Sulfamethoxazol
Übersicht
Beschreibung
Sulfamethoxazole is a synthetic antibiotic belonging to the sulfonamide class. It is commonly used in combination with trimethoprim to treat a variety of bacterial infections, including those of the urinary tract, respiratory system, and gastrointestinal tract . Sulfamethoxazole is known for its broad-spectrum antimicrobial activity and has become a crucial component in the fight against bacterial diseases .
Wirkmechanismus
Target of Action
Sulfamethoxazole is a sulfonamide antibiotic that primarily targets bacterial dihydropteroate synthase . This enzyme plays a crucial role in the synthesis of folic acid, which is essential for bacterial growth and division .
Mode of Action
Sulfamethoxazole inhibits bacterial dihydrofolic acid synthesis due to its structural similarity to an endogenous substrate, para-aminobenzoic acid (PABA) . Most bacteria meet their need for folic acid by synthesizing it from PABA, as opposed to Animalia that require exogenous folic acid sources . By inhibiting the synthesis of dihydrofolic acid, sulfamethoxazole prevents the formation of nucleic acids and proteins necessary for bacterial growth and division .
Biochemical Pathways
Sulfamethoxazole interferes with the biosynthesis of nucleic acids and proteins in bacteria by blocking two consecutive steps in the pathway . The first step is the conversion of PABA to dihydropteroate, which is inhibited by sulfamethoxazole. The second step, inhibited by trimethoprim, is the conversion of dihydrofolic acid to tetrahydrofolate . The combined action of these two drugs results in a synergistic effect, effectively halting bacterial growth .
Pharmacokinetics
Sulfamethoxazole is primarily metabolized by arylamine N-acetyltransferase (NAT) enzymes, which are responsible for acetylation of sulfamethoxazole at its N4 position . Sulfamethoxazole may also undergo oxidation at its C5 and N4 atoms, the latter of which is catalyzed by CYP2C9 . The drug is excreted renally, and its elimination half-life is approximately 10 hours .
Result of Action
The result of sulfamethoxazole’s action is the inhibition of bacterial growth and division . By preventing the synthesis of folic acid, an essential component for the production of nucleic acids and proteins, sulfamethoxazole effectively halts the growth of susceptible bacteria . This makes it useful for the treatment of a variety of bacterial infections, including those of the urinary, respiratory, and gastrointestinal tracts .
Action Environment
The action of sulfamethoxazole can be influenced by various environmental factors. For instance, the presence of additional carbon sources can affect the biodegradation of sulfamethoxazole . Moreover, the degradation efficiency of sulfamethoxazole can be affected by temperature and pH . It’s also worth noting that sulfamethoxazole is a ubiquitous pollutant in the environment due to extensive consumption, excretion, and disposal . This widespread presence can lead to the development of bacterial resistance, posing a significant challenge for the treatment of bacterial infections .
Wissenschaftliche Forschungsanwendungen
Sulfamethoxazol hat eine breite Palette von Anwendungen in der wissenschaftlichen Forschung:
Wirkmechanismus
This compound übt seine Wirkung aus, indem es die bakterielle Folat-Synthese stört . Es hemmt das Enzym Dihydropteroatsynthase, das für die Bildung von Dihydrofolsäure aus Para-Aminobenzoesäure essentiell ist . Diese Hemmung verhindert die Synthese von Nukleinsäuren und Proteinen, die für das Wachstum und die Teilung von Bakterien notwendig sind . In Kombination mit Trimethoprim, das die Reduktion von Dihydrofolsäure zu Tetrahydrofolat hemmt, wirken die beiden Wirkstoffe synergistisch, um aufeinanderfolgende Schritte im Folat-Stoffwechselweg zu blockieren .
Biochemische Analyse
Biochemical Properties
Sulfamethoxazole interacts with various enzymes and proteins. For instance, it has been observed to inhibit the activity of carbonic anhydrase (CA), stimulating the activity of Rubisco . This interaction plays a significant role in its biochemical reactions .
Cellular Effects
Sulfamethoxazole affects various types of cells and cellular processes. It influences cell function, including impact on cell signaling pathways, gene expression, and cellular metabolism . For example, in fish, it has been observed to cause variations in blood profile and biochemical parameters .
Molecular Mechanism
At the molecular level, Sulfamethoxazole exerts its effects through binding interactions with biomolecules, enzyme inhibition or activation, and changes in gene expression . It has been found to regulate the diversion of protoporphyrin IX and the chlorophyll cycle .
