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    Chemistry

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    Also known as: 22071-15-4, 2-(3-benzoylphenyl)propanoic acid, Orudis, 2-(3-benzoylphenyl)propionic acid, Actron, Capisten
    Molecular Formula
    C16H14O3
    Molecular Weight
    254.28  g/mol
    InChI Key
    DKYWVDODHFEZIM-UHFFFAOYSA-N
    FDA UNII
    90Y4QC304K
    Ketoprofen
    An IBUPROFEN-type anti-inflammatory analgesic and antipyretic. It is used in the treatment of rheumatoid arthritis and osteoarthritis.
    Ketoprofen is a Nonsteroidal Anti-inflammatory Drug. The mechanism of action of ketoprofen is as a Cyclooxygenase Inhibitor.
    1 2D Structure

    Ketoprofen

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    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)
    2.1.3 InChI Key
    DKYWVDODHFEZIM-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC(C1=CC(=CC=C1)C(=O)C2=CC=CC=C2)C(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    90Y4QC304K
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 19,583 Rp

    2. 2-(3-benzoylphenyl)propionic Acid

    3. Alrheumat

    4. Alrheumum

    5. Benzoylhydratropic Acid

    6. Orudis

    7. Profenid

    8. Rp 19583

    9. Rp, 19,583

    10. Rp-19583

    11. Rp19583

    2.3.2 Depositor-Supplied Synonyms

    1. 22071-15-4

    2. 2-(3-benzoylphenyl)propanoic Acid

    3. Orudis

    4. 2-(3-benzoylphenyl)propionic Acid

    5. Actron

    6. Capisten

    7. Oruvail

    8. M-benzoylhydratropic Acid

    9. Alrheumat

    10. Ketoprofene

    11. Profenid

    12. Aneol

    13. 3-benzoylhydratropic Acid

    14. Alrheumun

    15. Epatec

    16. Iso-k

    17. Orudis (tn)

    18. Rp-19583

    19. Ketoprofeno

    20. Ketoprophene

    21. 2-[3-(phenylcarbonyl)phenyl]propanoic Acid

    22. Ketorin

    23. Sector

    24. (rs)-ketoprofen

    25. 2-(m-benzoylphenyl)propionic Acid

    26. Actron Ketoprofen

    27. Racemic Ketoprofen

    28. Benzeneacetic Acid, 3-benzoyl-.alpha.-methyl-

    29. 3-benzoyl-alpha-methylbenzeneacetic Acid

    30. Ru 4733

    31. Ketoprofen (actron)

    32. Chebi:6128

    33. Chembl571

    34. Nsc-758144

    35. Propionic Acid, 2-(3-benzoylphenyl)-

    36. (s)-ketoprofen;dexketoprofen

    37. 19583 Rp

    38. Hydratropic Acid, M-benzoyl-

    39. L'acide (benzoyl-3-phenyl)-2-propionique

    40. Mls000079024

    41. Idea-033

    42. R.p. 19,583

    43. 90y4qc304k

    44. Orudis Kt

    45. 1189508-77-7

    46. 19583rp

    47. Ru-4733

    48. Kefenid

    49. Ketopron

    50. Menamin

    51. Meprofen

    52. Orugesic

    53. Oscorel

    54. Smr000040181

    55. Fastum

    56. Ketoprofen 100 Microg/ml In Acetonitrile

    57. Lertus

    58. Toprec

    59. Toprek

    60. Dexal

    61. Dsstox_cid_771

    62. R.p. 19583

    63. Racemic-ketoprofen

    64. Dsstox_rid_75783

    65. Dsstox_gsid_20771

    66. Ketoprofenum

    67. Rp 19583

    68. Ketoprofene [inn-french]

    69. Ketoprofenum [inn-latin]

    70. Ketoprofeno [inn-spanish]

    71. Ketoprofen (+-)

    72. (+-)-m-benzoylhydratropic Acid

    73. Benzeneacetic Acid, 3-benzoyl-alpha-methyl-

