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Chemistry

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Also known as: 112093-28-4, Z-endoxifen, 4-hydroxy-n-desmethyltamoxifen, Endoxifen z-isomer, N-desmethyl-4-hydroxytamoxifen, (z)-endoxifen
Molecular Formula
C25H27NO2
Molecular Weight
373.5  g/mol
InChI Key
MHJBZVSGOZTKRH-IZHYLOQSSA-N
FDA UNII
46AF8680RC

Endoxifen
1 2D Structure

Endoxifen

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-[(Z)-1-[4-[2-(methylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]phenol
2.1.2 InChI
InChI=1S/C25H27NO2/c1-3-24(19-7-5-4-6-8-19)25(20-9-13-22(27)14-10-20)21-11-15-23(16-12-21)28-18-17-26-2/h4-16,26-27H,3,17-18H2,1-2H3/b25-24-
2.1.3 InChI Key
MHJBZVSGOZTKRH-IZHYLOQSSA-N
2.1.4 Canonical SMILES
CCC(=C(C1=CC=C(C=C1)O)C2=CC=C(C=C2)OCCNC)C3=CC=CC=C3
2.1.5 Isomeric SMILES
CC/C(=C(\C1=CC=C(C=C1)O)/C2=CC=C(C=C2)OCCNC)/C3=CC=CC=C3
2.2 Other Identifiers
2.2.1 UNII
46AF8680RC
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 4-hydroxy-n-demethyltamoxifen

2. 4-hydroxy-n-desmethyltamoxifen

3. 4-hydroxy-n-desmethyltamoxifen, (z)-isomer

4. Z-endoxifen

2.3.2 Depositor-Supplied Synonyms

1. 112093-28-4

2. Z-endoxifen

3. 4-hydroxy-n-desmethyltamoxifen

4. Endoxifen Z-isomer

5. N-desmethyl-4-hydroxytamoxifen

6. (z)-endoxifen

7. 110025-28-0

8. (z)-4-hydroxy-n-desmethyl Tamoxifen (mixture Of Isomers)

9. 4ohndtam

10. Nsc-749798

11. N-desmethyl-4-hydroxy Tamoxifen (approx. 1:1 E/z Mixture)

12. 4-hydroxy-n-desmethyl-tamoxifen

13. Chebi:80555

14. 46af8680rc

15. 4-[(z)-1-[4-[2-(methylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]phenol

16. (z)-4-hydroxy-n-desmethyl Tamoxifen (contains Up To 10% E Isomer)

17. Unii-46af8680rc

18. 4-hydroxy-n-desmethyltamoxifen, (z)-isomer

19. 4-hydroxy-n-desmethyl Tamoxifen

20. (z)-4-(1-(4-(2-(methylamino)ethoxy)phenyl)-2-phenylbut-1-en-1-yl)phenol

21. Endoxifenz-isomer

22. Phenol, 4-((1z)-1-(4-(2-(methylamino)ethoxy)phenyl)-2-phenyl-1-buten-1-yl)-

23. Endoxifen(e/z=1:1)

24. Endoxifen [who-dd]

25. Chembl1093458

26. Schembl10107920

27. Gtpl10203

28. Dtxsid80149880

29. Ex-a645

30. Phenol, 4-[(1z)-1-[4-[2-(methylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]-

31. Bcp15866

32. Ex-a1970

33. 4-[1-[4-[2-(methylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]phenol

34. Bdbm50435003

35. Hy-18719e

36. Nsc746494

37. Nsc749798

38. Nsc777380

39. Zinc22056306

40. Nsc 749798

41. Nsc-746494

42. Nsc-777380

43. Ncgc00386714-01

44. Ac-36810

45. Be172975

46. Bs-42369

47. B7481

48. Cs-0028594

49. (z)-4-hydroxy-n-desmethyl Tamoxifen (endoxifen)

50. A894656

51. N-desmethyl-4-hydroxytamoxifen, Mixture Of Isomers

52. 4-hydroxy-n-desmethyl Tamoxifen ((e/z)-endoxifen)

