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Indometacin
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Name

Indometacin

 EINECS 200-186-5
CAS No. 53-86-1 Density 1.327 g/cm3
PSA 68.53000 LogP 3.92730
Solubility ethanol: 50 mg/mL Melting Point 155-162 °C
Formula C19H16ClNO4 Boiling Point 499.363 °C at 760 mmHg
Molecular Weight 357.793 Flash Point 255.806 °C
Transport Information UN 2811 6.1/PG 1 Appearance White crystalline powder
Safety 28-36/37-45-26 Risk Codes 28-36/37/38
Molecular Structure Molecular Structure of 53-86-1 (Indometacin) Hazard Symbols VeryT+, IrritantXi
Synonyms

Indole-3-aceticacid, 1-(p-chlorobenzoyl)-5-methoxy-2-methyl- (8CI);1-(4-Chlorobenzoyl)-2-methyl-5-methoxyindole-3-acetic acid;1-(p-Chlorobenzoyl)-5-methoxy-2-methylindole-3-acetic acid;Amuno;Chrono-Indocid 75;Confortid;Dolovin;Elmetacin;Flam;Indo-Rectolmin;Indo-Tablinen;IndoRich;Indocid;Indocid(pharmaceutical);Indomecol;Indomee;Indomethine;Indomod;Indoptic;Indoptol;Infrocin;Innamit;Mezolin;Mikametan;Mobilan;NSC 77541;Tannex;Vonum;a-[1-(p-Chlorobenzoyl)-2-methyl-5-methoxy-3-indolyl]aceticacid;

Article Data 106

Indometacin Synthetic route

16401-99-3

indomethacin ethyl ester

53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Conditions
ConditionsYield
With sodium hydroxide In methanol; water for 1h; Reflux;99%
With lithium hydroxide monohydrate In water at 25℃; for 6h;657 mg
2882-15-7

5-Methoxy-2-methylindole-3-acetic acid

122-01-0

4-chloro-benzoyl chloride

53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Conditions
ConditionsYield
Stage #1: 5-Methoxy-2-methylindole-3-acetic acid With potassium tert-butylate In tetrahydrofuran at -78℃; for 1h; Large scale;
Stage #2: 4-chloro-benzoyl chloride In tetrahydrofuran at 20℃; for 16h; Large scale;		97%
Stage #1: 5-Methoxy-2-methylindole-3-acetic acid With potassium tert-butylate In tetrahydrofuran at -78℃; for 1h;
Stage #2: 4-chloro-benzoyl chloride In tetrahydrofuran at 20℃; for 16h;		95%
With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hexamethylsilazane 1.) THF; Multistep reaction;
122-01-0

4-chloro-benzoyl chloride

17536-38-8

ethyl 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetate

53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Conditions
ConditionsYield
Stage #1: ethyl 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetate With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.333333h; Inert atmosphere;
Stage #2: 4-chloro-benzoyl chloride In tetrahydrofuran at 25℃; for 10h; Inert atmosphere;
Stage #3: With lithium hydroxide monohydrate; water In tetrahydrofuran at 25℃; for 6h; Inert atmosphere;		92%
24438-49-1

<1-(4-chlorobenzoyl)-2-methyl-5-methoxyindol-3-yl>acetaldehyde

53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Conditions
ConditionsYield
With N-hydroxyphthalimide; oxygen In acetonitrile at 80℃; for 30h; Schlenk technique;91%
With N-hydroxyphthalimide; oxygen In acetonitrile at 30℃; under 760.051 Torr; for 3h; Schlenk technique;91%
With sodium chlorite; sodium dihydrogenphosphate In tetrahydrofuran; water; tert-butyl alcohol at 20℃; for 0.5h; Schlenk technique;78%
With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene In tetrahydrofuran; water; tert-butyl alcohol at 20℃; for 0.5h;28.4 mg
26001-79-6

2-{1-[(4-chlorophenyl)carbonyl]-5-methoxy-2-methyl-1H-indol-3-yl}acetic acid benzyl ester

53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 0.666667h;84%
With palladium 10% on activated carbon; hydrogen In ethyl acetate
With 10% Pd/C; hydrogen In ethyl acetate
1601-18-9

indomethacin methyl ester

53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Conditions
ConditionsYield
With pyridine; lithium iodide for 20h; Reflux;84%
Stage #1: indomethacin methyl ester With pyridine; lithium iodide for 20h; Reflux;
Stage #2: With hydrogenchloride; water at 0℃;		83%
With pyridine; lithium iodide for 20h; Reflux;83%
75302-98-6

acemetacin tert-butyl ester

A

C20H18ClNO3

B

53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Conditions
ConditionsYield
With pyridine; iodine; aluminium In acetonitrile at 80℃; for 18h; chemoselective reaction;A 20%
B 70%

sodium 2-(4-chlorobenzoyl)-2-(4-methoxyphenyl)-1-hydrazosulfonate

123-76-2

levulinic acid

53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Conditions
ConditionsYield
With formic acid In acetic acid for 6h; Heating;66%
75302-98-6

acemetacin tert-butyl ester

A

53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

B

53164-05-9

acemetacin

Conditions
ConditionsYield
With iodine; aluminium In acetonitrile at 20℃; for 6h; chemoselective reaction;A 30%
B 66%
591-12-8

