Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C19H25NO.ClH |
| Molecular Weight | 319.869 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CCN(CC)CCOC1=CC=C(CC2=CC=CC=C2)C=C1
InChI
InChIKey=TXLHNFOLHRXMAU-UHFFFAOYSA-N
InChI=1S/C19H25NO.ClH/c1-3-20(4-2)14-15-21-19-12-10-18(11-13-19)16-17-8-6-5-7-9-17;/h5-13H,3-4,14-16H2,1-2H3;1H
| Molecular Formula | C19H25NO |
| Molecular Weight | 283.4079 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Tesmilifene is a small-molecule antineoplastic drug and chemopotentiator that was under development by YM BioSciences for the treatment of breast cancer. Tesmilifene was developed as a selective ligand of the antiestrogen binding sites without estrogen receptor affinity. Tesmilifene potentiates the cytotoxicity of a variety of chemotherapy drugs in vitro and in vivo. Tesmilifene in combination with doxorubicin provides an unexpected and very large survival advantage over doxorubicin alone in a randomized trial in phase III clinical trial in advanced breast cancer. Unfortunately, Tesmilifene application associated with high rate disease and treatment-related adverse events and poor quality of life. Based on these results further development of Tesmilifene was discontinued
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Effects of tesmilifene, a substrate of CYP3A and an inhibitor of P-glycoprotein, on the pharmacokinetics of intravenous and oral docetaxel in rats. | 2010-08 |
|
| Enhancement of cytotoxicity of natural product drugs against multidrug resistant variant cell lines of human head and neck squamous cell carcinoma and breast carcinoma by tesmilifene. | 2009-02-18 |
|
| Preferential killing of breast tumor initiating cells by N,N-diethyl-2-[4-(phenylmethyl)phenoxy]ethanamine/tesmilifene. | 2009-01-01 |
|
| N,N-diethyl-2-[4-(phenylmethyl) phenoxy] ethanamine (DPPE; tesmilifene), a chemopotentiating agent with hormetic effects on DNA synthesis in vitro, may improve survival in patients with metastatic breast cancer. | 2008-02 |
|
| On-demand generation of an efficient catalyst for pyridine formation from unactivated nitriles and alpha,omega-diynes using CoCl2-6H2O, dppe, and Zn. | 2007-03-01 |
|
| The phospholipidosis-lnducing potential of the chemopotentiating drug, N,N-Diethyl-2-[4-(phenylmethyl)phenoxy]ethanamine (DPPE, tesmilifene) correlates with its stimulation of phosphatidylserine synthesis and exposure on the plasma membrane in MCF-7 breast cancer cells. | 2007 |
|
| Quality of life analyses in a clinical trial of DPPE (tesmilifene) plus doxorubicin versus doxorubicin in patients with advanced or metastatic breast cancer: NCIC CTG Trial MA.19. | 2006-12 |
|
| Tesmilifene may enhance breast cancer chemotherapy by killing a clone of aggressive, multi-drug resistant cells through its action on the p-glycoprotein pump. | 2006 |
|
| Phase II trial of tesmilifene plus mitoxantrone and prednisone for hormone refractory prostate cancer: high subjective and objective response in patients with symptomatic metastases. | 2005-11 |
|
| Phase III study of N,N-diethyl-2-[4-(phenylmethyl) phenoxy]ethanamine (BMS-217380-01) combined with doxorubicin versus doxorubicin alone in metastatic/recurrent breast cancer: National Cancer Institute of Canada Clinical Trials Group Study MA.19. | 2004-01-15 |
|
| N,N-diethyl-2-[4-(phenylmethyl)phenoxy]ethanamine increases the permeability of primary mouse cerebral endothelial cell monolayers. | 2003-04 |
|
