Sulindac

Base Information

• Chemical Name: Sulindac
• CAS No.: 38194-50-2
• Deprecated CAS: 49627-22-7
• Molecular Formula: C20H17FO3S
• Molecular Weight: 356.418
• Hs Code.: 29309090
• European Community (EC) Number: 250-893-8,232-527-9,253-819-2
• NSC Number: 757344
• UNII: 184SNS8VUH
• DSSTox Substance ID: DTXSID4023624
• Nikkaji Number: J3.501G
• Wikipedia: Sulindac
• Wikidata: Q963093
• NCI Thesaurus Code: C850
• RXCUI: 10237
• Pharos Ligand ID: CLRLMAWF3NSM
• Metabolomics Workbench ID: 42934
• ChEMBL ID: CHEMBL15770
• Mol file: 38194-50-2.mol

Synonyms:Aclin;Apo Sulin;Apo-Sulin;Arthrobid;Arthrocine;Chibret;Clinoril;Copal;Kenalin;Klinoril;MK 231;MK-231;MK231;Novo Sundac;Novo-Sundac;Nu Sulindac;Nu-Sulindac;Sulindac;Sulindal

Chemical Property of Sulindac

Chemical Property:

• Appearance/Colour: yellow crystalline solid
• Vapor Pressure: 2.27E-14mmHg at 25°C
• Melting Point: 182-185 °C
• Refractive Index: 1.672
• Boiling Point: 581.6 °C at 760 mmHg
• PKA: pKa (25°) 4.7
• Flash Point: 305.6 °C
• PSA: 73.58000
• Density: 1.38 g/cm³
• LogP: 5.23120
• Storage Temp.: Store at RT
• Solubility.: Very slightly soluble in water, soluble in methylene chloride, sparingly soluble in ethanol (96 per cent). It dissolves in dilute solutions of alkali hydroxides.
• Water Solubility.: Soluble in water, methanol, ethanol.
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 356.08824374
• Heavy Atom Count: 25
• Complexity: 616

Purity/Quality:

99%, ^*data from raw suppliers

Sulindac ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-63-42/43
• Safety Statements: -

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: UVCB
• Drug Classes: Nonsteroidal Antiinflammatory Drugs
• Canonical SMILES: CC1=C(C2=C(C1=CC3=CC=C(C=C3)S(=O)C)C=CC(=C2)F)CC(=O)O
• Isomeric SMILES: CC\1=C(C2=C(/C1=C\C3=CC=C(C=C3)S(=O)C)C=CC(=C2)F)CC(=O)O
• Recent ClinicalTrials: The Prevention of Progression to Pancreatic Cancer Trial (The 3P-C Trial)
• Recent EU Clinical Trials: The intestinal disposition of sulindac in healthy volunteers
• Recent NIPH Clinical Trials: A randomized, double-blind, placebo-controlled trial for evaluating of suppressive effect of sulindac on branch duct type Intraductal papillary mucinous neoplasms
• Description: Many non-steroidal anti-inflammatory drugs (NSAIDs) are potent but non-selective inhibitors of both COX-1 and COX-2 in humans. Sulindac is one of the older NSAIDs, an isostere of indomethacin developed before the inducible form of COX-2 was discovered. Although a number of NSAIDs have been found to protect against digestive tract cancers, sulindac has an extensive epidemiology documenting reduced human colorectal cancer. In murine models, sulindac was found not only to inhibit the enzymatic activity of polyp-associated COX-2, but also to downregulate the expression of colonic COX-2 protein to control levels.
• Uses: Sulindac is used for relieving weak to moderate pain in rheumatoid arthritis and osteoarthritis. A non-steroidal anti-inflammatory agent. An anti-inflammatory Sulindac is a non-steroidal anti-inflammatory drug.
• Indications: Sulindac (Clinoril) is chemically related to indomethacin and is generally used for the same indications. It is a prodrug that is metabolized to an active sulfide metabolite and an inactive metabolite. The most frequently reported side effects are GI pain, nausea, diarrhea, and constipation. The incidence of these effects is lower than for indomethacin, presumably because sulindac is a prodrug and thus the active metabolite is not highly concentrated at the gastric mucosa. As with indomethacin, a rather high incidence of CNS side effects (dizziness, headache) also occurs.
• Therapeutic Function: Antiinflammatory
• Clinical Use: Sulindac is indicated for long-term use in the treatment of rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, and acute gouty arthritis. The usual maximum dosage is 400 mg/day, with starting doses recommended at 150 mg twice a day. It is recommended that sulindac be administered with food.
• Drug interactions: Potentially hazardous interactions with other drugs ACE inhibitors and angiotensin-II antagonists: antagonism of hypotensive effect; increased risk of nephrotoxicity and hyperkalaemia. Analgesics: avoid concomitant use of 2 or more NSAIDs, including aspirin (increased side effects); avoid with ketorolac (increased risk of side effects and haemorrhage). Antibacterials: possibly increased risk of convulsions with quinolones. Anticoagulants: effects of coumarins and phenindione enhanced; possibly increased risk of bleeding with heparins, dabigatran and edoxaban - avoid long term use with edoxaban. Antidepressants: increased risk of bleeding with SSRIs and venlaflaxine. Antidiabetic agents: effects of sulphonylureas enhanced. Antiepileptics: possibly increased phenytoin concentration. Antivirals: increased risk of haematological toxicity with zidovudine; concentration possibly increased by ritonavir. Ciclosporin: may potentiate nephrotoxicity. Cytotoxics: reduced excretion of methotrexate; increased risk of bleeding with erlotinib. Dimethyl sulfoxide: avoid concomitant use. Diuretics: increased risk of nephrotoxicity; antagonism of diuretic effect; hyperkalaemia with potassium-sparing diuretics. Lithium: excretion decreased. Pentoxifylline: increased risk of bleeding. Tacrolimus: increased risk of nephrotoxicity.

