Norethindrone


CAS No. : 68-22-4

Norethindrone,68-22-4
Product Details
Cat No:A000547
Synonyms:Norethisterone; 68-22-4; Norethisteron; Micronor; 19-Norethisterone
Molecular Formula:C20H26O2
Molecular Weight:298.4
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Appearance:Solid powder
Purity: > 98%
Cat No:A000547
Cas No:68-22-4
Product-Name:Norethindrone
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
Norethindrone is a steroidal progestin used in some combined oral contraceptive pills and progestogen-only pills, and is also available as a standalone drug. It can be used to treat premenstrual syndrome, painful periods, abnormal heavy bleeding, irregular periods, menopausal syndrome (in combination with estrogen), or to postpone a period. It is also commonly used to help prevent uterine hemorrhage in complicated non-surgical or pre-surgical gynecologic cases and in treating non responsive cyclical mastalgia. Norethisterone was the first orally highly active progestin to be synthesized.
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.
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.
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.
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.
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.
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.
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.
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.
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.
10: Petersen LH, Hala D, Carty D, Cantu M, Martinović 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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