    74. Sr-01000075949

    75. Rac Ketoprofen

    76. Ccris 4508

    77. (+-)-3-benzoyl-alpha-methylbenzeneacetic Acid

    78. (+/-)-m-benzoylhydratropic Acid

    79. (+) Ketoprofen

    80. Ncgc00016757-01

    81. Ketoprofen ,(s)

    82. Acide (benzoyl-3-phenyl)-2-propionique [french]

    83. Prestwick_617

    84. Einecs 244-759-8

    85. 2-[3-(benzoyl)phenyl]propanoic Acid

    86. Cas-22071-15-4

    87. Mfcd00055790

    88. Nexcede

    89. Ketoprofen-13c-d3

    90. 2-(3-benzoylphenyl)-propionic Acid

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

    92. Acide (benzoyl-3-phenyl)-2-propionique

    93. Spectrum_001309

    94. Ketoprofen [mi]

    95. Opera_id_509

    96. Ketoprofen [inn]

    97. Ketoprofen [jan]

    98. Prestwick0_000219

    99. Prestwick1_000219

    100. Prestwick2_000219

    101. Prestwick3_000219

    102. Spectrum2_000956

    103. Spectrum3_001479

    104. Spectrum4_000028

    105. Spectrum5_001254

    106. Ketoprofen [usan]

    107. M-benzoyl-hydratropic Acid

    108. Ketoprofen [vandf]

    109. Epitope Id:131783

    110. K 1751

    111. Ketoprofen [mart.]

    112. Schembl2896

    113. Ketoprofen [who-dd]

    114. (+/-)-ketoprofen

    115. Lopac0_000686

    116. Oprea1_117113

    117. Bspbio_000237

    118. Bspbio_003037

    119. Kbiogr_000435

    120. Kbioss_001789

    121. 22161-86-0

    122. Mls000028446

    123. Mls001201752

    124. Mls001306444

    125. Mls002548889

    126. Mls006011967

    127. Bidd:gt0443

    128. Divk1c_000598

    129. Spectrum1501215

    130. Unii-90y4qc304k

    131. Spbio_000952

    132. Spbio_002158

    133. Benzeneacetic Acid, 3-benzoyl-alpha-methyl-, (+-)-

    134. Bpbio1_000261

    135. Gtpl4795

    136. Ketoprofen (jp17/usp/inn)

    137. Ketoprofen [green Book]

    138. Ketoprofen, >=98% (tlc)

    139. Dtxsid6020771

    140. Ketoprofen [ep Impurity]

    141. Ketoprofen [orange Book]

    142. Dkywvdodhfezim-uhfffaoysa-

    143. Hms501n20

    144. Kbio1_000598

    145. Kbio2_001789

    146. Kbio2_004357

    147. Kbio2_006925

    148. Kbio3_002537

    149. 2-(3-benzoylphenyl)propanoicacid

    150. Ketoprofen [ep Monograph]

    151. Ketoprofen [usp Impurity]

    152. Ninds_000598

    153. Hms1568l19

    154. Hms1921b12

    155. Hms2089b16

    156. Hms2092l19

    157. Hms2095l19

    158. Hms2234h16

    159. Hms3259i05

    160. Hms3262i13

    161. Hms3372m08

    162. Hms3373g09

    163. Hms3649n10

    164. Hms3655c15

    165. Hms3712l19

    166. Hms3884k04

    167. Ketoprofen [usp Monograph]

    168. Pharmakon1600-01501215

    169. Bcp23428

    170. Hy-b0227

    171. 2-(3'-benzoylphenyl)propionic Acid

    172. 2-(3-benzoylphenyl) Propionic Acid

    173. Alpha(3-benzoylphenyl)propionic Acid

    174. Tox21_110594

    175. Tox21_200847

    176. Tox21_500686

    177. (.+/-.)-m-benzoylhydratropic Acid

    178. 2-(3-benzoylphenyl) Propionoic Acid

    179. Alpha-(m-benzoylphenyl)propionic Acid

    180. Bdbm50022271

    181. Ccg-39685

    182. Nsc758144

    183. S1645

    184. Stl450995

    185. (r)-(-)-ketoprofen-[13c,d3]

