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    Chemistry

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    Also known as: Norethisterone, 68-22-4, Micronor, Norethisteron, 19-norethisterone, Norlutin
    Molecular Formula
    C20H26O2
    Molecular Weight
    298.4  g/mol
    InChI Key
    VIKNJXKGJWUCNN-XGXHKTLJSA-N
    FDA UNII
    T18F433X4S
    Norethisterone
    A synthetic progestational hormone with actions similar to those of PROGESTERONE but functioning as a more potent inhibitor of ovulation. It has weak estrogenic and androgenic properties. The hormone has been used in treating amenorrhea, functional uterine bleeding, endometriosis, and for contraception.
    Norethindrone is a Progestin.
    1 2D Structure

    Norethisterone

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (8R,9S,10R,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
    2.1.2 InChI
    InChI=1S/C20H26O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,12,15-18,22H,4-11H2,2H3/t15-,16+,17+,18-,19-,20-/m0/s1
    2.1.3 InChI Key
    VIKNJXKGJWUCNN-XGXHKTLJSA-N
    2.1.4 Canonical SMILES
    CC12CCC3C(C1CCC2(C#C)O)CCC4=CC(=O)CCC34
    2.1.5 Isomeric SMILES
    C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=CC(=O)CC[C@H]34
    2.2 Other Identifiers
    2.2.1 UNII
    T18F433X4S
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 19-norpregn-4-en-20-yn-3-one, 17-hydroxy-, (17alpha)-

