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Enclomiphene

Synopsis

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Also known as: Trans-clomiphene, Enclomifene, 15690-57-0, Trans-clomifene, Enclomifeno, Enclomifenum

Molecular Formula

C₂₆H₂₈ClNO

Molecular Weight

406.0 g/mol

InChI Key

GKIRPKYJQBWNGO-OCEACIFDSA-N

FDA UNII

R6D2UI4FLS

The trans or (E)-isomer of clomiphene.

1 2D Structure

Enclomiphene

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[4-[(E)-2-chloro-1,2-diphenylethenyl]phenoxy]-N,N-diethylethanamine

2.1.2 InChI

InChI=1S/C26H28ClNO/c1-3-28(4-2)19-20-29-24-17-15-22(16-18-24)25(21-11-7-5-8-12-21)26(27)23-13-9-6-10-14-23/h5-18H,3-4,19-20H2,1-2H3/b26-25+

2.1.3 InChI Key

GKIRPKYJQBWNGO-OCEACIFDSA-N

2.2 Other Identifiers

2.2.1 UNII

R6D2UI4FLS

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Enclomifene

2. En-clomiphene

3. Enclomiphen

4. (e)-2-(p-(2-chloro-1,2-diphenylvinyl)phenoxy)triethylamine

5. Trans-clomiphene

2.3.2 Depositor-Supplied Synonyms

1. Trans-clomiphene

2. Enclomifene

3. 15690-57-0

4. Trans-clomifene

5. Enclomifeno

6. Enclomifenum

7. Isomer B

8. Rmi 16,289

9. Isomer-b

10. R6d2ui4fls

11. Ici 46476

12. Rmi-16,289

13. (e)-2-(p-(2-chloro-1,2-diphenylvinyl)phenoxy)triethylamine

14. Ici-46476

15. Rmi-16289

16. Dtxsid201318048

17. Trans-2-(4-(2-chloro-1,2-diphenylethenyl)phenoxy)-n,n-diethylethanamine

18. Ethanamine, 2-(4-(2-chloro-1,2-diphenylethenyl)phenoxy)-n,n-diethyl-, (e)-

19. Enclomiphen

20. En-clomiphene

21. Trans Clomiphene

22. 2-(4-((e)-2-chloro-1,2-di(phenyl)ethenyl)phenoxy)-n,n-diethylethanamine

23. 2-[4-[(e)-2-chloro-1,2-di(phenyl)ethenyl]phenoxy]-n,n-diethylethanamine

24. Clomiphene Trans-

25. Refchem:136761

26. Dtxcid50196644

27. (2-(4-((e)-2-chloro-1,2-diphenylethenyl)phenoxy)ethyl)diethylamine

28. Clomifene

29. Enclomiphene [usan]

30. Cisclomiphene

31. Enclomifene [inn]

32. Clomiphene Trans-form

33. Ethanamine, 2-[4-[(1e)-2-chloro-1,2-diphenylethenyl]phenoxy]-n,n-diethyl-

34. 2-[4-[(e)-2-chloro-1,2-diphenylethenyl]phenoxy]-n,n-diethylethanamine

35. Clomifeno

36. Enclomiphene (usan)

37. Transclomifenum

38. Clomifenum

39. 2-[4-[(e)-2-chloro-1,2-diphenyl-vinyl]phenoxy]-n,n-diethyl-ethanamine

40. Enclomifenum [inn-latin]

41. Enclomifeno [inn-spanish]

42. Clomiphene Citrate (z,e)

43. Unii-r6d2ui4fls

44. 2-{4-[(e)-2-chloro-1,2-diphenylethenyl]phenoxy}-n,n-diethylethanamine

45. Trans-enclomiphene

46. Clomifene (tn)

47. Clomifene (inn)

48. Ncgc00179503-02

49. 53q

50. Trans-2-(p-(2-chloro-1,2-diphenylvinyl)phenoxy)triethylamine

51. Prestwick2_000397

52. Prestwick3_000397

53. Chembl954

54. Schembl34893

55. Bspbio_000613

56. Mls001304092

57. Mls006011852

58. Bidd:er0223

59. Bidd:gt0216

60. Enclomiphene [who-dd]

61. {2-[4-(2-chloro-1,2-diphenylethenyl)phenoxy]ethyl}diethylamine

62. 2-(4-(2-chloro-1,2-diphenylethenyl)phenoxy)-n,n-diethylethanamine

63. 2-[4-(2-chloro-1,2-diphenylethenyl)phenoxy]-n,n-diethylethanamine

64. Bpbio1_000675

65. Gtpl7619

66. Bdbm55354

67. Cid_1548953

68. Cid_6420009

69. Hms2090o17

70. Hms2232e06

71. Clomiphene Trans-form [mi]

72. Mfcd00867469

73. Stk525981

74. Triethylamine, 2-(p-(2-chloro-1,2-diphenylvinyl)phenoxy)-, (e)-

