Oxaprozin: Synthesis, sar study, physico-chemical characteristics and pharmacology
Oksaprozin - sinteza, sar studija, fizičko-hemijska svojstva i farmakologija
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Приказ свих података о документуАпстракт
Oxaprozin (3-(4,5-diphenyloxazol-2-yl)propanoic acid) is a nonsteroidal anti-inflammatory drug (NSAID) used in the treatment of numerous inflammatory musculoskeletal diseases, including rheumatoid arthritis, osteoarthritis, tendonitis, ankylosing spondylitis and bursitis. It is the first representative member of the diaryl- substituted heterocyclic compounds, which have found clinical use as selective cyclooxygenase-2 (COX-2) inhibitors. The U.S. Food and Drug Administration (FDA) approved its official use in 1992. Both the anti-inflammatory and analgesic properties of oxaprozin are mainly due to the potent inhibition of COX. However, oxaprozin-induced benefits might be also regulated by other COX-independent pathways. It has been shown that oxaprozin induced direct proapoptotic effects in CD40L-treated human monocytes independently of COX inhibition. It also has several advantages in the treatment of inflammatory diseases in comparison to other NSAIDs such as aspirin, naproxen, indome...thacin and phenylbutazone, which enabled oxaprozin to become one of the most used NSAIDs in America. Oxaprozin, as other members of the group of NSAIDs, can cause gastrointestinal complications, but significantly lower due to relatively high pKa value. In this paper, the importance of oxaprozin in the treatment of arthritis and its pharmacokinetic properties were described, therewith its activity and side effects were compared with other commercially available anti-inflammatory drugs.
Oksaprozin (3-(4,5-difeniloksazol-2-il)propanska kiselina) jeste nesteroidni anti-inflamatorni agens koji se koristi za simptomatsko lečenje inflamacije, bola i reumatoidnih oboljenja. U ovom radu prikazani su različiti postupci dobijanja oksaprozina, njegovih derivata i detaljan opis mehanizma reakcija sinteze, kao i njegova fizička i hemijska svojstva. Pored osnovnih molekulskih osobina koje su značajne za aktivnost oksaprozina kao nesteroidnog anti-inflamatornog leka, navedeni su najznačajniji podaci SAR (eng. Structure-Activity Relationship) studije sintetisanih njegovih analoga. Istaknut je značaj oksaprozina u lečenju artritisa, njegova farmakokinetička svojstva i poređena je njegava aktivnost i sporedni efekti sa ostalim komercijalno dostupnim anti-inflamatornim lekovima.
Кључне речи:
oxaprozin / anti-inflammatory activity / inhibition of cyclooxygenases / pharmacokinetics / arthritis / Oksaprozin / anti-inflamatorna aktivnost / inhibicija ciklooksigenaza / farmakokinetika / ArtritisИзвор:
Hemijska industrija, 2011, 65, 5, 551-562Издавач:
- Association of Chemical Engineers of Serbia
Финансирање / пројекти:
- Проучавање синтезе, структуре и активности органских једињења природног и синтетског порекла (RS-MESTD-Basic Research (BR or ON)-172013)
DOI: 10.2298/HEMIND110426040B
ISSN: 0367-598X
WoS: 000300029700008
Scopus: 2-s2.0-80855144455
Институција/група
Tehnološko-metalurški fakultetTY - JOUR AU - Božić, Bojan AU - Trišović, Nemanja AU - Valentić, Nataša AU - Ušćumlić, Gordana AU - Petrović, Slobodan PY - 2011 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/1804 AB - Oxaprozin (3-(4,5-diphenyloxazol-2-yl)propanoic acid) is a nonsteroidal anti-inflammatory drug (NSAID) used in the treatment of numerous inflammatory musculoskeletal diseases, including rheumatoid arthritis, osteoarthritis, tendonitis, ankylosing spondylitis and bursitis. It is the first representative member of the diaryl- substituted heterocyclic compounds, which have found clinical use as selective cyclooxygenase-2 (COX-2) inhibitors. The U.S. Food and Drug Administration (FDA) approved its official use in 1992. Both the anti-inflammatory and analgesic properties of oxaprozin are mainly due to the potent inhibition of COX. However, oxaprozin-induced benefits might be also regulated by other COX-independent pathways. It has been shown that oxaprozin induced direct proapoptotic effects in CD40L-treated human monocytes independently of COX inhibition. It also has several advantages in the treatment of inflammatory diseases in comparison to other NSAIDs such as aspirin, naproxen, indomethacin and phenylbutazone, which enabled oxaprozin to become one of the most used NSAIDs in America. Oxaprozin, as other members of the group of NSAIDs, can cause gastrointestinal complications, but significantly lower due to relatively high pKa value. In this paper, the importance of oxaprozin in the treatment of arthritis and its pharmacokinetic properties were described, therewith its activity