    2. Conceplan

    3. Ethinylnortestosterone

    4. Micronor

    5. Monogest

    6. Nor Qd

    7. Nor-qd

    8. Norcolut

    9. Norcolute

    10. Norethindrone, (1 Beta)-isomer

    11. Norethisterone

    12. Norlutin

    13. Norpregneninolone

    14. Norqd

    2.3.2 Depositor-Supplied Synonyms

    1. Norethisterone

    2. 68-22-4

    3. Micronor

    4. Norethisteron

    5. 19-norethisterone

    6. Norlutin

    7. Anovule

    8. Gestest

    9. Norcolut

    10. Noriday

    11. Utovlan

    12. Camila

    13. Primolut-n

    14. Norethynodrone

    15. Conludag

    16. Micronovum

    17. Norluten

    18. Triella

    19. Mini-pill

    20. Nor-qd

    21. Mini-pe

    22. Noresthisterone

    23. Norethisteronum

    24. Conludaf

    25. Micronett

    26. Noralutin

    27. Norethyndron

    28. Norgestin

    29. Norluton

    30. Proluteasi

    31. Norfor

    32. Utovlar

    33. Norpregneninlone

    34. 19-nor-ethindrone

    35. Ethinylnortestosterone

    36. Noretisterona

    37. 17alpha-ethynyl-19-nortestosterone

    38. Ethynylnortestosterone

    39. 19-nor-17alpha-ethynyltestosterone

    40. Menzol

    41. 17alpha-ethinyl-19-nortestosterone

    42. Anhydrohydroxynorprogesterone

    43. Minovlar

    44. Nor-q.d.

    45. 19-norethinyltestosterone

    46. Norpregneninolone

    47. Ethinyl-19-nortestosterone

    48. Normapause

    49. 17alpha-ethynyl-4-estren-17-ol-3-one

    50. 17-alpha-ethynyl-19-nortestosterone

    51. 19-nor-17-alpha-ethynyltestosterone

    52. 19-norethindrone

    53. 19-nor-17-ethinyltestosterone

    54. 17alpha-ethinylestra-4-en-17beta-ol-3-one

    55. 17beta-hydroxy-19-norpregn-4-en-20-yn-3-one

    56. Nsc-9564

    57. 17-alpha-ethynyl-4-estren-17-ol-3-one

    58. 19-nor-17alpha-ethynyl-17beta-hydroxy-4-androsten-3-one

    59. 17alpha-ethynyl-17-hydroxy-4-estren-3-one

    60. Activella

    61. 19-nor-17alpha-ethynylandrosten-17beta-ol-3-one

    62. 4-estren-17alpha-ethynyl-17beta-ol-3-one

    63. 17alpha-ethynyl-19-norandrost-4-en-17beta-ol-3-one

    64. 17-hydroxy-19-nor-17alpha-pregn-4-en-20-yn-3-one

    65. 17-alpha-ethynyl-17-hydroxy-4-estren-3-one

    66. 17alpha-ethynyl-17beta-hydroxy-19-norandrost-4-en-3-one

    67. 17-beta-hydroxy-19-norpregn-4-en-20-yn-3-one

    68. Norethindrone (usp)

    69. Norethindrone [usp]

    70. Primolut N

    71. Norethisterone [inn]

    72. 19-nor-17-alpha-ethynylandrosten-17-beta-ol-3-one

    73. 17-ethynyl-17beta-hydroxyestr-4-en-3-one

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

    75. 17-hydroxy-19-nor-17-alpha-pregn-4-en-20-yn-3-one

    76. Anovulatorio

    77. Ciclovulan

    78. Microneth

    79. Norethadrone

    80. Norethynodron

    81. 19-nor-17-alpha-ethynyl-17-beta-hydroxy-4-androsten-3-one

    82. Estrinor

    83. Gencept

    84. Norethin

    85. Synphase

    86. Genora

    87. Milli

    88. Nelova

    89. Nodiol

    90. Noraethisteronum

    91. Norpregneninotone

    92. Chembl1162

    93. Combipatch

    94. Norcept-e

    95. 17alpha-ethynyl-19-nor-4-androsten-17beta-ol-3-one

    96. Norethindrone (norethisterone)

    97. Synphasic 28

    98. (17-alpha)-17-hydroxy-19-norpregn-4-en-20-yn-3-one

    99. Brevinor 21

    100. Brevinor 28

    101. Chebi:7627

    102. Trinovum 21

    103. Noriday 28

    104. Errin

    105. Jenest-28

    106. Ethynylmortestosterone

    107. Brevinor-1 21

    108. Brevinor-1 28

    109. T18f433x4s

    110. Tri-norinyl

    111. Ovysmen 1 35

    112. Noretisterone [dcit]

    113. Ortho-novum 1 35

    114. Ortho-novum 1 50

    115. Sc 4640

    116. Ortho-novum 7 7 7

    117. Ovysmen 0.5 35

    118. Ortho 1 35

    119. (8r,9s,10r,13s,14s,17r)-17-ethynyl-17-hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one

    120. Sc-4640

    121. Ortho 7 7 7

    122. Noretisterone

    123. 19-nortestosterone, 17-ethynyl-

    124. Norethisteronum [inn-latin]

    125. Noretisterona [inn-spanish]

    126. Dsstox_cid_3380

    127. Dsstox_rid_77005

    128. 17alpha-hydroxy-19-norpregn-4-en-20-yn-3-one

    129. Dsstox_gsid_23380

    130. Nora-be

    131. Norethisterone [progestins]

    132. (14beta,17alpha)-17-ethynyl-17-hydroxyestr-4-en-3-one

    133. Norethindirone

    134. 17-ethinyl-19-nortestosterone

    135. (17alpha)-17-ethynyl-17-hydroxyestra-4,8(14),9-trien-3-one

    136. 19-nor-17alpa-ethynyltestosterone

    137. Micronor (tn)

    138. (8r,9s,10r,13s,14s,17r)-17-ethynyl-17-hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3h-cyclopenta[a]phenanthren-3-one

