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| Clinical data | |
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| Trade names | Oruvail, others |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a686014 |
| License data | |
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| Routes of administration | By mouth,topical,intravenous |
| ATC code | |
| Legal status | |
| Legal status | |
| Pharmacokinetic data | |
| Protein binding | 99% |
| Eliminationhalf-life | 2–2.5 hours |
| Identifiers | |
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| CAS Number | |
| PubChemCID | |
| IUPHAR/BPS | |
| DrugBank |
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| ChemSpider |
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| KEGG |
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| ChEBI | |
| ChEMBL | |
| CompTox Dashboard(EPA) | |
| ECHA InfoCard | 100.040.676 |
| Chemical and physical data | |
| Formula | C16H14O3 |
| Molar mass | 254.285 g·mol−1 |
| 3D model (JSmol) | |
| Chirality | Racemic mixture |
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 N Y (what is this?) (verify) | |
Ketoprofen is one of thepropionic acid class ofnonsteroidal anti-inflammatory drugs (NSAID) withanalgesic andantipyretic effects.[3] It acts by inhibiting the body's production ofprostaglandin.
It was patented in 1967 and approved for medical use in 1980.[4]
Ketoprofen is generally prescribed for arthritis-related inflammatory pains or severe toothaches that result in the inflammation of the gums.
Ketoprofen topical patches are being used for treatment of musculoskeletal pain.[5][6][7]
Ketoprofen can also be used for treatment of some pain, especially nerve pain such assciatica,postherpetic neuralgia andreferred pain forradiculopathy, in the form of a cream, ointment, liquid, spray, or gel, which may also containketamine andlidocaine, along with other agents which may be useful, such ascyclobenzaprine,amitriptyline,acyclovir,gabapentin,orphenadrine and other drugs used as NSAIDs or adjuvant, atypical or potentiators for pain treatment.
Trials are going on for using this drug along withibuprofen for management oflymphedema.[citation needed] Animal trial and some human trials have shown significant improvement over placebo control. Dr Stanley G Rockson, ofStanford University is leading these researches.[citation needed]
A 2013systematic review indicated "The efficacy of orally administered ketoprofen in relieving moderate-severe pain and improving functional status and general condition was significantly better than that ofibuprofen and/ordiclofenac."[8] A 2017Cochrane systematic review investigating ketoprofen as a single-dose by mouth in acute, moderate-to-severe postoperative pain concluded that its efficacy is equivalent to drugs such as ibuprofen and diclofenac.[9]
There is evidence supporting topical ketoprofen for osteoarthritis but not other chronic musculoskeletal pain.[10]
In October 2020, the U.S.Food and Drug Administration (FDA) required thedrug label to be updated for all nonsteroidal anti-inflammatory medications to describe the risk of kidney problems in fetuses that result in low amniotic fluid.[11][12] They recommend avoiding NSAIDs in pregnant women at 20 weeks or later in pregnancy.[11][12]
Ketoprofen undergoes metabolism in the liver via conjugation withglucuronic acid (glucuronidation) byUGT enzymes, hydroxylation of thebenzoyl ring by theCYP3A4 andCYP2C9 enzymes, andreduction of itsketonemoiety (a carbonylfunctional group, i.e. with carbon-oxygen double bond)[13] by carbonyl reducing enzymes (CREs).[14][15] Ketoprofen is used for its antipyretic, analgesic, and anti-inflammatory properties by inhibitingcyclooxygenase-1 and -2 (COX-1 and COX-2) enzymes reversibly, which decreases production of proinflammatory prostaglandin precursors.[14][16]
The patches have been shown to provide rapid and sustained delivery to underlying tissues without significantly increasing levels of drug concentration in the blood when compared to the traditional oral administration.[7][17]
Ketoprofen has one stereogenic center in the side chain and hence exists as mirror-image twins. Majority of theprofens are marketed asracemic mixtures. For most of the NSAIDs the pharmacological activity resides in the (S)-enantiomers with their (R)-enantiomer virtually inactive. An interesting observation about most profens including ketoprofen is that they undergo unidirectional metabolic inversion,chiral inversion, of the (R)- acid to its (S)-mirror-image version with no other change in the molecule.[18][19][20]There have been concerns raised that Ketoprofen can break down into the parentbenzophenone molecule in skin exposed to strong summer or tropical UV light and this could pose a theoretical cancer risk. Given such a risk it is better to use other pain killers in such circumstances.
The earliest report of therapeutic use in humans is in 1972.[21]
Brand names in Australia include Orudis and Oruvail. It is available in Japan in a transdermal patch Mohrus Tape, made byHisamitsu Pharmaceutical. It is available in the UK as Ketoflam and Oruvail, in Ireland as Fastum Gel, in Estonia as Keto, Ketonal, and Fastum Gel, in Finland as Ketorin, Keto, Ketomex, and Orudis; in France as Profénid, Bi-Profénid, Toprec, and Ketum; in Italy as Ketodol, Fastum Gel, Lasonil, Orudis and Oki; in Greece as Okitask; in Poland as Ketonal, Ketonal active, Ketolek, in Serbia, Slovenia and Croatia as Knavon and Ketonal; in Romania as Ketonal and Fastum Gel; in Mexico as Arthril; in Norway as Zon and Orudis; in Russia as ОКИ (OKI), Fastum Gel and Ketonal; in Spain as Actron and Fastum Gel; in Albania as Oki and Fastum Gel; in Indonesia as Kaltrofen; and in Venezuela as Ketoprofeno as an injectable solution of 100 mg and 150 mg capsules.
In some countries, the optically pure (S)-enantiomer (dexketoprofen) is available; itstrometamol salt is said to be particularly rapidly reabsorbed from the gastrointestinal tract, having a rapid onset of effects.
Ketoprofen is a common NSAID,antipyretic, andanalgesic used in horses and other equines.[22] It is most commonly used for musculoskeletal pain, joint problems, and soft tissue injury, as well aslaminitis. It is also used to control fevers and preventendotoxemia. It is also used as a mild painkiller in smaller animals, generally following surgical procedures.
In horses, it is given at a dose of 2.2 mg/kg/day. Studies have shown that it does not inhibit5-lipoxygenase andleukotriene B4,[23] as originally claimed.[24] It is therefore not considered superior tophenylbutazone as previously believed, although clinical signs of lameness are reduced with its use.[25] In fact, phenylbutazone was shown superior to ketoprofen in cases of experimentally-induced synovitis when both drugs were used at labeled dosages.[26]
Experiments have found ketoprofen, likediclofenac, is a veterinary drug causing lethal effects inred-headed vultures. Vultures feeding on the carcasses of recently treated livestock develop acute kidney failure within days of exposure.[27]
This article incorporates text from this source, which is in thepublic domain:"FDA Warns that Using a Type of Pain and Fever Medication in Second Half of Pregnancy Could Lead to Complications".U.S.Food and Drug Administration (FDA) (Press release). 15 October 2020. Retrieved15 October 2020. This article incorporates text from this source, which is in thepublic domain:"NSAIDs may cause rare kidney problems in unborn babies".U.S. Food and Drug Administration. 21 July 2017. Retrieved15 October 2020.
| pyrazolones / pyrazolidines | |
|---|---|
| salicylates | |
| acetic acid derivatives and related substances | |
| oxicams | |
| propionic acid derivatives (profens) |
|
| n-arylanthranilic acids (fenamates) | |
| COX-2 inhibitors (coxibs) | |
| other | |
| NSAID combinations | |
Key:underline indicates initially developed first-in-class compound of specific group;#WHO-Essential Medicines;†withdrawn drugs;‡veterinary use. | |