53. J-002363

54. W-200834

55. Q27149598

56. N-desmethyl-4-hydroxy Tamoxifen(approx. 1:1 E/z Mixture)

57. (z)-4-hydroxy-n-desmethyl Tamoxifen(contains Up To 10% E Isomer)

58. (e/z)-4-(1-(4-(2-(methylamino)ethoxy)phenyl)-2-phenylbut-1-enyl)phenol

59. (z)-4-(1-(4-(2-(methylamino)ethoxy)phenyl)-2-phenylbut-1-enyl)phenol

60. 4-[(~{z})-1-[4-[2-(methylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]phenol

61. N-desmethyl-4-hydroxytamoxifen, Mixture Of Isomers, Analytical Standard

62. (e/z)-4-[1-[4-[2-(methylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]-phenol

63. 4-[(1z)-1-{4-[2-(methylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl]phenol

64. N-methyl-2-[4-[(e)-1-(4-hydroxyphenyl)-2-phenyl-1-butenyl]phenoxy]ethanamine

65. Phenol, 4-(1-(4-(2-(methylamino)ethoxy]phenyl)-2-phenyl-1-butenyl)-, (z)-

2.4 Create Date
2006-10-25
3 Chemical and Physical Properties
Molecular Weight 373.5 g/mol
Molecular Formula C25H27NO2
XLogP36.3
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count8
Exact Mass373.204179104 g/mol
Monoisotopic Mass373.204179104 g/mol
Topological Polar Surface Area41.5 Ų
Heavy Atom Count28
Formal Charge0
Complexity467
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 Metabolism/Metabolites

Endoxifen has known human metabolites that include Endoxifen O-glucuronide and Endoxifen O-sulfate.

Endoxifen is a known human metabolite of 4-Hydroxytamoxifen and N-Desmethyltamoxifen.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


Drugs in Development

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Details:

Endoxifen (z-endoxifen) is the most active metabolite of the FDA approved selective estrogen receptor modulator (SERM), tamoxifen. It has demonstrated that the anti-estrogenic effects and is being evaluated for ER+/HER2+ breast cancer.


Lead Product(s): Endoxifen

Therapeutic Area: Oncology Brand Name: Endoxifen

Study Phase: Phase IIProduct Type: Small molecule

Sponsor: Quantum Leap Healthcare

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable June 28, 2023

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01

euroPLX 86 Munich
Not Confirmed
euroPLX 86 Munich
Not Confirmed

Details : Endoxifen (z-endoxifen) is the most active metabolite of the FDA approved selective estrogen receptor modulator (SERM), tamoxifen. It has demonstrated that the anti-estrogenic effects and is being evaluated for ER+/HER2+ breast cancer.

Brand Name : Endoxifen

Molecule Type : Small molecule

Upfront Cash : Not Applicable

June 28, 2023

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Details:

Endoxifen (z-endoxifen) is the most active metabolite of the FDA approved selective estrogen receptor modulator (SERM), tamoxifen. It has demonstrated that the anti-estrogenic effects and is being evaluated for ER+/HER2+ breast cancer.


Lead Product(s): Endoxifen

Therapeutic Area: Oncology Brand Name: Endoxifen

Study Phase: Phase IIProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable June 12, 2023

blank

02

euroPLX 86 Munich
Not Confirmed
euroPLX 86 Munich
Not Confirmed

Details : Endoxifen (z-endoxifen) is the most active metabolite of the FDA approved selective estrogen receptor modulator (SERM), tamoxifen. It has demonstrated that the anti-estrogenic effects and is being evaluated for ER+/HER2+ breast cancer.

Brand Name : Endoxifen

Molecule Type : Small molecule

Upfront Cash : Not Applicable

June 12, 2023

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Details:

Under the agreement, Societal CDMO will provide a range of its Clinical Trial Services offerings focused on Atossa’s proprietary Selective Estrogen Receptor Modulator (SERM), (Z)-endoxifen, the most active metabolite of the FDA approved SERM, tamoxifen.


