GW501516

GW501516

Clinical data
Pregnancy category	N/A
Routes of administration	By mouth
ATC code	none
Legal status
Legal status	AU: Scheduled as illegal from June 2018 UK: Unscheduled US: Unscheduled
Identifiers
IUPAC name {2-methyl-4-[({4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methyl)sulfanyl]-2-methylphenoxy}acetic acid
CAS Number	317318-70-0 Y
PubChem CID	9803963
IUPHAR/BPS	2687
ChemSpider	7979723
UNII	7I2HA1NU22
ChEBI	CHEBI:73726 Y
ChEMBL	ChEMBL38943 N
CompTox Dashboard (EPA)	DTXSID3041037
Chemical and physical data
Formula	C21H18F3NO3S2
Molar mass	453.49 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C(COc1ccc(SCc2c(C)nc(c3ccc(C(F)(F)F)cc3)s2)cc1C)O
InChI InChI=1S/C21H18F3NO3S2/c1-12-9-16(7-8-17(12)28-10-19(26)27)29-11-18-13(2)25-20(30-18)14-3-5-15(6-4-14)21(22,23)24/h3-9H,10-11H2,1-2H3,(H,26,27) Key:YDBLKRPLXZNVNB-UHFFFAOYSA-N
NY (what is this?)  (verify)

GW501516 (also known as GW-501,516, GW1516, GSK-516, Cardarine, and on the black market as Endurobol^[1]) is a PPARδ receptor agonist that was invented in a collaboration between Ligand Pharmaceuticals and GlaxoSmithKline in the 1990s. It entered into clinical development as a drug candidate for metabolic and cardiovascular diseases, but was abandoned in 2007 because animal testing showed that the drug caused cancer to develop rapidly in several organs.^[2]

In 2007, research was published showing that high doses of GW501516 given to mice dramatically improved their physical performance; the work was widely discussed in popular media, and led to a black market for the drug candidate and to its abuse by athletes as a doping agent. The World Anti-Doping Agency (WADA) developed a test for GW501516 and other related chemicals and added them to the prohibited list in 2009; it has issued additional warnings to athletes that GW501516 is not safe.