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Substance Name: Ibuprofen [USAN:USP:INN:BAN:JAN]
RN: 15687-27-1
UNII: WK2XYI10QM
InChIKey: HEFNNWSXXWATRW-UHFFFAOYSA-N

Note

  • A nonsteroidal anti-inflammatory agent with analgesic properties used in the therapy of rheumatism and arthritis.

Molecular Formula

  • C13-H18-O2

Molecular Weight

  • 206.2832
 

Classification Codes

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

Names and Synonyms

Name of Substance

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

MeSH Heading

  • Ibuprofen

Synonyms

  • (+-)-2-(p-Isobutylphenyl)propionic acid
  • (+-)-alpha-Methyl-4-(2-methylpropyl)benzeneacetic acid
  • (+-)-Ibuprofen
  • (+-)-Ibuprophen
  • (+-)-p-Isobutylhydratropic acid
  • (4-Isobutylphenyl)-alpha-methylacetic acid
  • (RS)-Ibuprofen
  • (S)-4-Isobutyl-alpha-methylphenylacetic acid
  • 2-(4-Isobutylphenyl)propanoic acid
  • 4-Isobutyl-alpha-methylphenylacetic acid
  • 4-Isobutylhydratropic acid
  • Aches-N-Pain
  • Acide (isobutyl-4-phenyl)-2 propionique
  • Acide (isobutyl-4-phenyl)-2 propionique [French]
  • Act-3
  • Adex 200
  • Adran
  • Advil
  • Advil Liqui-Gels
  • Advil migraine
  • Advil Migraine Liqui-Gels
  • Advil, Children's
  • Ak+C2278tren
  • Alaxan
  • Algofen
  • Alivium
  • alpha-(4-Isobutylphenyl)propionic acid
  • alpha-Methyl-4-(2-methylpropyl)benzeneacetic acid
  • alpha-p-Isobutylphenylpropionic acid
  • Am-Fam 400
  • Amelior
  • Amersol
  • Anafen
  • Anco
  • Andran
  • Anflagen
  • Antagil
  • Antalfene
  • Antarene
  • Antiflam
  • Apo-Ibuprofen
  • Apsifen
  • Artofen
  • Artril
  • Artril 300
  • Balkaprofen
  • Bayer Select Pain Relief
  • Benzeneacetic acid, alpha-methyl-4-(2-methylpropyl), (+-)-
  • Benzeneacetic acid, alpha-methyl-4-(2-methylpropyl)-
  • Betaprofen
  • Bloom
  • Bluton
  • BRN 2049713
  • Brofen
  • Brufanic
  • Brufen
  • Brufen 400
  • Brufen Retard
  • Bruflam
  • Brufort
  • Buburone
  • Bufeno
  • Bufigen
  • Bukrefen
  • Bupron
  • Buracaps
  • Burana
  • Butacortelone
  • Butylenin
  • Caldolor
  • Cap-Profen
  • Carol
  • CCRIS 3223
  • Cesra
  • Children's Advil
  • Children's Advil-flavored
  • Children's elixsure
  • Children's ibuprofen
  • Children's Motrin
  • Citalgan
  • Cobo
  • Codral Period Pain
  • Combiflam
  • Cunil
  • Daiprophen
  • Dalsy
  • Dansida
  • Deep Relief
  • Dentigoa
  • Dibufen
  • Dignoflex
  • Dolgit
  • Dolibu
  • Dolmaral
  • DOLO PUREN
  • Dolocyl
  • Dolofen
  • Dolofen-F
  • Dolofin
  • Dolofort
  • Dologel
  • Dolomax
  • Doloren
  • Dolormin
  • Doltibil
  • Dolven
  • Donjust B
  • Dorival
  • Drin
  • Duafen
  • Dularbuprofen
