NorethindroneCAS# 68-22-4 |
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Quality Control & MSDS
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Chemical structure
3D structure
| Cas No. | 68-22-4 | SDF | Download SDF |
| PubChem ID | 6230 | Appearance | Powder |
| Formula | C20H26O2 | M.Wt | 298.42 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Synonyms | Norethisterone | ||
| Solubility | Soluble in DMSO > 10 mM | ||
| Chemical 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 | ||
| SMILES | CC12CCC3C(C1CCC2(C#C)O)CCC4=CC(=O)CCC34 | ||
| Standard InChIKey | VIKNJXKGJWUCNN-XGXHKTLJSA-N | ||
| Standard 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 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Norethindrone is a female progestin approved by FDA for the treatment of endometriosis, uterine bleeding caused by abnormal hormone levels, and secondary amenorrhea.In Vivo:Norethindrone acetate could be a cost-effective alternative with relatively mild side effects in the treatment of symptomatic endometriosis. Subjects treated with norethindrone acetate obtain dysmenorrhea and noncyclic pelvic pain relief[1]. Norethindrone acetate alone is a well-tolerated, effective option to manage pain and bleeding for all stages of endometriosis. Post-Norethindrone acetate bleeding scores are improved regardless of prior hormonal regimen, and post-Norethindrone acetate pain scores improved in all patients except for those previously prescribed GnRH-agonist plus add-back[2]. Norethindrone acetate shows low acute toxicity in experimental animals and is consistent with the lack of toxicity seen in humans. Administration of norethindrone acetate alone to rodents at several multiples of the human dose results in no treatment related mortality, hematological changes, behavioral changes, or organ pathology[3]. Norethindrone acetate administration leads to significant and proportional reductions of the concentrations of triglycerides, cholesterol and phospholipids of plasma lipoproteins of density <1.006 of rats fed a high carbohydrate diet. Norethindrone acetate (0.1 mM) also significantly inhibits the incorporation of both palmitate and glycerol into triglycerides of isolated hepatocytes from fed rats[4]. References: | |||||
Norethindrone Dilution Calculator
Norethindrone Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 3.351 mL | 16.7549 mL | 33.5098 mL | 67.0196 mL | 83.7745 mL |
| 5 mM | 0.6702 mL | 3.351 mL | 6.702 mL | 13.4039 mL | 16.7549 mL |
| 10 mM | 0.3351 mL | 1.6755 mL | 3.351 mL | 6.702 mL | 8.3775 mL |
| 50 mM | 0.067 mL | 0.3351 mL | 0.6702 mL | 1.3404 mL | 1.6755 mL |
| 100 mM | 0.0335 mL | 0.1675 mL | 0.3351 mL | 0.6702 mL | 0.8377 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Norethindrone is a synthetic progestin, which mimic the actions of the endogenous ovarian hormone progesterone.
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Unilateral Erythema Nodosum following Norethindrone Acetate, Ethinyl Estradiol, and Ferrous Fumarate Combination Therapy.[Pubmed:27110414]
Case Rep Obstet Gynecol. 2016;2016:5726416.
Erythema nodosum is a septal panniculitis that typically presents as symmetric, tender nodules on the anterior aspects of bilateral lower extremities. Nearly half of cases are due to secondary causes, with oral contraceptive pills being the leading pharmaceutical cause. However, to our knowledge, there has yet to be a published association with Norethindrone acetate, ethinyl estradiol, and ferrous fumarate. We report our experience with a 30-year-old woman who developed unilateral tender nodules within a month of starting 1 mg Norethindrone acetate and 20 mcg ethinyl estradiol daily. Of note, she had previously taken oral contraceptives with the same estrogen agent but different progesterone, without problems. We conclude that systemically triggered erythema nodosum can present with lesions localized to one extremity. When a patient presents with tender, firm nodules, clinicians should consider the possibility of erythema nodosum and its triggers, such as oral contraceptives. Additionally, should a patient on hormonal therapy develop erythema nodosum, changing the progesterone agent may allow the patient to continue similar therapy without developing symptoms.
