CAS No.53-86-1,Indometacin Suppliers

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Basic Information

Molecular Structure:
CAS No.:	53-86-1
Name:	Indometacin
Article Data:	106
Cas Database

Formula:	C₁₉H₁₆ClNO₄
Molecular Weight:	357.793
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;
EINECS:	200-186-5
Density:	1.327 g/cm³
Melting Point:	155-162 °C
Boiling Point:	499.363 °C at 760 mmHg
Flash Point:	255.806 °C
Solubility:	ethanol: 50 mg/mL
Appearance:	White crystalline powder
Hazard Symbols:	T+, Xi
Risk Codes:	28-36/37/38
Safety:	28-36/37-45-26
Transport Information:	UN 2811 6.1/PG 1
PSA:	68.53000
LogP:	3.92730

Synthetic route

: 16401-99-3
indomethacin ethyl ester

: 53-86-1
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

...Expand

Raw Materials

122-01-0

Downstream Products

104-88-1

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Chemistry

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

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.

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.

Consensus Reports

Reported in EPA TSCA Inventory.

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 NO_x.
Hazard Codes of Indometacin (CAS NO.53-86-1): Very T+, Irritant Xi
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

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- .