2-(3-benzoylphenyl)propanoic acid

• ChemBase ID: 882
• Molecular Formular: C16H14O3
• Molecular Mass: 254.28056
• Monoisotopic Mass: 254.09429431
• SMILES: OC(=O)C(c1cc(ccc1)C(=O)c1ccccc1)C
• Canonical SMILES: OC(=O)C(c1cccc(c1)C(=O)c1ccccc1)C
• InChI: InChI=1S/C16H14O3/c1-11(16(18)19)13-8-5-9-14(10-13)15(17)12-6-3-2-4-7-12/h2-11H,1H3,(H,18,19)
• InChIKey: DKYWVDODHFEZIM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3-benzoylphenyl)propanoic acid
• IUPAC Traditional name: 2-(3-benzoylphenyl)propanoic acid; ketoprofen
• Brand Name: Actron; Alrheumat; Alrheumun; Capisten; Dexal; Epatec; Fastum; Iso-K; Kefenid; Ketopron; Lertus; Menamin; Meprofen; Orudis; Orudis KT; Orugesic; Oruvail; Oscorel; Profenid; Toprec; Toprek
• Synonyms: Alrheumat; 2-(3-benzoylphenyl)propanoic acid; Orudis; Oruvail; Ketoflam; Orudis KT; m-Benzoylhydratropic acid; Ketoprofen; 2-[3-Benzoylphenyl]propionic acid; Ketoprofen; 2-(3-Benzoylphenyl)propionic acid; 3-Benzoyl-α-methylbenzeneacetic Acid; RP-19583; Alreumat; Alrheumun; Capisten; Epatec; Fastum; Ketofen; Menamin; Toprec; rac Ketoprofen; 2-(3-苯甲酰苯基)丙酸; 酮洛芬

Database IDs

• CAS Number: 22071-15-4
• EC Number: 244-759-8
• MDL Number: MFCD00055790
• PubChem SID: 160964345; 24896217; 24860779; 24278504; 46505715
• PubChem CID: 3825
• CHEBI ID: 6128
• ATC CODE: M01AE03; M01AE17; M02AA10
• CHEMBL: 571
• Chemspider ID: 3693
• DrugBank ID: DB01009
• KEGG ID: D00132
• Unique Ingredient Identifier: 90Y4QC304K
• Wikipedia Title: Ketoprofen
• Medline Plus: a686014

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.882609
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.9908713
• LogD (pH = 7.4): 0.39084414
• Log P: 3.6133335
• Molar Refractivity: 72.5156 cm^3
• Polarizability: 28.005615 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.29
• LOG S: -4.08
• Solubility (Water): 2.13e-02 g/l

PROPERTIES

Physical Property

• Solubility: 51 mg/L; Chloroform
• Apperance: White Solid
• Melting Point: 75 - 78°C; 91-93°C; 94°C
• Hydrophobicity(logP): 2.761; 3.2

Safety Information

• Storage Condition: -20°C; -20°C Freezer; Room Temperature (15-30°C)
• Storage Warning: IRRITANT
• RTECS: UE7570000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; III
• Australian Hazchem: 2X
• Risk Statements: 25-36/37/38; R:25
• Safety Statements: 26-45; S:28-29-36/37/39-45
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154
• TSCA Listed: false
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H319-H335
• GHS Precautionary statements: P261-P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3

Pharmacology Properties

• Admin Routes: Oral, topical, intravenous (veterinary use)
• Half Life: 2-2.5 hours
• Protein Bound: 99%
• Legal Status: Prescription-only medicine
• Pregnancy Category: C (D in 3rd trimester)
• Gene Information: human ... ALB(213), IL8RA(3577), PTGS1(5742), PTGS2(5743)
• Mechanism of Action: Bradykinin antagonist; Leukotriene synthesis inhibitor; Prostaglandin-antagonist

Product Information

• Purity: ≥98% (TLC); 95%; 95+%
• Grade: VETRANAL™, analytical standard
• Salt Data: Free Base
• Suitability: meets USP testing specifications
• Application(s): Analgesic; Antiinflammatory
• Empirical Formula (Hill Notation): C16H14O3

DETAILS

MP Biomedicals - 02155154

(2-[3-Benzoylphenyl]propionic acid)

DrugBank - DB01009

• Drug Groups: approved
• Description: Ketoprofen, a propionic acid derivative, is a nonsteroidal anti-inflammatory agent (NSAIA) with analgesic and antipyretic properties.
• Indication: For symptomatic treatment of acute and chronic rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, primary dysmenorrhea and mild to moderate pain associated with musculotendinous trauma (sprains and strains), postoperative (including dental surgery) or postpartum pain.
• Pharmacology: Ketoprofen is a nonsteroidal anti-inflammatory agent (NSAIA) with analgesic and antipyretic properties. Ketoprofen has pharmacologic actions similar to those of other prototypical NSAIDs, which inhibit prostaglandin synthesis. Ketoprofen is used to treat rheumatoid arthritis, osteoarthritis, dysmenorrhea, and alleviate moderate pain.
• Toxicity: LD₅₀=62.4 mg/kg (rat, oral). ;

  Symptoms of overdose include drowsiness, vomiting and abdominal pain.

