Celekoksib

Celekoksib
Klinički podaci
Prodajno ime	Celebra, Celebrex
Drugs.com	Monografija
Način primene	Oralno
Identifikatori
CAS broj	169590-42-5
ATC kod	L01XX33 (WHO), M01AH01
PubChem	CID 2662
DrugBank	DB00482
ChemSpider	2562
KEGG	C07589
ChEBI	CHEBI:3520
ChEMBL	CHEMBL118

Celekoksib je COX-2 selektivni nesteroidni anti-inflamatorni lek. Jedno od imena pod kojima se prodaje je Celebrex.

Hemijske osobine

Celekoksib je organsko jedinjenje, koje sadrži 17 atoma ugljenika i ima molekulsku masu od 381,372 Da.^[1]^[2]^[3]^[4]^[5]^[6]^[7]^[8]

Osobine

Osobina	Vrednost
Broj akceptora vodonika	3
Broj donora vodonika	1
Broj rotacionih veza	4
Particioni koeficijent^[9] (ALogP)	4,4
Rastvorljivost^[10] (logS, log(mol/L))	-6,4
Polarna površina^[11] (PSA, Å²)	86,4

Reference

^ Malhotra, S.; Shafiq, N.; Pandhi, P. (2004 Mar 23). „COX-2 inhibitors: a CLASS act or Just VIGORously promoted”. MedGenMed. 6 (1): 6. PMC 1140734 . PMID 15208519. Проверите вредност парамет(а)ра за датум: |date= (помоћ)
^ Silverstein, Fred E.; Faich, Gerald; Goldstein, Jay L.; Simon, Lee S.; Pincus, Theodore; Whelton, Andrew; Makuch, Robert; Eisen, Glenn; Agrawal, Naurang M.; Stenson, William F.; Burr, Aimee M.; Zhao, William W.; Kent, Jeffrey D.; Lefkowith, James B.; Verburg, Kenneth M.; Geis, G. Steven (2000 Sep 13). „Gastrointestinal Toxicity with Celecoxib vs Nonsteroidal Anti-inflammatory Drugs for Osteoarthritis and Rheumatoid Arthritis”. JAMA. 284 (10): 1247—55. PMID 10979111. doi:10.1001/jama.284.10.1247. Проверите вредност парамет(а)ра за датум: |date= (помоћ)
^ Solomon, Scott D.; McMurray, John J.V.; Pfeffer, Marc A.; Wittes, Janet; Fowler, Robert; Finn, Peter; Anderson, William F.; Zauber, Ann; Hawk, Ernest; Bertagnolli, Monica (2005 Mar 17). „Cardiovascular risk associated with celecoxib in a clinical trial for colorectal adenoma prevention”. N Engl J Med. 352 (11): 1071—80. PMID 15713944. doi:10.1056/NEJMoa050405. Проверите вредност парамет(а)ра за датум: |date= (помоћ) Feb 15.
^ Yelland MJ, Nikles CJ, McNairn N, Del Mar CB, Schluter PJ, Brown RM: Celecoxib compared with sustained-release paracetamol for osteoarthritis: a series of n-of-1 trials. Rheumatology (Oxford). Yelland, M. J.; Nikles, C. J.; McNairn, N.; Del Mar, C. B.; Schluter, P. J.; Brown, R. M. (2007 Jan). „Celecoxib compared with sustained-release paracetamol for osteoarthritis: A series of n-of-1 trials”. Rheumatology (Oxford, England). 46 (1): 135—40. PMID 16777855. doi:10.1093/rheumatology/kel195. Проверите вредност парамет(а)ра за датум: |date= (помоћ) Jun 15.
^ Bertagnolli, Monica M.; Eagle, Craig J.; Zauber, Ann G.; Redston, Mark; Solomon, Scott D.; Kim, Kyungmann; Tang, Jie; Rosenstein, Rebecca B.; Wittes, Janet; Corle, Donald; Hess, Timothy M.; Woloj, G. Mabel; Boisserie, Frédéric; Anderson, William F.; Viner, Jaye L.; Bagheri, Donya; Burn, John; Chung, Daniel C.; Dewar, Thomas; Foley, T. Raymond; Hoffman, Neville; MacRae, Finlay; Pruitt, Ronald E.; Saltzman, John R.; Salzberg, Bruce; Sylwestrowicz, Thomas; Gordon, Gary B.; Hawk, Ernest T. (2006 Aug 31). „Celecoxib for the prevention of sporadic colorectal adenomas”. N Engl J Med. 355 (9): 873—84. PMID 16943400. doi:10.1056/NEJMoa061355. Проверите вредност парамет(а)ра за датум: |date= (помоћ)
^ Sandberg, Mia; Yasar, Ümit; Strömberg, Patrik; Höög, Jan-Olov; Eliasson, Erik (2002 Oct). „Oxidation of celecoxib by polymorphic cytochrome P450 2C9 and alcohol dehydrogenase”. Br J Clin Pharmacol. 54 (4): 423—9. PMC 1874434 . PMID 12392591. doi:10.1046/j.1365-2125.2002.01660.x. Проверите вредност парамет(а)ра за датум: |date= (помоћ)
^ Knox, C.; Law, V.; Jewison, T.; Liu, P.; Ly, S.; Frolkis, A.; Pon, A.; Banco, K.; Mak, C.; Neveu, V.; Djoumbou, Y.; Eisner, R.; Guo, A. C.; Wishart, D. S. (2011). „DrugBank 3.0: A comprehensive resource for 'omics' research on drugs”. Nucleic Acids Research. 39 (Database issue): D1035—41. PMC 3013709 . PMID 21059682. doi:10.1093/nar/gkq1126.
^ Wishart, D. S.; Knox, C.; Guo, A. C.; Cheng, D.; Shrivastava, S.; Tzur, D.; Gautam, B.; Hassanali, M. (2008). „DrugBank: A knowledgebase for drugs, drug actions and drug targets”. Nucleic Acids Research. 36 (Database issue): D901—6. PMC 2238889 . PMID 18048412. doi:10.1093/nar/gkm958.
^ Ghose, Arup K.; Viswanadhan, Vellarkad N.; Wendoloski, John J. (1998). „Prediction of Hydrophobic (Lipophilic) Properties of Small Organic Molecules Using Fragmental Methods: An Analysis of ALOGP and CLOGP Methods”. The Journal of Physical Chemistry A. 102 (21): 3762—3772. Bibcode:1998JPCA..102.3762G. doi:10.1021/jp980230o.
^ Tetko, Igor V.; Tanchuk, Vsevolod Yu.; Kasheva, Tamara N.; Villa, Alessandro E. P. (2001). „Estimation of Aqueous Solubility of Chemical Compounds Using E-State Indices”. Journal of Chemical Information and Computer Sciences. 41 (6): 1488—1493. PMID 11749573. doi:10.1021/ci000392t.
^ Ertl, Peter; Rohde, Bernhard; Selzer, Paul (2000). „Fast Calculation of Molecular Polar Surface Area as a Sum of Fragment-Based Contributions and Its Application to the Prediction of Drug Transport Properties”. Journal of Medicinal Chemistry. 43 (20): 3714—3717. PMID 11020286. doi:10.1021/jm000942e.

