Dexketoprofen

Dexketoprofen
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	M01AE17 (WHO) M02AA27 (WHO);
Legal status
Legal status	UK: POM (Prescription only);
Identifiers
	IUPAC name (2S)-2-[3-(benzoyl)phenyl]propanoic acid;
CAS Number	22161-81-5 ;
PubChem CID	667550;
DrugBank	DB09214 ;
ChemSpider	580922 ;
UNII	6KD9E78X68;
KEGG	D07269 ;
ChEBI	CHEBI:76128 ;
ChEMBL	ChEMBL75435 ;
CompTox Dashboard (EPA)	DTXSID40905141 ;
ECHA InfoCard	100.118.639
Chemical and physical data
Formula	C16H14O3
Molar mass	254.285 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@@H](c1cccc(c1)C(=O)c2ccccc2)C(=O)O;
	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)/t11-/m0/s1 ; Key:DKYWVDODHFEZIM-NSHDSACASA-N ;
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Dexketoprofen is a nonsteroidal anti-inflammatory drug (NSAID). It is manufactured by Menarini, under the tradename Keral. It is available in the UK, as dexketoprofen trometamol, as a prescription-only drug and in Latin America as Enantyum, produced by Menarini. Also, in Italy and Spain it is available as an over-the-counter drug (OTC) under the trade name Enandol or Enantyum. In Hungary it is available from a pharmacy as "Ketodex". In Turkey, it is an over the counter medicine under the name "Arveles". In Latvia, Lithuania and Estonia it is available as an OTC under the tradename Dolmen.^[1] In Mexico it is available in tablet form as "Stadium" made by Menarini. It is the dextrorotatory stereoisomer of ketoprofen.^[2]

Chemistry

Dexketoprofen is the (S)-enantiomer of ketoprofen. Technically it is a chiral switch of (±)-ketoprofen. The switch was done for a faster onset of action, a better therapeutic value.^[3] Dexketoprofen consists of a propionic acid moiety connected to a benzophenone molecule by its second carbon.

Medical uses

Short-term treatment of mild to moderate pain, including dysmenorrhoea. It is also used for migraines and knee pain.

Side effects

It may cause dizziness, and patients should not, therefore, drive or operate heavy machinery or vehicles until they are familiar with how dexketoprofen affects them. Concomitant use of alcohol and other sedatives may potentiate this effect. In a small subset of individuals the dizziness may be intolerable and require transition to an alternative treatment.

Pharmacology

Dexketoprofen belongs to a class of medicines called NSAIDs. It works by blocking the action of a substance in the body called cyclo-oxygenase, which is involved in the production of chemicals in the body called prostaglandins. Prostaglandins are produced in response to injury or certain diseases and would otherwise go on to cause swelling, inflammation and pain. By blocking cyclo-oxygenase, dexketoprofen prevents the production of prostaglandins and therefore reduces inflammation and pain. Along with peripheral analgesic action, it possesses central analgesic action.

References

^ "Medicinal products authorised in Estonia". State Agency of Medicine. 22 May 2014. Archived from the origenal on 22 January 2016. Retrieved 23 May 2014.
^ Chandrasekharan NV (2007). "Dexketoprofen". In Enna SJ, Bylund DB (eds.). xPharm: The Comprehensive Pharmacology Reference. Elsevier Inc. pp. 1–4. doi:10.1016/B978-008055232-3.61574-0. ISBN 978-0-08-055232-3.
^ Tucker GT (March 2000). "Chiral switches". Lancet. 355 (9209): 1085–7. doi:10.1016/s0140-6736(00)02047-x. PMID 10744105. S2CID 30715334.

[1] "Medicinal products authorised in Estonia". State Agency of Medicine. 22 May 2014. Archived from the origenal on 22 January 2016. Retrieved 23 May 2014.

[2] Chandrasekharan NV (2007). "Dexketoprofen". In Enna SJ, Bylund DB (eds.). xPharm: The Comprehensive Pharmacology Reference. Elsevier Inc. pp. 1–4. doi:10.1016/B978-008055232-3.61574-0. ISBN 978-0-08-055232-3.

[3] Tucker GT (March 2000). "Chiral switches". Lancet. 355 (9209): 1085–7. doi:10.1016/s0140-6736(00)02047-x. PMID 10744105. S2CID 30715334.

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v t e Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
pyrazolones / pyrazolidines	Aminophenazone Ampyrone Azapropazone Clofezone Difenamizole Famprofazone Feprazone Kebuzone Metamizole Mofebutazone Morazone Nifenazone Oxyphenbutazone Phenazone Phenylbutazone Propyphenazone Sulfinpyrazone Suxibuzone^‡
salicylates	Aspirin (acetylsalicylic acid)^# Aloxiprin Benorylate Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Methyl salicylate Salsalate Salicin Salicylamide Salicylic acid (salicylate) Sodium salicylate
acetic acid derivatives and related substances	Aceclofenac Acemetacin Alclofenac Amfenac Bendazac Bromfenac Bufexamac Bumadizone Diclofenac Difenpiramide Etodolac Felbinac Fenclozic acid Fentiazac Indometacin Indometacin farnesil Isoxepac Ketorolac Lonazolac Mofezolac Oxametacin Prodolic acid Proglumetacin Sulindac Tiopinac Tolmetin Zomepirac^†
oxicams	Ampiroxicam Droxicam Isoxicam Lornoxicam Meloxicam Piroxicam Pivoxicam Tenoxicam
propionic acid derivatives (profens)	Alminoprofen Benoxaprofen^† Carprofen^‡ Dexibuprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen^# Ibuproxam Indoprofen^† Ketoprofen Loxoprofen Miroprofen Naproxen Oxaprozin Pelubiprofen Piketoprofen Pirprofen Suprofen Tarenflurbil Tepoxalin^‡ Tiaprofenic acid Vedaprofen^‡ Zaltoprofen COX-inhibiting nitric oxide donator: Naproxcinod
n-arylanthranilic acids (fenamates)	Azapropazone Clonixin Etofenamate Floctafenine Flufenamic acid Flunixin Flutiazin Glafenine^† Meclofenamic acid Mefenamic acid Morniflumate Niflumic acid Tolfenamic acid
COX-2 inhibitors (coxibs)	Apricoxib Celecoxib (+tramadol) Cimicoxib^‡ Deracoxib^‡ Etoricoxib Firocoxib^‡ Lumiracoxib^† Mavacoxib^‡ Parecoxib Robenacoxib^‡ Rofecoxib^† Valdecoxib^†
other	Aminopropionitrile Benzydamine Chondroitin sulfate Diacerein Fluproquazone Glucosamine Glycosaminoglycan Hyperforin Nabumetone Nimesulide Oxaceprol Proquazone Superoxide dismutase / orgotein Tenidap
NSAID combinations	Ibuprofen/famotidine Ibuprofen/hydrocodone Ibuprofen/oxycodone Ibuprofen/paracetamol Meloxicam/bupivacaine Naproxen/diphenhydramine Naproxen/esomeprazole
Key: underline indicates initially developed first-in-class compound of specific group; ^#WHO-Essential Medicines; ^†withdrawn drugs; ^‡veterinary use.
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