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Synopsis

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Chemistry

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Also known as: 89778-27-8, Fareston, Toremifene citrate [usan], Toremifene (citrate), Fc 1157a, Nk 622

Molecular Formula

C₃₂H₃₆ClNO₈

Molecular Weight

598.1 g/mol

InChI Key

IWEQQRMGNVVKQW-OQKDUQJOSA-N

FDA UNII

2498Y783QT

A first generation selective estrogen receptor modulator (SERM). Like TAMOXIFEN, it is an estrogen agonist for bone tissue and cholesterol metabolism but is antagonistic on mammary and uterine tissue.

1 2D Structure

Toremifene Citrate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[4-[(Z)-4-chloro-1,2-diphenylbut-1-enyl]phenoxy]-N,N-dimethylethanamine;2-hydroxypropane-1,2,3-tricarboxylic acid

2.1.2 InChI

InChI=1S/C26H28ClNO.C6H8O7/c1-28(2)19-20-29-24-15-13-23(14-16-24)26(22-11-7-4-8-12-22)25(17-18-27)21-9-5-3-6-10-21;7-3(8)1-6(13,5(11)12)2-4(9)10/h3-16H,17-20H2,1-2H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/b26-25-;

2.1.3 InChI Key

IWEQQRMGNVVKQW-OQKDUQJOSA-N

2.1.4 Canonical SMILES

CN(C)CCOC1=CC=C(C=C1)C(=C(CCCl)C2=CC=CC=C2)C3=CC=CC=C3.C(C(=O)O)C(CC(=O)O)(C(=O)O)O

2.1.5 Isomeric SMILES

CN(C)CCOC1=CC=C(C=C1)/C(=C(/CCCl)\C2=CC=CC=C2)/C3=CC=CC=C3.C(C(=O)O)C(CC(=O)O)(C(=O)O)O

2.2 Other Identifiers

2.2.1 UNII

2498Y783QT

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Citrate, Toremifene

2. Fareston

3. Fc 1157a

4. Fc-1157a

5. Fc1157a

6. Toremifene

7. Toremifene Citrate (1:1)

8. Toremifene, (e)-isomer

2.3.2 Depositor-Supplied Synonyms

1. 89778-27-8

2. Fareston

3. Toremifene Citrate [usan]

4. Toremifene (citrate)

5. Fc 1157a

6. Nk 622

7. Nsc 613680

8. Fc-1157a

9. 89778-27-8 (citrate)

10. Nsc-613680

11. Nsc613680

12. 2-(p-((z)-4-chloro-1,2-diphenyl-1-butenyl)phenoxy)-n,n-dimethylethylamine Citrate (1:1)

13. 2498y783qt

14. Toremifene Citrate (fareston, Acapodene)

15. Dsstox_cid_1367

16. Dsstox_rid_76113

17. Dsstox_gsid_21367

18. (z)-2-(4-(4-chloro-1,2-diphenylbut-1-en-1-yl)phenoxy)-n,n-dimethylethan-1-amine 2-hydroxypropane-1,2,3-tricarboxylate

19. Ethanamine, 2-(4-(4-chloro-1,2-diphenyl-1-butenyl)phenoxy)-n,n-dimethyl-, (z)-, 2-hydroxy-1,2,3-propanetricarboxylate (1:1)

20. (2-{4-[(1z)-4-chloro-1,2-diphenylbut-1-en-1-yl]phenoxy}ethyl)dimethylamine; 2-hydroxypropane-1,2,3-tricarboxylic Acid

21. 2-({4-[(1z)-4-chloro-1,2-diphenylbut-1-en-1-yl]phenyl}oxy)-n,n-dimethylethanamine 2-hydroxypropane-1,2,3-tricarboxylate (salt)

22. Cas-89778-27-8

23. Ccris 6719

24. Unii-2498y783qt

25. 2-[p-[(z)-4-chloro-1,2-diphenyl-1-butenyl]phenoxy]-n,n-dimethylethylamine Citrate (1:1)

26. Cpd000469213

27. Schembl4564

28. (z)-4-chloro-1,2-diphenyl-1-(4-(2-(n,n-dimethylamino)ethoxy)phenyl)-1-butene Citrate (1:1)