    139. Smr000499579

    140. Ccris 484

    141. Norethisterone (norethindrone)

    142. Primolut-n (tn)

    143. Camila (tn)

    144. N.e.e.

    145. 19-nor-17-ethinyl Testosterone

    146. Hsdb 3370

    147. 19-nor-ethinyl--4,5-testosterone

    148. Einecs 200-681-6

    149. Brn 1915671

    150. 19-norpregn-4-en-20-yn-3-one, 17-hydroxy-, (17.alpha.)-

    151. Heather Whole

    152. Unii-t18f433x4s

    153. Ai3-26422

    154. 17-alpha-ethinylestra-4-en-17-beta-ol-3-one

    155. Cas-68-22-4

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

    157. Ncgc00094738-01

    158. Ent

    159. Net

    160. Prestwick_646

    161. Calluna Vulgaris Whole

    162. 17-alpha-19-norpregn-4-en-20-yn-3-one, 17-hydroxy-

    163. 17alpha-ethinyl-17beta-hydroxy-delta(sup:4)-estren-3-one

    164. 19-nor-17alpha-pregn-4-en-20-yn-3-one, 17-hydroxy-

    165. 17-alpha-ethinyl-17-beta-hydroxy-delta(sup:4)-estren-3-one

    166. 17-alpha-ethynyl-17-beta-hydroxy-19-norandrost-4-en-3-one

    167. Norethisterone (jp17)

    168. Prestwick0_000253

    169. Prestwick1_000253

    170. Prestwick2_000253

    171. Prestwick3_000253

    172. Norethindrone [mi]

    173. 17-hydroxy-19-nor-17.alpha.-pregn-4-en-20-yn-3-one

    174. Ec 200-681-6

    175. Norethindrone [hsdb]

    176. Norethisterone [jan]

    177. Schembl23390

    178. Bspbio_000066

    179. Levonorgestrel Ep Impurity U

    180. Norethindrone [vandf]

    181. Mls001076679

    182. Mls001163874

    183. Norethisterone / Norethindrone

    184. Spbio_002285

    185. Norethindrone [usp-rs]

    186. Norethisterone [mart.]

    187. Bpbio1_000074

    188. Gtpl2880

    189. 17-ethynyl-19-nortestosterone

    190. Norethisterone [who-dd]

    191. Norethisterone [who-ip]

    192. (17alpha)-17-hydroxy-19-norpregn-4-en-20-yn-3-one

    193. Dtxsid9023380

    194. 17-ethinyl-19-nor-testosterone

    195. 19-nor-17-alpha-pregn-4-en-20-yn-3-one, 17-hydroxy-

    196. Hms1568d08

    197. Hms2090d21

    198. Hms2095d08

    199. Hms2231e18

    200. Hms3259c16

    201. Hms3712d08

    202. Norethindrone [orange Book]

    203. Bcp28306

    204. Hy-b0554

    205. 17alpha-pregn-4-en-20-yn-3-one

    206. Norethindrone [usp Impurity]

    207. Norethisterone [ep Impurity]

    208. Tox21_111322

    209. Tox21_302427

    210. 19-norethindrone, >=98%, Powder

    211. Bdbm50148732

    212. Lmst02030097

    213. Norethindrone [usp Monograph]

    214. S4040

    215. Zinc85205451

    216. Norinyl Component Norethindrone

    217. Vyfemla Component Norethindrone

    218. Akos005267172

    219. Aranelle Component Norethindrone

    220. Brevicon Component Norethindrone

    221. Norethisteronum [who-ip Latin]

    222. Taytulla Component Norethindrone

    223. Tox21_111322_1

    224. Ccg-220253

    225. Db00717

    226. Nc00576

    227. Femcon Fe Component Norethindrone

    228. Ncgc00179669-01

    229. Ncgc00179669-02

    230. Ncgc00179669-04

    231. Ncgc00255187-01

    232. Ac-11100

    233. Ac-33117

    234. As-56451

    235. Cpd000499579

    236. Norethindrone Component Of Aranelle

    237. Norquest Fe Component Norethindrone

    238. 17alpha-ethynyl-17-hydroxyest-4-en-3-one

    239. 17alpha-ethynyl-3-oxo-4-estren-17beta-ol

    240. Norethindrone Component Of Femcon Fe

    241. N0449

    242. Norethindrone Component Of Norquest Fe

    243. 17alpha-ethynyl-17-hydroxy-estr-4-en-3-one

    244. Lo Minastrin Fe Component Norethindrone

    245. Norethisterone 100 Microg/ml In Acetonitrile

    246. C05028

    247. C76161

    248. D00182

    249. Levonorgestrel Impurity U [ep Impurity]

    250. Minastrin 24 Fe Component Norethindrone

    251. 17alpha-ethynyl-17beta-hydroxyestr-4-en-3-one

    252. 17beta-hydroxy-17alpha-ethynylestr-4-en-3-one

    253. 067n596

    254. 17-alpha-ethynyl-17-beta-hydroxy-4-estren-3-one

    255. A836053

    256. Q421352

    257. Sr-01000765382

    258. 17alpha-ethinyl-17alpha-ethinyl-19-nortestosterone

    259. Sr-01000765382-3

    260. W-104686

    261. 13-methyl-17alpha-ethynyl-17-hydroxygon-4-en-3-one

    262. 17-hydroxy-17-alpha-19-norpregn-4-en-20-yn-3-one

    263. 17-hydroxy-19-nor-17alpha-pregn-4-en-20yn-3-one

    264. 19-norethindrone, Vetranal(tm), Analytical Standard

    265. Brd-k92073408-001-03-3

    266. Brd-k92073408-001-16-5

    267. Norethisterone Acetate Impurity A [ep Impurity]

    268. 17-hydroxy-(17alpha)-19-norpregn-4-en-20-yn-3-one

    269. 17-ethynyl-17-hydroxyestr-4-en-3-one (acd/name 4.0)

    270. Norethisterone, British Pharmacopoeia (bp) Reference Standard

    271. Norethisterone, European Pharmacopoeia (ep) Reference Standard

    272. Norethindrone, United States Pharmacopeia (usp) Reference Standard

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

    274. Norethindrone (norethisterone), Pharmaceutical Secondary Standard; Certified Reference Material

    275. Norethisterone; 19-norethisterone; 17?-ethynyl-19-nortestosterone; 17-hydroxy-19-nor-17?-pregn-4-en-20-yn-3-one

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 298.4 g/mol
    Molecular Formula C20H26O2
    XLogP33
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count1
    Exact Mass298.193280068 g/mol
    Monoisotopic Mass298.193280068 g/mol
    Topological Polar Surface Area37.3 Ų
    Heavy Atom Count22
    Formal Charge0
    Complexity594
    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 12  
    Drug NameActivella
    PubMed HealthEstradiol/Norethindrone
    Drug ClassesContraceptive, Estrogen/Progestin Combination, Monophasic Contraceptive Combination
    Active Ingredientnorethindrone acetate; Estradiol
    Dosage FormTablet
    Routeoral; Oral
    Strength0.5mg; 1mg; 1mg/0.5mg; 0.1mg
    Market StatusPrescription
    CompanyAmneal Pharms; Novo Nordisk

