Nitrosothiol esters of diclofenac: Synthesis and pharmacological characterization as gastrointestinal-sparing prodrugs

Journal of Medicinal Chemistry

Volumn 43, Issue 21, 2000, Pages 4005-4016

  Bandarage, U K ^a   Chen, L ^a   Fang, X ^a   Garvey, D S ^a   Glavin, A ^a   Janero, D R ^a   Letts, L G ^a   Mercer, G J ^a   Saha, J K ^a   Schroeder, J D ^a   Shumway, M J ^a   Tam, S W ^a  

^a NitroMed Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 [METHYL[(NITROTHIOCYCLOHEXYL)METHYL]AMINO]ETHYL 2 [2 [(2,6 DICHLOROPHENYL)AMINO]PHENYL]ACETATE; 2 ETHYL 2 (NITROSOTHIO)BUTYL 2 [2 [(2,6 DICHLOROPHENYL)AMINO]PHENYL]ACETATE; 2 METHYL 2 (NITROSOTHIO)PROPYL 2 [2 [(2,6 DICHLOROPHENYL)AMINO]PHENYL]ACETATE; 3 [METHYL[(NITROSOTHIOCYCLOHEXYL)METHYL]AMINO]PROPYL 2 [2 [(2,6 DICHLOROPHENYL)AMINO]PHENYL]ACETATE; [(NITROSOTHIO)CYCLOHEXYL]METHYL 2 [2 [(2,6 DICHLOROPHENYL)AMINO]PHENYL]ACETATE; CARRAGEENAN; DICLOFENAC DERIVATIVE; NONSTEROID ANTIINFLAMMATORY AGENT; UNCLASSIFIED DRUG;

ANALGESIC ACTIVITY; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG BIOAVAILABILITY; DRUG SAFETY; DRUG SYNTHESIS; MALE; MOUSE; NONHUMAN; PAW EDEMA; RAT; STOMACH LESION; WRITHING TEST;

ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; BIOLOGICAL AVAILABILITY; DICLOFENAC; MALE; MICE; NITROSO COMPOUNDS; PRODRUGS; RATS; RATS, SPRAGUE-DAWLEY; STOMACH; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0034687219     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm000178w     Document Type: Article

References (43)

1. Review of Diclofenac and Evaluation of Its Place in Therapy as a Nonsteroidal Anti-inflammatory Agent
2. Synthesis and Quantitative Structure-activity Relationship of Diclofenac Analogous
3. Non Steroidal Anti-inflammatory Drugs
4. The Art and Science of Nonsteroidal Antiinflammatory Drug Selection
5. Morpholinoalkyl Ester Prodrug of Diclofenac: Synthesis, In vitro and In vivo Evaluation
6. Pharmacological Properties of Diclofenac Sodium and Its Metabolites
7. Mitogen Inducible Prostaglandin G/H Synthase: A New Target for Non Steroidal Antiinflammatory Drugs
8. Inducible Isoforms of Cyclooxgenase and Nitric Oxide Synthase in Inflammation
9. Exacerbation of Inflammation-associated Colonic Injury in Rat through Inhibition of Cyclooxygenase-2
10. Pharmacology of Diclofenac Sodium
11. International Experience with Diclofenac in Rheumatoid Arthritis
12. Efficacy and Safety of Diclofenac Sodium in Rheumatoid Arthritis. Experience in the United States
13. NSAID Gastropathy: Epidemilogy
14. Mechanism of Nonsteroidal Antiinflammatory Drug (NSAID) Induced Gastrointestinal Damage-Potential for Development of Gastrointestinal Tract Safe NSAIDs
15. Synthesis and Pharmacological Evalution of Oligoethylene Ester Derivatives as Indomethacin Oral Prodrugs
16. Selective Inhibitors of COX-2
17. Overview: The Mechanism of Action of Antiinfiammatory Drugs
18. COX-2 Inhibitors
19. Gastrointestinal Toxicity of Non Steroidal Antiinflammatory Drugs
20. Prostaglandin Synthase 2 Gene Disruption Causes Severe Renal Pathology in the Mouse
21. Novel Nonsteroidal Antiinflammatory Drug Derivatives with Markedly Reduced Ulcerogenic Properties in the Rats
22. A Diclofenac Derivative without Ulcerogenic Properties
23. A Nitric Oxide-releasing Nonsteroidal Antiinflammatory Drug Accelerates Gastric Ulcer Healing in Rats
24. Effect of a Nitric Oxide-Releasing Naproxen Derivative on Hypertension and Gastric Damage Induced by Chronic Nitric Oxide Inhibition in the Rat
25. Nitric Oxide-Releasing Non-Steroidal Antiinflammatory Drugs: A Novel Approach for Reducing Gastrointestinal Toxicity
26. Nitric Oxide-releasing Nonsteroidal Antiinflammatory Drugs: Novel Gastrointestinal-sparing drugs
27. Clinical Pharmacology of Organic Nitrate
28. S-Nitrosothioh A Class of Nitric Donor Drugs
29. Nitric oxide (NO)-related Pharmaceuticals: Contemporary Approaches to Therapeutic NO Modulation
30. Redox Signaling: Nitrosylation and Related Target Interactions of Nitric Oxide
31. Nitrosylated Bovine Serum Albumin Derivatives as Pharmacologically Active Nitric Oxide Congeners
32. An Unusually Stable Thionitrite from N-acetyl-D,L-penicillamine: X-ray Crystal and Molecular Structure of 2-(Acetyl-amino)-2-carboxy-1,1-dimethyl thionitrite
33. NO, Nitrosonium ions, Nitrosothiols and Iron-nitrosyls in Biology: A Chemist's Perspective
34. New Thionitrites: Synthesis, Stability and Nitric Oxide Generation
35. Deoxyribonucleoside 3'-O-(2-thio- and 2-oxo-'spiro'-4,4-pentamethylene-1,3,2-oxathiaphospholane)s: Monomers for Stereocontrolled Synthesis of Oligo(deoxyribonucleoside phosphorothioate)s and Chimeric PS/PO Oligonucleotides
36. The Analgesic Properties of Piroxicam in Animals and Correlation with Experimentally Determined Plasma Levels
37. Carrageenan-induced Edema in Hind Paw of the Rat as an Assay for Antilnflammatory Drugs
38. Effect of Endothelium-Derived Relaxing Factor on the Gastric Lesion Induced by HCl in Rats
39. Nitrosothiol-Based NO-Donors Inhibit the Gastrointestinal Mucesal Damaging Actions of NSAIDs
40. Sulfhydryl Compounds may Mediate Gastric Cytoprotection
41. Gastointestinal Safety of Nitric Oxide-Derived Aspirin is Related to Inhibition of ICE- Like Cysteine Proteases in Rats
42. Rapid Chromatographic Technique for Preparative Separations with Moderate Resolution
43. A Rapid and Sensitive High-parfomance Liquid Chromatographic Method for the Determination of Diclofenac Sodium in Serum and its Use in Pharmacekinetic Studies