Lead Product(s): Endoxifen

Therapeutic Area: Oncology Brand Name: Endoxifen

Study Phase: Phase IIProduct Type: Small molecule

Sponsor: Atossa Therapeutics

Deal Size: Undisclosed Upfront Cash: Undisclosed

Deal Type: Agreement May 23, 2023

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03

euroPLX 86 Munich
Not Confirmed
euroPLX 86 Munich
Not Confirmed

Details : Under the agreement, Societal CDMO will provide a range of its Clinical Trial Services offerings focused on Atossa’s proprietary Selective Estrogen Receptor Modulator (SERM), (Z)-endoxifen, the most active metabolite of the FDA approved SERM, tamoxifen...

Brand Name : Endoxifen

Molecule Type : Small molecule

Upfront Cash : Undisclosed

May 23, 2023

blank

Details:

(Z)-endoxifen is the most active metabolite of the FDA approved selective estrogen receptor modulator (SERM), tamoxifen. It has demonstrated that the anti-estrogenic effects and is being evaluated for ER+/HER2+ breast cancer.


Lead Product(s): Endoxifen

Therapeutic Area: Oncology Brand Name: Undisclosed

Study Phase: Phase IIProduct Type: Small molecule

Sponsor: Quantum Leap Healthcare

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable March 21, 2023

blank

04

euroPLX 86 Munich
Not Confirmed
euroPLX 86 Munich
Not Confirmed

Details : (Z)-endoxifen is the most active metabolite of the FDA approved selective estrogen receptor modulator (SERM), tamoxifen. It has demonstrated that the anti-estrogenic effects and is being evaluated for ER+/HER2+ breast cancer.

Brand Name : Undisclosed

Molecule Type : Small molecule

Upfront Cash : Not Applicable

March 21, 2023

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Details:

Endoxifen, an active metabolite of tamoxifen, which is an FDA-approved drug to treat ovarian and breast cancer. Endoxifen administered to breast cancer patients prior to surgery.


Lead Product(s): Endoxifen

Therapeutic Area: Oncology Brand Name: Undisclosed

Study Phase: Phase IIProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable June 07, 2021

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05

euroPLX 86 Munich
Not Confirmed
euroPLX 86 Munich
Not Confirmed

Details : Endoxifen, an active metabolite of tamoxifen, which is an FDA-approved drug to treat ovarian and breast cancer. Endoxifen administered to breast cancer patients prior to surgery.

Brand Name : Undisclosed

Molecule Type : Small molecule

Upfront Cash : Not Applicable

June 07, 2021

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Details:

The study results show that treatment with Atossa’s proprietary Endoxifen for 20 days prior to unilateral mastectomy and for 18 months after surgery as an adjuvant did not lead to vasomotor symptoms commonly associated with tamoxifen.


Lead Product(s): Endoxifen

Therapeutic Area: Oncology Brand Name: Undisclosed

Study Phase: Phase IIProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable July 30, 2020

blank

06

euroPLX 86 Munich
Not Confirmed
euroPLX 86 Munich
Not Confirmed

Details : The study results show that treatment with Atossa’s proprietary Endoxifen for 20 days prior to unilateral mastectomy and for 18 months after surgery as an adjuvant did not lead to vasomotor symptoms commonly associated with tamoxifen.

Brand Name : Undisclosed

Molecule Type : Small molecule

Upfront Cash : Not Applicable

July 30, 2020

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Details:

Completed treating a sufficient number of patients to permit an initial report of study results from the pilot portion of the study.


Lead Product(s): Endoxifen

Therapeutic Area: Oncology Brand Name: Undisclosed

Study Phase: Phase IIProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable April 02, 2020

blank

07

euroPLX 86 Munich
Not Confirmed
euroPLX 86 Munich
Not Confirmed

Details : Completed treating a sufficient number of patients to permit an initial report of study results from the pilot portion of the study.

Brand Name : Undisclosed

Molecule Type : Small molecule

Upfront Cash : Not Applicable

April 02, 2020

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