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Substance Name: Indomethacin [USAN:USP]
RN: 53-86-1
UNII: XXE1CET956
InChIKey: CGIGDMFJXJATDK-UHFFFAOYSA-N

Note

  • A non-steroidal anti-inflammatory agent (NSAID) that inhibits the enzyme cyclooxygenase necessary for the formation of prostaglandins and other autacoids. It also inhibits the motility of polymorphonuclear leukocytes.

Molecular Formula

  • C19-H16-Cl-N-O4

Molecular Weight

  • 357.7914
 

Classification Codes

  • Analgesics
  • Analgesics, Non-Narcotic
  • Anti-Inflammatory
  • Anti-Inflammatory Agents
  • 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

Names and Synonyms

Name of Substance

  • Indometacin [INN]
  • Indomethacin
  • Indomethacin [USAN:USP]

MeSH Heading

  • Indomethacin

Synonyms

  • (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
  • 1-p-Cloro-benzoil-5-metoxi-2-metilindol-3-acido acetico [Spanish]
  • 1H-Indole-3-acetic acid, 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-
  • 5-22-05-00239 (Beilstein Handbook Reference)
  • alpha-(1-(p-Chlorobenzoyl)-2-methyl-5-methoxy-3-indolyl)acetic acid
  • Amuno
  • Artracin
  • Artrinovo
  • Artrivia
  • BRN 0497341
  • CCRIS 3502
  • Confortid
  • Dolovin
  • EC 200-186-5
  • EINECS 200-186-5
  • FLAM
  • HSDB 3101
  • Idomethine
  • Imbrilon
  • Inacid
  • Indacin
  • Indo-lemmon
  • Indo-rectolmin
  • Indo-tablinen
  • Indocid
  • Indocin
  • Indocin SR
  • Indole-3-acetic acid, 1-(p-chlorobenzoyl)-5-methoxy-2-methyl-
  • Indomecol
  • Indomed
  • Indomee
  • Indomet 140
  • Indometacin
  • Indometacina
  • Indometacina [INN-Spanish]
  • Indometacine
  • Indometacine [INN-French]
  • Indometacinum
  • Indometacinum [INN-Latin]
  • Indometacyna
  • Indometacyna [Polish]
  • Indomethacin
  • Indomethacine
  • Indomethacinum
  • Indomethazine
  • Indometicina
  • Indometicina [Spanish]
  • Indoptic
  • Indoptol
  • Inflazon
  • Infrocin
  • Inteban SP
  • Kwas 1-(p-chlorobenzoilo)-2-metylo-5-metoksy-3-indolilooctowy
  • Kwas 1-(p-chlorobenzoilo)-2-metylo-5-metoksy-3-indolilooctowy [Polish]
  • Lausit
  • Metacen
  • Metartril
  • Methazine
  • Metindol
  • Mezolin
  • Mikametan
  • Mobilan
  • N-p-Chlorbenzoyl-5-methoxy-2-methylindole-3-acetic acid
  • NCI-C56144
  • Osmosin
  • Reumacide
  • Sadoreum
  • Tannex
  • Tivorbex
  • UNII-XXE1CET956

Systematic Names

  • 1H-Indole-3-acetic acid, 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-
  • Indole-3-acetic acid, 1-(p-chlorobenzoyl)-5-methoxy-2-methyl-
  • Indometacin
  • Indomethacin

Superlist Name

  • Indomethacin

Registry Numbers

CAS Registry Number

  • 53-86-1

FDA UNII

  • XXE1CET956

Other Registry Numbers

  • 37242-43-6
  • 503560-73-4
  • 91853-74-6

Related Registry Numbers

  • 74252-25-8 (hydrochloride salt, tri-hydrate)
  • 7681-54-1 (hydrochloride salt)

System Generated Number

  • 0000053861

Structure Descriptors

InChI

InChI=1S/C19H16ClNO4/c1-11-15(10-18(22)23)16-9-14(25-2)7-8-17(16)21(11)19(24)12-3-5-13(20)6-4-12/h3-9H,10H2,1-2H3,(H,22,23)

InChIKey

CGIGDMFJXJATDK-UHFFFAOYSA-N

Smiles

COc1ccc2c(c1)c(CC(=O)O)c(C)n2C(=O)c3ccc(Cl)cc3

Toxicity

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: OTHER CHANGES

LIVER: "HEPATITIS, FIBROUS (CIRRHOSIS, POST-NECROTIC SCARRING)"		 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) KIDNEY, URETER, AND BLADDER: HEMATURIA

BEHAVIORAL: STIFFNESS		 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: URINE VOLUME DECREASED

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"		 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.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 158 deg C   EXP
pKa Dissociation Constant 4.5 (none)   EXP
log P (octanol-water) 4.27 (none)   EXP
Water Solubility 0.937 mg/L 25 EXP
Vapor Pressure 9.89E-11 mm Hg 25 EST
Henry's Law Constant 3.13E-14 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.03E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.