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    Chemistry

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    Also known as: Norethisterone acetate, 19-norethindrone acetate, 51-98-9, Aygestin, Norlutin acetate, Orlutate
    Molecular Formula
    C22H28O3
    Molecular Weight
    340.5  g/mol
    InChI Key
    IMONTRJLAWHYGT-ZCPXKWAGSA-N
    FDA UNII
    9S44LIC7OJ
    Norethisterone Acetate
    Acetate ester of norethindrone that is used as a long-term contraceptive (CONTRACEPTIVE AGENTS).
    1 2D Structure

    Norethisterone Acetate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [(8R,9S,10R,13S,14S,17R)-17-ethynyl-13-methyl-3-oxo-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate
    2.1.2 InChI
    InChI=1S/C22H28O3/c1-4-22(25-14(2)23)12-10-20-19-7-5-15-13-16(24)6-8-17(15)18(19)9-11-21(20,22)3/h1,13,17-20H,5-12H2,2-3H3/t17-,18+,19+,20-,21-,22-/m0/s1
    2.1.3 InChI Key
    IMONTRJLAWHYGT-ZCPXKWAGSA-N
    2.1.4 Canonical SMILES
    CC(=O)OC1(CCC2C1(CCC3C2CCC4=CC(=O)CCC34)C)C#C
    2.1.5 Isomeric SMILES
    CC(=O)O[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@H]34)C)C#C
    2.2 Other Identifiers
    2.2.1 UNII
    9S44LIC7OJ
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Aygestin

    2. Estr-4-en-3-one, 17-(acetyloxy)-17-ethynyl-, (17beta)-

    3. Norethindrone Acetate, (17alpha)-(+-)-isomer

    4. Norethindrone Acetate, (17alpha)-isomer

    5. Norethisterone Acetate

    6. Norlutate

    2.3.2 Depositor-Supplied Synonyms

    1. Norethisterone Acetate

    2. 19-norethindrone Acetate

    3. 51-98-9

    4. Aygestin

    5. Norlutin Acetate

    6. Orlutate

    7. Norethisteron Acetate

    8. Norlutate

    9. Enta

    10. 19-norethisterone Acetate

    11. Primolut-nor

    12. Norethindrone 17-acetate

    13. Norethysterone Acetate

    14. 19-norethynyltestosterone Acetate

    15. Norethynyltestosterone Acetate

    16. (17-alpha)-norethindrone Acetate

    17. 17alpha-ethynyl-19-nortestosterone Acetate

    18. Norethindrone Acetate [usp]

    19. Sh 420

    20. Milligynon

    21. Miniphase

    22. Progylut

    23. Norethynyltestosterone

    24. Milli-anovlar

    25. Norlutin A

    26. Norlutine Acetate

    27. 17-alpha-ethinyl-19-nortestosterone Acetate

    28. 17-alpha-ethynyl-19-nortestosterone Acetate

    29. 17-hydroxy-19-nor-17alpha-pregn-4-en-20-yn-3-one Acetate

    30. Nsc-22844

    31. Norethisterone 17-acetate

    32. 17alpha-ethinyl-19-nortestosterone 17beta-acetate

    33. 17alpha-ethinyl-19-nortestosterone-17beta-acetate

    34. 17alpha-ethynyl-17-hydroxyestr-4-en-3-one Acetate

    35. 9s44lic7oj

    36. 17-alpha-ethinyl-19-nortestosterone-17-beta-acetate

    37. 17-alpha-ethynyl-17-hydroxyestr-4-en-3-one Acetate

    38. 17-acetoxy-19-nor-17alpha-pregn-4-en-20-yn-3-one

    39. 17-acetoxy-19-nor-17-alpha-pregn-4-en-20-yn-3-one

    40. 17alpha-ethynyl-17beta-acetoxy-19-norandrost-4-en-3-one

    41. 17beta-acetoxy-19-nor-17alpha-pregn-4-en-20-yn-3-one

    42. Chebi:7628

    43. [(8r,9s,10r,13s,14s,17r)-17-ethynyl-13-methyl-3-oxo-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] Acetate

