TESMILIFENE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H25NO
Molecular Weight	283.4079
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN(CC)CCOC1=CC=C(CC2=CC=CC=C2)C=C1

InChI

InChIKey=NFIXBCVWIPOYCD-UHFFFAOYSA-N

InChI=1S/C19H25NO/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

HIDE SMILES / InChI

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14722035 | https://www.ncbi.nlm.nih.gov/pubmed/16217292 | https://www.ncbi.nlm.nih.gov/pubmed/16823511

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H1 receptor 315 Target ID: P35367 Gene ID: 3269.0 Gene Symbol: HRH1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/2886214	Antagonist 2778
Multidrug resistance protein 1 8 Target ID: P08183 Gene ID: 5243.0 Gene Symbol: ABCB1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16413681	Activator 1430

PubMed

Title	Date	PubMed
Increased histidine decarboxylase expression during in vitro monocyte maturation; a possible role of endogenously synthesised histamine in monocyte/macrophage differentiation.	2001 Aug	11556524
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 Nov	16217292
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 Dec	16823511
Preferential killing of breast tumor initiating cells by N,N-diethyl-2-[4-(phenylmethyl)phenoxy]ethanamine/tesmilifene.	2009 Jan 1	19118039

Patents

Sample Use Guides

In Vivo Use Guide

5.3 mg/kg Tesmilifene + 20 mg/m^2 Doxorubicin

Route of Administration: Intravenous

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:31:41 GMT 2023` Edited by `admin` on `Sat Dec 16 17:31:41 GMT 2023`
Record UNII	I43T3ID6G2
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TESMILIFENE

Official Name

English

TESMILIFENE [MI]

Common Name

English

tesmilifene [INN]

Common Name

English

Tesmilifene [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C481