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Tesmilifene

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Chemistry

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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

Tesmilifene

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 Formula	C₁₉H₂₅NO
Molecular Weight	283.4 g/mol
XLogP3	4.6
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	8
Exact Mass	283.193614421 g/mol
Monoisotopic Mass	283.193614421 g/mol
Topological Polar Surface Area	12.5 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	250
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.

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