Grundinformationen
- CAS
33005-95-7- Standard-SMILES
CC(C(=O)O)c1ccc(C(=O)c2ccccc2)s1- InChIKey
GUHPRPJDBZHYCJ-UHFFFAOYSA-N- Summenformel
- C14H12O3S
- Durchschnittliche Molmasse
- 260,31 g/mol
- Monoisotopische Masse
- 260,05071541
Überblick
Tiaprofenic acid is an aromatic ketone that is thiophene substituted at C-2 by benzoyl and at C-4 by a 1-carboxyethyl group. It has a role as a non-steroidal anti-inflammatory drug and a drug allergen. It is a monocarboxylic acid, a member of thiophenes and an aromatic ketone.
Namen und Bezeichner
- Bevorzugter Name
- Tiaprofenic Acid
- IUPAC
- 2-(5-benzoylthiophen-2-yl)propanoic acid
- Lokaler Name
- Tiaprofeninsure
- Englischer Name
- Tiaprofenic acid
- Summenformel
- C14H12O3S
- Molmasse
- 260.31
Namen und Synonyme
tiaprofenic acid33005-95-7Surgam2-(5-benzoylthiophen-2-yl)propanoic acidTiaprofensaeureAcido tiaprofenicotiaprofenAcide tiaprofenique5-Benzoyl-alpha-methyl-2-thiopheneacetic acidAcidum tiaprofenicum2-(5-Benzyl-2-thienyl)propionsaeureFC 3001
Weitere Namen anzeigen
TiaprofenicSuralganSurgam SATiaprofenicAci
RU 15060TiaprofenateDTXSID5023665alpha-methyl-5-benzoyl-2-thienylacetic acid1LS1T6R34CRU-15060CHEBI:322215-benzoyl-alpha-methylthiophene-2-acetic acid
Datenbank-Bezeichner
- CAS
33005-95-7- PubChem CID
- 5468
- DTXSID
DTXSID5023665- ChEMBL
CHEMBL365795- ChEBI
CHEBI:32221- UNII
- 1LS1T6R34C
- EC Number
- 251-329-3
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3,3
- Polarare Oberfläche (TPSA)
- 82,6 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 4
- Schwere Atome
- 18
- Formalladung
- 0
- Komplexität
- 323
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals
LogP2.86
Solubility3.24e-02 g/L
Human DrugsPharmaceuticals
Melting Point96 °C
Physical DescriptionSolid
Collision Cross Section155.1 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
Physikochemische Eigenschaften
- Schmelzpunkt
- 96 ° · 96° (isopropyl ether)
- Siedepunkt
- 373.57 °C · 373.57°C (rough estimate)
- Dichte
- 1.2959 · 1.2959 (rough estimate)
- Brechungsindex
- 1.505 · 1.5050 (estimate)
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
Danger
H301 (88.9%): Toxic if swallowed [Danger Acute toxicity, oral]
P203, P261, P264, P264+P265, P270, P271, P273, P280, P301+P316, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P318, 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 9 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Hazard Classes and CategoriesAcute Tox. 3 (88.9%)
Toxikologische Informationen
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Tiaprofenic acid
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Sicherheitsdaten
- wgk
- WGK 3
- ridadr
- UN 2811 6.1/PG III
- hs_code
- 2934.99.3000
- RTECS-Nr.
- XM7580000
- hazard_class
- 6.1
- packing_group
- III
- Speicherklasse
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- Acute Tox. 3 OralRepr. 2
Chemie und Industrie
Pharmakologische Informationen
ATC Code
M - Musculo-skeletal system
QM - Musculo-skeletal system
Pharmacodynamics
Tiaprofenic acid is a non-steroidal anti-inflammatory drug of the arylpropionic acid (profen) class, used to treat pain, especially arthritic pain. The typical adult dose is 300mg twice daily. This drug is not recommended for use in the pediatric population.
Mechanism of Action
Tiaprofenic acid belongs to a group of medicines called non-steroidal anti-inflammatory drugs (NSAIDs). It works by blocking the production of a chemical (prostaglandin) which the body produces in response to injury or certain diseases. This prostaglandin would otherwise go on to cause swelling, pain and inflammation.
Biological Half-Life1.5-2.5 hours
Metabolism/MetabolitesHepatic (10%). Sparingly metabolised in the liver to two inactive metabolites.
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 ExcretionBioavailability is 90% following oral administration.
Cellular LocationsCytoplasm
Metabolite PathwaysTiaprofenic Acid Action Pathway
Zugehörige Reaktionen
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