    2 of 12  
    Drug NameCamila
    PubMed HealthNorethindrone (By mouth)
    Drug ClassesContraceptive, Contraceptive, Progestin, Endocrine-Metabolic Agent
    Drug LabelEach light pink Camila tablet provides a continuous oral contraceptive regimen of 0.35 mg norethindrone USP daily, and has the following inactive ingredients: corn starch, FD&C red no. 40 aluminum lake, lactose monohydrate, magnesium stearate, povi...
    Active IngredientNorethindrone
    Dosage FormTablet
    RouteOral-28
    Strength0.35mg
    Market StatusPrescription
    CompanyBarr

    3 of 12  
    Drug NameErrin
    PubMed HealthNorethindrone (By mouth)
    Drug ClassesContraceptive, Contraceptive, Progestin, Endocrine-Metabolic Agent
    Active IngredientNorethindrone
    Dosage FormTablet
    RouteOral-28
    Strength0.35mg
    Market StatusPrescription
    CompanyBarr

    4 of 12  
    Drug NameMicronor
    PubMed HealthNorethindrone (By mouth)
    Drug ClassesContraceptive, Contraceptive, Progestin, Endocrine-Metabolic Agent
    Drug LabelEach tablet contains 0.35 mg norethindrone. Inactive ingredients include corn starch, D&C Green No. 5, D&C Yellow No. 10, lactose, magnesium stearate, and povidone....
    Active IngredientNorethindrone
    Dosage FormTablet
    RouteOral-28
    Strength0.35mg
    Market StatusPrescription
    CompanyJanssen Pharms

    5 of 12  
    Drug NameNorethindrone
    Drug LabelEach light pink Camila tablet provides a continuous oral contraceptive regimen of 0.35 mg norethindrone USP daily, and has the following inactive ingredients: corn starch, FD&C red no. 40 aluminum lake, lactose monohydrate, magnesium stearate, povi...
    Active IngredientNorethindrone
    Dosage FormTablet
    RouteOral-28
    Strength0.35mg
    Market StatusPrescription
    CompanyNovast Labs; Lupin; Famy Care; Glenmark Generics; Haupt Pharma

    6 of 12  
    Drug NameNor-qd
    Drug LabelEach yellow Nor-QD tablet provides a continuous oral contraceptive regimen of 0.35 mg norethindrone daily, and the inactive ingredients include D&C Yellow No. 10, FD&C Yellow No. 6, lactose, magnesium stearate, povidone, and starch.The chemical na
    Active IngredientNorethindrone
    Dosage FormTablet
    RouteOral-28
    Strength0.35mg
    Market StatusPrescription
    CompanyWatson Labs (utah)

    7 of 12  
    Drug NameActivella
    PubMed HealthEstradiol/Norethindrone
    Drug ClassesContraceptive, Estrogen/Progestin Combination, Monophasic Contraceptive Combination
    Active Ingredientnorethindrone acetate; Estradiol
    Dosage FormTablet
    Routeoral; Oral
    Strength0.5mg; 1mg; 1mg/0.5mg; 0.1mg
    Market StatusPrescription
    CompanyAmneal Pharms; Novo Nordisk

    8 of 12  
    Drug NameCamila
    PubMed HealthNorethindrone (By mouth)
    Drug ClassesContraceptive, Contraceptive, Progestin, Endocrine-Metabolic Agent
    Drug LabelEach light pink Camila tablet provides a continuous oral contraceptive regimen of 0.35 mg norethindrone USP daily, and has the following inactive ingredients: corn starch, FD&C red no. 40 aluminum lake, lactose monohydrate, magnesium stearate, povi...
    Active IngredientNorethindrone
    Dosage FormTablet
    RouteOral-28
    Strength0.35mg
    Market StatusPrescription
    CompanyBarr

    9 of 12  
    Drug NameErrin
    PubMed HealthNorethindrone (By mouth)
    Drug ClassesContraceptive, Contraceptive, Progestin, Endocrine-Metabolic Agent
    Active IngredientNorethindrone
    Dosage FormTablet
    RouteOral-28
    Strength0.35mg
    Market StatusPrescription
    CompanyBarr

    10 of 12  
    Drug NameMicronor
    PubMed HealthNorethindrone (By mouth)
    Drug ClassesContraceptive, Contraceptive, Progestin, Endocrine-Metabolic Agent
    Drug LabelEach tablet contains 0.35 mg norethindrone. Inactive ingredients include corn starch, D&C Green No. 5, D&C Yellow No. 10, lactose, magnesium stearate, and povidone....
    Active IngredientNorethindrone
    Dosage FormTablet
    RouteOral-28
    Strength0.35mg
    Market StatusPrescription
    CompanyJanssen Pharms

    11 of 12  
    Drug NameNorethindrone
    Drug LabelEach light pink Camila tablet provides a continuous oral contraceptive regimen of 0.35 mg norethindrone USP daily, and has the following inactive ingredients: corn starch, FD&C red no. 40 aluminum lake, lactose monohydrate, magnesium stearate, povi...
    Active IngredientNorethindrone
    Dosage FormTablet
    RouteOral-28
    Strength0.35mg
    Market StatusPrescription
    CompanyNovast Labs; Lupin; Famy Care; Glenmark Generics; Haupt Pharma

