柳氮磺胺吡啶
货号:
B1682708
CAS 编号:
599-79-1
分子量:
398.4 g/mol
InChI 键:
NCEXYHBECQHGNR-UHFFFAOYSA-N
注意:
仅供研究使用。不适用于人类或兽医用途。
描述
作用机制
柳氮磺胺吡啶通过多种机制发挥作用：
抗炎作用： 抑制促炎细胞因子和前列腺素的产生，减少结肠炎症.
免疫调节作用： 通过影响 T 细胞功能和细胞因子产生来调节免疫反应.
抗菌活性： 磺胺吡啶成分具有抗菌特性，有助于控制肠道菌群.
科学研究应用
生化分析
Biochemical Properties
Sulfasalazine and its metabolites, 5-aminosalicylic acid and sulfapyridine, are involved in various biochemical reactions .
Cellular Effects
Sulfasalazine 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 Sulfasalazine and its metabolites can inhibit leukotrienes and prostaglandins by blocking the cyclo-oxygenase .
Temporal Effects in Laboratory Settings
In laboratory settings, Sulfasalazine-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 Sulfasalazine vary with different dosages in animal models . The effects of Sulfasalazine and the analogues olsalazine, 5-aminosalicylic acid, and 4-aminosalicylic acid, in different experimental animal models have been reviewed .
Metabolic Pathways
Sulfasalazine is involved in various metabolic pathways. It is broken down by intestinal bacteria into sulfapyridine and 5-aminosalicylic acid . Sulfasalazine 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
Sulfasalazine is generally administered as enteric-coated tablets which release the drug in the small intestine . Some Sulfasalazine 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 Sulfasalazine and its effects on its activity or function are not well studied. It is known that Sulfasalazine 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 .
准备方法
合成路线及反应条件
柳氮磺胺吡啶是通过一系列化学反应合成的，起始原料为磺胺吡啶和水杨酸。 该过程涉及重氮化反应，然后进行偶联反应 . 以下是合成过程的简化概述：
重氮化反应： 将磺胺吡啶溶解在含有盐酸和亚硝酸钠的水溶液中，形成重氮盐。
偶联反应： 将重氮盐与水杨酸在氢氧化钠溶液中反应，生成柳氮磺胺吡啶.
工业生产方法
在工业环境中，柳氮磺胺吡啶的合成遵循类似的步骤，但规模更大。 反应经过精心控制，以确保高产率和纯度。 最终产品通常被制成片剂或肠溶衣制剂，以提高生物利用度并减少胃肠道副作用 .
化学反应分析
反应类型
柳氮磺胺吡啶会经历多种类型的化学反应，包括：
常见的试剂和条件
水解： 由结肠中的细菌酶催化。
氧化： 通常涉及肝脏中的细胞色素 P450 酶。
还原： 可以在肠道中的厌氧条件下发生.
形成的主要产物
磺胺吡啶： 具有抗菌特性的活性代谢物。
5-氨基水杨酸： 一种在结肠局部起作用的抗炎剂.
相似化合物的比较
类似化合物
美沙拉嗪（5-氨基水杨酸）： 具有抗炎特性，但缺少磺胺成分.
柳氮磺胺吡啶衍生物： 柳氮磺胺吡啶的修饰版本，具有改变的药代动力学特性.
独特性
柳氮磺胺吡啶的独特性在于它既是抗炎剂又是抗菌剂的双重作用。 它能够代谢成两种活性成分，磺胺吡啶和 5-氨基水杨酸，为治疗炎症性疾病提供了多方面的途径 .
属性
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 | |
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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
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| 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 | |
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| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3395 | |
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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
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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. | |
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 | |
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| URL | https://www.drugbank.ca/drugs/DB00795 | |
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| Record name | Salazosulfapyridine | |
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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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| 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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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
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