From Wikipedia, the free encyclopedia
Chemical compound
Miproxifene phosphate
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Other names | TAT-59; Iproxifene |
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Routes of administration |
Oral |
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[4-[(E)-1-[4-[2-(Dimethylamino)ethoxy]phenyl]-2-(4-propan-2-ylphenyl)but-1-enyl]phenyl] dihydrogen phosphate
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CAS Number | |
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PubChem
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KEGG | |
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Formula | C29H36NO5P |
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Molar mass | 509.583 g·mol−1 |
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3D model (
JSmol) | |
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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
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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
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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]
References
-
^ Miller WR, Ingle JN (8 March 2002).
Endocrine Therapy in Breast Cancer. CRC Press. pp. 53–.
ISBN
978-0-203-90983-6.
- ^
a
b
c
d
"Miproxifene". AdisInsight. Springer Nature Switzerland AG.
- ^
a
b 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.
- ^
a
b 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.
- ^
a
b
c Ottow E, Weinmann H (8 September 2008).
Nuclear Receptors as Drug Targets. John Wiley & Sons. pp. 90–.
ISBN
978-3-527-62330-3.
-
^ 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.
-
^ 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.
-
^ 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.
External links
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ERTooltip Estrogen receptor | Agonists |
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2-Hydroxyestrone
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3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol
-
3α-Androstanediol
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3α,5α-Dihydrolevonorgestrel
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3β,5α-Dihydrolevonorgestrel
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3α-Hydroxytibolone
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3β-Hydroxytibolone
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3β-Androstanediol
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4-Androstenediol
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4-Androstenedione
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4-Fluoroestradiol
-
4-Hydroxyestradiol
-
4-Hydroxyestrone
-
4-Methoxyestradiol
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4-Methoxyestrone
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5-Androstenediol
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7-Oxo-DHEA
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7α-Hydroxy-DHEA
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7α-Methylestradiol
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7β-Hydroxyepiandrosterone
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8,9-Dehydroestradiol
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8,9-Dehydroestrone
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8β-VE2
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10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)
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11β-Chloromethylestradiol
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11β-Methoxyestradiol
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15α-Hydroxyestradiol
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16α-Fluoroestradiol
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16α-Hydroxy-DHEA
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16α-Iodoestradiol
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16α-LE2
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16β-Hydroxyestrone
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16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)
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17α-Estradiol (
alfatradiol)
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17α-Dihydroequilenin
-
17α-Dihydroequilin
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17α-Epiestriol (16α-hydroxy-17α-estradiol)
-
17α-Ethynyl-3α-androstanediol
-
17α-Ethynyl-3β-androstanediol
-
17β-Dihydroequilenin
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17β-Dihydroequilin
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17β-Methyl-17α-dihydroequilenin
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Hippulin
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Hydroxyestrone diacetate
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Lynestrenol phenylpropionate
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agnuside,
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Mixed (
SERMsTooltip Selective estrogen receptor modulators) | |
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Antagonists |
- Coregulator-binding modulators:
ERX-11
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GPERTooltip G protein-coupled estrogen receptor | Agonists | |
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Antagonists | |
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Unknown | |
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