  • Duobrus
  • Dura-Ibu
  • Duralbuprofen
  • Dysdolen
  • Easifon
  • Ebufac
  • EC 239-784-6
  • EINECS 239-784-6
  • Emflam
  • Emflam-200
  • Epobron
  • Eputex
  • Ergix
  • Esprenit
  • Exneural
  • Faspic
  • Femafen
  • Femapirin
  • Femidol
  • Fenbid
  • Fendol
  • Fenspan
  • Fibraflex
  • Gelufene
  • Gofen
  • Grefen
  • Gynofug
  • Haltran
  • Hemagene Tailleur
  • HSDB 3099
  • Hydratropic acid, p-isobutyl-
  • IB-100
  • Ibol
  • Ibren
  • Ibu
  • Ibu-slo
  • Ibu-slow
  • Ibu-Tab
  • Ibu-tab 200
  • Ibubest
  • Ibubeta
  • Ibucasen
  • Ibudol
  • Ibudolor
  • Ibufen
  • Ibuflamar
  • Ibufug
  • Ibugel
  • Ibugen
  • Ibugesic
  • Ibuhexal
  • Ibulagic
  • Ibular
  • Ibulav
  • Ibuleve
  • Ibulgan
  • Ibumed
  • Ibumerck
  • Ibumetin
  • Ibupirac
  • Ibuprin
  • Ibuprocin
  • Ibuprofen
  • Ibuprofene
  • Ibuprofene [INN-French]
  • Ibuprofeno
  • Ibuprofeno [INN-Spanish]
  • Ibuprofenum
  • Ibuprofenum [INN-Latin]
  • Ibuprohm
  • Ibusal
  • Ifen
  • Inabrin
  • Inflam
  • IP-82
  • Ipren
  • Irfen
  • Isodol
  • Jenaprofen
  • Junifen
  • Junior Strength Advil
  • Junior Strength ibuprofen
  • Junior Strength Motrin
  • Kesan
  • Kontagripp Mono
  • Kratalgin
  • Lamidon
  • Librofem
  • Lidifen
  • Liptan
  • Lopane
  • Malafene
  • Manypren
  • Medipren
  • Melfen
  • Mensoton
  • Midol
  • Midol 200
  • Midol IB Cramp Relief
  • Midol Liquid Gels
  • Moment
  • Motrin
  • Motrin IB
  • Motrin Migraine Pain
  • Mynosedin
  • Nagifen-D
  • Napacetin
  • Narfen
  • Neo-Helvagit
  • Neo-Mindol
  • Neobrufen
  • Nerofen
  • Noalgil
  • Nobafon
  • Nobfelon
  • Nobfen
  • Nobgen
  • Noritis
  • Norton
  • Novadol
  • Novo Dioxadol
  • Novo-Profen
  • Novogent
  • Novoprofen
  • NSC 256857
  • Nuprilan
  • Nuprin
  • Nurofen
  • Optifen
  • Opturem
  • Oralfene
  • Ostarin
  • Ostofen
  • Ozonol
  • p-Isobutyl-2-phenylpropionic acid
  • p-Isobutylhydratropic acid
  • Paduden
  • Panafen
  • Pantrop
  • Paxofen
  • PediaProfen
  • Pediatric Advil
  • Perofen
  • Perrigo ibuprofen
  • Proartinal
  • Profen
  • Proflex
  • Provon
  • Quadrax
  • Rafen
  • Ranofen
  • RD 13621
  • Rebugen
  • Relcofen
  • Rhinadvil
  • Rofen
  • Roidenin
  • Rufen
  • Rufin
  • Rupan
  • Sadefen
  • Salivia
  • Schmerz-Dolgit
  • Sednafen
  • Seklodin
  • Seskafen
  • Siyafen
  • Solpaflex
  • Solufen
  • Stelar
  • Sugafen
  • Suprafen
  • Suspren
  • Syntofene
  • Tab-profen
  • Tabalon
  • Tabalon 400
  • Tatanal
  • Tempil
  • Tofen
  • Togal N
  • Tonal
  • Trendar
  • U 18573
  • U-18,573
  • UCB 79171
  • UNII-WK2XYI10QM
  • Unipron
  • Upfen
  • Uprofen
  • Urem
  • VUFB 9649
  • Zafen
  • Zofen

