Sulfasalazine
Vue d'ensemble
Description
Sulfasalazine is a medication primarily used to treat inflammatory bowel diseases such as ulcerative colitis and Crohn’s disease, as well as rheumatoid arthritis . It is a member of the sulfonamide class of drugs and is known for its anti-inflammatory and immunomodulatory properties . This compound was first introduced in the 1940s and has since become a staple in the treatment of various inflammatory conditions .
Mécanisme D'action
Target of Action
Sulfasalazine is primarily targeted at inflammatory molecules . It is metabolized by intestinal bacteria into two compounds, mesalazine and sulfapyridine, which carry out the main pharmacological activity of this compound .
Mode of Action
Research has found that this compound and its metabolites, mesalazine and sulfapyridine, can inhibit leukotrienes and prostaglandins by blocking the cyclo-oxygenase .
Biochemical Pathways
this compound is known to affect the prostaglandin synthesis pathway . It inhibits the formation of prostaglandins, which are key mediators of inflammation . This results in local anti-inflammatory effects in the colon .
Pharmacokinetics
this compound has a bioavailability of less than 15% . It has an elimination half-life of 5-10 hours . About 10-15% of a this compound dose is absorbed as unchanged drug from the small intestine . Part of an oral dose of this compound passes intact into the colon where the azo-linkage is cleaved by intestinal flora to form sulfapyridine and 5-aminosalicylic acid (mesalamine) .
Result of Action
this compound is a disease-modifying anti-rheumatic drug (DMARD) used to treat and manage autoimmune diseases including rheumatoid arthritis and an inflammatory bowel disease called ulcerative colitis . It helps to reduce pain and swelling and lowers inflammation in your body . It limits the damage that rheumatoid arthritis causes to your joints, helping to prevent disease progression .
Action Environment
The action of this compound is influenced by the presence of intestinal bacteria, which metabolize the drug into its active components . The medication is broken down by intestinal bacteria into sulfapyridine and 5-aminosalicylic acid . These metabolites are then able to exert their anti-inflammatory effects in the colon .
Applications De Recherche Scientifique
Sulfasalazine has a wide range of applications in scientific research:
Analyse Biochimique
Biochemical Properties
Sulfasalazine and its metabolites, 5-aminosalicylic acid and sulfapyridine, are involved in various biochemical reactions .
Cellular Effects
This compound has been found to have significant effects on various types of cells and cellular processes. It helps to reduce pain and swelling and lowers inflammation in the body . It limits the damage that rheumatoid arthritis causes to joints, helping to prevent disease progression .
Molecular Mechanism
One proposed mechanism is the inhibition of prostaglandins, resulting in local anti-inflammatory effects in the colon . It is also thought that this compound and its metabolites can inhibit leukotrienes and prostaglandins by blocking the cyclo-oxygenase .
Temporal Effects in Laboratory Settings
In laboratory settings, this compound-induced cytopenia, nephrotoxicity, and hepatotoxicity are uncommon during long-term treatment . Some guidelines recommend 3 monthly monitoring blood tests indefinitely during long-term treatment while others recommend stopping monitoring after 1 year .
Dosage Effects in Animal Models
The effects of this compound vary with different dosages in animal models . The effects of this compound and the analogues olsalazine, 5-aminosalicylic acid, and 4-aminosalicylic acid, in different experimental animal models have been reviewed .
Metabolic Pathways
This compound is involved in various metabolic pathways. It is broken down by intestinal bacteria into sulfapyridine and 5-aminosalicylic acid . This compound could improve therapy by sensitizing to cisplatin through killing CD44v9-positive cells and modifying the metabolic pathways, in particular tryptophan degradation (i.e., kynurenine pathway, serotonin pathway) and nucleic acid metabolism .
Transport and Distribution
This compound is generally administered as enteric-coated tablets which release the drug in the small intestine . Some this compound is absorbed in the small intestine but is limited due to transport back to the intestine by breast cancer resistance protein (ATP-binding cassette subfamily G member 2) .
Subcellular Localization
The subcellular localization of this compound and its effects on its activity or function are not well studied. It is known that this compound is too big to be absorbed by the small intestine, but bacteria in the colon can break the bond between 5-ASA and sulfapyridine, which frees 5-ASA to work locally in the colon to help in ulcerative colitis .
Méthodes De Préparation
Synthetic Routes and Reaction Conditions
Sulfasalazine is synthesized through a series of chemical reactions starting with sulfapyridine and salicylic acid. The process involves a diazotization reaction followed by a coupling reaction . Here is a simplified outline of the synthesis:
Diazotization Reaction: Sulfapyridine is dissolved in an aqueous solution containing hydrochloric acid and sodium nitrite to form a diazonium salt.
Coupling Reaction: The diazonium salt is then reacted with salicylic acid in a sodium hydroxide solution to produce this compound.
Industrial Production Methods
In industrial settings, the synthesis of this compound follows similar steps but on a larger scale. The reactions are carefully controlled to ensure high yield and purity. The final product is often formulated into tablets or enteric-coated preparations to improve bioavailability and reduce gastrointestinal side effects .
Analyse Des Réactions Chimiques
Types of Reactions
Sulfasalazine undergoes several types of chemical reactions, including:
Oxidation and Reduction: This compound can undergo oxidation and reduction reactions, particularly in the liver where it is metabolized.
Substitution Reactions: The compound can participate in substitution reactions, especially in the presence of strong nucleophiles or electrophiles.
Common Reagents and Conditions
Hydrolysis: Catalyzed by bacterial enzymes in the colon.
Oxidation: Often involves cytochrome P450 enzymes in the liver.
Reduction: Can occur under anaerobic conditions in the gut.
