Basic information
- CAS
33005-95-7- Standard SMILES
CC(C(=O)O)c1ccc(C(=O)c2ccccc2)s1- InChIKey
GUHPRPJDBZHYCJ-UHFFFAOYSA-N- Molecular formula
- C14H12O3S
- Average molar mass
- 260.31 g/mol
- Monoisotopic mass
- 260.05071541
Overview
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.
Names & identifiers
- Preferred name
- Tiaprofenic Acid
- IUPAC
- 2-(5-benzoylthiophen-2-yl)propanoic acid
- English name
- Tiaprofenic acid
- Molecular formula
- C14H12O3S
- Molecular weight
- 260.31
Names & synonyms
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
Show more names
TiaprofenicSuralganSurgam SATiaprofenicAci
RU 15060TiaprofenateDTXSID5023665alpha-methyl-5-benzoyl-2-thienylacetic acid1LS1T6R34CRU-15060CHEBI:322215-benzoyl-alpha-methylthiophene-2-acetic acid
Database identifiers
- CAS
33005-95-7- PubChem CID
- 5468
- DTXSID
DTXSID5023665- ChEMBL
CHEMBL365795- ChEBI
CHEBI:32221- UNII
- 1LS1T6R34C
- EC Number
- 251-329-3
- Nikkaji
- J3.176C
Properties
Computed structural properties
- XLogP
- 3.3
- Topological polar surface area
- 82.6 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 323
Experimental & physicochemical properties
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)]
Physicochemical properties
- Melting point
- 96 ° · 96° (isopropyl ether)
- Boiling point
- 373.57 °C · 373.57°C (rough estimate)
- Density
- 1.2959 · 1.2959 (rough estimate)
- refractive index
- 1.505 · 1.5050 (estimate)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
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.
Hazard information
Hazard Classes and CategoriesAcute Tox. 3 (88.9%)
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Tiaprofenic acid
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Safety data
- wgk
- WGK 3
- rtecs
- XM7580000
- ridadr
- UN 2811 6.1/PG III
- hs_code
- 2934.99.3000
- Signal word
- Danger
- Symbol(GHS)
- GHS06,GHS08
- hazard_class
- 6.1
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- packing_group
- III
Chemistry & industry
Pharmacology
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
Related reactions
3 records
Compound notes
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