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38194-50-2

Basic Information
CAS No.: 38194-50-2
Name: 1H-Indene-3-aceticacid, 5-fluoro-2-methyl-1-[[4-(methylsulfinyl)phenyl]methylene]-, (1Z)-
Molecular Structure:
Molecular Structure of 38194-50-2 (1H-Indene-3-aceticacid, 5-fluoro-2-methyl-1-[[4-(methylsulfinyl)phenyl]methylene]-, (1Z)-)
Formula: C20H17FO3S
Molecular Weight: 356.42
Synonyms: 1H-Indene-3-aceticacid, 5-fluoro-2-methyl-1-[[4-(methylsulfinyl)phenyl]methylene]-, (Z)-;(Z)-5-Fluoro-2-methyl-1-[p-(methylsulfinyl)benzylidene]indene-3-acetic acid;Aflodac;Arthrocine;Artribid;Clinoril;Clisundac;Imbaral;MK 231;Mobilin;Reumofil;Reumyl;Sudac;
EINECS: 253-819-2
Density: 1.38 g/cm3
Melting Point: 182-185 °C
Boiling Point: 581.6 °C at 760 mmHg
Flash Point: 305.6 °C
Solubility: Soluble in water, methanol, ethanol.
Appearance: yellow crystalline solid
Hazard Symbols: HarmfulXn
Risk Codes: 22-63-42/43
Safety: -
Transport Information: UN 3249
PSA: 73.58000
LogP: 5.23120
Downstream Products
2387-23-7
59973-80-7
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  • Sulindac

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    Sulindac

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  • 1H-Indene-3-aceticacid, 5-fluoro-2-methyl-1-[[4-(methylsulfinyl)phenyl]methylene]-, (1Z)-

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    1H-Indene-3-aceticacid, 5-fluoro-2-methyl-1-[[4-(methylsulfinyl)phenyl]methylene]-, (1Z)-

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  • Sulindac

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    Sulindac

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Specification

The CAS registry number of Sulindac is 38194-50-2. The IUPAC name is 2-[(3Z)-6-fluoro-2-methyl-3-[(4-methylsulfinylphenyl)methylidene]inden-1-yl]acetic acid. In addition, the molecular formula is C20H17FO3S. What's more, it is a non-steroidal anti-inflammatory drug which is derived from sulfinylindene. It is useful in the treatment of acute or chronic inflammatory conditions.

Physical properties about this chemical are: (1)ACD/LogP: 3.59; (2)ACD/LogD (pH 5.5): 2.33; (3)ACD/LogD (pH 7.4): 0.55; (4)ACD/BCF (pH 5.5): 17.3; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 117.35; (7)ACD/KOC (pH 7.4): 1.94; (8)#H bond acceptors: 3; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 4; (11)Polar Surface Area: 62.58 Å2; (12)Index of Refraction: 1.672; (13)Molar Refractivity: 96.22 cm3; (14)Molar Volume: 256.7 cm3; (15)Polarizability: 38.14 ×10-24cm3; (16)Surface Tension: 65.9 dyne/cm; (17)Density: 1.38 g/cm3; (18)Flash Point: 305.6 °C; (19)Enthalpy of Vaporization: 91.48 kJ/mol; (20)Boiling Point: 581.6 °C at 760 mmHg; (21)Vapour Pressure: 2.27E-14 mmHg at 25°C.

Preparation of Sulindac: At first, 5-fluorine-2-methyl-3-oxo-2,3-dihydro-1H-indene can react with 2-nitrilylacetic acid to give a product(Ⅰ) through condensation reaction. Then the Sulindac can be prepared by reacting product(Ⅰ) with p-methylthiobenzaldehyde through condensation and oxidation reaction.

Sulindac can can be prepared by reacting product(Ⅰ) reacts with p-methylthiobenzaldehyde through condensation and oxidation reaction

Uses of Sulindac: it may be used in the treatment of preterm labor. In addition, it can react with N-hydroxy-succinimide to get [6-fluoro-3-(4-methanesulfinyl-benzylidene)-2-methyl-3H-inden-1-yl]-acetic acid 2,5-dioxo-pyrrolidin-1-yl ester. This reaction will need reagent DCC and solvent tetrahydrofuran. The reaction time is 1 hour at reaction temperature of 0 °C. The yield is about 35%.

Sulindac can react with N-hydroxy-succinimide to get [6-fluoro-3-(4-methanesulfinyl-benzylidene)-2-methyl-3H-inden-1-yl]-acetic acid 2,5-dioxo-pyrrolidin-1-yl ester

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful if swallowed. And it may cause sensitization by inhalation and skin contact. Moreover, it may has risk of harm to the unborn child. Besides, it should not be used by persons with a history of major allergic reactions (urticaria or anaphylaxis).

You can still convert the following datas into molecular structure:
(1)SMILES: O=S(c1ccc(cc1)\C=C3/c2ccc(F)cc2\C(=C3C)CC(=O)O)C
(2)InChI: InChI=1/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-
(3)InChIKey: MLKXDPUZXIRXEP-MFOYZWKCBF

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
infant LDLo oral 12mg/kg/2D-I (12mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH

BLOOD: HEMORRHAGE
Acta Paediatrica. Vol. 85, Pg. 884, 1996.
man TDLo oral 34mg/kg/6D-I (34mg/kg)   Journal of Rheumatology. Vol. 13, Pg. 1084, 1986.
man TDLo oral 43mg/kg/10D-I (43mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

LIVER: LIVER FUNCTION TESTS IMPAIRED

BLOOD: LEUKOPENIA
JAMA, Journal of the American Medical Association. Vol. 244, Pg. 269, 1980.
man TDLo oral 343mg/kg (343mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

BLOOD: "CHANGES IN SERUM COMPOSITION (E.G., TP, BILIRUBIN, CHOLESTEROL)"
Journal of Toxicology, Clinical Toxicology. Vol. 33, Pg. 173, 1995.
mouse LD50 intraperitoneal 305mg/kg (305mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 13, Pg. 637, 1982.
mouse LD50 oral 507mg/kg (507mg/kg)   Drugs in Japan Vol. 6, Pg. APP-6, 1982.
mouse LD50 subcutaneous 398mg/kg (398mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 13, Pg. 637, 1982.
rat LD50 intraperitoneal 289mg/kg (289mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 13, Pg. 637, 1982.
rat LD50 oral 264mg/kg (264mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 30, Pg. 1398, 1980.
rat LD50 subcutaneous 336mg/kg (336mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 13, Pg. 637, 1982.
women LDLo oral 112mg/kg/2W-I (112mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE"
Journal of Rheumatology. Vol. 10, Pg. 512, 1983.
women TDLo oral 8mg/kg/10H-I (8mg/kg) BEHAVIORAL: ANOREXIA (HUMAN

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Journal of Clinical Gastroenterology. Vol. 8, Pg. 569, 1986.