    186. 2-(3-benzoylphenyl)propanoic Acid #

    187. Alpha-(3-benzoylphenyl)propionic Acid

    188. Akos007930512

    189. Alpha-(m-benzoylphenyl) Propionic Acid

    190. Ketoprofen 100 Microg/ml In Methanol

    191. Tox21_110594_1

    192. Ac-1486

    193. Bcp9000810

    194. Db01009

    195. Ketoprofen [usan:usp:inn:ban:jan]

    196. Ks-5031

    197. Lp00686

    198. Nc00459

    199. Nsc 758144

    200. Sdccgsbi-0050664.p004

    201. Idi1_000598

    202. (rs)-2-(3-benzoylphenyl)propanoic Acid

    203. Ncgc00015578-02

    204. Ncgc00015578-03

    205. Ncgc00015578-04

    206. Ncgc00015578-05

    207. Ncgc00015578-07

    208. Ncgc00015578-08

    209. Ncgc00015578-10

    210. Ncgc00015578-12

    211. Ncgc00015578-23

    212. Ncgc00094043-01

    213. Ncgc00094043-02

    214. Ncgc00094043-03

    215. Ncgc00094043-04

    216. Ncgc00258401-01

    217. Ncgc00261371-01

    218. Bk166172

    219. ((c)i)-ketoprofen-d4(propionic-d4 Acid)

    220. 3-benzoyl-.alpha.-methylbenzeneacetic Acid

    221. Bcp0726000302

    222. Sbi-0050664.p003

    223. (+/-)-2-(3-benzoylphenyl)propionic Acid

    224. L''acide (benzoyl-3-phenyl)-2-propionique

    225. Unm-0000306100

    226. Ab00052249

    227. Am20060549

    228. Eu-0100686

    229. Ft-0602834

    230. Ft-0670646

    231. Ft-0670647

    232. K0038

    233. Ketoprofen, Meets Usp Testing Specifications

    234. Orudis, Profenid, Dexal, Keduril, Ketofen,

    235. Sw196784-3

    236. Bim-0050664.0001

    237. C01716

    238. D00132

    239. D78110

    240. Ketoprofen, Vetranal(tm), Analytical Standard

    241. Ab00052249-17

    242. Ab00052249-19

    243. Ab00052249-20

    244. Ab00052249_21

    245. Ab00052249_22

    246. 071k154

    247. A815896

    248. Q409192

    249. Q-201268

    250. Sr-01000075949-1

    251. Sr-01000075949-6

    252. Sr-01000075949-9

    253. (.+/-.)-3-benzoyl-.alpha.-methylbenzeneacetic Acid

    254. Brd-a97739905-001-05-9

    255. Brd-a97739905-001-15-8

    256. Sr-01000075949-18

    257. F2173-0960

    258. Z1695709452

    259. (+/-)-3-benzoyl-.alpha.-methylbenzeneacetic Acid

    260. Ketoprofen, British Pharmacopoeia (bp) Reference Standard

    261. Ketoprofen, European Pharmacopoeia (ep) Reference Standard

    262. Ketoprofen, United States Pharmacopeia (usp) Reference Standard

    263. N-fmoc-3-amino-4-(4-tert-butoxy-phenyl)-butyricacid

    264. Ketoprofen, Pharmaceutical Secondary Standard; Certified Reference Material

    265. 154907-35-4

    2.4 Create Date
    2005-03-25
    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 Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameKetoprofen
    PubMed HealthKetoprofen (By mouth)
    Drug ClassesAnalgesic, Antimigraine, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent
    Drug LabelKetoprofen is a non-steroidal anti-inflammatory drug. The chemical name for ketoprofen is 2-(3-benzoylphenyl)-propionic acid with the following structural formula:C16H14O3M.W. 254.29It has a pKa of 5.94 in methanol: water (3:1) an...
    Active IngredientKetoprofen
    Dosage FormCapsule; Capsule, extended release
    RouteOral
    Strength200mg; 25mg; 150mg; 75mg; 100mg; 50mg
    Market StatusPrescription
    CompanyActavis Labs Fl; Teva; Dorado Pharma; Mylan