Major Products Formed
Sulfapyridine: An active metabolite with antibacterial properties.
5-Aminosalicylic Acid: An anti-inflammatory agent that acts locally in the colon.
Comparaison Avec Des Composés Similaires
Similar Compounds
Mesalazine (5-Aminosalicylic Acid): Shares the anti-inflammatory properties but lacks the sulfonamide component.
Sulfasalazine Derivatives: Modified versions of this compound with altered pharmacokinetic properties.
Uniqueness
This compound is unique due to its dual action as both an anti-inflammatory and antibacterial agent. Its ability to be metabolized into two active components, sulfapyridine and 5-aminosalicylic acid, provides a multifaceted approach to treating inflammatory diseases .
Propriétés
IUPAC Name |
2-hydroxy-5-[[4-(pyridin-2-ylsulfamoyl)phenyl]diazenyl]benzoic acid |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C18H14N4O5S/c23-16-9-6-13(11-15(16)18(24)25)21-20-12-4-7-14(8-5-12)28(26,27)22-17-3-1-2-10-19-17/h1-11,23H,(H,19,22)(H,24,25) |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
NCEXYHBECQHGNR-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
C1=CC=NC(=C1)NS(=O)(=O)C2=CC=C(C=C2)N=NC3=CC(=C(C=C3)O)C(=O)O |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C18H14N4O5S |
Source
|
| Record name | SALICYLAZOSULFAPYRIDINE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20999 | |
| 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. | |
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID0021256 |
Source
|
| Record name | Sulfasalazine | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID0021256 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
398.4 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Physical Description |
Salicylazosulfapyridine appears as odorless yellow or brownish-yellow to orange powder. Tasteless. (NTP, 1992) It is a sulfa drug used as an antibiotic. |
Source
|
| Record name | SALICYLAZOSULFAPYRIDINE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20999 | |
| 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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Solubility |
less than 1 mg/mL at 77 °F (NTP, 1992), Practically insoluble in water, Very slightly soluble in ethanol; practically insoluble in diethyl ether, chloroform, and benzene; soluble in aqueous solution of alkali hydroxides |
Source
|
| Record name | SALICYLAZOSULFAPYRIDINE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20999 | |
| 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 | Sulfasalazine | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3395 | |
| 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. | |
Mechanism of Action |
Although the exact mechanism of action of sulfasalazine is not fully understood, it is thought to be mediated through the inhibition of various inflammatory molecules. Research have found that sulfasalazine and its metabolites, mesalazine and sulfapyridine, can inhibit leukotrienes and prostaglandins by blocking the cyclo-oxygenase and lipoxygenase pathway. Specific enzymes that were investigated include phospholipase A2, cyclooxygenase-1 (COX-1), cyclooxygenase-2 (COX2), and arachidonate 5-lipoxygenase., Sulfonamide combined with an anti-inflammatory drug. Sulfasalazine has little effect and salicylic acid (mesalamine) has anti-inflammatory effects. ... When administered as the combination of salicylic acid and the sulfonamide, sulfapyridine, the salicylic acid is released by colonic bacteria to produce an anti-inflammatory effect. The anti-inflammatory effect is believed to be through antiprostaglandin action, antileukotriene activity, or both., ... The purpose of the present study was to determine whether sulfasalazine therapy affected NF-kappaB activation and the expression of pro-inflammatory cytokines in patients with ulcerative colitis. ... A total of 38 patients with moderate ulcerative colitis were investigated. Twenty-one patients received sulfasalazine. Seventeen patients did not receive any medication. Biopsy specimens were obtained from inflamed mucosa and analyzed for NF-kappaB DNA binding activity, NF-kappaBp65/IkappaBalpha protein expression and the levels of pro-inflammatory cytokine mRNA using electrophoretic mobility shift assay, western blot analysis, immunohistochemical staining and reverse transcription-polymerase chain reaction (RT-PCR) analysis, respectively. Increased activation of NF-kappaB and high levels of the expression of interleukin (IL)-1beta mRNA and IL-8 mRNA were detected in biopsy specimens from patients with ulcerative colitis. Therapeutic administration of sulfasalazine effectively downregulated the activation of NF-kappaB and the expression of IL-1beta mRNA and IL-8 mRNA while IkappaBalpha levels were stable. /The authors concluded that/ the therapeutic benefits for ulcerative colitis of sulfasalazine might at least in part be attributed to its ability to inhibit NF-kappaB activation, resulting in the downregulation of pro-inflammatory cytokine mRNA expression. |
Source
|
| Record name | Sulfasalazine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00795 | |
| 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 | Sulfasalazine | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3395 | |
| 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 |
Minute, brownish-yellow crystals, Light brownish yellow to bright yellow fine powder | |
CAS No. |
599-79-1 |
Source
|
| Record name | SALICYLAZOSULFAPYRIDINE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20999 | |
| 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 | Sulfasalazine | |
| Source | CAS Common Chemistry | |
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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 | Sulfasalazine [USAN:USP:INN:BAN] | |
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| Record name | Sulfasalazine | |
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| URL | https://www.drugbank.ca/drugs/DB00795 | |
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| Record name | Salazosulfapyridine | |
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| Record name | SULFASALAZINE | |
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| Record name | Sulfasalazine | |
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| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3395 | |
| 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. | |
Melting Point |
464 to 473 °F (decomposes) (NTP, 1992), 220 °C (decomposes) |
Source
|
| Record name | SALICYLAZOSULFAPYRIDINE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20999 | |
| 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 | Sulfasalazine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00795 | |
| 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 | Sulfasalazine | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3395 | |
| 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. | |
Retrosynthesis Analysis
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| Top-N result to add to graph | 6 |
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