Miproxifene phosphate

Miproxifene phosphate

Clinical data
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
Synonyms	TAT-59; Iproxifene
CAS Number	115767-74-3
PubChem CID	3034829
ChemSpider	2299219
UNII	QAK0B78ZCL
KEGG	D01853
Chemical and physical data
Formula	C29H36NO5P
Molar mass	509.58 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

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