OSU-03012

OSU-03012
Names
	IUPAC name 2-Amino-N-[4-[5-phenanthren-2-yl-3-(trifluoromethyl)pyrazol-1-yl]phenyl]acetamide
	Other names AR-12
Identifiers
CAS Number	742112-33-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:131196 ;
ChemSpider	8202849;
IUPHAR/BPS	8005;
PubChem CID	10027278;
UNII	EX3O2Q61UV ;
CompTox Dashboard (EPA)	DTXSID50225206 ;
	InChI InChI=1S/C26H19F3N4O/c27-26(28,29)24-14-23(33(32-24)20-10-8-19(9-11-20)31-25(34)15-30)18-7-12-22-17(13-18)6-5-16-3-1-2-4-21(16)22/h1-14H,15,30H2,(H,31,34) Key: YULUCECVQOCQFQ-UHFFFAOYSA-N; InChI=1/C26H19F3N4O/c27-26(28,29)24-14-23(33(32-24)20-10-8-19(9-11-20)31-25(34)15-30)18-7-12-22-17(13-18)6-5-16-3-1-2-4-21(16)22/h1-14H,15,30H2,(H,31,34) Key: YULUCECVQOCQFQ-UHFFFAOYAU;
	SMILES C1=CC=C2C(=C1)C=CC3=C2C=CC(=C3)C4=CC(=NN4C5=CC=C(C=C5)NC(=O)CN)C(F)(F)F;
Properties
Chemical formula	C26H19F3N4O
Molar mass	460.460 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

OSU-03012 (AR-12) is a celecoxib derivative with anticancer and anti-microbial activity. Unlike celecoxib, OSU-03012 does not inhibit COX, but inhibits several other important enzymes instead which may be useful in the treatment of some forms of cancer,^[1]^[2] When combined with PDE5 inhibitors such as sildenafil or tadalafil, OSU-03012 was found to show enhanced anti-tumour effects in cell culture.^[3]

^ Booth, L; Cruickshanks, N; Ridder, T; Chen, CS; Grant, S; Dent, P (Dec 2012). "OSU-03012 interacts with lapatinib to kill brain cancer cells". Cancer Biology and Therapy. 13 (14): 1501–11. doi:10.4161/cbt.22275. PMC 3542242. PMID 22990204.
^ Ma, Y; McCarty, SK; Kapuriya, NP; Brendel, VJ; Wang, C; Zhang, X; Jarjoura, D; Saji, M; Chen, CS; Ringel, MD (Aug 2013). "Development of p21 activated kinase-targeted multikinase inhibitors that inhibit thyroid cancer cell migration". Journal of Clinical Endocrinology and Metabolism. 98 (8): E1314–22. doi:10.1210/jc.2012-3937. PMC 3733855. PMID 23709653.
^ Booth, L; Roberts, JL; Cruickshanks, N; Grant, S; Poklepovic, A; Dent, P (Oct 2014). "Regulation of OSU-03012 toxicity by ER stress proteins and ER stress-inducing drugs". Molecular Cancer Therapeutics. 13 (10): 2384–98. doi:10.1158/1535-7163.MCT-14-0172. PMC 4185238. PMID 25103559. (This paper currently has an expression of concern, see doi:10.1158/1535-7163.MCT-19-0666)

[1] Booth, L; Cruickshanks, N; Ridder, T; Chen, CS; Grant, S; Dent, P (Dec 2012). "OSU-03012 interacts with lapatinib to kill brain cancer cells". Cancer Biology and Therapy. 13 (14): 1501–11. doi:10.4161/cbt.22275. PMC 3542242. PMID 22990204.

[2] Ma, Y; McCarty, SK; Kapuriya, NP; Brendel, VJ; Wang, C; Zhang, X; Jarjoura, D; Saji, M; Chen, CS; Ringel, MD (Aug 2013). "Development of p21 activated kinase-targeted multikinase inhibitors that inhibit thyroid cancer cell migration". Journal of Clinical Endocrinology and Metabolism. 98 (8): E1314–22. doi:10.1210/jc.2012-3937. PMC 3733855. PMID 23709653.

[3] Booth, L; Roberts, JL; Cruickshanks, N; Grant, S; Poklepovic, A; Dent, P (Oct 2014). "Regulation of OSU-03012 toxicity by ER stress proteins and ER stress-inducing drugs". Molecular Cancer Therapeutics. 13 (10): 2384–98. doi:10.1158/1535-7163.MCT-14-0172. PMC 4185238. PMID 25103559. (This paper currently has an expression of concern, see doi:10.1158/1535-7163.MCT-19-0666)

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