Temporal Effects in Laboratory Settings
In laboratory settings, the effects of Sulfamethoxazole change over time. It has been observed that its biodegradation capacity is sustainable within a certain cycle . Information on the product’s stability, degradation, and any long-term effects on cellular function have been observed in in vitro or in vivo studies .
Dosage Effects in Animal Models
The effects of Sulfamethoxazole vary with different dosages in animal models. For instance, in a study on fish, effects were based on chronic toxicity of environmentally relevant dosages of 25, 50, 100, and 200 μg/L of Sulfamethoxazole for 28 days .
Metabolic Pathways
Sulfamethoxazole is involved in various metabolic pathways. It interacts with enzymes or cofactors, and also affects metabolic flux or metabolite levels .
Transport and Distribution
Sulfamethoxazole is transported and distributed within cells and tissues . It interacts with transporters or binding proteins, and also affects its localization or accumulation .
Subcellular Localization
The subcellular localization of Sulfamethoxazole and its effects on its activity or function have been studied . It includes any targeting signals or post-translational modifications that direct it to specific compartments or organelles .
Vorbereitungsmethoden
Synthetische Routen und Reaktionsbedingungen
Sulfamethoxazol wird durch eine Reihe von chemischen Reaktionen synthetisiert. Eine gängige Methode beinhaltet die Reaktion von 3-Amino-5-Methylisoxazol mit 4-Aminobenzolsulfonylchlorid in Gegenwart einer Base . Die Reaktion findet typischerweise unter kontrollierten Temperaturbedingungen statt, um die Bildung des gewünschten Produkts zu gewährleisten.
Industrielle Produktionsverfahren
In industriellen Umgebungen wird this compound durch die Kombination von this compound mit Trimethoprim in einem bestimmten Verhältnis, oft 5:1, hergestellt . Der Prozess beinhaltet die Verwendung von Hilfsstoffen wie Ethanolamin, Propylenglykol, Ethanol, Natriummetabisulfit und Wasser für Injektionszwecke . Die Mischung wird gleichmäßig gerührt, beprobt und auf Gehalt und pH-Wert gemessen, bevor sie filtriert, aseptisch abgefüllt und verschlossen wird .
Analyse Chemischer Reaktionen
Arten von Reaktionen
Sulfamethoxazol unterliegt verschiedenen chemischen Reaktionen, darunter Oxidations-, Reduktions- und Substitutionsreaktionen .
Gängige Reagenzien und Bedingungen
Oxidation: this compound kann mit Reagenzien wie Wasserstoffperoxid oder Kaliumpermanganat oxidiert werden.
Reduktion: Reduktionsreaktionen können Reagenzien wie Natriumborhydrid beinhalten.
Substitution: Substitutionsreaktionen verwenden häufig Reagenzien wie Halogene oder Alkylierungsmittel.
Hauptprodukte, die gebildet werden
Die Hauptprodukte, die aus diesen Reaktionen entstehen, sind Sulfansäure, 3-Amino-5-Methylisoxazol und verschiedene Isomere .
Vergleich Mit ähnlichen Verbindungen
Sulfamethoxazol gehört zur Klasse der Sulfonamid-Antibiotika, die Verbindungen wie Sulfamethazin, Sulfamethizol und Sulfadiazin umfasst . Im Vergleich zu diesen Verbindungen ist this compound einzigartig in seiner strukturellen Ähnlichkeit mit Para-Aminobenzoesäure, die es ihm ermöglicht, die Dihydropteroatsynthase effektiv zu hemmen . Dieses strukturelle Merkmal macht es besonders effektiv gegen eine breite Palette bakterieller Infektionen .
Liste ähnlicher Verbindungen
- Sulfamethazin
- Sulfamethizol
- Sulfadiazin
Die breite Aktivität von this compound und seine Fähigkeit, synergistisch mit Trimethoprim zu wirken, machen es zu einem wertvollen Antibiotikum sowohl in klinischen als auch in Forschungsumgebungen .