    44. 17-hydroxy-19-nor-17-alpha-pregn-4-en-20-yn-3-one Acetate

    45. 17beta-hydroxy-19-nor-17alpha-pregn-4-en-20-yn-3-one Acetate

    46. 17-acetyloxy(17-alpha)-19-norpregn-4-estren-17-beta-ol-acetate-3-one

    47. Sh-420

    48. Gestakadin

    49. Monogest

    50. 19-nor-17alpha-ethynyltestosterone Acetate

    51. Nsc 22844

    52. 17.alpha.-ethynyl-19-nortestosterone Acetate

    53. Norethindrone Acetate (usp)

    54. Norethisterone Acetate (jan)

    55. Norlutin-a

    56. 17-hydroxy-19-nor-17.alpha.-pregn-4-en-20-yn-3-one Acetate

    57. Norethisterone Acetate [jan]

    58. (17beta)-17-ethynyl-3-oxoestr-4-en-17-yl Acetate

    59. Ccris 485

    60. Ethinyl-nortestosterone Acetate

    61. Einecs 200-132-0

    62. Unii-9s44lic7oj

    63. Brn 2064104

    64. Sh-420c

    65. 19-norpregn-4-en-20-yn-3-one, 17-(acetyloxy)-, (17.alpha.)-

    66. Ncgc00183366-01

    67. Aygestin (tn)

    68. Norethindrone-acetate

    69. Norethisteroni Acetas

    70. 17.alpha.-ethinyl-19-nortestosterone Acetate

    71. 19-nor-17alpha-pregn-4-en-20-yn-3-one, 17-acetoxy-

    72. Estr-4-en-3-one, 17alpha-ethynyl-17-hydroxy-, Acetate

    73. (17-alpha)-17-(acetyloxy)-19-norpregn-4-en-20-yn-3-one

    74. 17-alpha-ethynyl-17-beta-acetoxy-19-norandrost-4-en-3-one

    75. Dsstox_cid_1071

    76. Norethisterone Acetate (norethindrone Acetate)

    77. 17-acetoxy-19-nor-17.alpha.-pregn-4-en-20-yn-3-one

    78. 17.alpha.-ethinyl-19-nortestosterone 17.beta.-acetate

    79. 19-nor-17.alpha.-pregn-4-en-20-yn-3-one, 17-acetoxy-

    80. Dsstox_rid_77006

    81. Dsstox_gsid_23381

    82. Schembl37530

    83. 17.beta.-acetoxy-19-nor-17.alpha.-pregn-4-en-20-yn-3-one

    84. 17-acetyloxy(17.alpha.)-19-norpregn-4-estren-17.beta.-ol-acetate-3-one

    85. 17.beta.-hydroxy-19-nor-17.alpha.-pregn-4-en-20-yn-3-one Acetate

    86. Chembl1201146

    87. Dtxsid4023381

    88. 19-nor-17-alpha-pregn-4-en-20-yn-3-one, 17-acetoxy-

    89. Hms3259a16

    90. Norethindrone Acetate [mi]

    91. 19-nor-17alpha-pregn-4-en-20-yn-3-one, 17-hydroxy-, Acetate

    92. 19-norpregn-4-en-20-yn-3-one, 17-(acetyloxy)-, (17alpha)

    93. Bcp11908

    94. Hy-b1710

    95. Nsc22844

    96. Zinc1849528

    97. Tox21_113371

    98. Mfcd00271615

    99. Norethindrone Acetate [vandf]

    100. S5785

    101. Akos016010517

    102. Norethindrone Acetate [usp-rs]

    103. Norethisterone Acetate [mart.]

    104. Cs-7730

    105. Nc00575

    106. Norethisterone Acetate [who-dd]

    107. Norethisterone Acetate [who-ip]

    108. Cas-51-98-9

    109. Ncgc00159500-02

    110. Ncgc00183366-07

    111. (1s,11s,15s,2r,10r,14r)-14-ethynyl-15-methyl-5-oxotetracyclo[8.7.0.0<2,7>.0<11 ,15>]heptadec-6-en-14-yl Acetate

    112. As-13383

    113. Cpd001906776

    114. Norethindrone Acetate [orange Book]

    115. 17a-ethynyl-19-nortestosterone 17b-acetate

    116. Femhrt Component Norethindrone Acetate

    117. N0450

    118. Norethindrone Acetate [usp Monograph]

    119. Norethisterone Acetate [ep Monograph]

    120. Norethisteroni Acetas [who-ip Latin]

    121. En300-49856

    122. Oriahnn Component Norethindrone Acetate

    123. Activella Component Norethindrone Acetate

    124. C08152

    125. D00953

    126. Myfembree Component Norethindrone Acetate

    127. T72561

    128. Combipatch Component Norethindrone Acetate

    129. Norethindrone Acetate Component Of Femhrt

    130. Norethindrone Acetate Component Of Oriahnn

    131. Estrostep Fe Component Norethindrone Acetate

    132. Norethindrone Acetate Component Of Activella

    133. Norethindrone Acetate Component Of Myfembree

    134. Norethindrone Acetate Component Of Combipatch

    135. Tri-legest Fe Component Norethindrone Acetate

    136. 17.alpha.-ethynyl-17-hydroxyestr-4-en-3-one Acetate

    137. 19-nor-17.alpha.-pregn-4-en-20-yn-3-one, Acetate

    138. Brd-k96037667-001-01-4

    139. Lo Loestrin Fe Component Norethindrone Acetate

    140. Norethindrone Acetate Component Of Estrostep Fe

    141. Q47495694

    142. 17.alpha.-ethinyl-19-nortestosterone-17.beta.-acetate

    143. Norethindrone Acetate Component Of Lo Loestrin Fe

    144. Norethindrone Acetate Component Of Tri-legest Fe

    145. Wln: L E5 B666 Ov Mutj E Fov1 F1uu1 -b&ef

    146. (17alpha)-3-oxo-19-norpregn-4-en-20-yn-17-yl Acetate

    147. 17.alpha.-ethynyl-17.beta.-acetoxy-19-norandrost-4-en-3-one

    148. 19-norethindrone Acetate, Vetranal(tm), Analytical Standard

    149. Norethindrone Acetate, United States Pharmacopeia (usp) Reference Standard

    150. Norethisterone Acetate, European Pharmacopoeia (ep) Reference Standard

    151. Norethisterone Acetate For System Suitability, European Pharmacopoeia (ep) Reference Standard

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 340.5 g/mol
    Molecular Formula C22H28O3
    XLogP33.5
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count3
    Exact Mass340.20384475 g/mol
    Monoisotopic Mass340.20384475 g/mol
    Topological Polar Surface Area43.4 Ų
    Heavy Atom Count25
    Formal Charge0
    Complexity695
    Isotope Atom Count0
    Defined Atom Stereocenter Count6
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameNorethindrone acetate
    PubMed HealthNorethindrone Acetate/Ethinyl Estradiol/Ferrous Fumarate (By mouth)
    Drug LabelAYGESTIN (norethindrone acetate tablets, USP) - 5 mg oral tablets.AYGESTIN (norethindrone acetate tablets, USP), (17-hydroxy-19-nor-17-pregn-4-en-20-yn-3-one acetate), a synthetic, orally active progestin, is the acetic acid ester of norethindr...
    Active IngredientNorethindrone acetate
    Dosage FormTablet
    RouteOral
    Strength5mg
    Market StatusPrescription
    CompanyAmneal Pharms; Glenmark Generics; Barr

    2 of 2  
    Drug NameNorethindrone acetate
    PubMed HealthNorethindrone Acetate/Ethinyl Estradiol/Ferrous Fumarate (By mouth)
    Drug LabelAYGESTIN (norethindrone acetate tablets, USP) - 5 mg oral tablets.AYGESTIN (norethindrone acetate tablets, USP), (17-hydroxy-19-nor-17-pregn-4-en-20-yn-3-one acetate), a synthetic, orally active progestin, is the acetic acid ester of norethindr...
    Active IngredientNorethindrone acetate
    Dosage FormTablet
    RouteOral
    Strength5mg
    Market StatusPrescription
    CompanyAmneal Pharms; Glenmark Generics; Barr

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Contraceptive Agents, Hormonal

    Contraceptive agents that act on the ENDOCRINE SYSTEM. (See all compounds classified as Contraceptive Agents, Hormonal.)

    Contraceptive Agents, Female

    Chemical substances or agents with contraceptive activity in females. Use for female contraceptive agents in general or for which there is no specific heading. (See all compounds classified as Contraceptive Agents, Female.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Progestin [EPC]; Progesterone Congeners [CS]

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    04-Jan-2021
    01-Oct-2024
    KGS
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    Average Price (USD/KGS)

    Number of Transactions

    Total Quantity (KGS)

    Total Value (USD)

    Quantity (KGS) & Unit rate (USD/KGS) over time

    API Imports and Exports

    Importing Country Total Quantity
    (KGS)    		 Average Price
    (USD/KGS)    		 Number of Transactions

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    DRUG PRODUCT COMPOSITIONS

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    DOSAGE - TABLET;ORAL-28 - 0.02MG;1MG

    USFDA APPLICATION NUMBER - 17354

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    DOSAGE - TABLET;ORAL-21 - 0.03MG;1.5MG

    USFDA APPLICATION NUMBER - 17355

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    DOSAGE - TABLET;ORAL-21 - 0.03MG;1.5MG

    USFDA APPLICATION NUMBER - 17875

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    DOSAGE - TABLET;ORAL-21 - 0.02MG;1MG **Federa...DOSAGE - TABLET;ORAL-21 - 0.02MG;1MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 17876

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    DOSAGE - TABLET;ORAL-21 - 0.02MG,0.03MG,0.035...DOSAGE - TABLET;ORAL-21 - 0.02MG,0.03MG,0.035MG;1MG,1MG,1MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 20130

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    DOSAGE - TABLET;ORAL - 0.02MG;1MG **Federal R...DOSAGE - TABLET;ORAL - 0.02MG;1MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 203667

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    DOSAGE - INJECTABLE, TABLET;INTRAMUSCULAR, OR...DOSAGE - INJECTABLE, TABLET;INTRAMUSCULAR, ORAL - 11.25MG/VIAL,N/A;N/A,5MG

    USFDA APPLICATION NUMBER - 203696

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    DOSAGE - INJECTABLE, TABLET;INTRAMUSCULAR, OR...DOSAGE - INJECTABLE, TABLET;INTRAMUSCULAR, ORAL - 3.75MG/VIAL,N/A;N/A,5MG

    USFDA APPLICATION NUMBER - 203696

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    DOSAGE - CAPSULE;ORAL - 0.02MG;1MG

    USFDA APPLICATION NUMBER - 204426

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    DOSAGE - TABLET, CHEWABLE, TABLET;ORAL - 0.01...DOSAGE - TABLET, CHEWABLE, TABLET;ORAL - 0.01MG,0.01MG,N/A;1MG,N/A,N/A

    USFDA APPLICATION NUMBER - 204654

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    DOSAGE - FILM, EXTENDED RELEASE;TRANSDERMAL -...DOSAGE - FILM, EXTENDED RELEASE;TRANSDERMAL - 0.05MG/24HR;0.14MG/24HR

    USFDA APPLICATION NUMBER - 20870

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    DOSAGE - FILM, EXTENDED RELEASE;TRANSDERMAL -...DOSAGE - FILM, EXTENDED RELEASE;TRANSDERMAL - 0.05MG/24HR;0.25MG/24HR

    USFDA APPLICATION NUMBER - 20870

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    DOSAGE - TABLET;ORAL - 0.5MG;0.1MG **Federal ...DOSAGE - TABLET;ORAL - 0.5MG;0.1MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 20907

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    DOSAGE - TABLET;ORAL - 1MG;0.5MG

    USFDA APPLICATION NUMBER - 20907

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    DOSAGE - TABLET;ORAL - 0.0025MG;0.5MG

    USFDA APPLICATION NUMBER - 21065

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    DOSAGE - TABLET;ORAL - 0.005MG;1MG **Federal ...DOSAGE - TABLET;ORAL - 0.005MG;1MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 21065

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    DOSAGE - TABLET;ORAL - 0.02MG;1MG **Federal R...DOSAGE - TABLET;ORAL - 0.02MG;1MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 21871

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    DOSAGE - TABLET;ORAL - 0.01MG,0.01MG;1MG,N/A

    USFDA APPLICATION NUMBER - 22501

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