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Chemistry

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Also known as: Clomiphene citrate, 50-41-9, Zuclomiphene citrate, Cis-clomiphene citrate, Clomid, Zuclomid
Molecular Formula
C32H36ClNO8
Molecular Weight
598.1  g/mol
InChI Key
PYTMYKVIJXPNBD-OQKDUQJOSA-N
FDA UNII
UY5X264QZV

Clomiphene Citrate
A triphenyl ethylene stilbene derivative which is an estrogen agonist or antagonist depending on the target tissue. Note that ENCLOMIPHENE and ZUCLOMIPHENE are the (E) and (Z) isomers of Clomiphene respectively.
1 2D Structure

Clomiphene Citrate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-[4-[(Z)-2-chloro-1,2-diphenylethenyl]phenoxy]-N,N-diethylethanamine;2-hydroxypropane-1,2,3-tricarboxylic acid
2.1.2 InChI
InChI=1S/C26H28ClNO.C6H8O7/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;7-3(8)1-6(13,5(11)12)2-4(9)10/h5-18H,3-4,19-20H2,1-2H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/b26-25-;
2.1.3 InChI Key
PYTMYKVIJXPNBD-OQKDUQJOSA-N
2.1.4 Canonical SMILES
CCN(CC)CCOC1=CC=C(C=C1)C(=C(C2=CC=CC=C2)Cl)C3=CC=CC=C3.C(C(=O)O)C(CC(=O)O)(C(=O)O)O
2.1.5 Isomeric SMILES
CCN(CC)CCOC1=CC=C(C=C1)/C(=C(/C2=CC=CC=C2)\Cl)/C3=CC=CC=C3.C(C(=O)O)C(CC(=O)O)(C(=O)O)O
2.2 Other Identifiers
2.2.1 UNII
UY5X264QZV
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Chloramiphene

2. Citrate, Clomiphene

3. Clomid

4. Clomide

5. Clomifen

6. Clomifene

7. Clomiphene

8. Clomiphene Citrate

9. Clomiphene Hydrochloride

10. Clostilbegit

11. Dyneric

12. Gravosan

13. Hydrochloride, Clomiphene

14. Klostilbegit

15. Serophene

2.3.2 Depositor-Supplied Synonyms

1. Clomiphene Citrate

2. 50-41-9

3. Zuclomiphene Citrate

4. Cis-clomiphene Citrate

5. Clomid

6. Zuclomid

7. Clomiphene A Citrate

8. 7619-53-6

9. Clomiphene Citrate Salt

10. Milophene

11. Serophene

12. (z)-clomiphene Citrate

13. Chloramiphene

14. Omifin

15. Rmi 16289

16. Clomivid

17. Clomphid

18. Dyneric

19. Genozym

20. Ikaclomin

21. Clomifene Citrate (serophene)

22. Zuclomiphene (citrate)

23. Uy5x264qzv

24. Mrl 41

25. Nsc-151466

26. 2-(4-(2-chloro-1,2-diphenylvinyl)phenoxy)-n,n-diethylethanamine 2-hydroxypropane-1,2,3-tricarboxylate

27. Nsc 35770

28. Rmi 16312

29. 2-[4-[(z)-2-chloro-1,2-diphenylethenyl]phenoxy]-n,n-diethylethanamine;2-hydroxypropane-1,2,3-tricarboxylic Acid

30. Ethanamine, 2-(4-((1z)-2-chloro-1,2-diphenylethenyl)phenoxy)-n,n-diethyl-, 2-hydroxy-1,2,3-propanetricarboxylate (1:1)

31. Ethanamine, 2-[4-(2-chloro-1,2-diphenylethenyl)phenoxy]-n,n-diethyl-,2-hydroxy-1,2,3-propanetricarboxylate (1:1)

32. Mer-41

33. Mrl-41

34. Unii-uy5x264qzv

35. Nsc 151466

36. Nsc-35770

37. Cas-50-41-9

38. Clomiphene Citrate, Cis-

39. Triethylamine, 2-(p-(2-chloro-1,2-diphenylvinyl)phenoxy)-, Citrate (1:1), (z)-

40. Mls001332629

41. Mls002207099

42. Schembl223472

43. Spectrum1500196

44. Sgcut00109

45. Chembl1213137

46. Hms501h04

47. Hy-b1617a

48. Hms1920o19

49. Hms2091g06

50. Hms2232d12

51. Pharmakon1600-01500196

52. Amy33425

53. Bcp03057

54. To_000032

55. Ccg-39553

56. Nsc151466

57. Nsc756698

58. S2561

59. Akos005111131

60. Bcp9000541

61. Ds-6814

62. Fd12066

63. Nsc-756698

64. Ncgc00017008-01

65. Ncgc00017008-02

66. Ncgc00017008-03

67. Ncgc00094626-01

68. Ncgc00094626-02

69. Ncgc00164385-01

70. Ac-19685

71. Ac-32011

72. Ethanamine, 2-(4-(2-chloro-1,2-diphenylethenyl)phenoxy)-n,n-diethyl-, (z)-, 2-hydroxy-1,2,3-propanetricarboxylate (1:1)