75. Akos005459442

76. Db06735

77. Ncgc00179503-01

78. Ncgc00179503-12

79. Da-63191

80. Smr000718756

81. Smr004703502

82. Hy-118861

83. Cs-0069846

84. Ns00121637

85. C06917

86. D07726

87. D08910

88. H20724

89. 911c455

90. Brd-k04218075-048-03-4

91. 1-(p-.beta.-diethylaminoethoxyphenyl)-1,2-diphenyl-2-chloroethylene

92. 1-[(e)-2-chloro-1,2-diphenylethenyl]-4-methoxybenzene; Clomiphene

93. 2-{4-[(e)-2-chloro-1,2-diphenylethenyl]phenoxy}-n,n-diethylethan-1-amine

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₂₆H₂₈ClNO
Molecular Weight	406.0 g/mol
XLogP3	7.2
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	9
Exact Mass	Da
Monoisotopic Mass	Da
Topological Polar Surface Area	12.5
Heavy Atom Count	29
Formal Charge	0
Complexity	481
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	1

4 Drug and Medication Information

4.1 Drug Indication

Used mainly in female infertility due to anovulation (e.g. due to polycystic ovary syndrome) to induce ovulation.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Estrogen Antagonists

Compounds which inhibit or antagonize the action or biosynthesis of estrogenic compounds.

Fertility Agents, Female

Compounds which increase the capacity to conceive in females.

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)

5.2 ATC Code

G - Genito urinary system and sex hormones

G03 - Sex hormones and modulators of the genital system

G03G - Gonadotropins and other ovulation stimulants

G03GB - Ovulation stimulants, synthetic

G03GB02 - Clomifene

ATCvet Code

QG - Genito urinary system and sex hormones

QG03 - Sex hormones and modulators of the genital system

QG03G - Gonadotropins and other ovulation stimulants

QG03GB - Ovulation stimulants, synthetic

QG03GB02 - Clomifene

G03GB02

5.3 Absorption, Distribution and Excretion

Absorption

Based on early studies with 14 C-labeled clomifene, the drug was shown to be readily absorbed orally in humans.

Route of Elimination

Based on early studies with 14C-labeled clomiphene citrate, the drug was shown to be readily absorbed orally in humans and excreted principally in the feces. Mean urinary excretion was approximately 8% with fecal excretion of about 42%.

5.4 Metabolism/Metabolites

Hepatic

5.5 Biological Half-Life

5-7 days

5.6 Mechanism of Action

Clomifene has both estrogenic and anti-estrogenic properties, but its precise mechanism of action has not been determined. Clomifene appears to stumulate the release of gonadotropins, follicle-stimulating hormone (FSH), and leuteinizing hormone (LH), which leads to the development and maturation of ovarian follicle, ovulation, and subsequent development and function of the coprus luteum, thus resulting in pregnancy. Gonadotropin release may result from direct stimulation of the hypothalamic-pituitary axis or from a decreased inhibitory influence of estrogens on the hypothalamic-pituitary axis by competing with the endogenous estrogens of the uterus, pituitary, or hypothalamus. Clomifene has no apparent progestational, androgenic, or antrandrogenic effects and does not appear to interfere with pituitary-adrenal or pituitary-thyroid function.

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