Natural Product (NP) Details

General Information of the NP (ID: NP5783)
Name
Toremifene
Synonyms
toremifene; Farestone; 89778-26-7; Toremifeno; Toremifenum; UNII-7NFE54O27T; GTx-006; Z-Toremifene; {2-[4-(4-Chloro-1,2-diphenyl-but-1-enyl)-phenoxy]-ethyl}-dimethyl-amine; 7NFE54O27T; CHEBI:9635; Toremifenum [Latin]; Toremifeno [Spanish]; 89778-26-7 (free base); 2-[4-[(Z)-4-chloro-1,2-diphenylbut-1-enyl]phenoxy]-N,N-dimethylethanamine; 2-{4-[(1Z)-4-chloro-1,2-diphenylbut-1-en-1-yl]phenoxy}-N,N-dimethylethanamine; Ethanamine, 2-(4-((1Z)-4-chloro-1,2-diphenyl-1-butenyl)phenoxy)-N,N-dimethyl-; Toremifene Base; GTx 006; Toremifene [INN:BAN]; Estrimex; Toremifene (INN); C26H28ClNO; CCRIS 8745; (E)-Toremifene; 89778-29-0; (Z)-2-(4-(4-Chloro-1,2-diphenyl-1-butenyl)phenoxy)-N,N-dimethylethanamine; 2-(para-((Z)-4-Chloro-1,2-diphenyl-1-butenyl)phenoxy)-N,N-dimethylethylamine (IUPAC); SCHEMBL7465; CHEMBL1655; BIDD:PXR0202; BIDD:ER0222; BIDD:GT0211; GTPL4325; DTXSID3023689; BDBM58492; cid_3005572; HY-B0005A; HMS2090B22; HMS3714P06; BBL029023; DL-519; MFCD00801070; STK626445; ZINC12404516; AKOS005559276; AC-1751; CCG-220952; CS-1268; DB00539; 2-({4-[(1Z)-4-chloro-1,2-diphenylbut-1-en-1-yl]phenyl}oxy)-N,N-dimethylethanamine; 2-{4-[(1Z)-4-chloro-1,2-diphenylbut-1-en-1-yl]phenoxy}-N,N-dimethylethan-1-amine; Ethanamine, 2-(4-(4-chloro-1,2-diphenyl-1-butenyl)phenoxy)-N,N-dimethyl-, (Z)-; MRF-0000351; NCGC00160530-02; NCGC00160530-13; J33.157K; K600; SBI-0206902.P001; 78T267; C08166; D08620; W-5124; 29515-EP2272827A1; 29515-EP2275420A1; 29515-EP2280012A2; 29515-EP2281815A1; 29515-EP2295055A2; 29515-EP2295416A2; 29515-EP2295426A1; 29515-EP2295427A1; 29515-EP2298748A2; 29515-EP2298764A1; 29515-EP2298765A1; 29515-EP2301933A1; 29515-EP2305640A2; 29515-EP2305642A2; 29515-EP2305671A1; 29515-EP2311453A1; 29515-EP2311808A1; 29515-EP2311825A1; 29515-EP2311827A1; 29515-EP2311829A1; 29515-EP2311840A1; 29515-EP2311842A2; AB00698360-07; AB00698360-09; AB00698360-10; AB00698360_11; AB00698360_12; A843306; Q3993743; SR-01000763502-5; BRD-K51350053-048-06-6; (2-{4-[(1Z)-4-chloro-1,2-diphenylbut-1-en-1-yl]phenoxy}ethyl)dimethylamine; 2-[4-[(Z)-4-chloranyl-1,2-diphenyl-but-1-enyl]phenoxy]-N,N-dimethyl-ethanamine; 2-[4-[(Z)-4-chloro-1,2-di(phenyl)but-1-enyl]phenoxy]-N,N-dimethylethanamine; 2-[4-[(Z)-4-chloro-1,2-diphenyl-but-1-enyl]phenoxy]ethyl-dimethyl-amine;citric acid; 2-[4-[(Z)-4-chloranyl-1,2-diphenyl-but-1-enyl]phenoxy]-N,N-dimethyl-ethanamine;2-oxidanylpropane-1,2,3-tricarboxylic acid; 275360-73-1; T0R
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Species Origin Homo sapiens ...     Click to Show/Hide
Homo sapiens
Kingdom: Metazoa
Phylum: Chordata
Class: Mammalia
Order: Primates
Family: Hominidae
Genus: Homo
Species: Homo sapiens
Disease Breast cancer [ICD-11: 2C60] Approved [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -4.821
 
