Grundinformationen
- Standard-SMILES
C[C@H](C(=O)O)c1cccc(C(=O)c2ccccc2)c1- InChIKey
DKYWVDODHFEZIM-NSHDSACASA-N- Summenformel
- C16H14O3
- Durchschnittliche Molmasse
- 254,28 g/mol
- Monoisotopische Masse
- 254,09429431
Überblick
Dexketoprofen is a monocarboxylic acid that is (S)-hydratropic acid substituted at position 3 on the phenyl ring by a benzoyl group. A cyclooxygenase inhibitor, it is used to relieve short-term pain, such as muscular pain, dental pain and dysmenorrhoea. It has a role as a non-steroidal anti-inflammatory drug, a non-narcotic analgesic, a cyclooxygenase 2 inhibitor and a cyclooxygenase 1 inhibitor. It is a member of benzophenones and a monocarboxylic acid. It is functionally related to a (S)-hydratropic acid.
Namen und Bezeichner
- Bevorzugter Name
- Dexketoprofen
- IUPAC
- (2S)-2-(3-benzoylphenyl)propanoic acid
- Englischer Name
- (S)-(+)-Ketoprofen
- Summenformel
- C16H14O3
- Molmasse
- 254.28
Namen und Synonyme
DEXKETOPROFEN22161-81-5(S)-Ketoprofen(+)-KetoprofenArveles(+)-3-Benzoylhydratropic acidHydratropic acid, m-benzoyl-, (+)-Ketoprofen, (s)-(+)-(S)-m-Benzoylhydratropic aciddexketoprofeneDexketoprofeno(S)-3-Benzoyl-alpha-methylbenzeneacetic acid
Weitere Namen anzeigen
(2S)-2-(3-Benzoylphenyl)propanoic acidKeralDexktoprofenDexketoprofeexketoprofenlevoketoprofenDexketoprofen API
6KD9E78X68CHEBI:76128DTXSID40905141Benzeneacetic acid, 3-benzoyl-alpha-methyl-, (S)-dexketoprofen sodiumdexketoprofenumRefChem:132392M01AE17
Datenbank-Bezeichner
- CAS
22161-81-5- PubChem CID
- 667550
- DTXSID
DTXSID40905141- ChEMBL
CHEMBL75435- ChEBI
CHEBI:76128- UNII
- 6KD9E78X68
- EC Number
- 606-944-5
- Nikkaji
- J389.200J
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
Physikochemische Eigenschaften
- Schmelzpunkt
- 75 · 75-78 °C(lit.)
- Siedepunkt
- 431.3 · 431.3±28.0 °C(Predicted)
- Dichte
- 1.198 · 1.198±0.06 g/cm3(Predicted)
- storage temp.
- Sealed in dry,Room Temperature
- Löslichkeit
- 2 O; · insoluble in H2O; ≥10.6 mg/mL in DMSO; ≥20.55 mg/mL in EtOH
- pka
- 4.23 · 4.23±0.10(Predicted)
- Aggregatzustand
- White solid.
- Farbe
- White to off-white
- InChI
- InChI=1/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)/t11-/s3
- InChIKey
- DKYWVDODHFEZIM-LBPXTSNRNA-N
- SMILES
- C1(=CC=CC([C@H](C)C(=O)O)=C1)C(=O)C1=CC=CC=C1 |&1:5,r|
- CAS Datenbank
- 22161 · 22161-81-5(CAS DataBase Reference)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 2.4% (1 of 42) of reports.
Danger
H301 (97.6%): Toxic if swallowed [Danger Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 42 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory InformationStatus: Active Update: 06-11-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/17708
Hazard Classes and CategoriesAcute Tox. 3 (97.6%)
Toxikologische Informationen
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
DEXKETOPROFEN
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Sicherheitsdaten
- wgk
- 3
- ridadr
- UN 2811 6.1/PG 3
- RTECS-Nr.
- CY1572790
- risk_code
- 22-36/37/38-50/53-25
- hazard_code
- Xn,T
- safety_code
- 26-60-61-45
- Speicherklasse
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- Acute Tox. 3 OralAquatic Acute 1Eye Irrit. 2Skin Irrit. 2STOT SE 3
Chemie und Industrie
Pharmakologische Informationen
ATC Code
M - Musculo-skeletal system
M - Musculo-skeletal system
QM - Musculo-skeletal system
QM - Musculo-skeletal system
Protein BindingHighly protein bound.
PharmacodynamicsThis drug is an isomer of ketoprofen. Dexketoprofen a propionic acid derivative with analgesic, anti-inflammatory, and antipyretic properties.
Mechanism of ActionIt is a non-steroidal anti-inflammatory drug (NSAID) that reduces prostaglandin synthesis via inhibition of cyclooxygenase pathway (both COX-1 and COX-2) activity.
Biological Half-Life1.65 h
Metabolism/Metabolites
Dexketoprofen is highly lipophilic, and is metabolized in the liver by glucuronidation. In one study, after oral administration of 25 mg of dexketoprofen to young healthy adults, Tmax was approximately 30 min for a Cmax of 3.7 ± 0.72 mg/l. Dexketoprofen trometamol is metabolized by the hepatic cytochrome P450 enzymes (CYP2C8 and CYP2C9). Dexketoprofen trometamol has a number of metabolites, with hydroxyl derivatives making up the greatest volume. In humans, hydroxylation plays a minor role. Dexketoprofen is primarily conjugated to an acyl-glucuronide
MeSH Pharmacological Classification
Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.
Absorption, Distribution and Excretion
After oral ingestion, the Dexketoprofen onset of action is within 30 minutes. The plasma half-life of Dexketoprofen is about 4-6 hours. The Cmax is about 30 minutes
Approximately 70 to 80% of the ingested dose is recovered in the urine during the first 12 hours post-ingestion, mainly as the acyl-conjugated form of the drug.
<0.25 L/kg
Mainly cleared via glucuronide conjugation and followed by renal excretion, mainly unchanged.
Cellular LocationsMembrane
Anwendungen
VerwendenAnti-inflammatory; analgesic
Anbieter50 Anbieter
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Ergänzende Hinweise
DefinitionChEBI: A monocarboxylic acid that is (S)-hydratropic acid substituted at position 3 on the phenyl ring by a benzoyl group. A cyclooxygenase inhibitor, it is used to relieve short-term pain, such as muscular pain, dental pain and dysmenorrhoea.
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