5-methyl-2-furanone

16390-07-1

N1-(4-chlorobenzoyl)-4-methoxyphenylhydrazine

A

2882-15-7

5-Methoxy-2-methylindole-3-acetic acid

B

53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Conditions
ConditionsYield
With sulfuric acid In acetonitrile for 24h; Fischer indole reaction; Heating;A n/a
B 65%

Indometacin Chemical Properties

Molecular Structure:

Molecular Formula: C19H16ClNO4
Molecular Weight: 357.7876
IUPAC Name: 2-[1-(4-Chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
CAS NO: 53-86-1
Classification Code: Analgesics ; Analgesics, Non-Narcotic; Anti-Inflammatory Agents; Anti-inflammatory; Anti-inflammatory agents, non-steroidal; Antirheumatic Agents; Cardiovascular Agents; Cyclooxygenase inhibitors; Drug / Therapeutic Agent; Enzyme Inhibitors; Gout suppressants; Human Data; Mutation data; Peripheral Nervous System Agents; Reproductive Control Agents; Reproductive Effect; Sensory System Agents; Tocolytic agents; Tumor data
Melting point: 155-162 °C 
Index of Refraction: 1.619
Molar Refractivity: 94.59 cm3
Molar Volume: 269.5 cm3
Surface Tension: 47.4 dyne/cm
Density: 1.32 g/cm3
Flash Point: 255.8 °C
Enthalpy of Vaporization: 80.85 kJ/mol
Boiling Point: 499.4 °C at 760 mmHg
Vapour Pressure: 8.61E-11 mmHg at 25 °C
EINECS of Indometacin (CAS NO.53-86-1): 200-186-5

Indometacin Uses

  Indometacin (CAS NO.53-86-1) is a non-steroidal anti-inflammatory drug commonly used to reduce fever, pain, stiffness, and swelling. It works by inhibiting the production of prostaglandins, molecules known to cause these symptoms.

Indometacin Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 oral 320mg/kg (320mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 30, Pg. 1398, 1980.
cat LDLo intravenous 20200ug/kg (20.2mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 33, Pg. 726, 1983.
dog LD50 intravenous 100mg/kg (100mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 30, Pg. 1398, 1980.
dog LD50 oral 160mg/kg (160mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 2, Pg. 70, 1968.
guinea pig LD skin > 100mg/kg (100mg/kg) BEHAVIORAL: EXCITEMENT Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 14, Pg. 3185, 1986.
guinea pig LD50 intraperitoneal 143mg/kg (143mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 30, Pg. 1398, 1980.
guinea pig LD50 intravenous 180mg/kg (180mg/kg)   Journal de Pharmacologie. Vol. 2, Pg. 259, 1971.
guinea pig LD50 oral 100mg/kg (100mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 2, Pg. 70, 1968.
hamster LD50 oral 81mg/kg (81mg/kg)   Archives of Toxicology, Supplement. Vol. 7, Pg. 365, 1984.
human TDLo oral 113mg/kg/8W-I (113mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

GASTROINTESTINAL: OTHER CHANGES		 Arzneimittel-Forschung. Drug Research. Vol. 33, Pg. 636, 1983.
infant TDLo intravenous 200ug/kg (0.2mg/kg) BLOOD: HEMORRHAGE Journal of Pediatrics. Vol. 107, Pg. 312, 1985.
infant TDLo oral 400ug/kg/2D-I (0.4mg/kg) GASTROINTESTINAL: NECROTIC GHANGES Journal of Pediatrics. Vol. 107, Pg. 484, 1985.
mammal (species unspecified) LD50 oral 8mg/kg (8mg/kg)   Indian Journal of Medical Research. Vol. 81, Pg. 621, 1985.
man LDLo oral 15mg/kg/2W-I (15mg/kg) BLOOD: APLASTIC ANEMIA Israel Journal of Medical Sciences. Vol. 17, Pg. 433, 1981.
man TDLo multiple routes 3557mg/kg/5Y- (3557mg/kg) SENSE ORGANS AND SPECIAL SENSES: "RETINAL CHANGES (PIGMENTARY DEPOSITIONS, RETINITIS, OTHER): EYE" American Journal of Ophthalmology. Vol. 73, Pg. 846, 1972.
man TDLo oral 714ug/kg (0.714mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Allergy. Vol. 54, Pg. 90, 1999.
man TDLo oral 4286ug/kg/2D- (4.286mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" Postgraduate Medical Journal. Vol. 72, Pg. 186, 1996.
man TDLo oral 22500ug/kg/3W (22.5mg/kg) LIVER: "HEPATITIS, FIBROUS (CIRRHOSIS, POST-NECROTIC SCARRING)"

