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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 CYCLOOXYGENASE, which is 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
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
Classification Codes
- Analgesics
- Analgesics, Non-Narcotic
- Anti-Inflammatory
- Anti-Inflammatory Agents
- Anti-Inflammatory Agents, Non-Steroidal
- Antirheumatic Agents
- Antiviral (COVID-19)
- 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
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Links to Resources
NLM Resources (File Locators)
Regulatory Agencies (Superlist Locators)
Other Resources (Internet Locators)
Search for this InChIKey on the Web
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
- NSC 757061
- 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-NSmiles
COc1ccc2c(c1)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.