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    Clomiphene Citrate

    ACTIVE PHARMA INGREDIENTS

    DEVELOPMENTS

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    2D Structure
    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

    2D Structure

    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]