Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H17FO3S |
Molecular Weight | 356.411 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[S@+]([O-])C1=CC=C(\C=C2/C(C)=C(CC(O)=O)C3=C2C=CC(F)=C3)C=C1
InChI
InChIKey=MLKXDPUZXIRXEP-HCQJPZKZSA-N
InChI=1S/C20H17FO3S/c1-12-17(9-13-3-6-15(7-4-13)25(2)24)16-8-5-14(21)10-19(16)18(12)11-20(22)23/h3-10H,11H2,1-2H3,(H,22,23)/b17-9+/t25-/m0/s1
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/21383205Curator's Comment: The description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/017911s073lbl.pdf
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21383205
Curator's Comment: The description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/017911s073lbl.pdf
(S)-Sulindac is the (S)-enantiomer of nonsteroidal anti-inflammatory drug (NSAID) Sulindac, that is marketed in the U.S. by Merck as Clinoril. Sulindac is a prodrug, derived from sulfinyl-indene, that is converted in vivo to an active sulfide compound by liver methionine sulfoxide reductases (Msr). The (Msr) family of enzymes includes two major classes, MsrA and MsrB, that specifically reduce the S- and R-epimers of Sulindac. Reduction of (S)-Sulindac to Sulindac Sulfide catalyzed by methionine sulfoxide reductase (Msr)-A. The oxidation of both epimers to sulindac sulfone is catalyzed primarily by the microsomal cytochrome P450 (P450) system. (S)-Sulindac increases the activity of the P450 system better than (R)-sulindac, but both epimers increase primarily the enzymes that oxidize (R)-sulindac. Both epimers can protect normal lung cells against oxidative damage and enhance the killing of lung cancer cells exposed to oxidative stress.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2094253 |
0.02 µM [EC50] | ||
Target ID: Q9UJ68 Gene ID: 4482.0 Gene Symbol: MSRA Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/21383205 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | SULINDAC Approved UseCLINORIL is indicated for acute or long-term use in the relief of signs and symptoms of the following:
1. Osteoarthritis
2. Rheumatoid arthritis**
3. Ankylosing spondylitis
4. Acute painful shoulder (Acute subacromial bursitis/supraspinatus tendinitis)
5. Acute gouty arthritis Launch Date1988 |
|||
Primary | SULINDAC Approved UseCLINORIL is indicated for acute or long-term use in the relief of signs and symptoms of the following:
1. Osteoarthritis
2. Rheumatoid arthritis**
3. Ankylosing spondylitis
4. Acute painful shoulder (Acute subacromial bursitis/supraspinatus tendinitis)
5. Acute gouty arthritis Launch Date1988 |
|||
Primary | SULINDAC Approved UseCLINORIL is indicated for acute or long-term use in the relief of signs and symptoms of the following:
1. Osteoarthritis
2. Rheumatoid arthritis**
3. Ankylosing spondylitis
4. Acute painful shoulder (Acute subacromial bursitis/supraspinatus tendinitis)
5. Acute gouty arthritis Launch Date1988 |
Sample Use Guides
CLINORIL (Sulindac) should be administered orally twice a day with food. The maximum dosage is 400 mg per day. Dosages above 400 mg per day are not recommended. In osteoarthritis, rheumatoid arthritis, and ankylosing spondylitis, the recommended starting dosage is 150 mg twice a day. The dosage may be lowered or raised depending on the response.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21383205
Fresh rat liver was minced and then homogenized using 5 strokes in a Potter-Elvehjem homogenizer with 3 volumes of 50 mM Tris-Cl, pH 7.4. The homogenate was centrifuged for 15 min at 10,000g, the pellet was discarded, and the supernatant was spun at 100,000g for 2 h to obtain crude microsomes. The microsomes were washed by resuspension in 3 volumes of the above buffer and centrifugation at 100,000g for 1 h. The microsomal pellet was finally resuspended in 3 volumes of the above buffer, aliquoted, and frozen at -80°C. The protein concentration was 25 mg/ml. In a total volume of 100 mkl, 20 nmol of each sulindac epimer were incubated with 20 to 80 mkg of microsomes and a NADPH-regenerating system (1.5 mM NADPH, 5 mM glucose 6-phosphate, 150 ng of glucose-6-phosphate dehydrogenase, and 5 mM MgCl2) in potassium phosphate buffer (pH 7.4, 100 mM) for 60 min at 37°C. The reaction was then stopped with 3 volumes of acetonitrile and centrifuged. The supernatant was fractionated by HPLC as described above.
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RM8X801977
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11865478
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1316775-70-8
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SUBSTANCE RECORD