View source for Chemistry:NNC 45-0095

{{Short description|Chemical compound}}
{{Drugbox
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| IUPAC_name = 4-(1-ethylpyrrolo[2,1,5-''cd'']indolizin-2-yl)phenol
| image = NNC 45-0095.svg
| width = 

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| class = [[Chemistry:Selective estrogen receptor modulator|Selective estrogen receptor modulator]]

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<!-- Identifiers -->
| CAS_number_Ref = 
| CAS_number = 217318-90-6
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| PubChem = 9903336
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| ChemSpiderID_Ref = 
| ChemSpiderID = 8078990
| UNII = IS4M82C29X
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| ChEMBL = 420017
| synonyms = NNC-450095

<!--Chemical data-->
| C=18 | H=15 | N=1 | O=1
| SMILES = CCC1=C(C2=CC=C3N2C1=CC=C3)C4=CC=C(C=C4)O
| StdInChI_Ref = 
| StdInChI = 1S/C18H15NO/c1-2-15-16-5-3-4-13-8-11-17(19(13)16)18(15)12-6-9-14(20)10-7-12/h3-11,20H,2H2,1H3
| StdInChIKey_Ref = 
| StdInChIKey = GBHFDPQPLXKNIU-UHFFFAOYSA-N
}}

'''NC 45-0095''' is a synthetic [[Medicine:Nonsteroidal|nonsteroidal]] [[Chemistry:Selective estrogen receptor modulator|selective estrogen receptor modulator]] (SERM) which was under development by [[Company:Novo Nordisk|Novo Nordisk]] for the treatment of postmenopausal osteoporosis but was never marketed.<ref name="pmid10714509">{{cite journal | vauthors = Jørgensen AS, Jacobsen P, Christiansen LB, Bury PS, Kanstrup A, Thorpe SM, Bain S, Naerum L, Wassermann K | display-authors = 6 | title = Synthesis and pharmacology of a novel pyrrolo[2,1,5-cd] indolizine (NNC 45-0095), a high affinity non-steroidal agonist for the estrogen receptor | journal = Bioorganic & Medicinal Chemistry Letters | volume = 10 | issue = 4 | pages = 399–402 | date = February 2000 | pmid = 10714509 | doi = 10.1016/S0960-894X(00)00015-9 }}</ref><ref name="SharmaKumar2014">{{cite journal| vauthors = Sharma V, Kumar V |title=Indolizine: a biologically active moiety|journal=Medicinal Chemistry Research|volume=23|issue=8|year=2014|pages=3593–3606|issn=1054-2523|doi=10.1007/s00044-014-0940-1|s2cid=2643469}}</ref><ref name="pmid14683521">{{cite journal | vauthors = Wallace OB, Richardson TI, Dodge JA | title = Estrogen receptor modulators: relationships of ligand structure, receptor affinity and functional activity | journal = Current Topics in Medicinal Chemistry | volume = 3 | issue = 14 | pages = 1663–1682 | date = 2003 | pmid = 14683521 | doi = 10.2174/1568026033451727 }}</ref><ref name="RahmanReitz2010">{{cite book | vauthors = Meegan MJ, Lloyd DG | chapter = Understanding the Molecular Mechanism of Action of Estrogen Receptor Modulators. Frontiers in Medicinal Chemistry-Online | date = January 2005 | volume = 2 | issue = 1 | pages = 183-231 (206) | veditors = Atta-ur-Rahman, Reitz AB |title=Frontiers in Medicinal Chemistry|chapter-url=https://books.google.com/books?id=tCyDoIHToBQC&pg=PA206 |publisher=Bentham Science Publishers|isbn=978-1-60805-205-9 }}</ref><ref name="AdisInsight">{{Cite web|url=https://adisinsight.springer.com/drugs/800014610|title=NNC 450095 | work = AdisInsight | publisher = Springer Nature Switzerland AG }}</ref> It is a [[Chemistry:Partial agonist|partial agonist]] of the [[Biology:Estrogen receptor|estrogen receptor]] ({{abbrlink|IC<sub>50</sub>|half-maximal inhibitory concentration}} (for [[Physics:Molecular binding|binding]] inhibition) = 9.5&nbsp;nM; {{abbrlink|EC<sub>50</sub>|half-maximal effective concentration}} = 13&nbsp;nM) with mixed [[Chemistry:Estrogen (medication)|estrogen]]ic and antiestrogenic activity, and shows full estrogenic activity in [[Biology:Bone|bone]] and [[Biology:Uterus|uterus]] ({{abbrlink|E<sub>max</sub>|maximal efficacy}} (relative to [[Chemistry:Moxestrol|moxestrol]], in Ishikawa [[Medicine:Endometrial cancer|endometrial cancer]] cell line) = 105%).<ref name="pmid10714509" /><ref name="RahmanReitz2010" /> The compound is a [[Chemistry:Pyrrole|pyrrolo]][[Chemistry:Indolizine|indolizine]] [[Chemistry:Chemical derivative|derivative]].<ref name="pmid10714509" /><ref name="SharmaKumar2014" /> Its development was discontinued by 2003.<ref name="AdisInsight" />

== See also ==
* [[Biology:List of selective estrogen receptor modulators|List of selective estrogen receptor modulators]]

== References ==
{{Reflist}}

{{Estrogen receptor modulators}}

[[Category:Abandoned drugs]]
[[Category:Indolizines]]
[[Category:Phenols]]
[[Category:Pyrroles]]
[[Category:Selective estrogen receptor modulators]]


{{Sourceattribution|NNC 45-0095}}