    2 of 2  
    Drug NameKetoprofen
    PubMed HealthKetoprofen (By mouth)
    Drug ClassesAnalgesic, Antimigraine, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent
    Drug LabelKetoprofen is a non-steroidal anti-inflammatory drug. The chemical name for ketoprofen is 2-(3-benzoylphenyl)-propionic acid with the following structural formula:C16H14O3M.W. 254.29It has a pKa of 5.94 in methanol: water (3:1) an...
    Active IngredientKetoprofen
    Dosage FormCapsule; Capsule, extended release
    RouteOral
    Strength200mg; 25mg; 150mg; 75mg; 100mg; 50mg
    Market StatusPrescription
    CompanyActavis Labs Fl; Teva; Dorado Pharma; Mylan

    4.2 Drug 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.

    FDA Label

    Treatment of musculoskeletal and connective tissue pain

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    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.

    5.2 MeSH Pharmacological Classification

    Cyclooxygenase Inhibitors

    Compounds or agents that combine with cyclooxygenase (PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES) and thereby prevent its substrate-enzyme combination with arachidonic acid and the formation of eicosanoids, prostaglandins, and thromboxanes. (See all compounds classified as Cyclooxygenase Inhibitors.)

    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 FDA Pharmacological Classification
    5.3.1 Active Moiety
    KETOPROFEN
    5.3.2 FDA UNII
    90Y4QC304K
    5.3.3 Pharmacological Classes
    Cyclooxygenase Inhibitors [MoA]; Nonsteroidal Anti-inflammatory Drug [EPC]; Anti-Inflammatory Agents, Non-Steroidal [CS]
    5.4 ATC Code

    M02AA10

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    M - Musculo-skeletal system

    M01 - Antiinflammatory and antirheumatic products

    M01A - Antiinflammatory and antirheumatic products, non-steroids

    M01AE - Propionic acid derivatives

    M01AE03 - Ketoprofen

    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

    M02AA10 - Ketoprofen

    5.5 Absorption, Distribution and Excretion

    Absorption

    Ketoprofen is rapidly and well-absorbed orally, with peak plasma levels occurring within 0.5 to 2 hours.

    Route of Elimination

    In a 24 hour period, approximately 80% of an administered dose of ketoprofen is excreted in the urine, primarily as the glucuronide metabolite.

    Clearance

    Oral-dose cl=6.9 +/- 0.8 L/h [Ketoprofen Immediate-release capsules (4 50 mg)]

    Oral-dose cl=6.8 +/- 1.8 L/h [Ketoprofen Extended-release capsules (1 200 mg)]

    0.08 L/kg/h

    0.7 L/kg/h [alcoholic cirrhosis patients]

    5.6 Metabolism/Metabolites

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

    Ketoprofen has known human metabolites that include Ketoprofen glucuronide.

    S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

    5.7 Biological Half-Life

    Conventional capsules: 1.1-4 hours

    Extended release capsules: 5.4 hours due to delayed absorption (intrinsic clearance is same as conventional capsules)

