Miproxifene: Difference between revisions

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{{Short description|Selective estrogen receptor modulator}}
{{Drugbox
{{Drugbox
| Verifiedfields =
| verifiedfields = changed
| Watchedfields =  
| verifiedrevid = 477002123
| verifiedrevid =  
| IUPAC_name = 1-[4-[(Z)-1,2-diphenylbut-1-enyl]phenoxy]-3-(dimethylamino)propan-2-ol
| IUPAC_name = 4-[(''Z'')-1-[4-[2-(Dimethylamino)ethoxy]phenyl]-2-(4-propan-2-ylphenyl)but-1-enyl]phenol
| image = Miproxifene.png
| image = Miproxifene.svg
| width = 200px
| width = 250
| CAS_number = 129912-70-1
| PubChem = 3033965
| ChemSpiderID = 2298535
| UNII = 0X9U0Q2R8K
| KEGG = D05082
| ChEMBL = 2104010
| C=25
| H=29
| N=1
| O=2
| smiles = CC/C(=C(/c1ccc(OCC(CN(C)C)O)cc1)\c2ccccc2)c3ccccc3
}}


<!--Clinical data-->
'''Miproxifene''' is a [[selective estrogen receptor modulator]] (SERM) that has been studied for its potential use in the treatment of [[breast cancer]]. It is a derivative of [[tamoxifen]], a well-known SERM used in the treatment and prevention of breast cancer.
| tradename =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B            / C / D / X -->
| pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA =
| legal_UK =
| legal_US =
| legal_status =
| routes_of_administration =


<!--Pharmacokinetic data-->
==Mechanism of Action==
| bioavailability =  
Miproxifene functions by binding to [[estrogen receptors]] in the body, particularly those found in breast tissue. By doing so, it can block the effects of estrogen, a hormone that can promote the growth of certain types of breast cancer cells. This mechanism is similar to that of other SERMs, which can act as estrogen antagonists in some tissues while acting as agonists in others.
| protein_bound =  
| metabolism =  
| elimination_half-life =  
| excretion =


<!-- Identifiers -->
==Pharmacology==
| CAS_number_Ref =  
Miproxifene is designed to have a more favorable profile compared to tamoxifen, with the aim of reducing side effects and improving efficacy. The drug's structure allows it to selectively modulate estrogen receptor activity, potentially offering benefits in terms of reduced risk of [[endometrial cancer]] and other estrogen-related side effects.
| CAS_number = 129612-87-9
| CAS_supplemental =  
| ATC_prefix =  
| ATC_suffix =
| ATC_supplemental =
| PubChem = 3037015
| IUPHAR_ligand =
| DrugBank_Ref =
| DrugBank =
| ChemSpiderID_Ref =
| ChemSpiderID = 2300875
| UNII = BGJ4Z7930W
| KEGG =
| ChEBI =
| ChEMBL = 2074961


<!--Chemical data-->
==Clinical Development==
| C=29 | H=35 | N=1 | O=2
Miproxifene has been the subject of various clinical trials to assess its safety and efficacy in the treatment of breast cancer. These studies have focused on its ability to reduce tumor size and prevent the progression of the disease. However, as of the latest updates, miproxifene has not been approved for clinical use and remains an investigational drug.
| 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
| StdInChI_Ref =  
| StdInChI = 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-
| StdInChIKey_Ref =
| StdInChIKey = FVVPWVFWOOMXEZ-ZIADKAODSA-N
| synonyms = DP-TAT-59
}}


