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38194-50-2 molecular structure
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2-{5-fluoro-1-[(4-methanesulfinylphenyl)methylidene]-2-methyl-1H-inden-3-yl}acetic acid

ChemBase ID: 487
Molecular Formular: C20H17FO3S
Molecular Mass: 356.4105832
Monoisotopic Mass: 356.08824362
SMILES and InChIs

SMILES:
S(=O)(c1ccc(C=C2C(=C(c3c2ccc(F)c3)CC(=O)O)C)cc1)C
Canonical SMILES:
OC(=O)CC1=C(C)C(=Cc2ccc(cc2)S(=O)C)c2c1cc(F)cc2
InChI:
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)
InChIKey:
MLKXDPUZXIRXEP-UHFFFAOYSA-N

Cite this record

CBID:487 http://www.chembase.cn/molecule-487.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-{5-fluoro-1-[(4-methanesulfinylphenyl)methylidene]-2-methyl-1H-inden-3-yl}acetic acid
2-[(1Z)-5-fluoro-1-[(4-methanesulfinylphenyl)methylidene]-2-methyl-1H-inden-3-yl]acetic acid
IUPAC Traditional name
sulindac
Brand Name
Clinoril
Synonyms
Sulindac
Clinoril
Aflodac
Sulreuma
(Z)-2-(5-fluoro-2-methyl-1-(4-(methylsulfinyl)benzylidene)-1H-inden-3-yl)acetic acid
Sulindac
Z-5-Fluoro-2-methyl-1-[p-(methlsulfinyl)benzylidene]indene-3-acetic acid
MK-231
(1Z)-5-Fluoro-2-methyl-1-[(4-(methylsulfinyl)phenyl]methylene]-1H-indene-3-acetic Acid
cis-5-Fluoro-2-methyl-1-[(p-methylsulfinyl)benzylidenyl]indene-3-acetic Acid
Algocetil
Arthrocine
Artribid
Citireuma
Clisundac
Imbaral
MK 231
Mobilin
Reumofil
Reumyl
Sudac
Sulindac
Sulindac sulfoxide
Sulinol
cis-Sulindac
(Z)-5-氟-2-甲基-1-[4-(甲亚硫酰苯基)亚甲基]-1H-茚-3-醋酸
舒林酸
CAS Number
38194-50-2
EC Number
253-819-2
MDL Number
MFCD00599589
PubChem SID
24899604
24277737
160963950
PubChem CID
5352