Analysis of Adherence, Persistence, and Surgery Among Endometriosis Patients Treated with Leuprolide Acetate Plus Norethindrone Acetate Add-Back Therapy.[Pubmed:27123918]
J Manag Care Spec Pharm. 2016 May;22(5):573-87.
BACKGROUND: Endometriosis affects over 10 million women in the United States. Depot leuprolide acetate (LA), a gonadotropin-releasing hormone agonist, has been used extensively for the treatment of women with endometriosis but is associated with hypoestrogenic symptoms and bone mineral density loss. The concomitant use of add-back therapies, specifically Norethindrone acetate (NETA), can alleviate these adverse effects. OBJECTIVE: To compare adherence to and persistence with LA treatment and time to endometriosis-related surgery among women treated with NETA and women treated with LA plus other add-back therapies or LA only. METHODS: This retrospective analysis was conducted using Truven Health MarketScan Commercial Claims and Encounters Database. Women with a diagnosis of endometriosis (ICD-9-CM code 617.xx) who initiated LA (index date) in 2005-2011 were selected for inclusion. Additional requirements were 12 months of continuous enrollment pre- and post-index and no evidence of endometriosis-related surgeries pre-index or up to 30 days post-index; no pre-index use of estrogen or noncontraceptive hormones; and no diagnoses of uterine fibroids, malignant neoplasms, infertility, or pregnancy. Patients were characterized as using NETA; other add-back therapies (estrogens, progestins, or estrogen-progestin combinations); or no add-back therapy. Adherence to and persistence with LA were measured over the 6 months following the index date using outpatient medical and pharmacy claims. Patients were considered adherent if their proportion of days covered was greater than or equal to 0.80. Persistence was operationalized as time to discontinuation, defined as a continuous gap of > 60 days without LA on hand. Time to endometriosis-related surgery (laparotomy, laparoscopy, excision/ablation/fulguration, oophorectomy, and hysterectomy) was measured over the 12 months following the index date. Surgeries were identified from inpatient and outpatient medical claims using procedure codes. Outcomes were compared among cohorts using multivariable logistic and Cox proportional hazards regression models controlling for demographics and baseline clinical characteristics. RESULTS: The final sample included 3,114 women, with a mean age of 36.9 years. The majority of women used LA only with no add-back therapy (n = 1,963, 63.0%), while 15.1% (n = 470) used NETA, and 21.9% (N = 681) used other add-back therapies. During the 6-month follow-up, more patients in the LA plus NETA cohort were adherent to LA therapy compared with LA only (47.2% vs. 31.5%, P < 0.001), and fewer patients discontinued (37.9% vs. 59.6%, P < 0.001). Additionally, fewer patients underwent endometriosis-related surgery in the 12 months after LA initiation in the LA plus NETA cohort (12.6% vs. 16.9%, P = 0.021). In multivariable models, women who initiated LA plus NETA or LA plus other add-back therapies had a higher likelihood of being adherent to LA than LA only patients (OR = 1.91, 95% CI = 1.55-2.36 and OR = 1.95, 95% CI = 1.63-2.34) and lower likelihood of LA discontinuation (HR = 0.54, 95% CI = 0.46-0.63 and HR = 0.59, 95% CI = 0.52-0.68). NETA patients had a lower surgery rate in the 12-month post-index period compared with other add-back patients (HR = 0.68, 95% CI = 0.50-0.93) or LA only patients (HR = 0.69, 95% CI = 0.52-0.92). CONCLUSIONS: For women with endometriosis, treatment with LA and concomitant add-back therapies was associated with better adherence to and persistence with LA over the 6 months following initiation, compared with treatment with LA only. The increased adherence and persistence to LA may translate into decreased need for surgical intervention, although fewer endometriosis-related surgeries were only observed in the 12 months following LA initiation for patients using concomitant NETA add-back therapy. These results support an increased and earlier use of NETA add-back therapy among women who initiate LA. DISCLOSURES: This study was funded by AbbVie, which also markets the endometriosis drugs Lupron and Lupaneta Pack. AbbVie participated in the study design, research, data collection, analysis and interpretation, writing, review, and approval of this publication. Soliman and Castelli-Haley are employees of AbbVie and may own AbbVie stock or stock options. Bonafede and Farr are employees of Truven Health Analytics, which received a research contract to conduct this study with and on behalf of AbbVie. Winkel is a clinical professor in the Department of Obstetrics and Gynecology at Georgetown University in Washington, DC, and has served in a consulting role on research to AbbVie for this project. An earlier version of the current research was presented at the International Society for Pharmacoeconomics and Outcomes Research (ISPOR) 20th Annual International Meeting; Philadelphia, PA; May 2015. All authors participated in data analysis and interpretation and contributed to the development of the manuscript.