Eigenschaften
IUPAC Name |
4-amino-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C10H11N3O3S/c1-7-6-10(12-16-7)13-17(14,15)9-4-2-8(11)3-5-9/h2-6H,11H2,1H3,(H,12,13) |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
JLKIGFTWXXRPMT-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CC1=CC(=NO1)NS(=O)(=O)C2=CC=C(C=C2)N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C10H11N3O3S |
Source
|
| Record name | SULFAMETHOXAZOLE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/21046 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
| Explanation | CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data. | |
| Record name | sulfamethoxazole | |
| Source | Wikipedia | |
| URL | https://en.wikipedia.org/wiki/Sulfamethoxazole | |
| Description | Chemical information link to Wikipedia. | |
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID8026064 |
Source
|
| Record name | Sulfamethoxazole | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID8026064 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
253.28 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Physical Description |
Crystals or white powder. (NTP, 1992), Solid |
Source
|
| Record name | SULFAMETHOXAZOLE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/21046 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
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| Record name | Sulfamethoxazole | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0015150 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Solubility |
>38 [ug/mL] (The mean of the results at pH 7.4), less than 1 mg/mL at 68 °F (NTP, 1992), PRACTICALLY INSOL IN WATER, ETHER & CHLOROFORM; 1 G IN 50 ML ALCOHOL & ABOUT 4 ML ACETONE; DISSOLVES IN HCL HYDROGEN CHLORIDE OR SODIUM HYDROXIDE SOLN THROUGH SALT FORMATION, Insoluble in ethyl ether, In water, 610 mg/L at 37 °C, The solubility interactions of trimethoprim and sulfamethoxazole in binary solvents were studied using hexane (n-hexane)-ethyl acetate, ethyl acetate-methyl alcohol (methanol), and methyl alcohol-water as the solve mixtures. When solubilities were obtained for individual components, trimethoprim exhibited solvation in ethyl acetate-methyl alcohol mixtures, while sulfamethoxazole showed weaker solute-solvent interactions in the solvent series. At its peak, the solubility of sulfamethoxazole was about 8 times higher than that of trimethoprim when the drugs were combined. Sulfamethoxazole lowered trimethoprim solubility by 13-74%. Similarly, trimethoprim suppressed sulfamethoxazole solubility by 10-94%. In water, although mutual solubility was reduced, the solubility ratio of trimethoprim to sulfamethoxazole was 1:4 on the mol fraction scale., 4.59e-01 g/L |
Source
|
| Record name | SID855654 | |
| Source | Burnham Center for Chemical Genomics | |
| URL | https://pubchem.ncbi.nlm.nih.gov/bioassay/1996#section=Data-Table | |
| Description | Aqueous solubility in buffer at pH 7.4 | |
| Record name | SULFAMETHOXAZOLE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/21046 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
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| Record name | Sulfamethoxazole | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB01015 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | SULFAMETHOXAZOLE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3186 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
| Record name | Sulfamethoxazole | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0015150 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Mechanism of Action |
Sulfamethoxazole is a sulfonamide that inhibits bacterial dihydrofolic acid synthesis due to its structural similarity to an endogenous substrate, para-aminobenzoic acid (PABA). Most bacteria meet their need for folic acid by synthesizing it from PABA, as opposed to Animalia that require exogenous folic acid sources. Sulfamethoxazole competitively inhibits dihydropteroate synthase, the enzyme responsible for bacterial conversion of PABA to dihydrofolic acid. Inhibition of this pathway prevents the synthesis of tetrahydrofolate and, ultimately, the synthesis of bacterial purines and DNA, resulting in a bacteriostatic effect., Sulfonamides are usually bacteriostatic in action. Sulfonamides interfere with the utilization of p-aminobenzoic acid (PABA) in the biosynthesis of tetrahydrofolic acid (the reduced form of folic acid) cofactors in susceptible bacteria. Sulfonamides are structural analogs of PABA and appear to interfere with PABA utilization by competitively inhibiting the enzyme dihydropteroate synthase, which catalyzes the formation of dihydropteroic acid (a precursor of tetrahydrofolic acid) from PABA and pteridine; however, other mechanism(s) affecting the biosynthetic pathway also may be involved. Compounds such as pyrimethamine and trimethoprim, which block later stages in the synthesis of folic acid, act synergistically with sulfonamides. Only microorganisms that synthesize their own folic acid are inhibited by sulfonamides; animal cells and bacteria which are capable of utilizing folic acid precursors or preformed folic acid are not affected by these drugs. The antibacterial activity of the sulfonamides is reportedly