Miproxifene phosphate

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Miproxifene phosphate
Miproxifene phosphate.svg
Clinical data
Other namesTAT-59; Iproxifene
Routes of
administration 		Oral
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
Chemical and physical data
Formula C29H36NO5P
Molar mass 509.583 g·mol−1
3D model (JSmol)

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]

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Miproxifene (INN) is a nonsteroidal selective estrogen receptor modulator (SERM) of the triphenylethylene group that was never marketed. It is a derivative of afimoxifene (4-hydroxytamoxifen) in which an additional 4-isopropyl group is present in the β-phenyl ring. 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. 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. Miproxifene phosphate was under development for the treatment of breast cancer and reached phase III clinical trials for this indication but development was discontinued.

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Estrogen (medication)

An estrogen (E) is a type of medication which is used most commonly in hormonal birth control and menopausal hormone therapy, and as part of transgender hormone therapy for transgender women. They can also be used in the treatment of hormone-sensitive cancers like breast cancer and prostate cancer and for various other indications. Estrogens are used alone or in combination with progestogens. They are available in a wide variety of formulations and for use by many different routes of administration. Examples of estrogens include bioidentical estradiol, natural conjugated estrogens, synthetic steroidal estrogens like ethinylestradiol, and synthetic nonsteroidal estrogens like diethylstilbestrol. Estrogens are one of three types of sex hormone agonists, the others being androgens/anabolic steroids like testosterone and progestogens like progesterone.

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. 1 2 3 4 "Miproxifene". AdisInsight. Springer Nature Switzerland AG.
  3. 1 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.
  4. 1 2 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. 1 2 3 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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