    12 of 12  
    Drug NameNor-qd
    Drug LabelEach yellow Nor-QD tablet provides a continuous oral contraceptive regimen of 0.35 mg norethindrone daily, and the inactive ingredients include D&C Yellow No. 10, FD&C Yellow No. 6, lactose, magnesium stearate, povidone, and starch.The chemical na
    Active IngredientNorethindrone
    Dosage FormTablet
    RouteOral-28
    Strength0.35mg
    Market StatusPrescription
    CompanyWatson Labs (utah)

    4.2 Therapeutic Uses

    Contraceptives, Oral, Synthetic; Progestational Hormones, Synthetic

    National Library of Medicine's Medical Subject Headings online file (MeSH, 2009)

    AYGESTIN is indicated for the treatment of secondary amenorrhea, endometriosis, and abnormal uterine bleeding due to hormonal imbalance in the absence of organic pathology, such as submucous fibroids or uterine cancer. AYGESTIN is not intended, recommended or approved to be used with concomitant estrogen therapy in postmenopausal women for endometrial protection. /Included in US product label/

    US Natl Inst Health; DailyMed. Current Medication Information for AYGESTIN (norethindrone acetate) tablet (July 2007). Available from, as of February 14, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=21992

    Oral contraceptives are indicated for the prevention of pregnancy in women who elect to use this product as a method of contraception. /Included in US product label/

    US Natl Inst Health; DailyMed. Current Medication Information for BALZIVA (norethindrone and ethyl estradiol) kit (September 2009). Available from, as of February 28, 2011: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=11472

    Progestin-only oral contraceptives are indicated for the prevention of pregnancy. /Included in US product label/

    US Natl Inst Health; DailyMed. Current Medication Information for CAMILA (norethindrone) tablet (January 2011). Available from, as of February 28, 2011: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=37602

    For more Therapeutic Uses (Complete) data for NORETHINDRONE (6 total), please visit the HSDB record page.

    4.3 Drug Warning

    VET: MARKED RAT, MONKEY, & DOG FETAL MASCULINIZATION HAS BEEN OBSERVED AS IN HUMAN. EXCESSIVE DOSAGE DURING PREGNANCY MAY ALSO CAUSE FETAL DEATH, TERATOGENICITY, & DELAYED PARTURITION.

    Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 394

    Cigarette smoking increases the risk of serious cardiovascular side effects from oral contraceptive use. This risk increases with age and with heavy smoking (15 or more cigarettes per day) and is quite marked in women over 35 years of age. Women who use oral contraceptives should be strongly advised not to smoke.

    US Natl Inst Health; DailyMed. Current Medication Information for BALZIVA (norethindrone and ethyl estradiol) kit (September 2009). Available from, as of February 28, 2011: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=11472

    Norethindrone, like other progestins, may cause breakthrough bleeding, spotting, changes in menstrual flow, amenorrhea, changes in cervical erosion and secretions, edema, weight gain or loss, cholestatic jaundice, allergic rash with or without pruritus, melasma or chloasma, and mental depression.

    American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 3278

    When breakthrough bleeding or irregular vaginal bleeding occurs during norethindrone therapy, nonfunctional causes should be considered. Adequate diagnostic procedures should be performed in patients with undiagnosed vaginal bleeding.

    American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 3278

    For more Drug Warnings (Complete) data for NORETHINDRONE (44 total), please visit the HSDB record page.

    4.4 Minimum/Potential Fatal Human Dose

    3(?). 3= MODERATELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 0.5-5 G/KG, BETWEEN 1 OZ & 1 PINT FOR 70 KG PERSON (150 LB). /NORETHINDRONE WITH MESTRANOL/

    Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-174

    4.5 Drug Indication

    Norethisterone is indicated as an oral contraceptive when given as monotherapy or in combination with an estrogen component, such as [ethinylestradiol] or [estradiol]. In combination with an estrogen component, oral norethisterone is also indicated as a hormone replacement therapy in the treatment of postmenopausal osteoporosis and moderate-to-severe vasomotor symptoms arising from menopause. When applied via transdermal patch, the combination of norethisterone and estradiol is indicated for the treatment of hypoestrogenism, vulvovaginal atrophy, and moderate-severe vasomotor symptoms. Norethisterone, taken in combination with intramuscular [leuprolide], is also indicated for the symptomatic treatment of endometriosis-related pain.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Norethisterone is a synthetic oral progestin used for contraception or to treat other hormone-related conditions such as menopausal symptoms and endometriosis. As a synthetic progestin, norethisterone acts similarly to endogenous progesterone but with a much higher potency - it acts at the pelvic level to alter cervical and endometrial function, as well as via the inhibition of pituitary hormones that play a role in follicular maturation and ovulation. A small increase in the risk of developing breast cancer has been observed in patients using combined oral contraceptives, with some evidence also implicating progestin-only pills - patients starting hormonal contraception should be advised of this risk and should employ routine breast self-examinations to check for evidence of any developing masses.