Literatura

Hardman JG, Limbird LE, Gilman AG (2001). Goodman & Gilman's The Pharmacological Basis of Therapeutics (10. изд.). New York: McGraw-Hill. ISBN 0071354697. doi:10.1036/0071422803.
Thomas L. Lemke; David A. Williams, ур. (2007). Foye's Principles of Medicinal Chemistry (6. изд.). Baltimore: Lippincott Willams & Wilkins. ISBN 0781768799.

Spoljašnje veze

Celecoxib

Molimo Vas, obratite pažnju na važno upozorenje
u vezi sa temama iz oblasti medicine (zdravlja).

[1] Malhotra, S.; Shafiq, N.; Pandhi, P. (2004 Mar 23). „COX-2 inhibitors: a CLASS act or Just VIGORously promoted”. MedGenMed. 6 (1): 6. PMC 1140734 . PMID 15208519. Проверите вредност парамет(а)ра за датум: |date= (помоћ)

[2] Silverstein, Fred E.; Faich, Gerald; Goldstein, Jay L.; Simon, Lee S.; Pincus, Theodore; Whelton, Andrew; Makuch, Robert; Eisen, Glenn; Agrawal, Naurang M.; Stenson, William F.; Burr, Aimee M.; Zhao, William W.; Kent, Jeffrey D.; Lefkowith, James B.; Verburg, Kenneth M.; Geis, G. Steven (2000 Sep 13). „Gastrointestinal Toxicity with Celecoxib vs Nonsteroidal Anti-inflammatory Drugs for Osteoarthritis and Rheumatoid Arthritis”. JAMA. 284 (10): 1247—55. PMID 10979111. doi:10.1001/jama.284.10.1247. Проверите вредност парамет(а)ра за датум: |date= (помоћ)

[3] Solomon, Scott D.; McMurray, John J.V.; Pfeffer, Marc A.; Wittes, Janet; Fowler, Robert; Finn, Peter; Anderson, William F.; Zauber, Ann; Hawk, Ernest; Bertagnolli, Monica (2005 Mar 17). „Cardiovascular risk associated with celecoxib in a clinical trial for colorectal adenoma prevention”. N Engl J Med. 352 (11): 1071—80. PMID 15713944. doi:10.1056/NEJMoa050405. Проверите вредност парамет(а)ра за датум: |date= (помоћ) Feb 15.

