Norethindrone

For research use only. Not for therapeutic Use.

  • CAT Number: A000547
  • CAS Number: 68-22-4
  • Molecular Formula: C20H26O2
  • Molecular Weight: 298.43
  • Purity: ≥95%
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Norethindrone (Cat. No: A000547) is a synthetic progestin used in hormonal contraceptives, hormone replacement therapy, and to treat menstrual disorders such as amenorrhea and endometriosis. It works by mimicking natural progesterone, inhibiting ovulation, thickening cervical mucus, and altering the endometrial lining to prevent implantation. Norethindrone is available in oral tablet form, often combined with estrogen in contraceptive pills. Common side effects include changes in menstrual flow, headache, nausea, and breast tenderness. It is generally well-tolerated but should be used with caution in smokers and individuals with cardiovascular risk.


CAS Number 68-22-4
Synonyms

Norethisterone; 68-22-4; Norethisteron; Micronor; 19-Norethisterone

Molecular Formula C20H26O2
Purity ≥95%
Target Anti-infection
Storage -20°C
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
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
InChIKey VIKNJXKGJWUCNN-XGXHKTLJSA-N
SMILES CC12CCC3C(C1CCC2(C#C)O)CCC4=CC(=O)CCC34
Reference

1: Read WL, Trivedi S, Williams F. Norethindrone substituted for megestrol in the
treatment of metastatic endometrial carcinoma: Three cases. Gynecol Oncol Rep.
2017 Oct 2;22:75-77. doi: 10.1016/j.gore.2017.09.015. eCollection 2017 Nov.
PubMed PMID: 29062884; PubMed Central PMCID: PMC5647516.
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2: Retamero Delgado A, Marín-Casino M, Jiménez Martínez C. Limb Amputation After
Arterial Thromboembolism in a Patient Receiving Norethindrone. Ann Pharmacother.
2017 Jun;51(6):516-517. doi: 10.1177/1060028017695612. Epub 2017 Feb 1. PubMed
PMID: 28478714.
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3: Morotti M, Venturini PL, Biscaldi E, Racca A, Calanni L, Vellone VG, Stabilini
C, Ferrero S. Efficacy and acceptability of long-term norethindrone acetate for
the treatment of rectovaginal endometriosis. Eur J Obstet Gynecol Reprod Biol.
2017 Jun;213:4-10. doi: 10.1016/j.ejogrb.2017.03.033. Epub 2017 Mar 27. PubMed
PMID: 28384540.
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4: Brady PC, Missmer SA, Laufer MR. Hepatic Adenomas in Adolescents and Young
Women with Endometriosis Treated with Norethindrone Acetate. J Pediatr Adolesc
Gynecol. 2017 Jun;30(3):422-424. doi: 10.1016/j.jpag.2016.12.002. Epub 2016 Dec
23. PubMed PMID: 28024920.
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5: Townsend R, Dietz A, Hale C, Akhtar S, Kowalski D, Lademacher C, Lasseter K,
Pearlman H, Rammelsberg D, Schmitt-Hoffmann A, Yamazaki T, Desai A.
Pharmacokinetic Evaluation of CYP3A4-Mediated Drug-Drug Interactions of
Isavuconazole With Rifampin, Ketoconazole, Midazolam, and Ethinyl
Estradiol/Norethindrone in Healthy Adults. Clin Pharmacol Drug Dev. 2017
Jan;6(1):44-53. doi: 10.1002/cpdd.285. Epub 2016 Jul 25. PubMed PMID: 27273461;
PubMed Central PMCID: PMC5298035.
<br>

6: Soliman AM, Bonafede M, Farr AM, Castelli-Haley J, Winkel C. Analysis of
Adherence, Persistence, and Surgery Among Endometriosis Patients Treated with
Leuprolide Acetate Plus Norethindrone Acetate Add-Back Therapy. J Manag Care Spec
Pharm. 2016 May;22(5):573-87. doi: 10.18553/jmcp.2016.22.5.573. PubMed PMID:
27123918.
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7: Min MS, Fischer R, Fournier JB. Unilateral Erythema Nodosum following
Norethindrone Acetate, Ethinyl Estradiol, and Ferrous Fumarate Combination
Therapy. Case Rep Obstet Gynecol. 2016;2016:5726416. doi: 10.1155/2016/5726416.
Epub 2016 Mar 27. PubMed PMID: 27110414; PubMed Central PMCID: PMC4826688.
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8: Vercellini P, Bracco B, Mosconi P, Roberto A, Alberico D, Dhouha D, Somigliana
E. Norethindrone acetate or dienogest for the treatment of symptomatic
endometriosis: a before and after study. Fertil Steril. 2016
Mar;105(3):734-743.e3. doi: 10.1016/j.fertnstert.2015.11.016. Epub 2015 Dec 8.
PubMed PMID: 26677792.
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9: Wu M, Pan C, Yang M, Xu B, Lei X, Ma J, Cai L, Chen J. Chemical analysis of
fish bile extracts for monitoring endocrine disrupting chemical exposure in
water: Bisphenol A, alkylphenols, and norethindrone. Environ Toxicol Chem. 2016
Jan;35(1):182-90. doi: 10.1002/etc.3176. Epub 2015 Nov 30. PubMed PMID: 26206390.
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10: Petersen LH, Hala D, Carty D, Cantu M, Martinovi&#263; D, Huggett DB. Effects of
progesterone and norethindrone on female fathead minnow (Pimephales promelas)
steroidogenesis. Environ Toxicol Chem. 2015 Feb;34(2):379-90. doi:
10.1002/etc.2816. Epub 2015 Jan 6. PubMed PMID: 25470578.

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