Miproxifene

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

Miproxifene
Clinical data
Other namesDP-TAT-59
Identifiers
IUPAC name
  • 4-[(Z)-1-[4-[2-(Dimethylamino)ethoxy]phenyl]-2-(4-propan-2-ylphenyl)but-1-enyl]phenol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC29H35NO2
Molar mass429.604 g·mol−1
3D model (JSmol)
SMILES
  • CC/C(=C(\C1=CC=C(C=C1)O)/C2=CC=C(C=C2)OCCN(C)C)/C3=CC=C(C=C3)C(C)C
InChI
  • InChI=1S/C29H35NO2/c1-6-28(23-9-7-22(8-10-23)21(2)3)29(24-11-15-26(31)16-12-24)25-13-17-27(18-14-25)32-20-19-30(4)5/h7-18,21,31H,6,19-20H2,1-5H3/b29-28-
  • Key:FVVPWVFWOOMXEZ-ZIADKAODSA-N

References
  1. "Miproxifene". AdisInsight. Springer Nature Switzerland AG.
  2. 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.
  3. 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.
  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.


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