Product Name

Ketoprofen

CAS Number

22071-15-4

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Product Name:

Ketoprofen

CAS Number:

22071-15-4

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.

Mode of Action:

The anti-inflammatory effects of ketoprofen are believed to be due to inhibition cylooxygenase-2 (COX-2), an enzyme involved in prostaglandin synthesis via the arachidonic acid pathway. This results in decreased levels of prostaglandins that mediate pain, fever and inflammation. Ketoprofen is a non-specific cyclooxygenase inhibitor and inhibition of COX-1 is thought to confer some of its side effects, such as GI upset and ulceration. Ketoprofen is thought to have anti-bradykinin activity, as well as lysosomal membrane-stabilizing action. Antipyretic effects may be due to action on the hypothalamus, resulting in an increased peripheral blood flow, vasodilation, and subsequent heat dissipation.

Pharmacodynamics:

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.

Metabolism:

Rapidly and extensively metabolized in the liver, primarily via conjugation to glucuronic acid. No active metabolites have been identified.

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.

IUPAC:

2-(3-benzoylphenyl)propanoic acid

ATC:

M01AE03 M01AE17 M02AA10

PubChem:

3825

DrugBank:

DB01009 (APRD01059, DB05823)

Formula:

C₁₆H₁₄F₃N₃O₂S

Molecular Mass:

254.2806

Synonyms:

m-Benzoylhydratropic acid

SMILES:

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

AHFS Code:

28:08.04.92

InChi:

DKYWVDODHFEZIM-UHFFFAOYSA-N

General Reference:

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

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Ketoprofen

22071-15-4

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