29. Mls001306432

30. Mls006011608

31. Chebi:9636

32. Toremifene Citrate [mi]

33. Chembl1200675

34. Dtxsid2021367

35. Toremifene Citrate (jan/usan)

36. Toremifene Citrate [jan]

37. Hms2052c03

38. Hms2230p09

39. Hms3264l11

40. Pharmakon1600-01505682

41. Toremifene Citrate [vandf]

42. Toremifene Citrate [mart.]

43. Hy-b0005

44. Toremifene Citrate [who-dd]

45. Tox21_111877

46. Tox21_301740

47. Mfcd01729016

48. Nsc759190

49. S1776

50. Akos015888270

51. Ac-1985

52. Ccg-101072

53. Cs-1272

54. Ks-5242

55. Nc00322

56. Nsc-759190

57. 2-[4-[(z)-4-chloro-1,2-diphenyl-but-1-enyl]phenoxy]-n,n-dimethyl-ethanamine; Citric Acid

58. Toremifene Citrate [orange Book]

59. Ncgc00255310-01

60. 2-[4-[(z)-4-chloro-1,2-diphenylbut-1-enyl]phenoxy]-n,n-dimethylethanamine; 2-hydroxypropane-1,2,3-tricarboxylic Acid

61. Smr004703372

62. Toremifene Citrate Salt, >=98% (hplc)

63. Sw197702-3

64. T2832

65. D00967

66. 778t267

67. A843307

68. Sr-01000763502-3

69. Q27253831

70. 2-[p-[(z)-4-chloro-1,n- Dimethylethylamine Citrate (1:1)

71. (z)-2-[4-(4-chloro-1,2-diphenyl-1-butenyl)phenoxy]-n,n-dimethylethanamine Citrate

72. (z)-2-[4-(4-chloro-1,n- Dimethylethanamine, 2-hydroxy-1,2,3-propanetricarboxylate (1:1)

73. (z)-4-chloro-1-(4-dimethylaminoethoxyphenyl)-1,2-diphenyl-1-butene Citrate

74. (z)-2-(4-(4-chloro-1,2-diphenylbut-1-en-1-yl)phenoxy)-n,n-dimethylethanamine 2-hydroxypropane-1,2,3-tricarboxylate

75. (z)-2-(4-(4-chloro-1,2-diphenylbut-1-enyl)phenoxy)-n,n-dimethylethanamine 2-hydroxypropane-1,2,3-tricarboxylate

76. 2-[4-[(z)-4-chloranyl-1,2-diphenyl-but-1-enyl]phenoxy]-n,n-dimethyl-ethanamine; 2-oxidanylpropane-1,2,3-tricarboxylic Acid

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₃₂H₃₆ClNO₈
Molecular Weight	598.1 g/mol
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	14
Exact Mass	597.2129448 g/mol
Monoisotopic Mass	597.2129448 g/mol
Topological Polar Surface Area	145 Å²
Heavy Atom Count	42
Formal Charge	0
Complexity	710
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Indication

First line hormone treatment of hormone-dependent metastatic breast cancer in postmenopausal patients.

Fareston is not recommended for patients with estrogen receptor negative tumours.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Antineoplastic Agents, Hormonal

Antineoplastic agents that are used to treat hormone-sensitive tumors. Hormone-sensitive tumors may be hormone-dependent, hormone-responsive, or both. A hormone-dependent tumor regresses on removal of the hormonal stimulus, by surgery or pharmacological block. Hormone-responsive tumors may regress when pharmacologic amounts of hormones are administered regardless of whether previous signs of hormone sensitivity were observed. The major hormone-responsive cancers include carcinomas of the breast, prostate, and endometrium; lymphomas; and certain leukemias. (From AMA Drug Evaluations Annual 1994, p2079) (See all compounds classified as Antineoplastic Agents, Hormonal.)

Bone Density Conservation Agents

Agents that inhibit BONE RESORPTION and/or favor BONE MINERALIZATION and BONE REGENERATION. They are used to heal BONE FRACTURES and to treat METABOLIC BONE DISEASES such as OSTEOPOROSIS. (See all compounds classified as Bone Density Conservation Agents.)

Selective Estrogen Receptor Modulators

A structurally diverse group of compounds distinguished from ESTROGENS by their ability to bind and activate ESTROGEN RECEPTORS but act as either an agonist or antagonist depending on the tissue type and hormonal milieu. They are classified as either first generation because they demonstrate estrogen agonist properties in the ENDOMETRIUM or second generation based on their patterns of tissue specificity. (Horm Res 1997;48:155-63) (See all compounds classified as Selective Estrogen Receptor Modulators.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Selective Estrogen Receptor Modulators [MoA]; Estrogen Agonist/Antagonist [EPC]

5.3 ATC Code

L02BA02

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