    5.2 MeSH Pharmacological Classification

    Contraceptives, Oral, Synthetic

    Oral contraceptives which owe their effectiveness to synthetic preparations. (See all compounds classified as Contraceptives, Oral, Synthetic.)

    Contraceptives, Oral, Hormonal

    Oral contraceptives which owe their effectiveness to hormonal preparations. (See all compounds classified as Contraceptives, Oral, Hormonal.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    NORETHINDRONE
    5.3.2 FDA UNII
    T18F433X4S
    5.3.3 Pharmacological Classes
    Progestin [EPC]; Progesterone Congeners [CS]
    5.4 ATC Code

    G03FA01

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    G - Genito urinary system and sex hormones

    G03 - Sex hormones and modulators of the genital system

    G03A - Hormonal contraceptives for systemic use

    G03AC - Progestogens

    G03AC01 - Norethisterone

    G - Genito urinary system and sex hormones

    G03 - Sex hormones and modulators of the genital system

    G03D - Progestogens

    G03DC - Estren derivatives

    G03DC02 - Norethisterone

    5.5 Absorption, Distribution and Excretion

    Absorption

    The Cmax of norethisterone following oral administration of a single dose ranges from 5.39 to 7.36 ng/mL with a Tmax of 1-2 hours. AUC0-24 values following single oral doses range from approximately 30 to 37 ng*hr/mL. The oral bioavailability of norethisterone is approximately 64%. When applied transdermally, norethisterone is well-absorbed through the skin, reaches steady-state concentrations within 24 hours, and has a Cmax ranging from 617 to 1060 pg/mL at steady state. Norethisterone is often formulated as norethisterone acetate, which is completely and rapidly deacetylated to norethisterone following oral administration - the disposition of norethisterone acetate is indistinguishable from that of orally administered norethisterone.

    Route of Elimination

    Following administration of radio-labeled norethisterone, slightly more than 50% of the administered dose was eliminated in the urine and 20-40% was eliminated in the feces.

    Volume of Distribution

    The volume of distribution of norethisterone is approximately 4 L/kg. Sulfated metabolites of norethisterone, as well as small quantities of parent drug, have been shown to distribute into breast milk.

    Clearance

    The plasma clearance of norethisterone has been estimated as 0.4 L/hr/kg, and the intrinsic clearance is approximately 73-81 L/h.

    Norethindrone is 36% bound to sex hormone-binding globulin (SHBG) and 61% bound to albumin. Volume of distribution of norethindrone is about 4 L/kg.

    US Natl Inst Health; DailyMed. Current Medication Information for AYGESTIN (norethindrone acetate) tablet (July 2007). Available from, as of February 14, 2011: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=21992

    Plasma clearance value for norethindrone is approximately 0.4 L/hr/kg.

    US Natl Inst Health; DailyMed. Current Medication Information for AYGESTIN (norethindrone acetate) tablet (July 2007). Available from, as of February 14, 2011: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=21992

    In 25 BALB/c mice implanted subcutaneously with pellets containing 40% norethisterone and 60% cholesterol for 76-77 wk, absorption of norethisterone was estimated to be between 3.6 and 15.9 ug/day (mean, 7.7 ug/day).

    IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V21 452 (1979)

    Rabbits excrete norethisterone metabolites predominantly in the urine ... while rats excrete them to 80% in bile ... .

    IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V21 453 (1979)

    For more Absorption, Distribution and Excretion (Complete) data for NORETHINDRONE (8 total), please visit the HSDB record page.

    5.6 Metabolism/Metabolites

    Norethisterone is extensively metabolized, primarily in the liver, to a number of metabolites via partial and total reduction of its A-ring. The enzymes predominantly involved are 3- and 3-hydroxysteroid dehydrogenase (HSD) as well as 5- and 5-reductase. The 5-reduced metabolites, including 5-dihydronorethisterone and its derivatives, appear to carry biological activity while the 5-reduced metabolites appear inactive. Norethisterone and its metabolites are also extensively conjugated - most of the plasmatic metabolites are sulfate conjugates, while most of the urinary metabolites are glucuronide conjugates. The major metabolites in plasma are a disulfate conjugate of 3,5-tetrahydronorethisterone and a monosulfate conjugate of 3,5-tetrahydronorethisterone, while the major metabolite(s) in the urine are comprised of glucuronide and/or sulfate conjugates of 3,5-tetrahydronorethisterone. Norethisterone has also been observed to undergo some degree of metabolism via the cytochrome P450 enzyme system, predominantly by CYP3A4 and, to a much lesser extent, by CYP2C19, CYP1A2, and CYP2A6. The metabolites generated by these reactions have not been fully characterized.

    Norethindrone undergoes extensive biotransformation, primarily via reduction, followed by sulfate and glucuronide conjugation. The majority of metabolites in the circulation are sulfates, with glucuronides accounting for most of the urinary metabolites.