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 4.090206  H Acceptors
H Donor LogD (pH = 5.5) 1.5030619 
LogD (pH = 7.4) -0.17891507  Log P 2.9261546 
Molar Refractivity 99.5588 cm3 Polarizability 37.41637 Å3
Polar Surface Area 54.37 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.96  LOG S -4.15 
Solubility (Water) 2.51e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
Pactically insoluble in water below pH 4.5, but very soluble as the sodium salt or in buffers of pH 6 or higher (3000 mg/L). expand Show data source
Apperance
Yellowish Orange Solid expand Show data source
Melting Point
182-185°C expand Show data source
Hydrophobicity(logP)
3.5 expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer expand Show data source
Room Temperature (15-30°C) expand Show data source
RTECS
NK8226000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
UN Number
2811 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
3 expand Show data source
Risk Statements
63-22-42/43 expand Show data source
R:22 expand Show data source
Safety Statements
S:36/37/39 expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H301-H317-H334-H361 expand Show data source
GHS Precautionary statements
P261-P280-P301 + P310-P342 + P311 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand Show data source
RID/ADR
UN 2811 6.1/PG 3 expand Show data source
Gene Information
human ... ALB(213) expand Show data source
human ... ALB(213), PTGS2(5743) expand Show data source
Purity
≥99% expand Show data source
≥98.0% expand Show data source
95+% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Suitability
meets USP testing specifications expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals InterBioScreen InterBioScreen Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02195864 external link
Purity: >99%
Non-steroidal anti-inflammatory which inhibits cyclooxygenase and prostaglandin synthesis. Causes adenoma regression by apoptotic mechanism and induces apoptosis in HT-29 cells at levels which affect cell proliferation, morphology and cell phase distribution.
DrugBank - DB00605 external link
Item Information
Drug Groups approved
Description Sulindac is a nonsteroidal anti-inflammatory agent (NSAIA) of the arylalkanoic acid class that is marketed in the U.S. by Merck as Clinoril. Like other NSAIAs, it may be used in the treatment of acute or chronic inflammatory conditions. Sulindac is a prodrug, derived from sulfinylindene, that is converted in vivo to an active sulfide compound by liver enzymes. The sulfide metabolite then undergoes enterohepatic circulation; it is excreted in the bile and then reabsorbed from the intestine. This is thought to help maintain constant blood levels with reduced gastrointestinal side effects. Some studies have shown sulindac to be relatively less irritating to the stomach than other NSAIA's except for drugs of the cyclooxygenase-2 (COX-2) inhibitor class. The exact mechanism of its NSAIA properties is unknown, but it is thought to act on enzymes COX-1 and COX-2, inhibiting prostaglandin synthesis.
Indication For acute or long-term use in the relief of signs and symptoms of osteoarthritis, rheumatoid arthritis, ankylosing spondylitis, acute painful shoulder (acute subacromial bursitis/supraspinatus tendinitis), and acute gouty arthritis.
Pharmacology Sulindac is a non-steroidal anti-inflammatory indene derivative, also possessing analgesic and antipyretic activities.
Toxicity Acute oral toxicity (LD50) in rats is 264 mg/kg. Cases of overdose have been reported and rarely, deaths have occurred. The following signs and symptoms may be observed following overdose: stupor, coma, diminished urine output and hypotension.
Affected Organisms
Humans and other mammals
Biotransformation Undergoes two major biotransformations: reversible reduction to the sulfide metabolite, and irreversible oxidation to the sulfone metabolite. Sulindac and its sulfide and sulfone metabolites undergo extensive enterohepatic circulation. Available evidence indicates that the biological activity resides with the sulfide metabolite. Side chain hydroxylation and hydration of the double bond also occur.
Absorption Approximately 90% absorbed in humans following oral administration.
Half Life The mean half-life of sulindac is 7.8 hours while the mean half-life of the sulfide metabolite is 16.4 hours.
Protein Binding At 1 mcg/ml concentrations, approximately 93% sulindac and 98% of its sulfide metabolite are bound to human serum albumin.
Elimination Sulindac is excreted in rat milk; concentrations in milk were 10 to 20% of those levels in plasma. It is not known if sulindac is excreted in human milk. Approximately 50% of the administered dose of sulindac is excreted in the urine with the conjugated sulfone metabolite accounting for the major portion. Hepatic metabolism is an important elimination pathway.
Clearance * Renal cl=68.12 +/- 27.56 mL/min [NORMAL (19-41 yrs)]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Selleck Chemicals - S2007 external link
Research Area: Neurological Disease
Biological Activity:
Sulindac (Clinoril) is a non-steroidal anti-inflammatory drug of the arylalkanoic acid class. Like other NSAIDs, it is useful in the treatment of acute or chronic inflammatory conditions. Sulindac is a prodrug, derived from sulfinylindene that is converted in the body to an active NSAID. More specifically, the agent is converted by liver enzymes to a sulfide which is excreted in the bile and then reabsorbed from the intestine. This is thought to help maintain constant blood levels with reduced gastrointestinal side effects. [1]
Sigma Aldrich - S8139 external link
Biochem/physiol Actions
非甾体抗炎药;COX-1 的选择性抑制剂。
Application
Treatment of human colorectal cancer cell lines induces MRP1 and MRP3 but not other members of the MRP family. Reported to significantly increase the cytotoxicity of the anthracyclines (doxorubicin, daunorubicin and epirubicin), as well as teniposide, VP-16 and vincristine.
Sigma Aldrich - S4429 external link
Biochem/physiol Actions
非甾体抗炎药;COX-1 的选择性抑制剂。
Toronto Research Chemicals - S699215 external link
Sulindac is a non-steroidal anti-inflammatory drug.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • http://www.drugbank.ca/drugs/DB00605
  • • Bjorkman., et al.: Am. J. Med., 105, 17S (1998)
  • • Thakur, et al.: Am. J. Hypertens., 12, 925 (1998)
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PATENTS

PATENTS

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INTERNET

INTERNET

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