Pharmacokinetic Evaluation of CYP3A4-Mediated Drug-Drug Interactions of Isavuconazole With Rifampin, Ketoconazole, Midazolam, and Ethinyl Estradiol/Norethindrone in Healthy Adults.[Pubmed:27273461]
Clin Pharmacol Drug Dev. 2017 Jan;6(1):44-53.
This report describes the phase 1 trials that evaluated the metabolism of the novel triazole antifungal isavuconazole by cytochrome P450 3A4 (CYP3A4) and isavuconazole's effects on CYP3A4-mediated metabolism in healthy adults. Coadministration of oral isavuconazole (100 mg once daily) with oral rifampin (600 mg once daily; CYP3A4 inducer) decreased isavuconazole area under the concentration-time curve (AUCtau ) during a dosing interval by 90% and maximum concentration (Cmax ) by 75%. Conversely, coadministration of isavuconazole (200 mg single dose) with oral ketoconazole (200 mg twice daily; CYP3A4 inhibitor) increased isavuconazole AUC from time 0 to infinity (AUC0-infinity ) and Cmax by 422% and 9%, respectively. Isavuconazole was coadministered (200 mg 3 times daily for 2 days, then 200 mg once daily) with single doses of oral midazolam (3 mg; CYP3A4 substrate) or ethinyl estradiol/Norethindrone (35 mug/1 mg; CYP3A4 substrate). Following coadministration, AUC0-infinity increased 103% for midazolam, 8% for ethinyl estradiol, and 16% for Norethindrone; Cmax increased by 72%, 14%, and 6%, respectively. Most adverse events were mild to moderate in intensity; there were no deaths, and serious adverse events and adverse events leading to study discontinuation were rare. These results indicate that isavuconazole is a sensitive substrate and moderate inhibitor of CYP3A4.
Hepatic Adenomas in Adolescents and Young Women with Endometriosis Treated with Norethindrone Acetate.[Pubmed:28024920]
J Pediatr Adolesc Gynecol. 2017 Jun;30(3):422-424.
BACKGROUND: Endometriosis-ectopic implantation of endometrial-like tissue-affects 10% of female adolescents and adults. First-line treatment includes progesterone only (such as Norethindrone acetate [NET-A]) or combined estrogen/progestin oral contraceptive pills. Estrogen-containing contraceptives confer increased risk of hepatic adenomas, whereas the association with NET-A is very rarely reported. CASE: Three adolescents with stage I to II endometriosis managed with NET-A (up to 15 mg/d for 28-78 months) were diagnosed with hepatic adenomas at ages 17-22 years. They previously received estrogen-containing medications, which were stopped 24 months or longer before diagnosis of hepatic adenoma. SUMMARY AND CONCLUSION: NET-A in a dose greater than 10 mg/d might be associated with increased risk for hepatic adenomas, likely due to peripheral conversion to ethinyl estradiol. Use of NET-A might not be advisable in patients with known hepatic adenomas.
