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Tesmilifene

Tesmilifene structure

Tesmilifene 

structure
  • CAS No:

    98774-23-3

  • Formula:

    C19H25NO

  • Chemical Name:

    Tesmilifene

  • Synonyms:

    Ethanamine,N,N-diethyl-2-[4-(phenylmethyl)phenoxy]-;Triethylamine,2-(α-phenyl-p-tolyloxy)-;N,N-Diethyl-2-[4-(phenylmethyl)phenoxy]ethanamine;N,N-Diethyl-2-(p-benzylphenoxy)ethylamine;DPPE;Tesmilifene;2-(4-Benzylphenoxy)-N,N-diethylethanamine

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

N,N-diethyl-2-[4-(phenylmethyl)phenoxy]ethanamine is a diarylmethane.|Tesmilifene is a novel potentiator of chemotherapy which, when added to doxorubicin, achieved an unexpected and very large survival advantage over doxorubicin alone in a randomized trial in advanced breast cancer.

Tesmilifene Basic Attributes

283.415

283.41

I43T3ID6G2

DTXSID1045661

Characteristics

12.5

5.04

Transparent, colorless liquid

1.0±0.1 g/cm3

397.0±30.0 °C at 760 mmHg

116.8±26.9 °C

1.543

Drug Information

Intended for the treatment of various forms of cancer.

Drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists. Classical antihistaminics block the histamine H1 receptors only. (See all compounds classified as Histamine Antagonists.)|Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system. (See all compounds classified as Platelet Aggregation Inhibitors.)

Hepatic

Although the exact mechanism of action is not known, one study (PMID: 16413681) proposes that tesmilifene may be an activating p-gp substrate, which enables the p-gp pump to extrude typical p-gp substrates (such as anthracyclines or taxanes) more efficiently. This process consumes ATP, since the p-gp is absolutely, and highly dependent on ATP hydrolysis. The mechanism of cell death is likely to result not from the presence of chemotherapy inside the cell (in fact the chemotherapy is extruded) but, directly or indirectly, from the enhanced consumption of ATP. The ATP may be consumed below a threshold necessary for survival, or, (more likely) the enhanced ATP production required to maintain ATP levels may result in the generation of reactive oxygen species (ROS) to an extent that overwhelms the cell’s ability to inactivate them. The result would be additional cell death, but only in the mdr+ population. The doxorubicin would continue to act on the drug sensitive remainder of the cell population, but without the help of tesmilifene.

(2-(4-benzylphenoxy)ethyl)diethylamine

Computed Properties

Molecular Weight:283.4
XLogP3:4.6
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:8
Exact Mass:283.193614421
Monoisotopic Mass:283.193614421
Topological Polar Surface Area:12.5
Heavy Atom Count:21
Complexity:250
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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