DIMP (antiandrogen)

DIMP (developmental code name Ro 7-8117), or N-(3,5-dimethyl-4-isoxazolylmethyl)phthalimide, is a nonsteroidal antiandrogen (NSAA) structurally related to thalidomide (which also binds to and antagonizes the androgen receptor (AR))^[1][2][3] that was first described in 1973 and was never marketed.^[4] Along with flutamide, it was one of the earliest NSAAs to be discovered,^[5] and for this reason, has been described as a "classical" NSAA.^[1][2][3] The drug is a selective, competitive, silent antagonist of the AR,^[4][6] although it is described as an "only relatively weak competitor".^[7][8] Its relative binding affinity for the androgen receptor is about 2.6% of that of metribolone.^[9] DIMP possesses no androgenic, estrogenic, progestogenic, or antigonadotropic activity,^[4] but it does reverse the antigonadotropic effects of testosterone, indicating that, like other pure AR antagonists, it is progonadotropic.^[4]

Other namesRo 7-8117; N-(3,5-Dimethyl-4-isoxazolylmethyl)phthalimide

Drug classNonsteroidal antiandrogen

CAS Number

• 39962-28-2 ^Y

PubChem CID

• 135035

Quick facts Clinical data, Other names ...

DIMP

Clinical data
Other names	Ro 7-8117; N-(3,5-Dimethyl-4-isoxazolylmethyl)phthalimide
Drug class	Nonsteroidal antiandrogen
Identifiers
IUPAC name 2-[(3,5-dimethyl-1,2-oxazol-4-yl)methyl]-2,3-dihydro-1H-isoindole-1,3-dione
CAS Number	39962-28-2 Y
PubChem CID	135035
ChemSpider	118991
UNII	BW49C59ULP
ChEMBL	ChEMBL1710671
CompTox Dashboard (EPA)	DTXSID40193001
Chemical and physical data
Formula	C14H12N2O3
Molar mass	256.261 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1=C(C(=NO1)C)CN2C(=O)C3=CC=CC=C3C2=O
InChI InChI=1S/C14H12N2O3/c1-8-12(9(2)19-15-8)7-16-13(17)10-5-3-4-6-11(10)14(16)18/h3-6H,7H2,1-2H3 Key:SHPRUADECKZSMQ-UHFFFAOYSA-N

Close

DIMP is the lead antiandrogen of the phthalimide group of nonsteroidal AR ligands, and a variety of AR ligands with higher affinity for the AR have been derived from DIMP and thalidomide.^[10][11]