    5.8 Mechanism 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.

    API Reference Price

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VICTORIA BC V8W 3V6 CANADA Victoria, , CANADASDNF CANADA","customerAddress":"SCF.287, MOTOR MARKET,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1715625000,"product":"KETOPROFEN","address":"SCF.287, MOTOR MARKET,","city":"CHANDIGARH.","supplier":"PHARMASTER LABORATORIES LIMITED","supplierCountry":"CHINA","foreign_port":"SHANGHAI","customer":"SAURAV CHEMICALS","customerCountry":"INDIA","quantity":"900.00","actualQuantity":"900","unit":"KGS","unitRateFc":"67.5","totalValueFC":"61706.4","currency":"USD","unitRateINR":"5693.6","date":"14-May-2024","totalValueINR":"5124262.5","totalValueInUsd":"61706.4","indian_port":"JNPT","hs_no":"29163990","bill_no":"3478024","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"SHANGHAI","supplierAddress":"301-3800 FINNERTY RD, VICTORIA BC V8W 3V6, CANADASDNF Canada","customerAddress":"SCF.287, MOTOR MARKET,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1717785000,"product":"KETOPROFEN USP-KETOPROFEN 25 KG","address":"564\/A\/22, ROAD NO.92","city":"HYDERABAD,ANDHRA PRADESH","supplier":"EUROAPI","supplierCountry":"GERMANY","foreign_port":"FRANKFURT\/MAIN INT\\'L","customer":"VIATRIS","customerCountry":"INDIA","quantity":"50.00","actualQuantity":"50","unit":"KGS","unitRateFc":"210","totalValueFC":"11689.5","currency":"EUR","unitRateINR":"19414.5","date":"08-Jun-2024","totalValueINR":"970725","totalValueInUsd":"11689.5","indian_port":"Bombay Air","hs_no":"29183090","bill_no":"3903490","productDescription":"API","marketType":"REGULATED MARKET","country":"GERMANY","selfForZScoreResived":"Pharma Grade","supplierPort":"FRANKFURT\/MAIN INT\\'L","supplierAddress":"Industriepark Hochst D-65926 Frankfurt am MainSDNF Germany","customerAddress":"564\/A\/22, ROAD NO.92"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1718994600,"product":"KETOPROFEN USP-KETOPROFEN 25 KG","address":"564\/A\/22, ROAD NO.92","city":"HYDERABAD,ANDHRA PRADESH","supplier":"EUROAPI","supplierCountry":"GERMANY","foreign_port":"FRANKFURT\/MAIN INT\\'L","customer":"VIATRIS","customerCountry":"INDIA","quantity":"200.00","actualQuantity":"200","unit":"KGS","unitRateFc":"210","totalValueFC":"46125.7","currency":"EUR","unitRateINR":"19152","date":"22-Jun-2024","totalValueINR":"3830400","totalValueInUsd":"46125.7","indian_port":"Bombay Air","hs_no":"29183090","bill_no":"4135960","productDescription":"API","marketType":"REGULATED MARKET","country":"GERMANY","selfForZScoreResived":"Pharma Grade","supplierPort":"FRANKFURT\/MAIN INT\\'L","supplierAddress":"Industriepark Hochst D-65926 Frankfurt am MainSDNF Germany","customerAddress":"564\/A\/22, ROAD NO.92"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1724610600,"product":"KETOPROFEN","address":"ACME PLAZA, ANDHERI KURLA ROAD,","city":"MUMBAI, MAHARASHTRA.","supplier":"PHARMASTER NINGBO INT ","supplierCountry":"CHINA","foreign_port":"SHANGHAI","customer":"SUN PHARMACEUTICAL INDUSTRIES LIMITED","customerCountry":"INDIA","quantity":"725.00","actualQuantity":"725","unit":"KGS","unitRateFc":"88","totalValueFC":"65188.5","currency":"USD","unitRateINR":"7466.8","date":"26-Aug-2024","totalValueINR":"5413430","totalValueInUsd":"65188.5","indian_port":"JNPT","hs_no":"29420090","bill_no":"5255491","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"SHANGHAI","supplierAddress":"1101,11 FLOOR, NO.757 RILI ROAD,AUXCENTRAL BUILDING,YINZHOU DISTRICT,315100 NINGBO CHINA China","customerAddress":"ACME PLAZA, ANDHERI KURLA ROAD,"}]
    02-Jan-2021
    30-Aug-2024
    KGS
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    Average Price (USD/KGS)

    Number of Transactions

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    Quantity (KGS) & Unit rate (USD/KGS) over time

    API Imports and Exports

    Importing Country Total Quantity
    (KGS)    		 Average Price
    (USD/KGS)    		 Number of Transactions

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