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    [6-Hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophen-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone Hydrochloride

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    2D Structure
    Also known as: 82640-04-8, Raloxifene hcl, Evista, Keoxifene hydrochloride, Keoxifene, Optruma
    Molecular Formula
    C28H28ClNO4S
    Molecular Weight
    510.0  g/mol
    InChI Key
    BKXVVCILCIUCLG-UHFFFAOYSA-N
    FDA UNII
    4F86W47BR6
    A second generation selective estrogen receptor modulator (SERM) used to prevent osteoporosis in postmenopausal women. It has estrogen agonist effects on bone and cholesterol metabolism but behaves as a complete estrogen antagonist on mammary gland and uterine tissue.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [6-hydroxy-2-(4-hydroxyphenyl)-1-benzothiophen-3-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone;hydrochloride
    2.1.2 InChI
    InChI=1S/C28H27NO4S.ClH/c30-21-8-4-20(5-9-21)28-26(24-13-10-22(31)18-25(24)34-28)27(32)19-6-11-23(12-7-19)33-17-16-29-14-2-1-3-15-29;/h4-13,18,30-31H,1-3,14-17H2;1H
    2.1.3 InChI Key
    BKXVVCILCIUCLG-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1CCN(CC1)CCOC2=CC=C(C=C2)C(=O)C3=C(SC4=C3C=CC(=C4)O)C5=CC=C(C=C5)O.Cl
    2.2 Other Identifiers
    2.2.1 UNII
    4F86W47BR6
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Evista

    2. Keoxifene

    3. Keoxifene Hydrochloride

    4. Ly 139481

    5. Ly 156758

    6. Ly-139481

    7. Ly-156758

    8. Ly139481

    9. Ly156758

    10. Raloxifene

    11. Raloxifene Hcl

    2.3.2 Depositor-Supplied Synonyms

    1. 82640-04-8

    2. Raloxifene Hcl

    3. Evista

    4. Keoxifene Hydrochloride

    5. Keoxifene

    6. Optruma

    7. Raloxifene Teva

    8. (6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophen-3-yl)(4-(2-(piperidin-1-yl)ethoxy)phenyl)methanone Hydrochloride

    9. Raloxifene (hydrochloride)

    10. Ly 156758

    11. Ly156758

    12. Ly-156758

    13. Nsc-706725

    14. 2-(4-hydroxyphenyl)-3-({4-[2-(piperidin-1-yl)ethoxy]phenyl}carbonyl)-1-benzothiophen-6-ol Hydrochloride

    15. Chebi:50740

    16. Evista (raloxifene Hydrochloride)

    17. 4f86w47br6

    18. 6-hydroxy-2-(p-hydroxyphenyl)benzo(b)thien-3-yl-p-(2-piperidinoethoxy)phenyl Ketone, Hydrochloride

    19. Dsstox_cid_14181

    20. Dsstox_rid_79119

    21. Dsstox_gsid_34181

    22. [6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone Hydrochloride

    23. [6-hydroxy-2-(4-hydroxyphenyl)-1-benzothiophen-3-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone;hydrochloride

    24. Smr000058508

    25. Raloxifene Hydrochloride [usan]

    26. Ncgc00015889-05

    27. Cas-82640-04-8

    28. C28h27no4s.hcl

    29. Loxifen

    30. Unii-4f86w47br6

    31. Sr-01000076102

    32. Cdt-raloxifene

    33. Raloxifene-d4 Hcl

    34. Raloxifene Cloridrato

    35. Evista (tn)

    36. Mfcd01938233

    37. Prestwick_1035

    38. Raloxifene Hydrochloride [usan:usp]

    39. Methanone, Hydrochloride

    40. Cloridrato De Raloxifeno

    41. Clorhidrato De Raloxifeno

    42. Chlorhydrate De Raloxifene

    43. Ly139481 Hydrochloride

    44. Ly156758 Hydrochloride

    45. Chembl1116

    46. Schembl19077

    47. Mls000859902

    48. Mls001332533

    49. Mls001332534

    50. Mls002222293

    51. Raloxifene Hydrochloride, Solid

    52. Evista, Raloxifene Hydrochloride

    53. Raloxifene Hydrochloride- Bio-x

    54. Dtxsid1034181

    55. Ly156758 (keoxifene) Hcl

    56. Ly-139481 Hcl

    57. Hms1570n05

    58. Pharmakon1600-01505622

    59. Amy23426

    60. Bcp05713

    61. Raloxifene Hydrochloride (jan/usp)

    62. Tox21_110255

    63. Tox21_302369

    64. Tox21_501051

    65. Hy-13738a

    66. Nsc706725

    67. Nsc759285

    68. Raloxifene Hydrochloride [mi]

    69. S1227

    70. Raloxifene Hydrochloride [jan]

    71. Akos008131940

    72. Tox21_110255_1

    73. Ac-8390

    74. Ccg-213497

    75. Cs-1775

    76. Ds-2162

    77. Ks-1102

    78. Lp01051

    79. Nc00665

    80. Nsc 706725

    81. Nsc 759285

    82. Nsc-759285

    83. Raloxifene Hydrochloride [mart.]

    84. Raloxifene Hydrochloride [vandf]

    85. Ncgc00015889-03

    86. Ncgc00015889-11

    87. Ncgc00092353-01

    88. Ncgc00092353-03

    89. Ncgc00094334-01

    90. Ncgc00094334-02

    91. Ncgc00255153-01

    92. Ncgc00261736-01

    93. Raloxifene Hydrochloride [usp-rs]

    94. Raloxifene Hydrochloride [who-dd]

    95. Br164310

    96. Methanone, (6-hydroxy-2-(4-hydroxyphenyl)benzo(b)thien-3-yl)(4-(2-(1-piperidinyl)ethoxy)phenyl)-, Hydrochloride

    97. Methanone, [6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]-,hydrochloride (1:1)

    98. Raloxifene Hydrochloride [ema Epar]

    99. Eu-0101051

    100. Ft-0630912

    101. R0109

    102. Sw197106-5

    103. En300-52517

    104. Raloxifene Hydrochloride [orange Book]

    105. D02217

    106. R 1402

    107. Raloxifene Hydrochloride [ep Monograph]

    108. Raloxifene Hydrochloride [usp Impurity]

    109. Raloxifene Hydrochloride [usp Monograph]

    110. 640r048

    111. A840401

    112. Q-201656

    113. Sr-01000076102-2

    114. Sr-01000076102-9

    115. Q27122215

    116. (6-oxo-1,6-dihydro-pyridazin-3-yloxy)-aceticacid

    117. Raloxifene Hydrochloride, European Pharmacopoeia (ep) Reference Standard

    118. Raloxifene Hydrochloride, Pharmaceutical Secondary Standard; Certified Reference Material

    119. Raloxifene Hydrochloride, United States Pharmacopeia (usp) Reference Standard

    120. (6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophen-3-yl)-(4-(2-(piperidin-1-yl)ethoxy)phenyl)methanone Hydrochloride

    121. (6-oh-2-(4-oh-ph)benzo[b]thiophen-3-yl)(4-(2-(piperidin-1-yl)ethoxy)ph)methanone Hydrochloride

    122. [6-hydroxy-2-(4-hydroxyphenyl)-1-benzothien-3-yl][4-(2-piperidin-1-ylethoxy)phenyl]methanone Hydrochloride

    123. [6-hydroxy-2-(4-hydroxyphenyl)-benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]-methanone Hydrochloride

    124. [6-hydroxy-2-(4-hydroxyphenyl)benzo [b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]-methanone Hydrochloride

    125. [6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]-methanone Hydrochloride

    126. [6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]-methanone, Monohydrochloride

    127. [6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophen-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone Hydrochloride

    128. [6-hydroxy-2[4-hydroxyphenyl)benzo [b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone Hydrochloride

    129. [6-hydroxy-2[4-hydroxyphenyl)benzo [b]thien3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone Hydrochloride

    130. [6-hydroxy-2[4-hydroxyphenyl)benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone Hydrochloride

    131. 1-[2-(4-{[6-hydroxy-2-(4-hydroxyphenyl)-1-benzothiophen-3-yl]carbonyl}phenoxy)ethyl]piperidinium Chloride

    132. 6-hydroxy-2-(4-hydroxyphenyl)-3-[ 4-(2-piperidinoethoxy)benzoyl]benzo[b]thiophene, Hydrochloride

    133. 6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]-benzo[b]-thiophene Hydrochloride

    134. 6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]-benzo[b]thiophene Hydrochloride

    135. 6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thien-3-yl 4-[2-(1-piperidinyl)ethoxy]phenyl Methanone Hydrochloride

    136. 6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophen-3-yl 4-[2-(1-piperidinyl)ethoxy]phenyl Ketone Hydrochloride

    137. 6-hydroxy-2-(p-hydroxyphenyl)benzo(.beta.)thien-3-yl-p-(2-piperidinoethoxy)phenyl Ketone, Hydrochloride

    138. Methanone, (6-hydroxy-2-(4-hydroxyphenyl)benzo(.beta.)thien-3-yl)(4-(2-(1-piperidinyl)ethoxy)phenyl)-, Hydrochloride

    139. Methanone, [6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]-, Hydrochloride (1:1)

    140. Raloxifene Hydrochloride For Peak Identification, European Pharmacopoeia (ep) Reference Standard

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 510.0 g/mol
    Molecular Formula C28H28ClNO4S
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count7
    Exact Mass509.1427572 g/mol
    Monoisotopic Mass509.1427572 g/mol
    Topological Polar Surface Area98.2 Ų
    Heavy Atom Count35
    Formal Charge0
    Complexity655
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameEvista
    PubMed HealthRaloxifene (By mouth)
    Drug ClassesAntineoplastic Agent, Endocrine-Metabolic Agent
    Drug LabelEVISTA (raloxifene hydrochloride) is an estrogen agonist/antagonist, commonly referred to as a selective estrogen receptor modulator (SERM) that belongs to the benzothiophene class of compounds. The chemical structure is:The chemical designation is m...
    Active IngredientRaloxifene hydrochloride
    Dosage FormTablet
    Routeoral; Oral
    Strength60mg
    Market StatusPrescription
    CompanyLilly

    2 of 4  
    Drug NameRaloxifene hydrochloride
    Drug LabelEVISTA (raloxifene hydrochloride) is an estrogen agonist/antagonist, commonly referred to as a selective estrogen receptor modulator (SERM) that belongs to the benzothiophene class of compounds. The chemical structure is:The chemical designation is m...
    Active IngredientRaloxifene hydrochloride
    Dosage FormTablet
    Routeoral; Oral
    Strength60mg
    Market StatusTentative Approval; Prescription
    CompanyTeva Pharms Usa; Invagen Pharms; Watson Labs

    3 of 4  
    Drug NameEvista
    PubMed HealthRaloxifene (By mouth)
    Drug ClassesAntineoplastic Agent, Endocrine-Metabolic Agent
    Drug LabelEVISTA (raloxifene hydrochloride) is an estrogen agonist/antagonist, commonly referred to as a selective estrogen receptor modulator (SERM) that belongs to the benzothiophene class of compounds. The chemical structure is:The chemical designation is m...
    Active IngredientRaloxifene hydrochloride
    Dosage FormTablet
    Routeoral; Oral
    Strength60mg
    Market StatusPrescription
    CompanyLilly

    4 of 4  
    Drug NameRaloxifene hydrochloride
    Drug LabelEVISTA (raloxifene hydrochloride) is an estrogen agonist/antagonist, commonly referred to as a selective estrogen receptor modulator (SERM) that belongs to the benzothiophene class of compounds. The chemical structure is:The chemical designation is m...
    Active IngredientRaloxifene hydrochloride
    Dosage FormTablet
    Routeoral; Oral
    Strength60mg
    Market StatusTentative Approval; Prescription
    CompanyTeva Pharms Usa; Invagen Pharms; Watson Labs

    4.2 Drug Indication

    Optruma is indicated for the treatment and prevention of osteoporosis in post-menopausal women. A significant reduction in the incidence of vertebral, but not hip fractures has been demonstrated. When determining the choice of Optruma or other therapies, including oestrogens, for an individual postmenopausal woman, consideration should be given to menopausal symptoms, effects on uterine and breast tissues, and cardiovascular risks and benefits (see section 5. 1).

    Evista is indicated for the treatment and prevention of osteoporosis in post-menopausal women. A significant reduction in the incidence of vertebral, but not hip fractures has been demonstrated. When determining the choice of Evista or other therapies, including oestrogens, for an individual postmenopausal woman, consideration should be given to menopausal symptoms, effects on uterine and breast tissues, and cardiovascular risks and benefits.

    Raloxifene is indicated for the treatment and prevention of osteoporosis in postmenopausal women. A significant reduction in the incidence of vertebral, but not hip fractures has been demonstrated.

    When determining the choice of raloxifene or other therapies, including oestrogens, for an individual postmenopausal woman, consideration should be given to menopausal symptoms, effects on uterine and breast tissues, and cardiovascular risks and benefits.

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    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.)

    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.)

    Estrogen Antagonists

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

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Selective Estrogen Receptor Modulators [MoA]; Estrogen Agonist/Antagonist [EPC]
    5.3 ATC Code

    G03XC01

    G03XC01

    G03XC01