decreased in the presence of blood or purulent body exudates. /Sulfonamides/, /Sulfonamides inhibit bacterial growth by preventing para-aminobenzoic acid (PABA) from being incorporated/ into dihydropteroic acid, the immediate precursor of folic acid. Sensitive microorganisms are those that must synthesize their own folic acid; bacteria that can utilize preformed folate are not affected. Bacteriostasis induced by sulfonamides is counteracted by PABA competitively. Sulfonamides do not affect mammalian cells by this mechanism, since they require preformed folic acid and cannot synthesize it. /Sulfonamides/, Sulfonamides are broad-spectrum, bacteriostatic anti-infectives. They are structural analogs of para-aminobenzoic acid and competively inhibit a bacterial enzyme, dihydropteroate synthetase, that is responsible for incorporation of para-aminobenzoic acid into dihydrofolic acid. This blocks the synthesis of dihydrofolic acid and decreases the amount of metabolically active tetrahydrofolic acid, a cofactor for the synthesis of purines, thymidine, and DNA. /Sulfonamides/, The hydroxylamine and nitroso metabolites formed by N4-oxidation of sulfonamides are thought to be involved in the pathogenesis of idiosyncratic reactions to this class of drugs. Idiosyncratic reactions to sulfonamides are characterized by multisystemic toxicity, including hepatitis, nephritis, dermatitis, and blood dyscrasias (aplastic anemia, agranulocytosis). Previously it has been shown that cytochrome p-450 in the liver metabolizes sulfamethoxazole to its hydroxylamine metabolite. In this paper the N4-oxidation of sulfamethoxazole by activated monocytes and neutrophils (human and canine) to form sulfamethoxazole hydroxylamine and nitrosulfamethoxazole is reported. The presumed nitroso intermediate was not detected. Purified myeloperoxidase and prostaglandin H synthase were also capable of mediating the oxidation of sulfamethoxazole. The present studies suggest that myeloperoxidase is responsible for the observed oxidation by phagocytic cells. Oxidation by neutrophils may play a role in agranulocytosis, and oxidation by monocytes may facilitate antigen presentation. Extrahepatic bioactivation of sulfonamides by peroxidases in phagocytic cells and other tissues may be important in determining the range of adverse reactions to sulfonamides that occur., Hypersensitivity syndromes are severe drug induced side effects with skin rashes, fever and/or multiorgan-system abnormalities which are not pharmacologically related. ... These reactions are considered to be immune-mediated but the precise mechanisms are not completely understood. Clinical features, which resemble and EBV infection, and some immunological studies suggest that T-cell mediated immunity is involved in the pathogenesis of this rare disease. In the literature, allopurinol and anticonvulsant hypersensitivity syndromes are clinically well characterized entities, while the definition of hypersensitivity syndrome elicited by other drugs is rather confusing. ... Two patients, one with sulfamethoxazole- and one with allopurinol-induced hypersensitivity syndrome /are presented/. In both cases a lymphocyte transformation test (LTT) was performed and /investigators/ analyzed the T-cell activation parameters CD25 and HLA-DR on CD4- and CD8- T-cells to demonstrate in vivo activation of T-cells during the active disease. Both patients show increased activation of T-cells with elevated levels of HLA-DR on CD8+ cells. The T-cell activation correlated with the clinical course. /The/ data supports an immunological pathogenesis for hypersensitivity syndromes and the concept that drug specific T-cells are involved in hypersensitivity syndromes. |
Source
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| Record name | Sulfamethoxazole | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB01015 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | SULFAMETHOXAZOLE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3186 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
Impurities |
N-[4-[(5-methylisoxazol-3-yl)sulfamoyl]phenyl]acetamide; 4-[[(4-)aminophenyl)sulfonyl]amino]-N-(5-methylisoxazol-3-yl]benzenesulfonamide; 5-methylisoxazol-3-amine; 4-aminobenzenesulfonic acid; 4-aminobenzenesulfonamide; 4-amino-N-(3-methylisoxazol-5-yl)benzenesulfonamide |
Source
|
| Record name | SULFAMETHOXAZOLE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3186 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
Color/Form |
Yellow-white powder, Almost white, Crystals from dilute ethanol, WHITE TO OFF-WHITE CRYSTALLINE POWDER, Colorless crystalline powder | |
CAS No. |
723-46-6, 144930-01-8, 144993-89-5 |
Source
|
| Record name | SULFAMETHOXAZOLE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/21046 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
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| Record name | Sulfamethoxazole | |
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| Description | CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. | |
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| Record name | Benzenesulfonamide, 4-amino-N-(5-methyl-3-isoxazolyl)-, radical ion(1+) | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=144930-01-8 | |
