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 namesTAT-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
PubChem CID
ChemSpider
UNII
KEGG
Chemical and physical data
FormulaC29H36NO5P
Molar mass509.583 g·mol−1
3D model (JSmol)
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

References
  1. Miller WR, Ingle JN (8 March 2002). Endocrine Therapy in Breast Cancer. CRC Press. pp. 53–. ISBN 978-0-203-90983-6.
  2. "Miproxifene". AdisInsight. Springer Nature Switzerland AG.
  3. Stella V, Borchardt R, Hageman M, Oliyai R, Maag H, Tilley J (12 March 2007). Prodrugs: Challenges and Rewards. Springer Science & Business Media. pp. 168–169. ISBN 978-0-387-49782-2.
  4. Kelloff GJ, Hawk ET, Sigman CC (17 August 2008). Cancer Chemoprevention: Volume 2: Strategies for Cancer Chemoprevention. Springer. pp. 251–. ISBN 978-1-59259-768-0.
  5. Ottow E, Weinmann H (8 September 2008). Nuclear Receptors as Drug Targets. John Wiley & Sons. pp. 90–. ISBN 978-3-527-62330-3.
  6. Stromgaard K, Krogsgaard-Larsen P, Madsen U (19 August 2016). Textbook of Drug Design and Discovery, Fifth Edition. CRC Press. pp. 162–. ISBN 978-1-4987-0279-9.
  7. Yang HC, Yeh WK, McCarthy JR (22 November 2013). Enzyme Technologies: Pluripotent Players in Discovering Therapeutic Agent. Wiley. pp. 166–. ISBN 978-1-118-73989-1.
  8. Oettel M, Schillinger E (6 December 2012). Estrogens and Antiestrogens I: Physiology and Mechanisms of Action of Estrogens and Antiestrogens. Springer Science & Business Media. pp. 58–60. ISBN 978-3-642-58616-3.


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