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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| Verifiedfields =
| Verifiedfields =
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| IUPAC_name = 4-[(''Z'')-1-[4-(2-Aminoethoxy)phenyl]-2-phenylbut-1-enyl]phenol
| IUPAC_name = 4-[(''Z'')-1-[4-(2-Aminoethoxy)phenyl]-2-phenylbut-1-enyl]phenol
| image = Norendoxifen.svg
| image = Norendoxifen.svg
| width =200px
| width = 250


<!--Clinical data-->
<!--Clinical data-->
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| legal_US =
| legal_US =
| legal_status =
| legal_status =
| routes_of_administration =
| routes_of_administration =


<!--Pharmacokinetic data-->
<!--Pharmacokinetic data-->
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| metabolism =
| metabolism =
| elimination_half-life =
| elimination_half-life =
| excretion =
| excretion =


<!-- Identifiers -->
<!-- Identifiers -->
| CAS_number_Ref =
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 1217237-98-3
| CAS_number = 1217237-98-3
| UNII_Ref = {{fdacite|correct|FDA}}
⚫
| UNII = 51GJD354B5
| CAS_supplemental =
| CAS_supplemental =
| ATC_prefix =
| ATC_prefix =
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| ChemSpiderID_Ref =
| ChemSpiderID_Ref =
| ChemSpiderID = 32817000
| ChemSpiderID = 32817000
⚫
| UNII =
| KEGG =
| KEGG =
| ChEBI =
| ChEBI =
| ChEMBL = 2386284
| ChEMBL = 2386284
| synonyms = 4-Hydroxy-''N'',''N''-didesmethyltamoxifen


<!--Chemical data-->
<!--Chemical data-->
| C=24 | H=25 | N=1 | O=2
| C=24 | H=25 | N=1 | O=2
| smiles = CCC(=C(c1ccc(cc1)O)c2ccc(cc2)OCCN)c3ccccc3
| SMILES = CCC(=C(c1ccc(cc1)O)c2ccc(cc2)OCCN)c3ccccc3
| StdInChI = 1S/C24H25NO2/c1-2-23(18-6-4-3-5-7-18)24(19-8-12-21(26)13-9-19)20-10-14-22(15-11-20)27-17-16-25/h3-15,26H,2,16-17,25H2,1H3
| StdInChI = 1S/C24H25NO2/c1-2-23(18-6-4-3-5-7-18)24(19-8-12-21(26)13-9-19)20-10-14-22(15-11-20)27-17-16-25/h3-15,26H,2,16-17,25H2,1H3
| StdInChIKey = YCQBLTPGQSYLHD-UHFFFAOYSA-N
| StdInChIKey = YCQBLTPGQSYLHD-UHFFFAOYSA-N
| synonyms = N,N-Didesmethyl-4-hydroxytamoxifen
}}
}}


'''Norendoxifen''', also known as '''N,N-didesmethyl-4-hydroxytamoxifen''', is a [[non-steroidal]] [[aromatase inhibitor]] (AI) of the [[triphenylethylene]] group that was never marketed.<ref name="pmid21814747">{{cite journal | vauthors = Lu WJ, Xu C, Pei Z, Mayhoub AS, Cushman M, Flockhart DA | title = The tamoxifen metabolite norendoxifen is a potent and selective inhibitor of aromatase (CYP19) and a potential lead compound for novel therapeutic agents | journal = Breast Cancer Res. Treat. | volume = 133 | issue = 1 | pages = 99–109 | year = 2012 | pmid = 21814747 | doi = 10.1007/s10549-011-1699-4 | url = }}</ref> It is an [[active metabolite]] of the [[selective estrogen receptor modulator]] (SERM) [[tamoxifen]].<ref name="pmid21814747" /> Unlike tamoxifen, norendoxifen is not a SERM, and instead has been found to act as a [[potency (pharmacology)|potent]] and [[binding selectivity|selective]] [[competitive inhibition|competitive]] [[enzyme inhibitor|inhibitor]] of [[aromatase]] (K<sub>i</sub> = 35&nbsp;nM).<ref name="pmid21814747" /> Drugs with dual SERM and AI activity, such as [[4'-hydroxynorendoxifen]], have been developed from norendoxifen, and may have therapeutic potential as [[antiestrogen]]s in the treatment of [[estrogen receptor]]-positive [[breast cancer]].<ref name="pmid25751283">{{cite journal | vauthors = Lv W, Liu J, Skaar TC, Flockhart DA, Cushman M | title = Design and synthesis of norendoxifen analogues with dual aromatase inhibitory and estrogen receptor modulatory activities | journal = J. Med. Chem. | volume = 58 | issue = 6 | pages = 2623–48 | year = 2015 | pmid = 25751283 | pmc = 4687028 | doi = 10.1021/jm501218e | url = }}</ref>
'''Norendoxifen''', also known as '''4-hydroxy-''N'',''N''-didesmethyltamoxifen''', is a [[nonsteroidal]] [[aromatase inhibitor]] (AI) of the [[triphenylethylene]] group that was never marketed.<ref name="pmid21814747">{{cite journal | vauthors = Lu WJ, Xu C, Pei Z, Mayhoub AS, Cushman M, Flockhart DA | s2cid = 22096941 | title = The tamoxifen metabolite norendoxifen is a potent and selective inhibitor of aromatase (CYP19) and a potential lead compound for novel therapeutic agents | journal = Breast Cancer Research and Treatment | volume = 133 | issue = 1 | pages = 99–109 | date = May 2012 | pmid = 21814747 | doi = 10.1007/s10549-011-1699-4 | authorlink5 = Mark Cushman | authorlink6 = David Flockhart }}</ref> It is an [[active metabolite]] of the [[selective estrogen receptor modulator]] (SERM) [[tamoxifen]].<ref name="pmid21814747" /> Unlike tamoxifen, norendoxifen is not a SERM, and instead has been found to act as a [[potency (pharmacology)|potent]] and [[binding selectivity|selective]] [[competitive inhibition|competitive]] [[enzyme inhibitor|inhibitor]] of [[aromatase]] (''K''<sub>i</sub> = 35&nbsp;nM).<ref name="pmid21814747" /> Drugs with dual SERM and AI activity, such as [[4'-hydroxynorendoxifen]], have been developed from norendoxifen, and may have therapeutic potential as [[antiestrogen]]s in the treatment of [[estrogen receptor]]-positive [[breast cancer]].<ref name="pmid25751283">{{cite journal | vauthors = Lv W, Liu J, Skaar TC, Flockhart DA, Cushman M | title = Design and synthesis of norendoxifen analogues with dual aromatase inhibitory and estrogen receptor modulatory activities | journal = Journal of Medicinal Chemistry | volume = 58 | issue = 6 | pages = 2623–48 | date = March 2015 | pmid = 25751283 | pmc = 4687028 | doi = 10.1021/jm501218e | authorlink4 = David Flockhart | authorlink5 = Mark Cushman }}</ref>


