OSU-03012

OSU-03012

Names
IUPAC name 2-amino-N-[4-[5-phenanthren-2-yl-3-(trifluoromethyl)pyrazol-1-yl]phenyl]acetamide
Other names OSU-03012
Identifiers
CAS Number	742112-33-0
3D model (JSmol)	Interactive image
ChEBI	CHEBI:131196 Y
ChemSpider	8202849
IUPHAR/BPS	8005
PubChem CID	10027278
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	460.46 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, while also having activity via disruption of phosphoinositide-dependent kinase-1 activity. When combined with PDE5 inhibitors such as sildenafil or tadalafil, OSU-03012 was found to show enhanced anti-tumour,antibiotic and antiviral activity against a wide variety of organisms, with this activity thought to be mediated via inhibition of the chaperone protein BiP.

The European Commission has designated AR-12 as an orphan drug for use in combination with other drugs for treatment of two infections diseases, and tularaemia. AR-12 received an orphan drug designation in combination with the antifungal drug fluconazole for cryptococcosis of the brain. It also received this designation for tularaemia in combination with the antibacterial drug gentamicin.