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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| verifiedrevid =
| verifiedrevid =
| IUPAC_name = 4-[2-(4-Ethoxyphenyl)-4-methyl-1''H''-pyrrol-1-yl]benzenesulfonamide
| IUPAC_name = 4-[2-(4-Ethoxyphenyl)-4-methyl-1''H''-pyrrol-1-yl]benzenesulfonamide
| image = Apricoxib_structure.svg
| image = Apricoxib.svg


<!--Identifiers-->
<!--Identifiers-->
| CAS_number = 162011-90-7
| CAS_number = 197904-84-0
| ATC_prefix =
| ATC_prefix =
| ATC_suffix =
| ATC_suffix =
| ATC_supplemental =
| ATC_supplemental =
| PubChem = 9820073
| PubChem = 9820073
| DrugBank =
| DrugBank = DB12378
| ChemSpiderID = 7995822
| ChemSpiderID = 7995822
| UNII =
| UNII = 5X5HB3VZ3Z
| KEGG =
| KEGG = D08657
| ChEBI =
| ChEBI =
| ChEMBL =
| ChEMBL =

<!-- Legal status -->
| legal_status = Investigational


<!--Chemical data-->
<!--Chemical data-->
| C=19 | H=20 | N=2 | O=3 | S=1
| C=19 | H=20 | N=2 | O=3 | S=1
| molecular_weight = 356.4387 g/mol
| smiles = CCOC1=CC=C(C=C1)C2=CC(=CN2C3=CC=C(C=C3)S(=O)(=O)N)C
| smiles = CCOC1=CC=C(C=C1)C2=CC(=CN2C3=CC=C(C=C3)S(=O)(=O)N)C
| InChI = InChI=1S/C19H20N2O3S/c1-3-24-17-8-4-15(5-9-17)19-12-14(2)13-21(19)16-6-10-18(11-7-16)25(20,22)23/h4-13H,3H2,1-2H3,(H2,20,22,23)
| StdInChI = 1S/C19H20N2O3S/c1-3-24-17-8-4-15(5-9-17)19-12-14(2)13-21(19)16-6-10-18(11-7-16)25(20,22)23/h4-13H,3H2,1-2H3,(H2,20,22,23)
| InChIKey = JTMITOKKUMVWRT-UHFFFAOYSA-N
| StdInChIKey = JTMITOKKUMVWRT-UHFFFAOYSA-N
| StdInChI =
| StdInChIKey =
}}
}}


'''Apricoxib''' is an experimental anticancer drug and [[nonsteroidal anti-inflammatory drug]] (NSAID).<ref>{{cite web | url = https://ncithesaurus.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&code=C74021&ns=ncit | work = NCI Thesaurus | publisher = National Cancer Institute | title = Apricoxib (Code C74021) }}</ref> It is a [[COX-2 inhibitor]] which is intended to improve standard therapy response in molecularly-defined models of [[pancreatic cancer]].<ref>{{cite journal | vauthors = Kirane A, Toombs JE, Ostapoff K, Carbon JG, Zaknoen S, Braunfeld J, Schwarz RE, Burrows FJ, Brekken RA | display-authors = 6 | title = Apricoxib, a novel inhibitor of COX-2, markedly improves standard therapy response in molecularly defined models of pancreatic cancer | journal = Clinical Cancer Research | volume = 18 | issue = 18 | pages = 5031–42 | date = September 2012 | pmid = 22829202 | pmc = 3777527 | doi = 10.1158/1078-0432.CCR-12-0453 }}</ref> It was also studied in clinical trials for [[non-small-cell lung cancer]].<ref>{{cite journal | vauthors = Edelman MJ, Tan MT, Fidler MJ, Sanborn RE, Otterson G, Sequist LV, Evans TL, Schneider BJ, Keresztes R, Rogers JS, de Mayolo JA, Feliciano J, Yang Y, Medeiros M, Zaknoen SL | display-authors = 6 | title = Randomized, double-blind, placebo-controlled, multicenter phase II study of the efficacy and safety of apricoxib in combination with either docetaxel or pemetrexed in patients with biomarker-selected non-small-cell lung cancer | journal = Journal of Clinical Oncology | volume = 33 | issue = 2 | pages = 189–94 | date = January 2015 | pmid = 25452446 | pmc = 4890680 | doi = 10.1200/JCO.2014.55.5789 }}</ref> Development was abandoned in 2015 due to poor clinical trial results.<ref>{{cite web | title = Apricoxib | url = http://adisinsight.springer.com/drugs/800026002 | work = Adis Insight | publisher = Springer Nature Switzerland AG }}</ref>
'''Apricoxib''' is an experimental anticancer drug in Phase II clinical trials. It is a [[COX-2 inhibitor]] which improves standard therapy response in molecularly defined models of pancreatic cancer.<ref>{{Cite doi|10.1158/1078-0432.CCR-12-0453}}</ref>