Technology Process of Sulindac

There total 15 articles about Sulindac which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.9%

5-fluoro-2-methyl-1-(4-methylsulfanylbenzylidene)-3-indenylacetic acid (49627-27-2,61812-45-1,32004-67-4) → Sulindac (38194-50-2)

Guidance literature:

With peracetic acid; hydrazine; In toluene; at 10 ℃; for 12h; Solvent; Temperature; Reagent/catalyst; UV-irradiation;

Reference yield: 94.0%

5-fluoro-2-methyl-1-(4-methylsulfanylbenzylidene)-3-indenylacetic acid (49627-27-2,61812-45-1,32004-67-4) → 2-(5-fluoro-2-methyl-1-(4-(methylsulfinyl)benzylidene)-1H-inden-3-yl)acetic acid (38194-50-2,49627-22-7,53933-60-1,61812-46-2,149116-77-8,32004-68-5)

Guidance literature:

With oxygen; In methanol; water; at 20 ℃; for 13h; Irradiation; Green chemistry;

DOI:10.1039/d1gc02733f

Reference yield: 92.3%

5-fluoro-2-methyl-1-(4-methylthiobenzylidene)-3-indeneacetonitrile → Sulindac (38194-50-2)

Guidance literature:

With water; Mo₃WTe₈; acetic acid; at 80 ℃; for 2h; Reagent/catalyst; Irradiation;

upstream raw materials:

Glyoxilic acid

(+/-)-6-Fluoro-3-(4-methanesulfinylbenzyl)-2-methyl-1H-indene

6-Fluoro-2-methyl-3-(p-methylthiobenzyl)-1H-indene

sulindac sulfide

Downstream raw materials:

(Z)-N-benzyl-2-(5-fluoro-2-methyl-1-(4-(methylsulfinyl)benzylidene)-1H-inden-3-yl)acetamide

Refernces

• 1、 Xie, Gang,Cheng, Ka-Wing,Huang, Liqun,Rigas, Basil. "The in vitro metabolism of phospho-sulindac amide, a novel potential anticancer agent". . p. 249 - 255. Retrieved 2014.
• 2、 Ma, Lina,Zhou, Hua,Xu, Ming,Hao, Peipei,Kong, Xianggui,Duan, Haohong. "Integrating hydrogen production with anodic selective oxidation of sulfides over a CoFe layered double hydroxide electrode". . p. 938 - 945. Retrieved 2021/02/06.
• 3、 Fan, Qiangwen,Zhu, Longwei,Li, Xuhuai,Ren, Huijun,Wu, Guorong,Zhu, Haibo,Sun, Wuji. "Catalyst-free visible light-mediated selective oxidation of sulfides into sulfoxides under clean conditions". supporting information. p. 7945 - 7949. Retrieved 2021/11/01.