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(+)-Ketoprofen

(+)-Ketoprofen structure

CAS No:
22161-81-5
Formula:
C16H14O3
Chemical Name:
(+)-Ketoprofen
Synonyms:
Benzeneacetic acid,3-benzoyl-α-methyl-,(αS)-;Benzeneacetic acid,3-benzoyl-α-methyl-,(S)-;Hydratropic acid,m-benzoyl-,(+)-;(αS)-3-Benzoyl-α-methylbenzeneacetic acid;(+)-Ketoprofen;(S)-Ketoprofen;(+)-3-Benzoylhydratropic acid;(+)-2-(3-Benzoylphenyl)propionic acid;(2S)-2-(3-Benzoylphenyl)propionic acid;Dexketoprofen;(+)-(S)-m-Benzoylhydratropic acid;(S)-(+)-2-(3-Benzoylphenyl)propionic acid;(S)-2-(3-Benzoylphenyl)propionic acid;(+)-3-Benzoyl-α-methylbenzeneacetic acid;S-(+)-Ketoprofen;(S)-2-(3-Benzoylphenyl)propanoic acid;Arveles;(2S)-2-(3-Benzoylphenyl)propanoic acid
Categories:
Active Pharmaceutical Ingredients > Other Chemical Drugs

Description

S-(+)-Ketoprofen is a potent inhibitor of both COX-1 and COX-2 with IC50s of 1.9 and 27 nM, respectively.

Dexketoprofen is a monocarboxylic acid that is (S)-hydratropic acid substituted at position 3 on the phenyl ring by a benzoyl group. A cyclooxygenase inhibitor, it is used to relieve short-term pain, such as muscular pain, dental pain and dysmenorrhoea. It has a role as a non-steroidal anti-inflammatory drug, a cyclooxygenase 1 inhibitor, a cyclooxygenase 2 inhibitor and a non-narcotic analgesic. It is a monocarboxylic acid and a member of benzophenones. It derives from a (S)-hydratropic acid.|Dexketoprofen is a non-steroidal anti-inflammatory drug. It is available in the various countries in Europe, Asia and Latin America. It has analgesic, antipyretic and anti-inflammatory properties.

(+)-Ketoprofen Basic Attributes

Molecular Weight：

254.28

Exact Mass：

254.28

EC Number：

606-944-5

UNII：

6KD9E78X68

ATC Code：

M - Musculo-skeletal system

HScode：

2942000000

Characteristics

PSA：

54.4

XLogP3：

3.1

Appearance：

white or almost white, crystalline powder.

Density：

1.2±0.1 g/cm3

Melting Point：

72 °C @ Solvent: Diisopropyl ether, Ligroine

Boiling Point：

431.316°C at 760 mmHg

Flash Point：

228.8±20.5 °C

Refractive Index：

1.592

Safety Information

Packing level：

Ⅲ

Transport codes：

3077

wgk germany：

hazard class code：

safety instructions：

26-60-61

RTECS Number：

CY1572790

Marks：

Xn: Harmful;

Precautionary statement(s)：

P261-P273-P301 + P310-P305 + P351 + P338

Hazard Statements：

H301-H315-H319-H335-H400

Toxicity

Toxicity Summary：

Nausea and/or vomiting, stomach pain, diarrhea, digestive problems (dyspepsia) are the most common symptoms of toxicity. More toxicity symptoms include dizziness, sleepiness, disturbed sleep, nervousness, headache, palpitations, flushing, stomach problems, constipation, dry mouth, flatulence, skin rash, tiredness, pain, feeling feverish and shivering, and malaise. Severe toxicity can lead to thrombocytopenia and anemia with bleeding episodes. Dexketoprofen is associated with a small increased risk of myocardial infarction.

Protein Binding：

Highly protein bound.

Drug Information

Drug Indication：

For short-term treatment of mild to moderate pain, including dysmenorrhoea, musculoskeletal pain and toothache.

Pharmacology：

This drug is an isomer of ketoprofen. Dexketoprofen a propionic acid derivative with analgesic, anti-inflammatory, and antipyretic properties.

MeSH：

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. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)

Absorption：

After oral ingestion, the Dexketoprofen onset of action is within 30 minutes. The plasma half-life of Dexketoprofen is about 4-6 hours. The Cmax is about 30 minutes|Approximately 70 to 80% of the ingested dose is recovered in the urine during the first 12 hours post-ingestion, mainly as the acyl-conjugated form of the drug.|<0.25 L/kg|Mainly cleared via glucuronide conjugation and followed by renal excretion, mainly unchanged.

Metabolism/Metabolites：

Dexketoprofen is highly lipophilic, and is metabolized in the liver by glucuronidation. In one study, after oral administration of 25 mg of dexketoprofen to young healthy adults, Tmax was approximately 30 min for a Cmax of 3.7 ± 0.72 mg/l. Dexketoprofen trometamol is metabolized by the hepatic cytochrome P450 enzymes (CYP2C8 and CYP2C9). Dexketoprofen trometamol has a number of metabolites, with hydroxyl derivatives making up the greatest volume. In humans, hydroxylation plays a minor role. Dexketoprofen is primarily conjugated to an acyl-glucuronide

Biological Half-Life：

1.65 h

Mechanism of Action：

It is a non-steroidal anti-inflammatory drug (NSAID) that reduces prostaglandin synthesis via inhibition of cyclooxygenase pathway (both COX-1 and COX-2) activity.

MeSH Entry Terms：

Adolquir

(+)-Ketoprofen Use and Manufacturing

COX inhibitor Anti-inflammatory; analgesic

Computed Properties

Molecular Weight:254.28
XLogP3:3.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:254.094294304
Monoisotopic Mass:254.094294304
Topological Polar Surface Area:54.4
Heavy Atom Count:19
Complexity:331
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

Extract from the above information

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Dexketoprofen Tablets
Specifications	25mg

Dexketoprofen
Manufacturer	Huangshi Shixing Pharmaceutical Co., Ltd.

Dexketoprofen

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Registered Holders

Huangshi Shixing Pharmaceutical Co., Ltd.

China
Active
PKU HealthCare Corp., Ltd.

China
Active
NAGASE FINE CHEMICALS LTD

United States
Inactive

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