==See also==
== See also ==
*[[Tilmacoxib]]
*[[Tilmacoxib]]
*[[cimicoxib]]
*[[Cimicoxib]]
*[[NS-398]]
*[[NS-398]]
*[[Celecoxib]]
*[[Celecoxib]]


==References==
== References ==
{{Reflist|2}}
{{Reflist}}



{{Prostanoidergics}}
{{Prostanoidergics}}
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[[Category:COX-2 inhibitors]]
[[Category:COX-2 inhibitors]]
[[Category:Sulfonamides]]
[[Category:Sulfonamides]]
[[Category:Experimental cancer drugs]]
[[Category:Abandoned drugs]]


{{pharma-stub}}
{{musculoskeletal-drug-stub}}

Latest revision as of 00:01, 25 January 2023

Apricoxib
Legal status
Legal status
  • Investigational
Identifiers
  • 4-[2-(4-Ethoxyphenyl)-4-methyl-1H-pyrrol-1-yl]benzenesulfonamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H20N2O3S
Molar mass356.44 g·mol−1
3D model (JSmol)
  • CCOC1=CC=C(C=C1)C2=CC(=CN2C3=CC=C(C=C3)S(=O)(=O)N)C
  • InChI=1S/C19H20N2O3S/c1-3-24-17-8-4-15(5-9-17)19-12-14(2)13-21(19)16-6-10-18(11-7-16)25(20,22)23/h4-13H,3H2,1-2H3,(H2,20,22,23)
  • Key:JTMITOKKUMVWRT-UHFFFAOYSA-N

Apricoxib is an experimental anticancer drug and nonsteroidal anti-inflammatory drug (NSAID).[1] It is a COX-2 inhibitor which is intended to improve standard therapy response in molecularly-defined models of pancreatic cancer.[2] It was also studied in clinical trials for non-small-cell lung cancer.[3] Development was abandoned in 2015 due to poor clinical trial results.[4]

See also

[edit]

References

[edit]
  1. ^ "Apricoxib (Code C74021)". NCI Thesaurus. National Cancer Institute.
  2. ^ Kirane A, Toombs JE, Ostapoff K, Carbon JG, Zaknoen S, Braunfeld J, et al. (September 2012). "Apricoxib, a novel inhibitor of COX-2, markedly improves standard therapy response in molecularly defined models of pancreatic cancer". Clinical Cancer Research. 18 (18): 5031–42. doi:10.1158/1078-0432.CCR-12-0453. PMC 3777527. PMID 22829202.
  3. ^ Edelman MJ, Tan MT, Fidler MJ, Sanborn RE, Otterson G, Sequist LV, et al. (January 2015). "Randomized, double-blind, placebo-controlled, multicenter phase II study of the efficacy and safety of apricoxib in combination with either docetaxel or pemetrexed in patients with biomarker-selected non-small-cell lung cancer". Journal of Clinical Oncology. 33 (2): 189–94. doi:10.1200/JCO.2014.55.5789. PMC 4890680. PMID 25452446.
  4. ^ "Apricoxib". Adis Insight. Springer Nature Switzerland AG.
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