ChemFOnt: Showing chemical card for Suprofen (CFc000009322)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:25 UTC

Chemfont ID

CFc000009322

Molecule Identification

Common Name

Suprofen

Definition

Suprofen is only found in individuals that have used or taken this drug. It is an ibuprofen-type anti-inflammatory analgesic and antipyretic. It inhibits prostaglandin synthesis and has been proposed as an anti-arthritic. [PubChem]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 A₂). 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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+-)-2-(p-(2-Thenoyl)phenyl)propionic acid	ChEBI
2-(4-(2-Thenoyl)phenyl)propionsaeure	ChEBI
2-[4-(Thiophene-2-carbonyl)-phenyl]-propionic acid	ChEBI
4-(2-Thenoyl)hydratropsaeure	ChEBI
alpha-Methyl-4-(2-thienylcarbonyl)benzeneacetic acid	ChEBI
p-2-Thenoylhydratropic acid	ChEBI
PROFENAL	ChEBI
Suprofene	ChEBI
Suprofenum	ChEBI
SUTOPROFEN	ChEBI
(+-)-2-(p-(2-Thenoyl)phenyl)propionate	Generator
2-[4-(Thiophene-2-carbonyl)-phenyl]-propionate	Generator
a-Methyl-4-(2-thienylcarbonyl)benzeneacetate	Generator
a-Methyl-4-(2-thienylcarbonyl)benzeneacetic acid	Generator
alpha-Methyl-4-(2-thienylcarbonyl)benzeneacetate	Generator
Α-methyl-4-(2-thienylcarbonyl)benzeneacetate	Generator
Α-methyl-4-(2-thienylcarbonyl)benzeneacetic acid	Generator
p-2-Thenoylhydratropate	Generator

Chemical Formula

C₁₄H₁₂O₃S

Average Molecular Weight

260.308

Monoisotopic Molecular Weight

260.05071494

IUPAC Name

2-[4-(thiophene-2-carbonyl)phenyl]propanoic acid

Traditional Name

suprofen

CAS Registry Number

40828-46-4

SMILES

CC(C(O)=O)C1=CC=C(C=C1)C(=O)C1=CC=CS1

InChI Identifier

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)

InChI Key

MDKGKXOCJGEUJW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Aryl-phenylketones

Alternative Parents

Substituents

Aryl-phenylketone
2-phenylpropanoic-acid
P-cymene
Aromatic monoterpenoid
Monocyclic monoterpenoid
Monoterpenoid
Benzoyl
Thiophene carboxylic acid or derivatives
Benzenoid
Monocyclic benzene moiety
Heteroaromatic compound
Thiophene
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:9362 )
thiophenes (CHEBI:9362 )
aromatic ketone (CHEBI:9362 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0015008)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Suprofen Action Pathway (PathBank: SMP0000101)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.042 g/L	ALOGPS
logP	3.16	ALOGPS
logP	3.53	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	4.01	ChemAxon
pKa (Strongest Basic)	-7.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	69.41 m³·mol⁻¹	ChemAxon
Polarizability	26.84 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon