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Clomifene Citrate

Clomifene Citrate

Synopsis, 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

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

Clomifene 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 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	708
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 Information

1 of 6
Drug Name	Clomid
PubMed Health	Clomiphene (By mouth)
Drug Classes	Endocrine-Metabolic Agent, Female Reproductive Agent
Drug Label	Clomiphene 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 Ingredient	Clomiphene citrate
Dosage Form	Tablet
Route	Oral
Strength	50mg
Market Status	Prescription
Company	Sanofi Aventis Us

2 of 6
Drug Name	Clomiphene citrate
PubMed Health	Clomiphene (By mouth)
Drug Classes	Endocrine-Metabolic Agent, Female Reproductive Agent
Drug Label	ClomiPHENE 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 Ingredient	Clomiphene citrate
Dosage Form	Tablet
Route	Oral
Strength	50mg
Market Status	Prescription
Company	Par Pharm

3 of 6
Drug Name	Serophene
Active Ingredient	Clomiphene citrate
Dosage Form	Tablet
Route	Oral
Strength	50mg
Market Status	Prescription
Company	Emd Serono

4 of 6
Drug Name	Clomid
PubMed Health	Clomiphene (By mouth)
Drug Classes	Endocrine-Metabolic Agent, Female Reproductive Agent
Drug Label	Clomiphene 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 Ingredient	Clomiphene citrate
Dosage Form	Tablet
Route	Oral
Strength	50mg
Market Status	Prescription
Company	Sanofi Aventis Us

5 of 6
Drug Name	Clomiphene citrate
PubMed Health	Clomiphene (By mouth)
Drug Classes	Endocrine-Metabolic Agent, Female Reproductive Agent
Drug Label	ClomiPHENE 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 Ingredient	Clomiphene citrate
Dosage Form	Tablet
Route	Oral
Strength	50mg
Market Status	Prescription
Company	Par Pharm

6 of 6
Drug Name	Serophene
Active Ingredient	Clomiphene citrate
Dosage Form	Tablet
Route	Oral
Strength	50mg
Market Status	Prescription
Company	Emd 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]