| Description | CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. | |
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| Record name | Benzenesulfonamide, 4-amino-N-(5-methyl-3-isoxazolyl)-, radical ion(1-) | |
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| URL | https://commonchemistry.cas.org/detail?cas_rn=144993-89-5 | |
| Description | CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. | |
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| Record name | Sulfamethoxazole [USAN:USP:INN:BAN:JAN] | |
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| Record name | Sulfamethoxazole | |
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| URL | https://www.drugbank.ca/drugs/DB01015 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
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| Record name | sulfamethoxazole | |
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| Record name | sulfamethoxazole | |
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| Record name | Benzenesulfonamide, 4-amino-N-(5-methyl-3-isoxazolyl)- | |
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| Record name | Sulfamethoxazole | |
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| Record name | Sulfamethoxazole | |
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| Record name | Sulfamethoxazole | |
| Source | European Chemicals Agency (ECHA) | |
| URL | https://echa.europa.eu/information-on-chemicals | |
| Description | The European Chemicals Agency (ECHA) is an agency of the European Union which is the driving force among regulatory authorities in implementing the EU's groundbreaking chemicals legislation for the benefit of human health and the environment as well as for innovation and competitiveness. | |
| Explanation | Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. | |
| Record name | SULFAMETHOXAZOLE | |
| Source | FDA Global Substance Registration System (GSRS) | |
| URL | https://gsrs.ncats.nih.gov/ginas/app/beta/substances/JE42381TNV | |
| Description | The FDA Global Substance Registration System (GSRS) enables the efficient and accurate exchange of information on what substances are in regulated products. Instead of relying on names, which vary across regulatory domains, countries, and regions, the GSRS knowledge base makes it possible for substances to be defined by standardized, scientific descriptions. | |
| Explanation | Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. | |
| Record name | SULFAMETHOXAZOLE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3186 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
| Record name | Sulfamethoxazole | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0015150 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Melting Point |
333 °F (NTP, 1992), 167 °C, MP: 209-210 °C; crystals from alcohol /N4-Acetylsulfamethoxazole/, MP: 171 °C |
Source
|
| Record name | SULFAMETHOXAZOLE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/21046 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
| Explanation | CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data. | |
| Record name | Sulfamethoxazole | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB01015 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | SULFAMETHOXAZOLE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3186 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
| Record name | Sulfamethoxazole | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0015150 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Retrosynthesis Analysis
AI-Powered Synthesis Planning: Our tool employs the Template_relevance Pistachio, Template_relevance Bkms_metabolic, Template_relevance Pistachio_ringbreaker, Template_relevance Reaxys, Template_relevance Reaxys_biocatalysis model, leveraging a vast database of chemical reactions to predict feasible synthetic routes.
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Strategy Settings
| Precursor scoring | Relevance Heuristic |
|---|---|
| Min. plausibility | 0.01 |
| Model | Template_relevance |
| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
| Top-N result to add to graph | 6 |
Feasible Synthetic Routes
Q1: What is the mechanism of action of Sulfamethoxazole?
A1: Sulfamethoxazole is a sulfonamide antibiotic that acts as a competitive inhibitor of dihydropteroate synthase (FolP), a crucial enzyme in the bacterial folic acid synthesis pathway. [] It competes with para-aminobenzoic acid (PABA) for binding to FolP, ultimately disrupting the synthesis of dihydrofolic acid, a precursor to tetrahydrofolic acid, essential for bacterial DNA synthesis. []
Q2: What are the downstream effects of Sulfamethoxazole's inhibition of bacterial folic acid synthesis?
A2: Blocking folic acid synthesis hinders the production of nucleotides required for DNA replication and repair. [] This leads to the inhibition of bacterial growth and proliferation, ultimately causing bacterial cell death.
Q3: What is the molecular formula and weight of Sulfamethoxazole?
A3: The molecular formula of Sulfamethoxazole is C10H11N3O3S, and its molecular weight is 253.28 g/mol.
Q4: What is known about the stability of Sulfamethoxazole under various conditions?
