Sulindac sulfoxide
Sulindac
CAS: 38194-50-2
Molecular Formula: C20H17FO3S
Sulindac sulfoxide - Names and Identifiers
Sulindac sulfoxide - Physico-chemical Properties
| Molecular Formula | C20H17FO3S |
| Molar Mass | 356.41 |
| Density | 1.2581 (estimate) |
| Melting Point | 182-185°C |
| Boling Point | 581.6±50.0 °C(Predicted) |
| Flash Point | 305.6°C |
| Water Solubility | Soluble in water, methanol, ethanol. |
| Solubility | DMSO 71 mg/mL;Water <1 mg/mL;Ethanol 9 mg/mL. Slightly soluble in ethanol, acetone, ethyl acetate or chloroform, hardly soluble in methanol, insoluble in water |
| Vapor Presure | 2.27E-14mmHg at 25°C |
| Appearance | Yellow solid |
| Color | Light yellow to Brown |
| Maximum wavelength(λmax) | ['327nm(0.05mol/L methanolic HCl)(lit.)'] |
| Merck | 14,8982 |
| pKa | pKa (25°) 4.7 |
| Storage Condition | Sealed in dry,Store in freezer, under -20°C |
| Refractive Index | 1.672 |
| MDL | MFCD00599589 |
| Physical and Chemical Properties | Yellow crystal, odorless and tasteless. Deliquescence. Slightly soluble in ethanol, acetone, ethyl acetate or chloroform, difficult to dissolve in methanol. When the pH value is less than 4.5, it is not soluble in water. The solubility increases with the increase of pH value, and at pH 7, it is about 3.0mg/ml. Melting point 182~185 °c (decomposition). UV maximum absorption (0.1mol/L hydrogen chloride in methanol):327,285,256,226nm(E1 cm175,420,410,540). pKa(25 degrees C) 4.7. |
| Use | Used as anti-inflammatory analgesics, for rheumatic, rheumatoid arthritis, acute gout |
| In vitro study | In two colon cancer and other cell lines, Sulindac and its metabolites sulindacsulfide and sulindacsulfone also inhibit the NF-κB pathway due to Sulindac-mediated reduction of IKK beta kinase activity. Sulindac sulfide significantly reduced the number of cells by about 4-fold in both overgrown and undergrown HT-29 cells. Sulindac sulfid inhibits the growth of a variety of tumor cell lines derived from other tissues, as well as normal epithelial cells and fibroblasts. In CRC cell lines DLD1 and SW480, Sulindac sulfide inhibits beta-catenin/TCF-mediated gene transcription and reduces the level of non-phosphorylated beta-catenin. |
| In vivo study | In the murine model of familial adenomatous polyposis, Sulindac not only inhibits tumor formation, but also reduces small intestinal COX-2 and prostaglandin E(2) to baseline levels, restoring normal levels of apoptosis. In Min/mouse intestinal tissue, Sulindac not only reduced the number of tumors by 95%, but did not change the levels of PGE 2 and LTB 4. In Min/mouse intestinal tissue, Sulindac reduced tumor numbers by 82%, while arachidic acid levels remained elevated. In Min/mouse intestinal tissue, Sulindac caused 70-80% regression within 4 days, but did not have the same effect on colon lesions. |
Sulindac sulfoxide - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R22 - Harmful if swallowed R63 - Possible risk of harm to the unborn child R42/43 - May cause sensitization by inhalation and skin contact. |
| UN IDs | 3249 |
| WGK Germany | 3 |
| RTECS | NK8226000 |
| HS Code | 29309090 |
| Hazard Class | 6.1(b) |
| Packing Group | III |
Sulindac sulfoxide - Reference
| Reference Show more | 1. Wang Yian, Fu Yuxin, Li Haowen, etc. Preparation of sulindac nanosuspension and its anti-tumor effect in vitro and in vivo [J]. Modern medicine and clinic, 2020, 000(001): p. 16-21. 2. [IF = 3.535] Hui Jiang et al."Determination of lipid-water partition coefficient of neutral and ionic drugs by lipid chromatography." Electrophoresis. 2021 Aug;42(14-15):1436-1449 |
Sulindac sulfoxide - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| overview | sulindac (Sulindac) is an effective non-steroidal anti-inflammatory drug for the treatment of colon polyposis. From a structural point of view, sulindac is a sulfoxide drug. It has no efficacy for rheumatic and rheumatoid arthritis, but it can be converted by liver enzymes into sulfides that inhibit the synthesis of prostaglandins, and it can also be metabolized in the body. It is converted into sulfone compounds that can treat colon polyps and inhibit early cancer deterioration. Sulindac is a very small active precursor drug, which is metabolized into active sulfide after entering the human body. It can inhibit cyclooxygenase and reduce the synthesis of prostaglandins, thereby having analgesic, anti-inflammatory and antipyretic effects. |
| biological activity | Sulindac is a non-steroidal COX inhibitor, which effectively inhibits the synthesis of prostaglandins and is used to treat acute or chronic inflammation. |
| Target | Value |
| use | approved by FDA in 1978. As a prodrug, it does not have anti-inflammatory and analgesic activity, but has an effect on oral absorption and conversion into metabolic sulfide. Used for rheumatoid arthritis, arm and knee arthritis, ankylosing spondylitis, bursitis, acute gout, etc. used as anti-inflammatory analgesic, used for rheumatism, rheumatoid arthritis, acute gout, etc. |
| Production method | Method 1: 4-nitrophthalic acid is hydrogenated and reduced to 4-aminophthalic acid, and the Sehiernann reaction produces 4-fluoro-phthalic acid, which is esterified to diethyl 4-fluoro-phthalate, and ethyl propionate is condensed and cyclized under the action of sodium to form dihydroindene, which reacts with organic phosphine compound and introduces methyl acetate at the 3 position, then it performs a Grigne reaction with p-methylsulfinyl benzyl bromide, and finally hydrolyzes desulinic acid. Method 2: 5-fluoro-2-methyl-3-oxo-2, 3-dihydro-1H-indene was used as raw material, first condensed with 2-cyanoacetic acid, and then acetic acid was introduced at the 3 position. Then it is condensed with p-methylthio benzaldehyde, and finally oxidized to desulinac acid. Method 3: Similar to Method 2, only the sequence of side chain introduction is different. Method 4: 5-fluoro-2-methyl-1-oxo-2, 3-dihydro-Lh-indene and p-methylthiobenzyl chloride were subjected to a Grignite reaction, introducing p-methylthiobenzyl at the 1 position, then dehydrating in acid, forming a double bond at the 1 and 2 positions, then reacting with glyoxylic acid, introducing acetic acid at the 3 position, oxidizing with hydrogen peroxide, and finally acidification to shift the double bond to obtain sulindic acid. |
Last Update：2024-04-09 02:00:08
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