Systematic Names

  • Benzeneacetic acid, alpha-methyl-4-(2-methylpropyl)-
  • Hydratropic acid, p-isobutyl-
  • Ibuprofen

Mixture Names

  • Advil Cold & Sinus
  • Advil Cold and Sinus
  • Children's Elixsure IB
  • Combunox
  • Dristan Sinus
  • Motrin IB Gelcaps
  • Sine-Aid IB Caplets

Registry Numbers

CAS Registry Number

  • 15687-27-1

FDA UNII

  • WK2XYI10QM

Other Registry Numbers

  • 139466-08-3
  • 58560-75-1

Related Registry Numbers

  • 31121-93-4 (hydrochloride salt)
  • 79261-49-7 (potassium salt)

System Generated Number

  • 0015687271

Structure Descriptors

InChI

1S/C13H18O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15/h4-7,9-10H,8H2,1-3H3,(H,14,15)

InChIKey

HEFNNWSXXWATRW-UHFFFAOYSA-N

Smiles

CC(C)Cc1ccc(cc1)C(C)C(=O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child LDLo oral 469mg/kg (469mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Annals of Emergency Medicine. Vol. 15, Pg. 1308, 1986.
child TDLo oral 480mg/kg/17D- (480mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE" Journal of Pediatrics. Vol. 90, Pg. 657, 1977.
child TDLo oral 500mg/kg (500mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"
Annals of Pharmacotherpy. Vol. 31, Pg. 432, 1997.
guinea pig LD50 oral 495mg/kg (495mg/kg)   Archives of Toxicology, Supplement. Vol. 7, Pg. 365, 1984.
hamster LD50 oral 1690mg/kg (1690mg/kg)   Archives of Toxicology, Supplement. Vol. 7, Pg. 365, 1984.
mammal (species unspecified) LD50 oral 1gm/kg (1000mg/kg)   Acta Poloniae Pharmaceutica. For English translation, see APPFAR. Vol. 42, Pg. 545, 1985.
man LDLo oral 171mg/kg (171mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
British Medical Journal. Vol. 281, Pg. 1458, 1980.
man TDLo oral 120mg/kg/W-I (120mg/kg)   New York State Journal of Medicine. Vol. 78, Pg. 1239, 1978.
man TDLo oral 120mg/kg/W-I (120mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
New York State Journal of Medicine. Vol. 78, Pg. 1239, 1978.
man TDLo oral 180mg/kg/3W-I (180mg/kg) LIVER: "JAUNDICE, CHOLESTATIC" American Journal of Gastroenterology. Vol. 91, Pg. 1626, 1996.
man TDLo oral 429mg/kg (429mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY OBSTRUCTION
Journal of Toxicology, Clinical Toxicology. Vol. 32, Pg. 315, 1994.
man TDLo oral 800mg/kg (800mg/kg)   Postgraduate Medical Journal. Vol. 69, Pg. 575, 1993.
man TDLo oral 800mg/kg (800mg/kg) BEHAVIORAL: COMA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Postgraduate Medical Journal. Vol. 69, Pg. 575, 1993.
man TDLo oral 1028mg/kg (1028mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" American Journal of Emergency Medicine. Vol. 13, Pg. 375, 1995.
mouse LD50 intraperitoneal 320mg/kg (320mg/kg) GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Toxicology and Applied Pharmacology. Vol. 15, Pg. 310, 1969.
mouse LD50 oral 740mg/kg (740mg/kg) BEHAVIORAL: ANALGESIA Pharmaceutical Chemistry Journal Vol. 14, Pg. 119, 1980.
mouse LD50 rectal 620mg/kg (620mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Oyo Yakuri. Pharmacometrics. Vol. 24, Pg. 415, 1982.
mouse LD50 subcutaneous 395mg/kg (395mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 24, Pg. 415, 1982.
rabbit LD50 oral 1400mg/kg (1400mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 32, Pg. 1032, 1990.
rabbit LD50 rectal 830mg/kg (830mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 32, Pg. 1032, 1990.
rat LD50 intraperitoneal 626mg/kg (626mg/kg) BEHAVIORAL: ANALGESIA Arzneimittel-Forschung. Drug Research. Vol. 27, Pg. 1006, 1977.
rat LD50 oral 636mg/kg (636mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 34, Pg. 280, 1984.
rat LD50 rectal 530mg/kg (530mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Oyo Yakuri. Pharmacometrics. Vol. 24, Pg. 415, 1982.
rat LD50 subcutaneous 740mg/kg (740mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 24, Pg. 415, 1982.
women TDLo oral 8mg/kg (8mg/kg) BEHAVIORAL: HEADACHE JAMA, Journal of the American Medical Association. Vol. 239, Pg. 1062, 1978.
women TDLo oral 132mg/kg/6D-I (132mg/kg) BLOOD: THROMBOCYTOPENIA British Journal of Clinical Practice. Vol. 48, Pg. 51, 1994.
women TDLo unreported 96mg/kg/3D-I (96mg/kg) SENSE ORGANS AND SPECIAL SENSES: DIPLOPIA: EYE JAMA, Journal of the American Medical Association. Vol. 248, Pg. 649, 1982.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 76 deg C   EXP
pKa Dissociation Constant 4.91 (none)   EXP
log P (octanol-water) 3.97 (none)   EXP
Water Solubility 21 mg/L 25 EXP
Vapor Pressure 1.86E-04 mm Hg 25 EST
Henry's Law Constant 1.50E-07 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.16E-11 cm3/molecule-sec 25 EST

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