Drug Information
| Drug General Information | Top | |||
|---|---|---|---|---|
| Drug ID |
D0W9WF
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| Former ID |
DAP000623
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| Drug Name |
Ketoprofen
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| Synonyms |
Actron; Alrheumat; Alrheumum; Alrheumun; Aneol; Capisten; Dexal; Epatec; Fastum; Kefenid; Ketoprofene; Ketoprofeno; Ketoprofenum; Ketopron; Ketoprophene; Lertus; Menamin; Meprofen; Orudis; Orugesic; Oruvail; Oscorel; Profenid; Toprec; Toprek; Benzoylhydratropic Acid; Orudis KT; K 1751; RP 19583; RP19583; RU 4733; Arthril (TN); Fastum (TN); Fastum Gel (TN); Iso-K; Keto (TN); Ketoflam (TN); Ketomex (TN); Ketonal (TN); Ketoprofenas (TN); Ketoprofene (TN); Ketoprofene [INN-French]; Ketoprofeno [INN-Spanish]; Ketoprofenum (TN); Ketoprofenum [INN-Latin]; Ketorin (TN); Ketospray (TN); Lasonil (TN); M-Benzoylhydratropic acid; Oki (TN); Orudis (TN); Oruvail (TN); RP-19583; Racemic-Ketoprofen; Zon (TN); Bi-Profnid (TN); RP, 19,583; Ketoprofen (JP15/USP/INN); Ketoprofen [USAN:INN:BAN:JAN]; Orudis, Oruvail, Ketoflam, Orudis KT, Ketoprofen; Acide (benzoyl-3-phenyl)-2-propionique; Acide (benzoyl-3-phenyl)-2-propionique [French]; L'Acide (benzoyl-3-phenyl)-2-propionique; (+-)-m-Benzoylhydratropic acid; 2-(3-Benzoylphenyl)propanoic acid; 2-(3-Benzoylphenyl)propionic acid; 2-(m-Benzoylphenyl)propionic acid; 2-[3-(benzoyl)phenyl]propanoic acid; 2-[3-(phenylcarbonyl)phenyl]propanoic acid; 2-[3-Benzoylphenyl]propionic acid; 3-Benzoylhydratropic acid
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| Drug Type |
Small molecular drug
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| Indication | Musculoskeletal pain [ICD-11: MG30; ICD-10: R52.1, R52.2] | Approved | [1], [2] | |
| Pain [ICD-11: MG30-MG3Z] | Phase 3 | [3], [4] | ||
| Migraine [ICD-11: 8A80; ICD-10: G43, G43.9; ICD-9: 346] | Phase 2 | [5] | ||
| Osteoarthritis [ICD-11: FA00-FA05] | Phase 1 | [5] | ||
| Therapeutic Class |
Analgesics
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| Company |
ProEthic Pharmaceuticals
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| Structure |
 |
Download2D MOL |
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| Formula |
C16H14O3
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| Canonical SMILES |
CC(C1=CC(=CC=C1)C(=O)C2=CC=CC=C2)C(=O)O
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| 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)
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| InChIKey |
DKYWVDODHFEZIM-UHFFFAOYSA-N
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| CAS Number |
CAS 22071-15-4
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| PubChem Compound ID | ||||
| PubChem Substance ID |
4853, 857801, 5316933, 7847200, 7979680, 8149782, 8152423, 10321584, 10513923, 11335773, 11361012, 11364203, 11366765, 11369327, 11372636, 11373574, 11377489, 11461984, 11466247, 11467367, 11484688, 11485894, 11488772, 11491294, 11491843, 11495123, 11532908, 11533518, 15122326, 17405247, 24278504, 24860779, 24896217, 26612243, 26679814, 26747548, 26747549, 29222944, 46505715, 47216761, 47365167, 47588981, 47588982, 47588983, 47662267, 47736456, 47810738, 48184977, 48413934, 49698784
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| ChEBI ID |
CHEBI:6128
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| ADReCS Drug ID | BADD_D01231 | |||
| SuperDrug ATC ID |
M01AE03; M02AA10
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| SuperDrug CAS ID |
cas=022071154
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| Interaction between the Drug and Microbe | Top | |||
|---|---|---|---|---|
| The Metabolism of Drug Affected by Studied Microbe(s) | ||||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Bacteroidales | ||||
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Studied Microbe: Bacteroides
Show/Hide Hierarchy
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[6] | |||
| Hierarchy | ||||
| Microbial Enzyme | Beta glucuronidase | |||
| Metabolic Reaction | Hydrolysis | |||
| Metabolic Effect | Increase toxicity | |||
| Description | Ketoprofen can be metabolized by the beta glucuronidase of Bacteroides through hydrolysis, which results in the increase of the drug's toxicity. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Bifidobacteriales | ||||
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Studied Microbe: Bifidobacterium
Show/Hide Hierarchy
|
[6] | |||
| Hierarchy | ||||
| Microbial Enzyme | Beta glucuronidase | |||
| Metabolic Reaction | Hydrolysis | |||
| Metabolic Effect | Increase toxicity | |||
| Description | Ketoprofen can be metabolized by the beta glucuronidase of Bifidobacterium through hydrolysis, which results in the increase of the drug's toxicity. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Eubacteriales | ||||
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Studied Microbe: Clostridium
Show/Hide Hierarchy
|
[6] | |||
| Hierarchy | ||||
| Microbial Enzyme | Beta glucuronidase | |||
| Metabolic Reaction | Hydrolysis | |||
| Metabolic Effect | Increase toxicity | |||
| Description | Ketoprofen can be metabolized by the beta glucuronidase of Clostridium through hydrolysis, which results in the increase of the drug's toxicity. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Gut microbiota | ||||
| Studied Microbe: Gut microbiota unspecific | [6], [7], [8] | |||
| Metabolic Reaction | Deglucuronidation | |||
| Metabolic Effect | Increase side effect (diarrhea | |||
| Description | Ketoprofen can be metabolized by gut microbiota through deglucuronidation, which results in the increase of the drug's side effect (diarrhea; bowel distress; gastrointestinal lesions). | |||
| References | Top | |||
|---|---|---|---|---|
| REF 1 | URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4795). | |||
| REF 2 | FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (ANDA) 073516. | |||
| REF 3 | Ketoprofen-induced cyclooxygenase inhibition in renal medulla and platelets of rats treated with caffeine. Pharmacology. 2001;63(4):234-9. | |||
| REF 4 | Synthesis and biological testing of Acyl-CoA-ketoprofen conjugates as selective irreversible inhibitors of COX-2. Bioorg Med Chem. 2002 Mar;10(3):753-7. | |||
| REF 5 | Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA) | |||
| REF 6 | Gut microbiota modulates drug pharmacokinetics. Drug Metab Rev. 2018 Aug;50(3):357-368. | |||
| REF 7 | Gut microbiome interactions with drug metabolism, efficacy, and toxicity. Transl Res. 2017 Jan;179:204-222. | |||
| REF 8 | Predicting and Understanding the Human Microbiome's Impact on Pharmacology. Trends Pharmacol Sci. 2019 Jul;40(7):495-505. | |||
| REF 9 | Probing the skin permeation of fish oil/EPA and ketoprofen-3. Effects on epidermal COX-2 and LOX. Prostaglandins Leukot Essent Fatty Acids. 2007 Jun;76(6):357-62. | |||
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