A5: Sulfamethoxazole's stability can be influenced by factors like pH, temperature, and the presence of other compounds. For example, research has focused on the stability of Sulfamethoxazole in combination with Trimethoprim, demonstrating the potential formation of different solid phases depending on the pH and diluent used. []
Q5: How does the solubility of Sulfamethoxazole impact its efficacy?
A6: Sulfamethoxazole exhibits moderate hydrophilicity. [] Its solubility in various media can affect its dissolution rate, absorption, and ultimately, its bioavailability and efficacy. [] Further research on dissolution and solubility characteristics is crucial for optimizing its formulation and delivery.
Q6: Are there specific analytical methods for characterizing and quantifying Sulfamethoxazole?
A7: Several analytical methods exist for Sulfamethoxazole characterization and quantification, including high-performance liquid chromatography (HPLC), liquid chromatography-mass spectrometry (LC-MS), and UV-Vis spectrophotometry. [, , ]
Q7: What is the importance of analytical method validation for Sulfamethoxazole analysis?
A8: Validation of analytical methods is crucial for ensuring the accuracy, precision, and specificity of Sulfamethoxazole measurements. [] This is essential for reliable data interpretation in various research areas, including pharmacokinetic studies, quality control, and environmental monitoring.
Q8: What is known about the pharmacokinetics of Sulfamethoxazole?
A9: Research indicates that Sulfamethoxazole exhibits a wide range of pharmacokinetic parameters, including metabolic clearance, volume of distribution, and elimination half-life. [] Studies have focused on understanding its absorption, distribution, metabolism, and excretion (ADME) profile to optimize its dosing regimen, particularly in challenging cases like multidrug-resistant tuberculosis. []
Q9: How do the pharmacokinetic parameters of Sulfamethoxazole relate to its pharmacodynamic properties?
A10: Pharmacokinetic parameters like area under the curve (AUC) and time above the minimum inhibitory concentration (MIC) are essential for predicting Sulfamethoxazole efficacy. [] Studies have explored the relationship between these parameters to determine optimal dosing regimens and enhance treatment outcomes. []
Q10: Has Sulfamethoxazole efficacy been investigated in in vitro and in vivo models?
A11: Yes, Sulfamethoxazole has been extensively studied in both in vitro and in vivo settings. In vitro studies often involve cell-based assays to evaluate its bactericidal activity against various pathogens, including carbapenem-resistant Klebsiella pneumoniae. [] In vivo studies, typically using animal models, assess its efficacy in treating infections like Pneumocystis carinii pneumonia. [, , ]
Q11: What are the known mechanisms of resistance to Sulfamethoxazole?
A12: Bacterial resistance to Sulfamethoxazole can arise through several mechanisms, including mutations in the target enzyme FolP, overexpression of efflux pumps that reduce intracellular drug concentration, and the acquisition of resistance genes like sul1 and sul2. [, , ]
Q12: Is there cross-resistance between Sulfamethoxazole and other antibiotics?
A13: Yes, cross-resistance between Sulfamethoxazole and other antibiotics, particularly those inhibiting the folate pathway like Trimethoprim, is a concern. Studies have shown that resistance to Sulfamethoxazole is often linked to resistance to other antibiotics, such as those from the quinolone and tetracycline classes. [, ]
Q13: What are the known toxicities and safety concerns associated with Sulfamethoxazole?
A14: While generally considered safe, Sulfamethoxazole can cause various side effects, including skin rash, nausea, vomiting, and in rare cases, severe hypersensitivity reactions. [, , ] These adverse effects are often associated with its sulfonamide moiety and require careful monitoring, especially in patients with known allergies. []
Q14: Are there any specific drug delivery strategies being explored for Sulfamethoxazole?
A15: While traditional oral and intravenous administration routes are common for Sulfamethoxazole, research is exploring innovative drug delivery systems to enhance its targeting, bioavailability, and efficacy. This includes complexing Sulfamethoxazole with metals like gold to improve its activity against biofilms. []
Q15: What is the known environmental impact of Sulfamethoxazole?
A17: Sulfamethoxazole, like many pharmaceuticals, has been detected in wastewater and surface water, raising concerns about its potential ecotoxicological effects. [, ] Research is focusing on understanding its environmental fate, degradation pathways, and potential risks to aquatic organisms. [] Strategies to mitigate its environmental impact include optimizing wastewater treatment processes and promoting responsible disposal practices. []
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