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    Chemistry

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    Also known as: (s)-(+)-ketoprofen, 22161-81-5, (s)-ketoprofen, (+)-ketoprofen, (s)-2-(3-benzoylphenyl)propanoic acid, (2s)-2-(3-benzoylphenyl)propanoic acid
    Molecular Formula
    C16H14O3
    Molecular Weight
    254.28  g/mol
    InChI Key
    DKYWVDODHFEZIM-NSHDSACASA-N
    FDA UNII
    6KD9E78X68
    Dexketoprofen Trometamol
    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.
    1 2D Structure

    Dexketoprofen Trometamol

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S)-2-(3-benzoylphenyl)propanoic acid
    2.1.2 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
    2.1.3 InChI Key
    DKYWVDODHFEZIM-NSHDSACASA-N
    2.1.4 Canonical SMILES
    CC(C1=CC(=CC=C1)C(=O)C2=CC=CC=C2)C(=O)O
    2.1.5 Isomeric SMILES
    C[C@@H](C1=CC(=CC=C1)C(=O)C2=CC=CC=C2)C(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    6KD9E78X68
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Adolquir

    2. Badyket

    3. Dexketoprofen Trometamol

    4. Enangel

    5. Enantyum

    6. Keral

    7. Ketesse

    8. Quiralam

    9. Quirgel

    10. Sympal

    2.3.2 Depositor-Supplied Synonyms

    1. (s)-(+)-ketoprofen

    2. 22161-81-5

    3. (s)-ketoprofen

    4. (+)-ketoprofen

    5. (s)-2-(3-benzoylphenyl)propanoic Acid

    6. (2s)-2-(3-benzoylphenyl)propanoic Acid

    7. S-(+)-ketoprofen

    8. Dexketoprofen [inn]

    9. Arveles

    10. (+)-3-benzoylhydratropic Acid

    11. (+)-(s)-m-benzoylhydratropic Acid

    12. Hydratropic Acid, M-benzoyl-, (+)-

    13. Ketoprofen, (s)-

    14. (s)-3-benzoyl-alpha-methylbenzeneacetic Acid

    15. Chembl75435

    16. (s)-(+)-2-(3-benzoylphenyl)propionic Acid

    17. Chebi:76128

    18. 6kd9e78x68

    19. Dexketoprofen (inn)

    20. (2s)-2-[3-(benzenecarbonyl)phenyl]propanoic Acid

    21. Smr000857177

    22. Dexketoprofen [inn:ban]

    23. Unii-6kd9e78x68

    24. 9kl

    25. Mfcd00673316

    26. Biomolki_000007

    27. Biomolki2_000017

    28. Schembl66987

    29. Bmk1-b7

    30. Mls001333189

    31. Mls001333190

    32. Benzeneacetic Acid, 3-benzoyl-alpha-methyl-, (s)-

    33. Dexketoprofen [who-dd]

    34. Zinc5560

    35. (s)-(+)-ketoprofen, 99%

    36. Dtxsid40905141

    37. Hms2090m22

    38. Hms2234m14

    39. Bcp13810

    40. Hy-b2137

    41. Bdbm50088570

    42. S5192

    43. 2-(3-benzoyl-phenyl)-propionic Acid

    44. Akos015913672

    45. Ac-8103

    46. Ccg-100611

    47. Cs-8173

    48. Db09214

    49. Ncgc00142585-01

    50. Ncgc00142585-02

    51. As-17683

    52. Bk166230

    53. (s)-2-(3-benzoyl-phenyl)-propionic Acid

    54. (+)-2-(3-benzoylphenyl)propionic Acid

    55. (s)-(+)-2-(3-benzoylphenyl) Propionic Acid

    56. (s)-(+)-3-benzoyl-?-methylbenzeneacetic Acid

    57. D07269

    58. D94685

    59. (2s)-2-(3-benzoylphenyl)propionic Acid

    60. Ab00918363-05

    61. (s)-(+)-3-benzoyl-alpha-methylbenzeneacetic Acid

    62. 161k815

    63. A878675

    64. Q425440

    65. S-(+)-ketoprofen; (s)-ketoprofen; Dexketoprofen

    66. W-201922

    67. (.alpha.s)-3-benzoyl-.alpha.-methylbenzeneacetic Acid

    68. Benzeneacetic Acid, 3-benzoyl-.alpha.-methyl-, (.alpha.s)-

    69. Benzeneacetic Acid, 3-benzoyl-.alpha.-methyl-, (s)-

    70. Benzeneacetic Acid, 3-benzoyl-?-methyl-, (s)-hydratropic Acid, M-benzoyl-, (+)-

    2.4 Create Date
    2005-07-07
    3 Chemical and Physical Properties
    Molecular Weight 254.28 g/mol
    Molecular Formula C16H14O3
    XLogP33.1
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count4
    Exact Mass254.094294304 g/mol
    Monoisotopic Mass254.094294304 g/mol
    Topological Polar Surface Area54.4 Ų
    Heavy Atom Count19
    Formal Charge0
    Complexity331
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

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

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

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

    5.2 MeSH Pharmacological Classification

    Anti-Inflammatory Agents, Non-Steroidal

    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.)

    5.3 ATC Code

    M - Musculo-skeletal system

    M01 - Antiinflammatory and antirheumatic products

    M01A - Antiinflammatory and antirheumatic products, non-steroids

    M01AE - Propionic acid derivatives

    M01AE17 - Dexketoprofen

    M - Musculo-skeletal system

    M02 - Topical products for joint and muscular pain

    M02A - Topical products for joint and muscular pain

    M02AA - Antiinflammatory preparations, non-steroids for topical use

    M02AA27 - Dexketoprofen

    5.4 Absorption, Distribution and Excretion

    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

    Route of Elimination

    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.

    Volume of Distribution

    <0.25 L/kg

    Clearance

    Mainly cleared via glucuronide conjugation and followed by renal excretion, mainly unchanged.

    5.5 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

    5.6 Biological Half-Life

    1.65 h

    5.7 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.

    API Reference Price

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    04-Jan-2021
    29-Aug-2024
    KGS
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