    US Natl Inst Health; DailyMed. Current Medication Information for AYGESTIN (norethindrone acetate) tablet (July 2007). Available from, as of February 14, 2011: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=21992

    Norethisterone undergoes extensive ring A reduction to form dihydro- and tetrahydronorethisterone metabolites that undergo conjugation; it can also be aromatized. Low serum levels of ethinylestradiol have been measured in postmenopausal women following oral administration of relatively large doses of norethisterone acetate or norethisterone. On the basis of the area-under-the-curve (AUC) values that were determined for ethinylestradiol and norethisterone, it was shown that the mean conversion ratio of norethisterone to ethinylestradiol was 0.7 and 1.0% at doses of 5 and 10 mg, respectively. The authors calculated that this corresponds to an oral dose equivalent of about 6 ug ethinylestradiol/ mg of norethisterone acetate. Similarly, it was shown that a dose of 5 mg norethisterone administered orally was equivalent to about 4 ug ethinylestradiol/mg norethisterone.

    IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V91 145 (2007)

    After incubation of norethisterone with dog liver microsomes the 4beta,5beta-epoxide of norethisterone and a 6-oxygenated norethisterone derivative were obtained as minor metabolites ... .

    IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V21 453 (1979)

    Rabbit liver homogenates ... catalyze the deethinylation of norethisterone, giving rise to the metabolite oestr-4-ene-3,17-dione.

    IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V21 453 (1979)

    For more Metabolism/Metabolites (Complete) data for NORETHINDRONE (7 total), please visit the HSDB record page.

    Norethindrone has known human metabolites that include Norethindrone-O-glucuronide.

    S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

    5.7 Biological Half-Life

    The half-life of norethisterone has been variably estimated as 8-10 hours.

    The mean terminal elimination half-life of norethindrone following a single dose administration of AYGESTIN is approximately 9 hours.

    US Natl Inst Health; DailyMed. Current Medication Information for AYGESTIN (norethindrone acetate) tablet (July 2007). Available from, as of February 14, 2011: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=21992

    The plasma half-life, MCR and plasma metabolite levels at various time intervals have been studied in six women after an intravenous injection of 3H-norethindrone acetate. The disappearance curve due to norethindrone acetate showed an initial rapid disappearance of 3H with an average half-life of 7.5 minutes and a subsequent slow disapperance with a half-life of 51.5 hours. Norethindrone acetate was cleared from the plasma with an average MCR of 495 L/day. Norethindrone acetate is rapidly metabolised after an intravenous injection. Norethindrone, the main metabolite, disappears from the plasma with an average half-life of 34.8 hours. Norethindrone maintains a high level compared with norethindrone acetate at all time intervals up to 24 hours and an equilibrium is reached between the two at 24 to 48 hours.

    PMID:484634 Singh H et al; Am J Obstet Gynecol 135 (3): 409-14 (1979)

    The half-life (of the beta phase of a two-component model) of elimination ranged from 4.8 to 12.8 hr (mean, 7.6 hr) with no significant differences between oral and intravenous administration.

    IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V91 145 (2007)

    5.8 Mechanism of Action

    On a molecular level, progestins like norethisterone exert their effects on target cells via binding to progesterone receptors that result in downstream changes to target genes. Target cells are found in the reproductive tract, breast, pituitary, hypothalamus, skeletal tissue, and central nervous system. Contraceptive efficacy is derived mainly from changes to the cervical mucus, wherein norethisterone increases the cell content and viscosity of the mucous to impede sperm transport and migration. Norethisterone also induces a variety of changes to the endometrium - including atrophy, irregular secretion, and suppressed proliferation - that make it inhospitable for implantation. Working via a negative feedback loop, norethisterone also acts on both the hypothalamus and anterior pituitary to suppress the release of follicle-stimulating hormone (FSH) and luteinizing hormone (LH) from the anterior pituitary. Suppression of these hormones prevents follicular development, ovulation, and corpus luteum development. When used as a component of hormone replacement therapy in menopausal women, norethisterones value is mainly in suppressing the growth of the endometrium. As estrogen stimulates endometrial growth, the unopposed use of estrogen in postmenopausal women with an intact uterus can lead to endometrial hyperplasia which can increase the risk of endometrial cancer. The addition of a progestin to a hormone replacement therapy in this population protects against this endometrial hyperplasia and, therefore, lowers the risk associated with the use of hormone replacement therapies. Norethisterone, along with other progestins and endogenous progesterone, has a low affinity for other steroid receptors, such as the androgen receptor and glucocorticoid receptor. While affinity and agonistic activity at these receptors is minimal, it is thought that androgen receptor agonism is responsible for some of the adverse effects observed with progestin use (e.g. acne, serum lipid changes).

    Norethindrone shares the actions of progestins. Although the exact mechanism of action of progestin-only oral contraceptives is not known, norethindrone, when administered in usual contraceptive doses, appears to act principally by altering cervical mucus so that sperm migration into the uterus is inhibited. Progestational changes in the endometrium also occur which may inhibit implantation of the fertilized ovum in the uterus. In addition, continuous administration of low doses of norethindrone alters the rate of ovum transport by changing motility and secretion in fallopian tubes. Norethindrone prevents pregnancy even in the presence of ovulation. Norethindrone suppresses ovulation and causes ovarian and endometrial atrophy at high doses; the drug does not consistently suppress ovulation when administered in a continuous low-dose regimen. In low doses, norethindrone causes variable suppression of follicle-stimulating hormone (FSH) and luteinizing hormone (LH). Norethindrone has mild androgenic activity. At low doses, norethindrone also has some estrogenic activity.

