Ketoprofen
Grundinformationen
- CAS
22161-86-0- Standard-SMILES
CC(C(=O)O)c1cccc(C(=O)c2ccccc2)c1- InChIKey
DKYWVDODHFEZIM-UHFFFAOYSA-N- Summenformel
- C16H14O3
- Durchschnittliche Molmasse
- 254,28 g/mol
Überblick
Ketoprofen is an oxo monocarboxylic acid that consists of propionic acid substituted by a 3-benzoylphenyl group at position 2. It has a role as a non-steroidal anti-inflammatory drug, an antipyretic, an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor, a xenobiotic, an environmental contaminant and a drug allergen. It is a member of benzophenones and an oxo monocarboxylic acid. It is functionally related to a propionic acid.
Namen und Bezeichner
- Bevorzugter Name
- Ketoprofen
- IUPAC
- 2-(3-benzoylphenyl)propanoic acid
- Englischer Name
- Ketoprofene
- Molmasse
- 0
Namen und Synonyme
ketoprofen22071-15-42-(3-Benzoylphenyl)propanoic acid2-(3-Benzoylphenyl)propionic acidOrudisCapistenActronOruvailAlrheumatKetoprofeneAneolm-Benzoylhydratropic acid
Weitere Namen anzeigen
(RS)-2-(3-BENZOYLPHENYL)PROPIONIC ACID
3-Benzoylhydratropic acidIso-KKetoprofenoOrudis KTRP-19583SectorKetoprofenumKetorin
Datenbank-Bezeichner
- CAS
22161-86-0- ChEMBL
CHEMBL571- ChEBI
CHEBI:6128- UNII
- 90Y4QC304K
- EC Number
- 244-759-8
- Nikkaji
- J3.468A
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3,1
- Polarare Oberfläche (TPSA)
- 54,4 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 4
- Schwere Atome
- 19
- Formalladung
- 0
- Komplexität
- 331
Experimentelle und physikochemische Eigenschaften
Drugs
DEA NFLIS-Drug Category -> Analgesics
Pharmaceuticals -> NSAIDs
Pharmaceutical
Pharmaceuticals
LogP
3.2
3.12
Solubility2.13e-02 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Analgesic Agents; Anti-inflammatory Agents, Nonsteroidal
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Animal Drugs
Active Ingredients (Ketoprofen) -> FDA Greenbook
Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
Pharmaceuticals -> UK Veterinary Medicines Directorate List
Melting Point94 °C
Physical DescriptionSolid
Dissociation Constants
3.98
4
3.8
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 0.1% (1 of 672) of reports.
Danger
H301 (99.7%): Toxic if swallowed [Danger Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 672 reports by companies from 29 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory Information
Status: Active Update: 30-06-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/24605
Ketoprofen: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Benzeneacetic acid, 3-benzoyl-.alpha.-methyl-: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 3 (99.7%)
Toxikologische Informationen
Hepatotoxicity
Prospective studies show that 1% to 2% of patients taking ketoprofen experience at least transient serum aminotransferase elevations. These may resolve even with drug continuation. Marked aminotransferase elevations (>3 fold elevated) occur in
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Chemie und Industrie
Pharmakologische Informationen
ATC Code
M02AA10
M - Musculo-skeletal system
M - Musculo-skeletal system
QM - Musculo-skeletal system
QM - Musculo-skeletal system
Protein Binding99% bound, primarily to albumin
Pharmacodynamics
Ketoprofen is a nonsteroidal anti-inflammatory agent (NSAIA) with analgesic and antipyretic properties. Ketoprofen has pharmacologic actions similar to those of other prototypical NSAIDs, which inhibit prostaglandin synthesis. Ketoprofen is used to treat rheumatoid arthritis, osteoarthritis, dysmenorrhea, and alleviate moderate pain.
Mechanism of Action
The anti-inflammatory effects of ketoprofen are believed to be due to inhibition cylooxygenase-2 (COX-2), an enzyme involved in prostaglandin synthesis via the arachidonic acid pathway. This results in decreased levels of prostaglandins that mediate pain, fever and inflammation. Ketoprofen is a non-specific cyclooxygenase inhibitor and inhibition of COX-1 is thought to confer some of its side effects, such as GI upset and ulceration. Ketoprofen is thought to have anti-bradykinin activity, as well as lysosomal membrane-stabilizing action. Antipyretic effects may be due to action on the hypothalamus, resulting in an increased peripheral blood flow, vasodilation, and subsequent heat dissipation.
Biological Half-LifeConventional capsules: 1.1-4 hours <p>Extended release capsules: 5.4 hours due to delayed absorption (intrinsic clearance is same as conventional capsules)</p>
Metabolism/Metabolites
Rapidly and extensively metabolized in the liver, primarily via conjugation to glucuronic acid. No active metabolites have been identified.
Ketoprofen has known human metabolites that include Ketoprofen glucuronide.
FDA Pharmacological Classification
90Y4QC304K
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