LIVER: OTHER CHANGES		 British Medical Journal. Vol. 3, Pg. 155, 1967.
man TDLo oral 22500ug/kg/3W (22.5mg/kg) GASTROINTESTINAL: ULCERATION OR BLEEDING FROM LARGE INTESTINE Annals of Pharmacotherpy. Vol. 29, Pg. 883, 1994.
man TDLo rectal 2586mg/kg/3.5 (2586mg/kg) SENSE ORGANS AND SPECIAL SENSES: "RETINAL CHANGES (PIGMENTARY DEPOSITIONS, RETINITIS, OTHER): EYE" American Journal of Ophthalmology. Vol. 73, Pg. 846, 1972.
man TDLo unreported 499mg/kg/87W- (499mg/kg) BEHAVIORAL: STIFFNESS

KIDNEY, URETER, AND BLADDER: HEMATURIA		 Arthritis and Rheumatism. Vol. 20, Pg. 917, 1977.
mouse LD50 intramuscular 18200ug/kg (18.2mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 30, Pg. 1398, 1980.
mouse LD50 intraperitoneal 10mg/kg (10mg/kg)   Archivos de Farmacologia y Toxicologia. Vol. 8, Pg. 201, 1982.
mouse LD50 intravenous 30mg/kg (30mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 1198, 1969.
mouse LD50 oral 11841ug/kg (11.841mg/kg)   German Offenlegungsschrift Patent Document. Vol. #3005827,
mouse LD50 subcutaneous 18300ug/kg (18.3mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 30, Pg. 1398, 1980.
rabbit LD50 oral 135mg/kg (135mg/kg)   Drugs in Japan Vol. 6, Pg. 90, 1982.
rat LD skin > 250mg/kg (250mg/kg)   Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 14, Pg. 3185, 1986.
rat LD50 intramuscular 26300ug/kg (26.3mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 30, Pg. 1398, 1980.
rat LD50 intraperitoneal 13mg/kg (13mg/kg)   Toxicology and Applied Pharmacology. Vol. 38, Pg. 127, 1976.
rat LD50 intravenous 21mg/kg (21mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 31, Pg. 655, 1981.
rat LD50 oral 2420ug/kg (2.42mg/kg) GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH Arzneimittel-Forschung. Drug Research. Vol. 25, Pg. 1526, 1975.
rat LD50 rectal 31900ug/kg (31.9mg/kg)   Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 14, Pg. 2259, 1986.
rat LD50 subcutaneous 12mg/kg (12mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 2, Pg. 70, 1968.
women TDLo oral 2098ug/kg/1D- (2.098mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED		 Southern Medical Journal. Vol. 78, Pg. 1390, 1985.
women TDLo oral 10mg/kg (10mg/kg) BEHAVIORAL: COMA Japanese Journal of Toxicology. Vol. 12, Pg. 337, 1999.

Indometacin Consensus Reports

Reported in EPA TSCA Inventory.

Indometacin Safety Profile

A poison by ingestion, intravenous, intraperitoneal, and subcutaneous routes. Human systemic effects by ingestion: aplastic anemia, changes in kidney tubules, decreased urine volume, diarrhea, fibrous hepatitis, hemorrhage, hypermotility, liver changes, necrotic stomach changes, retinal changes. Human teratogenic effects by ingestion and intravenous routes: developmental abnormalities of the respiratory system and urogenital system, homeostasis, other neonatal effects. Experimental teratogenic and reproductive effects. Mutation data reported. When heated to decomposition it emits very toxic Cl− and NOx.
Hazard Codes of Indometacin (CAS NO.53-86-1): VeryT+,IrritantXi
Risk Statements: 28-36/37/38 
R28: Very toxic if swallowed. 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 28-36/37-45-26 
S28: After contact with skin, wash immediately with plenty of soap-suds. 
S36/37: Wear suitable protective clothing and gloves. 
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RIDADR: UN 2811 6.1/PG 1
WGK Germany: 3
F: 8-10
HazardClass:  6.1
PackingGroup:  I

Indometacin Specification

 Synonyms of Indometacin (CAS NO.53-86-1) are (1-p-Chlorobenzoyl-5-methoxy-2-methylindol-3-yl)acetic acid ; 1-(p-Chlorbenzoyl)-5-methoxy-2-methylindol-3-essigsaeure ; 1-(p-Chlorbenzoyl)-5-methoxy-2-methylindol-3-essigsaeure [German] ; 1-(p-Chlorobenzoyl)-2-methyl-5-methoxyindole-3-acetic acid ; 1-(p-Chlorobenzoyl)-5-methoxy-2-methylindole-3-acetic acid ; 1-p-Cloro-benzoil-5-metoxi-2-metilindol-3-acido acetico ; 1H-Indole-3-acetic acid, 1-(4-chlorobenzoyl)-5-methoxy-2-methyl- ; Indole-3-acetic acid, 1-(p-chlorobenzoyl)-5-methoxy-2-methyl- .

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