and side effects were compared with other commercially available anti-inflammatory drugs. AB - Oksaprozin (3-(4,5-difeniloksazol-2-il)propanska kiselina) jeste nesteroidni anti-inflamatorni agens koji se koristi za simptomatsko lečenje inflamacije, bola i reumatoidnih oboljenja. U ovom radu prikazani su različiti postupci dobijanja oksaprozina, njegovih derivata i detaljan opis mehanizma reakcija sinteze, kao i njegova fizička i hemijska svojstva. Pored osnovnih molekulskih osobina koje su značajne za aktivnost oksaprozina kao nesteroidnog anti-inflamatornog leka, navedeni su najznačajniji podaci SAR (eng. Structure-Activity Relationship) studije sintetisanih njegovih analoga. Istaknut je značaj oksaprozina u lečenju artritisa, njegova farmakokinetička svojstva i poređena je njegava aktivnost i sporedni efekti sa ostalim komercijalno dostupnim anti-inflamatornim lekovima. PB - Association of Chemical Engineers of Serbia T2 - Hemijska industrija T1 - Oxaprozin: Synthesis, sar study, physico-chemical characteristics and pharmacology T1 - Oksaprozin - sinteza, sar studija, fizičko-hemijska svojstva i farmakologija EP - 562 IS - 5 SP - 551 VL - 65 DO - 10.2298/HEMIND110426040B ER -
@article{ author = "Božić, Bojan and Trišović, Nemanja and Valentić, Nataša and Ušćumlić, Gordana and Petrović, Slobodan", year = "2011", abstract = "Oxaprozin (3-(4,5-diphenyloxazol-2-yl)propanoic acid) is a nonsteroidal anti-inflammatory drug (NSAID) used in the treatment of numerous inflammatory musculoskeletal diseases, including rheumatoid arthritis, osteoarthritis, tendonitis, ankylosing spondylitis and bursitis. It is the first representative member of the diaryl- substituted heterocyclic compounds, which have found clinical use as selective cyclooxygenase-2 (COX-2) inhibitors. The U.S. Food and Drug Administration (FDA) approved its official use in 1992. Both the anti-inflammatory and analgesic properties of oxaprozin are mainly due to the potent inhibition of COX. However, oxaprozin-induced benefits might be also regulated by other COX-independent pathways. It has been shown that oxaprozin induced direct proapoptotic effects in CD40L-treated human monocytes independently of COX inhibition. It also has several advantages in the treatment of inflammatory diseases in comparison to other NSAIDs such as aspirin, naproxen, indomethacin and phenylbutazone, which enabled oxaprozin to become one of the most used NSAIDs in America. Oxaprozin, as other members of the group of NSAIDs, can cause gastrointestinal complications, but significantly lower due to relatively high pKa value. In this paper, the importance of oxaprozin in the treatment of arthritis and its pharmacokinetic properties were described, therewith its activity and side effects were compared with other commercially available anti-inflammatory drugs., Oksaprozin (3-(4,5-difeniloksazol-2-il)propanska kiselina) jeste nesteroidni anti-inflamatorni agens koji se koristi za simptomatsko lečenje inflamacije, bola i reumatoidnih oboljenja. U ovom radu prikazani su različiti postupci dobijanja oksaprozina, njegovih derivata i detaljan opis mehanizma reakcija sinteze, kao i njegova fizička i hemijska svojstva. Pored osnovnih molekulskih osobina koje su značajne za aktivnost oksaprozina kao nesteroidnog anti-inflamatornog leka, navedeni su najznačajniji podaci SAR (eng. Structure-Activity Relationship) studije sintetisanih njegovih analoga. Istaknut je značaj oksaprozina u lečenju artritisa, njegova farmakokinetička svojstva i poređena je njegava aktivnost i sporedni efekti sa ostalim komercijalno dostupnim anti-inflamatornim lekovima.", publisher = "Association of Chemical Engineers of Serbia", journal = "Hemijska industrija", title = "Oxaprozin: Synthesis, sar study, physico-chemical characteristics and pharmacology, Oksaprozin - sinteza, sar studija, fizičko-hemijska svojstva i farmakologija", pages = "562-551", number = "5", volume = "65", doi = "10.2298/HEMIND110426040B" }
Božić, B., Trišović, N., Valentić, N., Ušćumlić, G.,& Petrović, S.. (2011). Oxaprozin: Synthesis, sar study, physico-chemical characteristics and pharmacology. in Hemijska industrija Association of Chemical Engineers of Serbia., 65(5), 551-562. https://doi.org/10.2298/HEMIND110426040B
Božić B, Trišović N, Valentić N, Ušćumlić G, Petrović S. Oxaprozin: Synthesis, sar study, physico-chemical characteristics and pharmacology. in Hemijska industrija. 2011;65(5):551-562. doi:10.2298/HEMIND110426040B .
Božić, Bojan, Trišović, Nemanja, Valentić, Nataša, Ušćumlić, Gordana, Petrović, Slobodan, "Oxaprozin: Synthesis, sar study, physico-chemical characteristics and pharmacology" in Hemijska industrija, 65, no. 5 (2011):551-562, https://doi.org/10.2298/HEMIND110426040B . .