MDCK Permeability
 -4.821
 
PAMPA
 +++
 
HIA
 - - -
 
Distribution
VDss
 0.927
 
PPB
 95.3%
 
BBB
 +++
 
Metabolism
CYP1A2 inhibitor
 - - -
CYP1A2 substrate
 +++
CYP2C19 inhibitor
 -
CYP2C19 substrate
 +++
CYP2C9 inhibitor
 - - -
CYP2C9 substrate
 +++
CYP2D6 inhibitor
 +++
CYP2D6 substrate
 - -
CYP3A4 inhibitor
 +
CYP3A4 substrate
 +++
CYP2B6 inhibitor
 +++
CYP2B6 substrate
 +++
CYP2C8 inhibitor
 +++
HLM Stability
 +++
 
Excretion
CLplasma
 11.355
 
T1/2
 0.922
Toxicity
DILI
 +
 
Rat Oral Acute Toxicity
 ++
 
FDAMDD
 +++
 
Respiratory
 +++
 
Human Hepatotoxicity
 +++
 
Ototoxicity
 +++
 
Drug-induced Nephrotoxicity
 +++
 
Drug-induced Neurotoxicity
 +++
 
Hematotoxicity
 +++
 
Genotoxicity
 +++
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
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Formula
C26H28ClNO
PubChem CID
3005573
Canonical SMILES
CN(C)CCOC1=CC=C(C=C1)C(=C(CCCl)C2=CC=CC=C2)C3=CC=CC=C3
InChI
1S/C26H28ClNO/c1-28(2)19-20-29-24-15-13-23(14-16-24)26(22-11-7-4-8-12-22)25(17-18-27)21-9-5-3-6-10-21/h3-16H,17-20H2,1-2H3/b26-25-
InChIKey
XFCLJVABOIYOMF-QPLCGJKRSA-N
CAS Number
CAS 89778-26-7
ChEBI ID
CHEBI:9635
TTD Drug ID
D04VFJ
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Atamestane      Breast cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model MCF-7 CVCL_0031 Invasive breast carcinoma Homo sapiens
                    Experimental
                    Result(s)		 Combination of toremifene plus atamestane was as effective as toremifene or tamoxifen alone but may not provide any additional benefit over toremifene alone or tamoxifen alone.
Target and Pathway
Target(s) Estrogen receptor (ESR)  Molecule Info  [3]
KEGG Pathway Estrogen signaling pathway Click to Show/Hide
2 Prolactin signaling pathway
3 Thyroid hormone signaling pathway
4 Endocrine and other factor-regulated calcium reabsorption
5 Proteoglycans in cancer
NetPath Pathway FSH Signaling Pathway Click to Show/Hide
2 EGFR1 Signaling Pathway
3 RANKL Signaling Pathway
Pathway Interaction Database Regulation of nuclear SMAD2/3 signaling Click to Show/Hide
2 Signaling events mediated by HDAC Class II
3 Plasma membrane estrogen receptor signaling
4 LKB1 signaling events
5 Regulation of Telomerase
6 ATF-2 transcription factor network
7 AP-1 transcription factor network
8 FOXM1 transcription factor network
9 Validated nuclear estrogen receptor alpha network
10 Signaling mediated by p38-alpha and p38-beta
11 FOXA1 transcription factor network
Reactome Nuclear signaling by ERBB4 Click to Show/Hide
2 Nuclear Receptor transcription pathway
WikiPathways Estrogen signaling pathway Click to Show/Hide
2 Nuclear Receptors Meta-Pathway
3 Estrogen Receptor Pathway
4 Signaling by ERBB4
5 JAK/STAT
6 Integrated Pancreatic Cancer Pathway
7 Leptin signaling pathway
8 miR-targeted genes in muscle cell - TarBase
9 Integrated Breast Cancer Pathway
10 Nuclear Receptors
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4325).
Reference 2 Toremifene-atamestane; alone or in combination: predictions from the preclinical intratumoral aromatase model. J Steroid Biochem Mol Biol. 2008 Jan;108(1-2):1-7.
Reference 3 Effect of selective estrogen receptor modulators on cell proliferation and estrogen receptor activities in normal human prostate stromal and epithe... Prostate Cancer Prostatic Dis. 2009;12(4):375-81.
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