Basic information
- Standard SMILES
CC(C(=O)O)c1ccc(C(=O)c2cccs2)cc1- InChIKey
MDKGKXOCJGEUJW-UHFFFAOYSA-N- Molecular formula
- C14H12O3S
- Average molar mass
- 260.31 g/mol
- Monoisotopic mass
- 260.05071524
Overview
Suprofen is an aromatic ketone that is thiophene substituted at C-2 by a 4-(1-carboxyethyl)benzoyl group. It has a role as a non-steroidal anti-inflammatory drug, a non-narcotic analgesic, an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor, an antirheumatic drug, a peripheral nervous system drug and a drug allergen. It is a monocarboxylic acid, a member of thiophenes and an aromatic ketone.
Names & identifiers
- Preferred name
- Suprofen
- IUPAC
- 2-[4-(thiophene-2-carbonyl)phenyl]propanoic acid
- English name
- Suprofen
- Molecular formula
- C14H12O3S
- Molecular weight
- 260.31
Names & synonyms
Show more names
Database identifiers
- CAS
40828-46-4- PubChem CID
- 5359
- DTXSID
DTXSID5045469- ChEMBL
CHEMBL956- ChEBI
CHEBI:9362- UNII
- 988GU2F9PE
- EC Number
- 255-096-9
- Nikkaji
- J16.410K
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
- 321
Experimental & physicochemical properties
LogP
2.2
2.83
Solubility
limited solubility
4.22e-02 g/L
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Pharmaceuticals
Dissociation Constants
4.3
3.91
Collision Cross Section
157.2 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
156.15 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 278 °C · 278°C
- Boiling point
- 373.57 °C · 373.57°C (rough estimate)
- Density
- 1.2959 · 1.2959 (rough estimate)
- refractive index
- 1.505 · 1.5050 (estimate)
- storage temp.
- -20 °C · Keep in dark place,Sealed in dry,Store in freezer, under -20°C
- solubility
- 30 mg/ml; · DMF: 30 mg/ml; DMSO: 30 mg/ml; Ethanol: 20 mg/ml; PBS (pH 7.2): 0.5 mg/ml
- pka
- 3.91 · 3.91(at 25℃)
- form
- Powder
- color
- White to off-white
- Water Solubility
- soluble
- InChI
- InChI=1S/C14H12O3S/c1-9(14(16)17)10-4-6-11(7-5-10)13(15)12-3-2-8-18-12/h2-9H,1H3,(H,16,17)
- InChIKey
- MDKGKXOCJGEUJW-UHFFFAOYSA-N
- SMILES
- C1(=CC=C(C(C)C(=O)O)C=C1)C(=O)C1SC=CC=1
- CAS DataBase Reference
- 40828 · 40828-46-4(CAS DataBase Reference)
- FDA UNII
- 988 GU2F9PE · 988GU2F9PE
- ATC code
- 1 AE07 · M01AE07
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 301 · H301
- Precautionary statements
- 301 · P301+P330+P331+P310
- RIDADR
- 3249 · 3249
- WGK Germany
- 3 · WGK 3
- HazardClass
- 6.1 · 6.1(b)
- PackingGroup
- III
- HS Code
- 2934990002 · 2934990002
- Storage Class
- 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- 3 Oral · Acute Tox. 3 Oral
- Toxicity
- 50 · LD50 (7 days post-drug) in mice, rats, guinea pigs, dogs (mg/kg): 590, 353, 280, 160 orally (Niemegeers)
Safety & regulation
GHS classification
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Safety data
- wgk
- WGK 3
- ridadr
- 3249
- hs_code
- 2934990002
- Toxicity
- LD50 (7 days post-drug) in mice, rats, guinea pigs, dogs (mg/kg): 590, 353, 280, 160 orally (Niemegeers)
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_class
- 6.1(b)
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- packing_group
- III
- Hazard statements
- H301
- Hazard Classifications
- Acute Tox. 3 Oral
- Precautionary statements
- P301+P330+P331+P310
Chemistry & industry
Pharmacology
ATC Code
M - Musculo-skeletal system
QM - Musculo-skeletal system
Pharmacodynamics
Suprofen is a non-steroidal anti-inflammatory analgesic and antipyretic. Ophthalmic anti-inflammatory medicines are used in the eye to lessen problems that can occur during or after some kinds of eye surgery. Sometimes, the pupil of the eye gets smaller during an operation (pupil constriction), making it more difficult for the surgeon to reach some areas of the eye. Suprofen is used to help prevent this.
Mechanism of Action
Suprofen binds to the cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) isoenzymes, preventing the synthesis of prostaglandins and reducing the inflammatory response. Cyclooxygenase catalyses the formation of prostaglandins and thromboxane from arachidonic acid (itself derived from the cellular phospholipid bilayer by phospholipase A<sub>2</sub>). Prostaglandins act (among other things) as messenger molecules in the process of inflammation. The overall result is a reduction in pain and inflammation in the eyes and the prevention of pupil constriction during surgery. Normally trauma to the anterior segment of the eye (especially the iris) increases endogenous prostaglandin synthesis which leads to constriction of the iris sphincter.
Metabolism/Metabolites
Primarily hepatic (mainly via cytochrome P450 isozyme 2C9).
Suprofen has known human metabolites that include Suprofen -sulfoxide, Thiophene-4,5-epoxide, and (2S,3S,4S,5R)-3,4,5-trihydroxy-6-[2-[4-(thiophene-2-carbonyl)phenyl]propanoyloxy]oxane-2-carboxylic acid.
MeSH Pharmacological Classification
Compounds with activity like OPIATE ALKALOIDS, acting at OPIOID RECEPTORS. Properties include induction of ANALGESIA or NARCOSIS.
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.
Agents that induce NARCOSIS. Narcotics include agents that cause somnolence or induced sleep (STUPOR); natural or synthetic derivatives of OPIUM or MORPHINE or any substance that has such effects. They are potent inducers of ANALGESIA and OPIOID-RELATED DISORDERS.
Compounds or agents that combine with cyclooxygenase (PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES) and thereby prevent its substrate-enzyme combination with arachidonic acid and the formation of eicosanoids, prostaglandins, and thromboxanes.
Uses & manufacturing
Applications
DescriptionSuprofen is an arylpropionic acid analgesic/antiinflammatory agent with close structural resemblance to ketoprofen. It is more potent in many assays than indomethacin and ketoprofen and appears better tolerated.
UsesProstaglandin biosynthesis inhibitor. Analgesic
UsesBridged pseudopelletierine derivative; specific serotonin (5HT3) receptor antagonist. Antiemetic.
Upstream & downstream products
Upstream raw materials
Suppliers50 total
Additional notes
DefinitionChEBI: An aromatic ketone that is thiophene substituted at C-2 by a 4-(1-carboxyethyl)benzoyl group.
Related reactions
Linked notes
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