can be performed using mammalian cell lines to evaluate the compound's cytotoxicity and effects on host cells.
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| Animal Protocol |
In vivo animal studies for Sulfameter are typically conducted in animal models of bacterial infection to evaluate its efficacy and pharmacokinetics. Rodent models of urinary tract infections or other susceptible bacterial infections are commonly used. Animals are administered Sulfameter orally or parenterally at various doses, and the infection progression is monitored by measuring bacterial load in tissues or blood. Blood samples are collected at different time points to determine the pharmacokinetic profile, including absorption, distribution, and elimination of the compound. These studies are crucial for validating the compound's in vivo efficacy and for establishing appropriate dosing regimens.
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| ADME/Pharmacokinetics |
Sulfameter is administered orally and has been studied in human pharmacokinetic trials. Six healthy patients each received 2 g of Sulfameter simultaneously with meals to assess its absorption. It exhibits a log P value of 0.46, indicating moderate lipophilicity, which influences its absorption and distribution. The compound demonstrates moderate liver toxicity with choleostatic liver toxicity and a low percentage of acute liver toxicity noted in clinical trials, but without significant cytolytic, chronic, or severe liver toxicity indications. Its long-acting nature is attributed to its slow elimination from the body.
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| Toxicity/Toxicokinetics |
Sulfameter shows moderate liver toxicity with choleostatic liver toxicity and a low percentage of acute liver toxicity noted in clinical trials. However, it does not exhibit significant cytolytic, chronic, or severe liver toxicity indications. The compound is considered safe for use as an antibacterial agent but should be used with caution in patients with pre-existing liver conditions. As with other sulfonamides, potential side effects include allergic reactions, gastrointestinal disturbances, and hematological effects. Its safety profile has been established through clinical use and research studies.
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| References |
Int J Clin Pharmacol Biopharm.1979 Jun;17(6):260-3;Clin Pharmacol Ther.1969 Jul-Aug;10(4):591-4.
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| Additional Infomation |
Sulfamethoxydiazepoxide is a sulfonamide drug composed of a pyrimidine ring with a methoxy substituent at the 5-position and a 4-aminobenzenesulfonamide group at the 2-position. It has anti-infective, renal protective, and leprosy-treating effects. It belongs to the pyrimidine, sulfonamide, and sulfonamide antibiotic classes. Its function is related to that of sulfonamide drugs. Long-acting sulfonamides are used to treat leprosy, urinary tract infections, and respiratory infections. Sulfamethoxydiazepoxide is a long-acting sulfonamide antibacterial drug used to treat urinary tract infections and leprosy. Long-acting sulfonamides are used to treat leprosy, urinary tract infections, and respiratory infections.
Sulfameter (Bayrena) is a long-acting sulfonamide antibacterial agent used primarily for the treatment of urinary tract infections and leprosy. Its mechanism of action involves competitive inhibition of dihydropteroate synthase (DHPS), a key enzyme in the bacterial folate synthesis pathway. The compound demonstrates a range of bioactivities, including anti-malarial and anti-viral properties in vitro. It is a research compound with a well-characterized pharmacological profile. Sulfameter is not approved for clinical use in all regions and is primarily utilized in research settings for antimicrobial studies. |
| Molecular Formula |
C11H12N4O3S
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| Molecular Weight |
280.3
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| Exact Mass |
280.063
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| CAS # |
651-06-9
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| Related CAS # |
Sulfameter-d4;1189483-96-2;Sulfameter-13C6
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| PubChem CID |
5326
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| Appearance |
White to off-white solid powder
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
539.4±56.0 °C at 760 mmHg
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| Melting Point |
214-216°C
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| Flash Point |
280.0±31.8 °C
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| Vapour Pressure |
0.0±1.4 mmHg at 25°C
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| Index of Refraction |
1.647
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| LogP |
0.42
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
19
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| Complexity |
368
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| Defined Atom Stereocenter Count |
0
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| SMILES |
S(C1C([H])=C([H])C(=C([H])C=1[H])N([H])[H])(N([H])C1=NC([H])=C(C([H])=N1)OC([H])([H])[H])(=O)=O
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| InChi Key |
GPTONYMQFTZPKC-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C11H12N4O3S/c1-18-9-6-13-11(14-7-9)15-19(16,17)10-4-2-8(12)3-5-10/h2-7H,12H2,1H3,(H,13,14,15)
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| Chemical Name |
4-amino-N-(5-methoxypyrimidin-2-yl)benzenesulfonamide
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| Synonyms |
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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 |
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| 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) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.92 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 25.0 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: ≥ 2.5 mg/mL (8.92 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 25.0 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (8.92 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.5676 mL | 17.8380 mL | 35.6761 mL | |
| 5 mM | 0.7135 mL | 3.5676 mL | 7.1352 mL | |
| 10 mM | 0.3568 mL | 1.7838 mL | 3.5676 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.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT05728229 | Completed | Drug: Supplement with SiderAl® Med | Fatigue Stroke |
Fondazione Policlinico Universitario Agostino Gemelli IRCCS |
November 7, 2022 | Not Applicable |
| NCT00933010 | Completed | Metabolic Syndrome | AstraZeneca | October 2009 | ||
| NCT06182189 | Recruiting | Other: Observation of patients with a benign prostatic hyperplasia condition |
Benign Prostatic Hyperplasia | IRCCS San Raffaele | December 1, 2014 | |
| NCT05431283 | Recruiting | Drug: Tofacitinib | Ulcerative Colitis Spondyloarthropathy |
Italian Group for the study of Inflammatory Bowel Disease (IG-IBD) |
April 25, 2022 |
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