  ;

  Side effects are usually mild and mainly involved the GI tract. Most common adverse GI effect is dyspepsia (11% of patients). May cause nausea, diarrhea, abdominal pain, constipation and flatulence in greater than 3% of patients.

• Affected Organisms: Humans and other mammals
• Biotransformation: Rapidly and extensively metabolized in the liver, primarily via conjugation to glucuronic acid. No active metabolites have been identified.
• Absorption: Ketoprofen is rapidly and well-absorbed orally, with peak plasma levels occurring within 0.5 to 2 hours.
• Half Life: Conventional capsules: 1.1-4 hours;

  Extended release capsules: 5.4 hours due to delayed absorption (intrinsic clearance is same as conventional capsules)

• Protein Binding: 99% bound, primarily to albumin
• Elimination: In a 24 hour period, approximately 80% of an administered dose of ketoprofen is excreted in the urine, primarily as the glucuronide metabolite.
• Clearance: * Oral-dose cl=6.9 +/- 0.8 L/h [Ketoprofen Immediate-release capsules (4 × 50 mg)]; * Oral-dose cl=6.8 +/- 1.8 L/h [Ketoprofen Extended-release capsules (1 × 200 mg)]; * 0.08 L/kg/h; * 0.7 L/kg/h [alcoholic cirrhosis patients]
• References: Kantor TG: Ketoprofen: a review of its pharmacologic and clinical properties. Pharmacotherapy. 1986 May-Jun;6(3):93-103. [Pubmed] ; Mazieres B: Topical ketoprofen patch. Drugs R D. 2005;6(6):337-44. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Selleck Chemicals - S1645

Research Area: Inflammation
Biological Activity:
Ketoprofen (Actron) is a non-selective NSAID exhibiting IC50 of 0.5 μM and 2.33 μM for human recombinant COX-1 and COX-2, respectively. [1] It is used for its antipyretic, analgesic, and anti-inflammatory properties by inhibiting cyclooxygenase-1 and -2 (COX-1 and COX-2) enzymes reversibly, which decreases production of pro-inflammatory prostaglandin precursors. [2] Based on in vitro IC(50) COX-1:IC(50) COX-2 ratios, robenacoxib was COX-2 selective (ratio=32.2), diclofenac (ratio=3.9) and meloxicam (ratio=2.7) were only weakly COX-2 preferential, and ketoprofen (ratio=0.049) was COX-1 selective. [3]References on Ketoprofen (Actron)[] J. vet. Pharmacol. Therap., 2010, 33, 444–452

Sigma Aldrich - K1751

Biochem/physiol Actions
非甾体抗炎药，对 COX-1 具有选择性。

Sigma Aldrich - 34016

Biochem/physiol Actions
Non-steroidal anti-inflammatory compound that is selective for COX-1.
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - K2012

Biochem/physiol Actions
非甾体抗炎药，对 COX-1 具有选择性。

Toronto Research Chemicals - K200800

Anti-inflammatory; analgesic.

REFERENCES

• Mazieres B: Topical ketoprofen patch. Drugs R D. 2005;6(6):337-44. Pubmed
• Kantor TG: Ketoprofen: a review of its pharmacologic and clinical properties. Pharmacotherapy. 1986 May-Jun;6(3):93-103. Pubmed
• http://en.wikipedia.org/wiki/Ketoprofen
• Ueno, K., et al.: J. Med. Chem., 19, 941 (1976)
• Liversidge, G.G., Anal. Profiles Drug Subs., 10, 443 (1976)
• Jamali, F., et al.: Clin. Pharmacokinet., 19, 197 (1976)
• Brogden, R.N. et al., Drugs, 1974, 8, 168, (rev, pharmacol)
• Allais, A. et al., Eur. J. Med. Chem. (Chim. Ther.), 1974, 9, 381, (synth, pharmacol)
• Pinna, G. et al., Farmaco, Ed. Sci., 1980, 35, 684, (synth)
• Comisso, G. et al., Gazz. Chim. Ital., 1980, 110, 123, (synth, abs config)
• Liversidge, G.G., Anal. Profiles Drug Subst., 1981, 10, 443, (rev)
• Kim, J.W. et al., Arch. Pharmacal Res., 1987, 10, 25, (resoln, abs config)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 3889
• Mitra, R.B. et al., Synth. Commun., 1988, 18, 2259, (synth)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 21
• Camps, P. et al., Synth. Commun., 1993, 23, 1739, (synth)
• Sonawane, H.R. et al., Tetrahedron, 1994, 50, 1243, (synth)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, BDU500