[4] Yelland MJ, Nikles CJ, McNairn N, Del Mar CB, Schluter PJ, Brown RM: Celecoxib compared with sustained-release paracetamol for osteoarthritis: a series of n-of-1 trials. Rheumatology (Oxford). Yelland, M. J.; Nikles, C. J.; McNairn, N.; Del Mar, C. B.; Schluter, P. J.; Brown, R. M. (2007 Jan). „Celecoxib compared with sustained-release paracetamol for osteoarthritis: A series of n-of-1 trials”. Rheumatology (Oxford, England). 46 (1): 135—40. PMID 16777855. doi:10.1093/rheumatology/kel195. Проверите вредност парамет(а)ра за датум: |date= (помоћ) Jun 15.

[5] Bertagnolli, Monica M.; Eagle, Craig J.; Zauber, Ann G.; Redston, Mark; Solomon, Scott D.; Kim, Kyungmann; Tang, Jie; Rosenstein, Rebecca B.; Wittes, Janet; Corle, Donald; Hess, Timothy M.; Woloj, G. Mabel; Boisserie, Frédéric; Anderson, William F.; Viner, Jaye L.; Bagheri, Donya; Burn, John; Chung, Daniel C.; Dewar, Thomas; Foley, T. Raymond; Hoffman, Neville; MacRae, Finlay; Pruitt, Ronald E.; Saltzman, John R.; Salzberg, Bruce; Sylwestrowicz, Thomas; Gordon, Gary B.; Hawk, Ernest T. (2006 Aug 31). „Celecoxib for the prevention of sporadic colorectal adenomas”. N Engl J Med. 355 (9): 873—84. PMID 16943400. doi:10.1056/NEJMoa061355. Проверите вредност парамет(а)ра за датум: |date= (помоћ)

[6] Sandberg, Mia; Yasar, Ümit; Strömberg, Patrik; Höög, Jan-Olov; Eliasson, Erik (2002 Oct). „Oxidation of celecoxib by polymorphic cytochrome P450 2C9 and alcohol dehydrogenase”. Br J Clin Pharmacol. 54 (4): 423—9. PMC 1874434 . PMID 12392591. doi:10.1046/j.1365-2125.2002.01660.x. Проверите вредност парамет(а)ра за датум: |date= (помоћ)

[7] Knox, C.; Law, V.; Jewison, T.; Liu, P.; Ly, S.; Frolkis, A.; Pon, A.; Banco, K.; Mak, C.; Neveu, V.; Djoumbou, Y.; Eisner, R.; Guo, A. C.; Wishart, D. S. (2011). „DrugBank 3.0: A comprehensive resource for 'omics' research on drugs”. Nucleic Acids Research. 39 (Database issue): D1035—41. PMC 3013709 . PMID 21059682. doi:10.1093/nar/gkq1126.

[8] Wishart, D. S.; Knox, C.; Guo, A. C.; Cheng, D.; Shrivastava, S.; Tzur, D.; Gautam, B.; Hassanali, M. (2008). „DrugBank: A knowledgebase for drugs, drug actions and drug targets”. Nucleic Acids Research. 36 (Database issue): D901—6. PMC 2238889 . PMID 18048412. doi:10.1093/nar/gkm958.

[9] Ghose, Arup K.; Viswanadhan, Vellarkad N.; Wendoloski, John J. (1998). „Prediction of Hydrophobic (Lipophilic) Properties of Small Organic Molecules Using Fragmental Methods: An Analysis of ALOGP and CLOGP Methods”. The Journal of Physical Chemistry A. 102 (21): 3762—3772. Bibcode:1998JPCA..102.3762G. doi:10.1021/jp980230o.

[10] Tetko, Igor V.; Tanchuk, Vsevolod Yu.; Kasheva, Tamara N.; Villa, Alessandro E. P. (2001). „Estimation of Aqueous Solubility of Chemical Compounds Using E-State Indices”. Journal of Chemical Information and Computer Sciences. 41 (6): 1488—1493. PMID 11749573. doi:10.1021/ci000392t.

[11] Ertl, Peter; Rohde, Bernhard; Selzer, Paul (2000). „Fast Calculation of Molecular Polar Surface Area as a Sum of Fragment-Based Contributions and Its Application to the Prediction of Drug Transport Properties”. Journal of Medicinal Chemistry. 43 (20): 3714—3717. PMID 11020286. doi:10.1021/jm000942e.

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