    American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 3119

    Norethindrone shares the pharmacologic actions of the progestins. In women with adequate endogenous estrogen, norethindrone transforms a proliferative endometrium into a secretory one. Norethindrone has been shown to have some estrogenic, androgenic, and anabolic activity. The drug inhibits the secretion of pituitary gonadotropins at usual dosages and thus prevents follicular maturation and ovulation.

    American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 3279

    Progestins enter target cells by passive diffusion and bind to cytosolic (soluble) receptors that are loosely bound in the nucleus. The steroid receptor complex initiates transcription, resulting in an increase in protein synthesis. /Progestins/

    USP. Convention. USPDI - Drug Information for the Health Care Professional. 20th ed. Volume I. Micromedex, Inc. Englewood, CO., 2000. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 2568

    Progestins are capable of affecting serum concentrations of other hormones, particularly estrogen. Estrogenic effects are modified by the progestins, either by reducing the availability or stability of the hormone receptor complex or by turning off specific hormone-responsive genes by direct interaction with the progestin receptor in the nucleus. In addition, estrogen priming is necessary to increase progestin effects by upregulating the number of progestin receptors and/or increasing progesterone production, causing a negative feedback mechanism that inhibits estrogen receptors. /Progestins/

    USP. Convention. USPDI - Drug Information for the Health Care Professional. 20th ed. Volume I. Micromedex, Inc. Englewood, CO., 2000. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 2568

    For more Mechanism of Action (Complete) data for NORETHINDRONE (9 total), please visit the HSDB record page.

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    19-Apr-2021
    26-Oct-2024
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    Aurobindo Receives FDA Approval for Emzahh (Norethindrone Tablets USP), 0.35mg

    Details:

    Norethisterone acts similarly to endogenous progesterone with a much higher potency, it acts at the pelvic level to alter cervical and endometrial function, as well as via the inhibition of pituitary hormones that play a role in follicular maturation and ovulation.


    Lead Product(s): Norethisterone

    Therapeutic Area: Obstetrics/Gynecology (Women’s Health) Brand Name: Emzahh-Generic

    Study Phase: ApprovedProduct Type: Small molecule

    Sponsor: Not Applicable

    Deal Size: Not Applicable Upfront Cash: Not Applicable

    Deal Type: Not Applicable January 10, 2023

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    Lead Product(s) : Norethisterone

    Therapeutic Area : Obstetrics/Gynecology (Women’s Health)

    Highest Development Status : Approved

    Partner/Sponsor/Collaborator : Not Applicable

    Deal Size : Not Applicable

    Deal Type : Not Applicable

    DEALS_DEV arrow-down

    Aurobindo Receives FDA Approval for Emzahh (Norethindrone Tablets USP), 0.35mg

    Details : Norethisterone acts similarly to endogenous progesterone with a much higher potency, it acts at the pelvic level to alter cervical and endometrial function, as well as via the inhibition of pituitary hormones that play a role in follicular maturation and...

    Brand Name : Emzahh-Generic

    Molecule Type : Small molecule

    Upfront Cash : Not Applicable

    January 10, 2023

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    DOSAGE - TABLET;ORAL-28 - 0.05MG;1MG

    USFDA APPLICATION NUMBER - 16659

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    DOSAGE - TABLET;ORAL-28 - 0.35MG **Federal Re...DOSAGE - TABLET;ORAL-28 - 0.35MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 16954

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    DOSAGE - TABLET;ORAL-28 - 0.35MG

    USFDA APPLICATION NUMBER - 17060

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    DOSAGE - TABLET;ORAL-28 - 0.035MG;1MG **Feder...DOSAGE - TABLET;ORAL-28 - 0.035MG;1MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 17919

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    DOSAGE - TABLET;ORAL-28 - 0.035MG,0.035MG,0.0...DOSAGE - TABLET;ORAL-28 - 0.035MG,0.035MG,0.035MG;0.5MG,1MG,0.5MG

    USFDA APPLICATION NUMBER - 18977

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    DOSAGE - TABLET;ORAL-28 - 0.035MG,0.035MG,0.0...DOSAGE - TABLET;ORAL-28 - 0.035MG,0.035MG,0.035MG;0.5MG,0.75MG,1MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 18985

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    DOSAGE - TABLET;ORAL - 0.035MG;0.4MG **Federa...DOSAGE - TABLET;ORAL - 0.035MG;0.4MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 21490

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    DOSAGE - TABLET, CHEWABLE;ORAL - 0.025MG;0.8M...DOSAGE - TABLET, CHEWABLE;ORAL - 0.025MG;0.8MG

    USFDA APPLICATION NUMBER - 22573

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