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Substance Name: Ketoprofen [USAN:USP:INN:BAN:JAN]
RN: 22071-15-4
UNII: 90Y4QC304K
InChIKey: DKYWVDODHFEZIM-UHFFFAOYSA-N

Note

  • An IBUPROFEN-type anti-inflammatory analgesic and antipyretic. It is used in the treatment of rheumatoid arthritis and osteoarthritis.

Molecular Formula

  • C16-H14-O3

Molecular Weight

  • 254.2836
 

Classification Codes

  • Analgesics
  • Analgesics, Non-Narcotic
  • Anti-Inflammatory
  • Anti-Inflammatory Agents
  • Anti-Inflammatory Agents, Non-Steroidal
  • Antirheumatic Agents
  • Cyclooxygenase Inhibitors
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data
  • Mutation Data
  • Peripheral Nervous System Agents
  • Reproductive Effect
  • Sensory System Agents

Names and Synonyms

Name of Substance

  • Ketoprofen
  • Ketoprofen [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Ketoprofen

Synonyms

  • (+-)-3-Benzoyl-alpha-methylbenzeneacetic acid
  • (+-)-m-Benzoylhydratropic acid
  • 19583 RP
  • 2-(3-Benzoylphenyl)propionic acid
  • 2-(m-Benzoylphenyl)propionic acid
  • 3-Benzoylhydratropic acid
  • Acide (benzoyl-3-phenyl)-2-propionique
  • Acide (benzoyl-3-phenyl)-2-propionique [French]
  • Actron
  • Alrheumun
  • Aneol
  • Benzeneacetic acid, 3-benzoyl-alpha-methyl-
  • Benzeneacetic acid, 3-benzoyl-alpha-methyl-, (+-)-
  • Capisten
  • CCRIS 4508
  • EINECS 244-759-8
  • Epatec
  • Hydratropic acid, m-benzoyl-, (+-)-
  • Ketoprofen
  • Ketoprofen (+-)
  • Ketoprofene
  • Ketoprofene [INN-French]
  • Ketoprofeno
  • Ketoprofeno [INN-Spanish]
  • Ketoprofenum
  • Ketoprofenum [INN-Latin]
  • Ketoprophene
  • m-Benzoylhydratropic acid
  • Orudis
  • Orudis KT
  • Oruvail
  • Profenid
  • R.P. 19,583
  • racemic-Ketoprofen
  • RP 19583
  • RU 4733
  • UNII-90Y4QC304K

Systematic Names

  • Benzeneacetic acid, 3-benzoyl-alpha-methyl-
  • Ketoprofen
  • Propionic acid, 2-(3-benzoylphenyl)-

Registry Numbers

CAS Registry Number

  • 22071-15-4

FDA UNII

  • 90Y4QC304K

Other Registry Numbers

  • 154907-35-4
  • 172964-50-0
  • 22161-86-0

System Generated Number

  • 0022071154

Structure Descriptors

InChI

1S/C16H14O3/c1-11(16(18)19)13-8-5-9-14(10-13)15(17)12-6-3-2-4-7-12/h2-11H,1H3,(H,18,19)

InChIKey

DKYWVDODHFEZIM-UHFFFAOYSA-N

Smiles

c1cc(ccc1)C(c1cccc(c1)[C@@H](C(O)=O)C)=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo unreported 300mg/kg/15D- (300mg/kg) BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES

GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: HEADACHE
New England Journal of Medicine. Vol. 300, Pg. 796, 1979.
guinea pig LD50 intravenous 450mg/kg (450mg/kg)   Journal de Pharmacologie. Vol. 2, Pg. 259, 1971.
guinea pig LD50 oral 1300mg/kg (1300mg/kg)   Journal de Pharmacologie. Vol. 2, Pg. 259, 1971.
human TDLo oral 714ug/kg (0.714mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Journal of Clinical Pharmacology. Vol. 24, Pg. 486, 1984.
man TDLo oral 5714ug/kg (5.714mg/kg)   Clinical Rheumatology. Vol. 10, Pg. 215, 1991.
man TDLo oral 5714ug/kg (5.714mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL" Clinical Rheumatology. Vol. 10, Pg. 215, 1991.
mouse LD50 intraperitoneal 300mg/kg (300mg/kg)   European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 11, Pg. 7, 1976.
mouse LD50 intravenous 500mg/kg (500mg/kg)   Journal de Pharmacologie. Vol. 2, Pg. 259, 1971.
mouse LD50 oral 360mg/kg (360mg/kg)   Polish Journal of Pharmacology and Pharmacy. Vol. 38, Pg. 107, 1986.
mouse LD50 subcutaneous 550mg/kg (550mg/kg)   Journal de Pharmacologie. Vol. 2, Pg. 259, 1971.
rat LD50 intraperitoneal 80mg/kg (80mg/kg)   Drugs in Japan Vol. 6, Pg. 265, 1982.
rat LD50 intravenous 350mg/kg (350mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 9, Pg. 222, 1978.
rat LD50 oral 62400ug/kg (62.4mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 34, Pg. 280, 1984.
rat LD50 rectal 84mg/kg (84mg/kg) GASTROINTESTINAL: PERITONITIS

GASTROINTESTINAL: ULCERATION OR BLEEDING FROM SMALL INTESTINE
Journal of Toxicological Sciences. Vol. 6, Pg. 209, 1981.
rat LD50 subcutaneous 100mg/kg (100mg/kg)   Journal de Pharmacologie. Vol. 2, Pg. 259, 1971.
women TDLo oral 11mg/kg/12H-I (11mg/kg) SKIN AND APPENDAGES (SKIN): SWEATING: OTHER

CARDIAC: PULSE RATE

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
Journal of Clinical Pyschopharmacology. Vol. 19, Pg. 95, 1999.
women TDLo oral 80mg/kg/10D-I (80mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" British Medical Journal. Vol. 292, Pg. 97, 1986.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 94 deg C   EXP
pKa Dissociation Constant 4.45 (none)   EXP
log P (octanol-water) 3.12 (none)   EXP
Water Solubility 51 mg/L 22 EXP
Vapor Pressure 3.72E-07 mm Hg 25 EST
Henry's Law Constant 2.12E-11 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 6.06E-12 cm3/molecule-sec 25 EST

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