Miproxifene phosphate

Miproxifene phosphate (former developmental code name TAT-59) is a nonsteroidal selective estrogen receptor modulator (SERM) of the triphenylethylene group^[1] that was under development in Japan for the treatment of breast cancer but was abandoned and never marketed.^[2][3][4][5] It reached phase III clinical trials for this indication before development was discontinued.^[2][5] The drug is a phosphate ester and prodrug of miproxifene (DP-TAT-59) with improved water solubility that was better suited for clinical development.^[2][3][6][7] Miproxifene has been found to be 3- to 10-fold as potent as tamoxifen in inhibiting breast cancer cell growth in in vitro models.^[2][5][4] It is a derivative of afimoxifene (4-hydroxytamoxifen) in which an additional 4-isopropyl group is present in the β-phenyl ring.^[8]

Miproxifene phosphate

Clinical data
Other names	TAT-59; Iproxifene
Routes of administration	Oral
Identifiers
IUPAC name [4-[(E)-1-[4-[2-(Dimethylamino)ethoxy]phenyl]-2-(4-propan-2-ylphenyl)but-1-enyl]phenyl] dihydrogen phosphate
CAS Number	115767-74-3
PubChem CID	3034829
ChemSpider	2299219
UNII	QAK0B78ZCL
KEGG	D01853
CompTox Dashboard (EPA)	DTXSID301031364
Chemical and physical data
Formula	C29H36NO5P
Molar mass	509.583 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC/C(=C(/C1=CC=C(C=C1)OCCN(C)C)\C2=CC=C(C=C2)OP(=O)(O)O)/C3=CC=C(C=C3)C(C)C
InChI InChI=1S/C29H36NO5P/c1-6-28(23-9-7-22(8-10-23)21(2)3)29(25-13-17-27(18-14-25)35-36(31,32)33)24-11-15-26(16-12-24)34-20-19-30(4)5/h7-18,21H,6,19-20H2,1-5H3,(H2,31,32,33)/b29-28+ Key:QZUHFMXJZOUZFI-ZQHSETAFSA-N