'''Miproxifene''' ([[International Nonproprietary Name|INN]]) (former developmental code name '''DP-TAT-59''') is a [[nonsteroidal]] [[selective estrogen receptor modulator]] (SERM) of the [[triphenylethylene]] group that was never marketed.<ref name="AdisInsight">http://webcache.googleusercontent.com/search?q=cache:FyhxGXFiLogJ:adisinsight.springer.com/drugs/800000796+&cd=1&hl=en&ct=clnk&gl=us</ref><ref name="StellaBorchardt2007">{{cite book|author1=Valentino Stella|author2=Ronald Borchardt|author3=Michael Hageman |author4=Reza Oliyai |author5=Hans Maag |author6=Jefferson Tilley|title=Prodrugs: Challenges and Rewards|url=https://books.google.com/books?id=qkjHxX5TgHEC&pg=PA168|date=12 March 2007|publisher=Springer Science & Business Media|isbn=978-0-387-49782-2|pages=168–169}}</ref> It is a [[chemical derivative|derivative]] of [[afimoxifene]] (4-hydroxytamoxifen) in which an additional 4-[[isopropyl group]] is present in the β-[[phenyl group|phenyl ring]].<ref name="OettelSchillinger2012">{{cite book|author1=Michael Oettel|author2=Ekkehard Schillinger|title=Estrogens and Antiestrogens I: Physiology and Mechanisms of Action of Estrogens and Antiestrogens|url=https://books.google.com/books?id=0BfrCAAAQBAJ&pg=PA58|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-58616-3|pages=58–60}}</ref> 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.<ref name="AdisInsight" /><ref name="KelloffHawk2008">{{cite book|author1=Gary J. Kelloff|author2=Ernest T. Hawk|author3=Caroline C. Sigman|title=Cancer Chemoprevention: Volume 2: Strategies for Cancer Chemoprevention|url=https://books.google.com/books?id=ldyg4-cem9UC&pg=PA251|date=17 August 2008|publisher=Springer|isbn=978-1-59259-768-0|pages=251–}}</ref><ref name="OttowWeinmann2008">{{cite book|author1=Eckhard Ottow|author2=Hilmar Weinmann|title=Nuclear Receptors as Drug Targets|url=https://books.google.com/books?id=iATfLbPgRugC&pg=PA90|date=8 September 2008|publisher=John Wiley & Sons|isbn=978-3-527-62330-3|pages=90–}}</ref> 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]].<ref name="AdisInsight" /><ref name="StellaBorchardt2007" /><ref name="StromgaardKrogsgaard-Larsen2016">{{cite book|author1=Kristian Stromgaard|author2=Povl Krogsgaard-Larsen|author3=Ulf Madsen|title=Textbook of Drug Design and Discovery, Fifth Edition|url=https://books.google.com/books?id=FcLBDAAAQBAJ&pg=PA162|date=19 August 2016|publisher=CRC Press|isbn=978-1-4987-0279-9|pages=162–}}</ref><ref name="YangYeh2013">{{cite book|author1=Hsiu-Chiung Yang|author2=Wu-Kuang Yeh|author3=J. R. McCarthy|title=Enzyme Technologies: Pluripotent Players in Discovering Therapeutic Agent|url=https://books.google.com/books?id=-nUqAgAAQBAJ&pg=PA166|date=22 November 2013|publisher=Wiley|isbn=978-1-118-73989-1|pages=166–}}</ref> Miproxifene phosphate was under development for the treatment of breast cancer and reached [[Phases of clinical research#Phase III|phase III]] [[clinical trial]]s for this indication but development was discontinued.<ref name="AdisInsight" />
==Potential Benefits==
The potential benefits of miproxifene include its ability to act as an effective anti-estrogen agent in breast tissue while minimizing adverse effects in other tissues. This selectivity could make it a valuable option for patients who are at risk of developing breast cancer or who have already been diagnosed with the disease.


==References==
==Side Effects==
{{reflist|30em}}
As with other SERMs, miproxifene may cause side effects, although its specific profile is still under investigation. Common side effects associated with SERMs include hot flashes, vaginal discharge, and an increased risk of thromboembolic events. The development of miproxifene aims to mitigate these risks while providing effective treatment.


{{Estrogen receptor modulators}}
==Related Pages==
* [[Tamoxifen]]
* [[Selective estrogen receptor modulator]]
* [[Breast cancer]]
* [[Estrogen receptor]]


[[Category:Phenols]]
[[Category:Dimethylamino compounds]]
[[Category:Hormonal antineoplastic drugs]]
[[Category:Human drug metabolites]]
[[Category:Selective estrogen receptor modulators]]
[[Category:Selective estrogen receptor modulators]]
[[Category:Triphenylethylenes]]
[[Category:Experimental cancer drugs]]
 
 
{{genito-urinary-drug-stub}}
{{antineoplastic-drug-stub}}
{{dictionary-stub1}}
<gallery>
File:Miproxifene.svg|Miproxifene
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File:Miproxifene.svg|Miproxifene
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Revision as of 19:11, 22 March 2025

Selective estrogen receptor modulator


Miproxifene
File:Miproxifene.png
INN
Drug class
Routes of administration
Pregnancy category
Bioavailability
Metabolism
Elimination half-life
Excretion
Legal status
CAS Number 129912-70-1
PubChem 3033965
DrugBank
ChemSpider 2298535
KEGG D05082


Miproxifene is a selective estrogen receptor modulator (SERM) that has been studied for its potential use in the treatment of breast cancer. It is a derivative of tamoxifen, a well-known SERM used in the treatment and prevention of breast cancer.

Mechanism of Action

Miproxifene functions by binding to estrogen receptors in the body, particularly those found in breast tissue. By doing so, it can block the effects of estrogen, a hormone that can promote the growth of certain types of breast cancer cells. This mechanism is similar to that of other SERMs, which can act as estrogen antagonists in some tissues while acting as agonists in others.

Pharmacology

Miproxifene is designed to have a more favorable profile compared to tamoxifen, with the aim of reducing side effects and improving efficacy. The drug's structure allows it to selectively modulate estrogen receptor activity, potentially offering benefits in terms of reduced risk of endometrial cancer and other estrogen-related side effects.

Clinical Development

Miproxifene has been the subject of various clinical trials to assess its safety and efficacy in the treatment of breast cancer. These studies have focused on its ability to reduce tumor size and prevent the progression of the disease. However, as of the latest updates, miproxifene has not been approved for clinical use and remains an investigational drug.

Potential Benefits

The potential benefits of miproxifene include its ability to act as an effective anti-estrogen agent in breast tissue while minimizing adverse effects in other tissues. This selectivity could make it a valuable option for patients who are at risk of developing breast cancer or who have already been diagnosed with the disease.

Side Effects

As with other SERMs, miproxifene may cause side effects, although its specific profile is still under investigation. Common side effects associated with SERMs include hot flashes, vaginal discharge, and an increased risk of thromboembolic events. The development of miproxifene aims to mitigate these risks while providing effective treatment.

Related Pages