Suprofen

HCID 5359CAS 40828-46-4

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

suprofen40828-46-4SutoprofenProfenalp-2-Thenoylhydratropic acidSulproltinSrendamSuprofeneTopalgicSuprofenumracemic suprofen2-[4-(thiophene-2-carbonyl)phenyl]propanoic acid
Show more names
ProfenolSuprolr25061AnemetSuprocilmaldocil
TN-7624-(2-Thenoyl)hydratropsaeureR-25061p-(2-thenoyl)hydratropic acidTN 7622-(4-(thiophene-2-carbonyl)phenyl)propanoic acid2-(4-(2-Thenoyl)phenyl)propionsaeureR-25,061

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

Experimental & physicochemical properties

LogP · 2 items

2.2

2.83

Solubility · 2 items

limited solubility

4.22e-02 g/L

Human Drugs · 3 items

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Pharmaceuticals

Melting Point124.3 °C
Physical DescriptionSolid
Dissociation Constants · 2 items

4.3

3.91

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

Safety & regulation

GHS classification

GHS Classification · 4 items

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

Hazard Classes and CategoriesAcute Tox. 3 (100%)

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

Chemistry & industry

Pharmacology

ATC Code · 2 items

M - Musculo-skeletal system

QM - Musculo-skeletal system

Protein Binding20%
Pharmacodynamics · 1 item

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 · 1 item

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 · 2 items

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 · 4 items

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

Use ClassificationPharmaceuticals
Applications · 3 items

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.

Suppliers50 total

北京华美互利生物化工010-56205725 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
成都乐美天医药科技有限公司17308096051 17308096051 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]

Additional notes

DefinitionChEBI: An aromatic ketone that is thiophene substituted at C-2 by a 4-(1-carboxyethyl)benzoyl group.

Related reactions

42 records

Linked notes

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