| Effect of alpha-FMH and DPPE on colony-forming properties of human peripheral progenitor cells. | 2002-07 |
|
| Cimetidine and a tamoxifen derivate reduce tumour formation in SCID mice xenotransplanted with a human melanoma cell line. | 2002-06 |
|
| Different h2 receptor antihistamines dissimilarly retard the growth of xenografted human melanoma cells in immunodeficient mice. | 2002 |
|
| Murine and human hematopoietic colony formation: a possible regulatory role for intracellular histamine. | 2002 |
|
| Increased histidine decarboxylase expression during in vitro monocyte maturation; a possible role of endogenously synthesised histamine in monocyte/macrophage differentiation. | 2001-08 |
|
| Inhibition of effects of endogenously synthesized histamine disturbs in vitro human dendritic cell differentiation. | 2001-04-02 |
|
| N,N-diethyl-2-[4-(phenylmethyl)phenoxy] ethanamine (DPPE) a chemopotentiating and cytoprotective agent in clinical trials: interaction with histamine at cytochrome P450 3A4 and other isozymes that metabolize antineoplastic drugs. | 2000 |
|
| Study of the in-vivo antioestrogenic action of N,N-diethyl-2-[4-(phenylmethyl)phenoxy]ethanamine HCl (DPPE), a novel intracellular histamine antagonist and antioestrogen binding site ligand. | 1990-05 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:04:59 GMT 2025
by
admin
on
Mon Mar 31 18:04:59 GMT 2025
|
| Record UNII |
1U4B477260
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Preferred Name | English | ||
|
Official Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
NCI_THESAURUS |
C2141
Created by
admin on Mon Mar 31 18:04:59 GMT 2025 , Edited by admin on Mon Mar 31 18:04:59 GMT 2025
|
||
|
NCI_THESAURUS |
C1821
Created by
admin on Mon Mar 31 18:04:59 GMT 2025 , Edited by admin on Mon Mar 31 18:04:59 GMT 2025
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
30669
Created by
admin on Mon Mar 31 18:04:59 GMT 2025 , Edited by admin on Mon Mar 31 18:04:59 GMT 2025
|
PRIMARY | |||
|
DBSALT002853
Created by
admin on Mon Mar 31 18:04:59 GMT 2025 , Edited by admin on Mon Mar 31 18:04:59 GMT 2025
|
PRIMARY | |||
|
CHEMBL26424
Created by
admin on Mon Mar 31 18:04:59 GMT 2025 , Edited by admin on Mon Mar 31 18:04:59 GMT 2025
|
PRIMARY | |||
|
92981-78-7
Created by
admin on Mon Mar 31 18:04:59 GMT 2025 , Edited by admin on Mon Mar 31 18:04:59 GMT 2025
|
PRIMARY | |||
|
m10591
Created by
admin on Mon Mar 31 18:04:59 GMT 2025 , Edited by admin on Mon Mar 31 18:04:59 GMT 2025
|
PRIMARY | Merck Index | ||
|
1U4B477260
Created by
admin on Mon Mar 31 18:04:59 GMT 2025 , Edited by admin on Mon Mar 31 18:04:59 GMT 2025
|
PRIMARY | |||
|
741196
Created by
admin on Mon Mar 31 18:04:59 GMT 2025 , Edited by admin on Mon Mar 31 18:04:59 GMT 2025
|
PRIMARY | |||
|
300000055346
Created by
admin on Mon Mar 31 18:04:59 GMT 2025 , Edited by admin on Mon Mar 31 18:04:59 GMT 2025
|
PRIMARY | |||
|
DTXSID70918805
Created by
admin on Mon Mar 31 18:04:59 GMT 2025 , Edited by admin on Mon Mar 31 18:04:59 GMT 2025
|
PRIMARY | |||
|
KK-80
Created by
admin on Mon Mar 31 18:04:59 GMT 2025 , Edited by admin on Mon Mar 31 18:04:59 GMT 2025
|
PRIMARY | |||
|
175534
Created by
admin on Mon Mar 31 18:04:59 GMT 2025 , Edited by admin on Mon Mar 31 18:04:59 GMT 2025
|
PRIMARY | |||
|
C952
Created by
admin on Mon Mar 31 18:04:59 GMT 2025 , Edited by admin on Mon Mar 31 18:04:59 GMT 2025
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
PARENT -> SALT/SOLVATE |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |