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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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MAHARASHTRA","supplier":"ASPEN API","supplierCountry":"NETHERLANDS","foreign_port":"AMSTERDAM, SCHIPHOL","customer":"GLENMARK PHARMACEUTICALS","customerCountry":"INDIA","quantity":"3.79","actualQuantity":"3.786","unit":"KGS","unitRateFc":"6000","totalValueFC":"24892.7","currency":"EUR","unitRateINR":"546000","date":"16-May-2024","totalValueINR":"2067156","totalValueInUsd":"24892.7","indian_port":"Bombay Air","hs_no":"29372300","bill_no":"3516467","productDescription":"API","marketType":"REGULATED MARKET","country":"NETHERLANDS","selfForZScoreResived":"Micronized","supplierPort":"AMSTERDAM, SCHIPHOL","supplierAddress":"KLOOSTERSTRAAT 6,5349 AB OSS.SDNFSDNF NETHERLANDS","customerAddress":"B\/2 MAHALAXMI CHAMBERS"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1715797800,"product":"NORETHINDRONE ACETATE (MICRONIZED) USP (BATCH NO. : L00049439)","address":"B\/2 MAHALAXMI CHAMBERS","city":"MUMBAI. 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MAHARASHTRA","supplier":"ASPEN API","supplierCountry":"NETHERLANDS","foreign_port":"AMSTERDAM, SCHIPHOL","customer":"GLENMARK PHARMACEUTICALS","customerCountry":"INDIA","quantity":"2.46","actualQuantity":"2.46","unit":"KGS","unitRateFc":"6000","totalValueFC":"16209.9","currency":"EUR","unitRateINR":"547200","date":"25-Jun-2024","totalValueINR":"1346112","totalValueInUsd":"16209.9","indian_port":"Bombay Air","hs_no":"29372300","bill_no":"4177959","productDescription":"API","marketType":"REGULATED MARKET","country":"NETHERLANDS","selfForZScoreResived":"Micronized","supplierPort":"AMSTERDAM, SCHIPHOL","supplierAddress":"KLOOSTERSTRAAT 6,5349 AB OSS.SDNFSDNF NETHERLANDS","customerAddress":"B\/2 MAHALAXMI CHAMBERS"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1719253800,"product":"NORETHINDRONE ACETATE (MICRONIZED) USP (BATCH NO. : L00049439)","address":"B\/2 MAHALAXMI CHAMBERS","city":"MUMBAI. 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04-Jan-2021
06-Jul-2024
KGS
overview
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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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Controlled & Modified Release

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Taste Masking

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Emulsifying Agents

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API Stability Enhancers

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Surfactant & Foaming Agents

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