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

• ChemBase ID: 748
• Molecular Formular: C14H12O3S
• Molecular Mass: 260.30828
• Monoisotopic Mass: 260.05071524
• SMILES: s1c(C(=O)c2ccc(C(C)C(=O)O)cc2)ccc1
• Canonical SMILES: OC(=O)C(c1ccc(cc1)C(=O)c1cccs1)C
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[4-(thiophene-2-carbonyl)phenyl]propanoic acid
• IUPAC Traditional name: 2-[4-(thiophene-2-carbonyl)phenyl]propanoic acid; suprofen
• Brand Name: Maldocil; Masterfen; Profenal; Srendam; Sulproltin; Suprocil; Suprol; Sutoprofen; Topalgic
• Synonyms: Suprofene [INN-French]; Suprofenum [INN-Latin]; Suprofen; Profenal; Suprofen (Profenal); α-Methyl-4-(2-thienylcarbonyl)benzeneacetic Acid; p-(2-Thenoyl)hydratropic Acid; Sutoprofen; R-25061; Masterfen; Srendam; Sulprotin; Supranol; Suprocil; Suprol; Topalgic

Database IDs

• CAS Number: 40828-46-4
• PubChem SID: 46508210; 160964211
• PubChem CID: 5359

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.011917
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.0281713
• LogD (pH = 7.4): 0.37402022
• Log P: 3.5262148
• Molar Refractivity: 69.4055 cm^3
• Polarizability: 26.688793 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.16
• LOG S: -3.79
• Solubility (Water): 4.22e-02 g/l

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Ethanol; limited solubility; Methanol,
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 116-118°C
• Hydrophobicity(logP): 2.2

Safety Information

• Storage Condition: -20°C Freezer

Pharmacology Properties

• Target: Others

Product Information

• Salt Data: Free Base

DETAILS

DrugBank - DB00870

• Drug Groups: approved
• Description: An ibuprofen-type anti-inflammatory analgesic and antipyretic. It inhibits prostaglandin synthesis and has been proposed as an anti-arthritic. [PubChem]
• Indication: Used as eye drops to inhibit the miosis (pupil constriction) that may occur during ocular surgery.
• Pharmacology: 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.
• Toxicity: Symptoms of overdose include bleeding in the eye or redness or swelling of the eye or the eyelid, blurred vision or other change in vision, fever or chills, itching or tearing, nausea or vomiting, pain, sensitivity to light, shortness of breath, sticky or matted eyelashes, swelling of face, throbbing pain, tightness in chest, troubled breathing, and wheezing.
• Affected Organisms: Humans and other mammals
• Biotransformation: Primarily hepatic (mainly via cytochrome P450 isozyme 2C9).
• Protein Binding: 20%
• External Links: Wikipedia; Drugs.com

Toronto Research Chemicals - S840000

Prostaglandin biosynthesis inhibitor. Analgesic.

REFERENCES

• Niemegeers, C.J.E., et al.: Arzneim.-Forsch., 25, 1537 (1975)