73. Bcp0726000214

74. Cs-0111663

75. Sw196898-3

76. C08161

77. Triethylamine,2-diphenylvinyl)phenoxy]-, Citrate

78. Sr-05000001591

79. Sr-05000001591-1

80. Q27291328

81. Triethylamine,2-diphenylvinyl)phenoxy]-, Citrate (1:1)

82. Triethylamine,2-diphenylvinyl)phenoxy]-, Citrate (1:1), (z)-

83. (2)2-[p-(2-chloro-1,2-diphenylvinyl)phenoxy]triethylamine Citrate (1:1)

84. 2-(4-[2-chloro-1,2-diphenylethenyl]phenoxy)-n,n-diethylethanamine Citrate Salt

85. {2-[4-(2-chloro-1,2-diphenylvinyl)phenoxy]ethyl}diethylamine 2-hydroxypropane-1,2,3-tricarboxylic Acid Salt

86. 2-({4-[(z)-2-chloro-1,2-diphenylethenyl]phenyl}oxy)-n,n-diethylethanamine 2-hydroxypropane-1,2,3-tricarboxylate (salt)

87. Ethanamine,2-diphenylethenyl)phenoxy]-n,n-diethyl-, (z)-, 2-hydroxy-1,2,3-propanetricarboxylate (1:1)

88. Ethanamine,2-diphenylethenyl)phenoxy]-n,n-diethyl-, 2-hydroxy-1,2,3-propanetricarboxylate (1:1)

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 598.1 g/mol
Molecular Formula C32H36ClNO8
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count9
Rotatable Bond Count14
Exact Mass597.2129448 g/mol
Monoisotopic Mass597.2129448 g/mol
Topological Polar Surface Area145 Ų
Heavy Atom Count42
Formal Charge0
Complexity708
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 6  
Drug NameClomid
PubMed HealthClomiphene (By mouth)
Drug ClassesEndocrine-Metabolic Agent, Female Reproductive Agent
Drug LabelClomiphene citrate tablets, USP is an orally administered, nonsteroidal, ovulatory stimulant designated chemically as 2-[p-(2chloro-1,2-diphenylvinyl)phenoxy] triethylamine citrate (1:1). It has the molecular formula of C26H28CINO C6H8O7 and a mo...
Active IngredientClomiphene citrate
Dosage FormTablet
RouteOral
Strength50mg
Market StatusPrescription
CompanySanofi Aventis Us

2 of 6  
Drug NameClomiphene citrate
PubMed HealthClomiphene (By mouth)
Drug ClassesEndocrine-Metabolic Agent, Female Reproductive Agent
Drug LabelClomiPHENE citrate is an orally administered, nonsteroidal, ovulatory stimulant designated chemically as 2-[p-(2-chloro-1,2-diphenylvinyl) phenoxy] triethylamine citrate (1:1). It has a molecular formula of C26H28CINO C6H8O7 and a molecular weig...
Active IngredientClomiphene citrate
Dosage FormTablet
RouteOral
Strength50mg
Market StatusPrescription
CompanyPar Pharm

3 of 6  
Drug NameSerophene
Active IngredientClomiphene citrate
Dosage FormTablet
RouteOral
Strength50mg
Market StatusPrescription
CompanyEmd Serono

4 of 6  
Drug NameClomid
PubMed HealthClomiphene (By mouth)
Drug ClassesEndocrine-Metabolic Agent, Female Reproductive Agent
Drug LabelClomiphene citrate tablets, USP is an orally administered, nonsteroidal, ovulatory stimulant designated chemically as 2-[p-(2chloro-1,2-diphenylvinyl)phenoxy] triethylamine citrate (1:1). It has the molecular formula of C26H28CINO C6H8O7 and a mo...
Active IngredientClomiphene citrate
Dosage FormTablet
RouteOral
Strength50mg
Market StatusPrescription
CompanySanofi Aventis Us

5 of 6  
Drug NameClomiphene citrate
PubMed HealthClomiphene (By mouth)
Drug ClassesEndocrine-Metabolic Agent, Female Reproductive Agent
Drug LabelClomiPHENE citrate is an orally administered, nonsteroidal, ovulatory stimulant designated chemically as 2-[p-(2-chloro-1,2-diphenylvinyl) phenoxy] triethylamine citrate (1:1). It has a molecular formula of C26H28CINO C6H8O7 and a molecular weig...
Active IngredientClomiphene citrate
Dosage FormTablet
RouteOral
Strength50mg
Market StatusPrescription
CompanyPar Pharm

6 of 6  
Drug NameSerophene
Active IngredientClomiphene citrate
Dosage FormTablet
RouteOral
Strength50mg
Market StatusPrescription
CompanyEmd Serono

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Fertility Agents, Female

Compounds which increase the capacity to conceive in females. (See all compounds classified as Fertility Agents, Female.)


Estrogen Antagonists

Compounds which inhibit or antagonize the action or biosynthesis of estrogenic compounds. (See all compounds classified as Estrogen Antagonists.)


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]

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13-Jan-2021
31-Aug-2024
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Quantity (KGS) & Unit rate (USD/KGS) over time

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