==See also==
==See also==
* [[Afimoxifene]] (4-hydroxytamoxifen)
* [[Afimoxifene]] (4-hydroxytamoxifen)
* [[Endoxifen]] (N-desmethyl-4-hydroxytamoxifen)
* [[Endoxifen]] (4-hydroxy-''N''-desmethyltamoxifen)


==References==
==References==
{{reflist|30em}}
{{Reflist}}

{{Steroid hormone metabolism modulators}}


[[Category:Amines]]
[[Category:Amines]]
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[[Category:Phenols]]
[[Category:Phenols]]
[[Category:Triphenylethylenes]]
[[Category:Triphenylethylenes]]



{{genito-urinary-drug-stub}}
{{genito-urinary-drug-stub}}

Revision as of 23:47, 22 January 2023

Norendoxifen
Clinical data
Other names4-Hydroxy-N,N-didesmethyltamoxifen
Identifiers
  • 4-[(Z)-1-[4-(2-Aminoethoxy)phenyl]-2-phenylbut-1-enyl]phenol
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC24H25NO2
Molar mass359.469 g·mol−1
3D model (JSmol)
  • CCC(=C(c1ccc(cc1)O)c2ccc(cc2)OCCN)c3ccccc3
  • InChI=1S/C24H25NO2/c1-2-23(18-6-4-3-5-7-18)24(19-8-12-21(26)13-9-19)20-10-14-22(15-11-20)27-17-16-25/h3-15,26H,2,16-17,25H2,1H3
  • Key:YCQBLTPGQSYLHD-UHFFFAOYSA-N

Norendoxifen, also known as 4-hydroxy-N,N-didesmethyltamoxifen, is a nonsteroidal aromatase inhibitor (AI) of the triphenylethylene group that was never marketed.[1] It is an active metabolite of the selective estrogen receptor modulator (SERM) tamoxifen.[1] Unlike tamoxifen, norendoxifen is not a SERM, and instead has been found to act as a potent and selective competitive inhibitor of aromatase (Ki = 35 nM).[1] Drugs with dual SERM and AI activity, such as 4'-hydroxynorendoxifen, have been developed from norendoxifen, and may have therapeutic potential as antiestrogens in the treatment of estrogen receptor-positive breast cancer.[2]

See also

References

  1. ^ a b c Lu WJ, Xu C, Pei Z, Mayhoub AS, Cushman M, Flockhart DA (May 2012). "The tamoxifen metabolite norendoxifen is a potent and selective inhibitor of aromatase (CYP19) and a potential lead compound for novel therapeutic agents". Breast Cancer Research and Treatment. 133 (1): 99–109. doi:10.1007/s10549-011-1699-4. PMID 21814747. S2CID 22096941.
  2. ^ Lv W, Liu J, Skaar TC, Flockhart DA, Cushman M (March 2015). "Design and synthesis of norendoxifen analogues with dual aromatase inhibitory and estrogen receptor modulatory activities". Journal of Medicinal Chemistry. 58 (6): 2623–48. doi:10.1021/jm501218e. PMC 4687028. PMID 25751283.
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