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    Tesmilifene

    ACTIVE PHARMA INGREDIENTS

    PharmaCompass
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    2D Structure
    Also known as: 98774-23-3, 2-(4-benzylphenoxy)-n,n-diethylethanamine, Tesmilifene [inn], N,n-diethyl-2-((4-phenylmethyl)phenoxy)ethanamine, Depmpe, Chembl26424
    Molecular Formula
    C19H25NO
    Molecular Weight
    283.4  g/mol
    InChI Key
    NFIXBCVWIPOYCD-UHFFFAOYSA-N
    FDA UNII
    I43T3ID6G2
    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.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-(4-benzylphenoxy)-N,N-diethylethanamine
    2.1.2 InChI
    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
    2.1.3 InChI Key
    NFIXBCVWIPOYCD-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CCN(CC)CCOC1=CC=C(C=C1)CC2=CC=CC=C2
    2.2 Other Identifiers
    2.2.1 UNII
    I43T3ID6G2
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (2-(4-benzylphenoxy)ethyl)diethylamine

    2. Bzphoet-diethylammonium Chloride

    3. Depmpe

    4. Dppe

    5. Dppe Hydrochloride

    6. Ethanamine, N,n-diethyl-2-(4-(phenylmethyl)phenoxy)-, (2ar-(2aalpha,4beta,4abeta,6beta,9alpha(alphar*,betas*),11alpha,12alpha,12aalpha,12balpha))-

    7. N,n-diethyl-2-((4-phenylmethyl)phenoxy)-ethanamine Hydrochloride

    8. N,n-diethyl-2-((4-phenylmethyl)phenoxy)ethanamine

    9. N,n-diethyl-2-((4-phenylmethyl)phenoxy)ethanamine Hydrochloride

    10. N,n-diethyl-2-(4-(phenylmethyl)phenoxy)ethanamine

    11. N,n-diethyl-2-(4-(phenylmethyl)phenoxy)ethanamine Hydrochloride

    12. Tesmilifene Hydrochloride

    2.3.2 Depositor-Supplied Synonyms

    1. 98774-23-3

    2. 2-(4-benzylphenoxy)-n,n-diethylethanamine

    3. Tesmilifene [inn]

    4. N,n-diethyl-2-((4-phenylmethyl)phenoxy)ethanamine

    5. Depmpe

    6. Chembl26424

    7. I43t3id6g2

    8. N,n-diethyl-2-[4-(phenylmethyl)phenoxy]ethanamine

    9. N,n-diethyl-2-[4-benzylphenoxy]ethanamine

    10. Ethanamine, N,n-diethyl-2-(4-(phenylmethyl)phenoxy)-

    11. Ncgc00024762-02

    12. N,n-diethyl-2-(4-benzylphenoxy)ethanamine

    13. Dsstox_cid_25661

    14. Dsstox_rid_81038

    15. Dsstox_gsid_45661

    16. Unii-i43t3id6g2

    17. Cas-98774-23-3

    18. Ethanamine, N,n-diethyl-2-[4-(phenylmethyl)phenoxy]-

    19. Ymb1002

    20. Tocris-0743

    21. Tesmilifene [mi]

    22. 2-((alpha-phenyl-p-tolyl)oxy)triethylamine

    23. Tesmilifene [who-dd]

    24. Schembl112525

    25. Zinc2139

    26. Dtxsid1045661

    27. Chebi:93414

    28. Bcp09123

    29. Tox21 110924

    30. Tox21_110924

    31. Bdbm50085260

    32. Tox21_110924_1

    33. Db04905

    34. [2-(4-benzylphenoxy)ethyl]diethylamine

    35. Ncgc00024762-01

    36. Ncgc00024762-03

    37. Ncgc00024762-04

    38. Ncgc00024762-05

    39. N,n-diethyl-2-(p-benzylphenoxy)ethylamine

    40. Db-103604

    41. [2-(4-benzyl-phenoxy)-ethyl]-diethyl-amine

    42. Triethylamine, 2-(.alpha.-phenyl-p-tolyloxy)-

    43. Brd-k80315159-051-01-2

    44. Q27095558

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 283.4 g/mol
    Molecular Formula C19H25NO
    XLogP34.6
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count8
    Exact Mass283.193614421 g/mol
    Monoisotopic Mass283.193614421 g/mol
    Topological Polar Surface Area12.5 Ų
    Heavy Atom Count21
    Formal Charge0
    Complexity250
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Intended for the treatment of various forms of cancer.

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Histamine Antagonists

    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.)

    Platelet Aggregation Inhibitors

    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.)

    5.2 Metabolism/Metabolites

    Hepatic

    5.3 Mechanism of Action

    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 cells 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.