Norethindrone
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 318378

CAS#: 68-22-4

Description: 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.

Chemical Structure

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Norethindrone
CAS# 68-22-4
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 318378
Name: Norethindrone
CAS#: 68-22-4
Chemical Formula: C20H26O2
Exact Mass: 298.19
Molecular Weight: 298.419
Elemental Analysis: C, 80.50; H, 8.78; O, 10.72

Price and Availability

Size Price Availability Quantity
5g USD -1
10g USD -1
10mg USD 180
25mg USD 200
50mg USD 220
100mg USD 250
200mg USD 350
500mg USD 380
1g USD 400
2g USD 450
Bulk inquiry

Synonym: Norethindrone, Norethisterone, 19-nor-17α-ethynyltestosterone, Utovlan

IUPAC/Chemical Name: (8R,9S,10R,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one

InChi Key: VIKNJXKGJWUCNN-XGXHKTLJSA-N

InChi Code: 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

SMILES Code: C[C@]12CC[C@H]3[C@@H](CCC4=CC(CC[C@H]34)=O)[C@@H]1CC[C@@]2(O)C#C

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: Norethindrone is a female progestin.
In vitro activity: Assays of cell viability, proliferation, migration, apoptosis, and colony formation were performed to investigate the pro-tumorigenesis effect of NET (norethisterone) and the effects of miR-181a on human breast epithelial MCF10A cells. NET significantly increased MCF10A cell viability, proliferation, migration, and colony formation, but reduced cellular apoptosis. In addition, NET increased the expression of progesterone receptor membrane component 1 (PGRMC1), EGFR, B-cell lymphoma 2, cyclin D1, and proliferating cell nuclear antigen, but decreased the expression of pro-apoptosis factors, such as Bax, caspase-7, and caspase-9. Reference: Transl Oncol. 2021 Jun;14(6):101068. https://pubmed.ncbi.nlm.nih.gov/33730679/
In vivo activity: Norethindrone acetate administration led to significant and proportional reductions of the concentrations of triglycerides, cholesterol and phospholipids of plasma lipoproteins of density less than 1.006 of rats fed a high carbohydrate diet. Norethindrone acetate (0.1 mM) also significantly inhibited the incorporation of both [9,10(-3)H] palmitate and [U-14C]glycerol into triglycerides of isolated hepatocytes from fed rats, by 11 to 16% (P less than 0.001). Reference: Atherosclerosis. 1983 Jan;46(1):41-8. https://pubmed.ncbi.nlm.nih.gov/6838693/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 42.5 142.42
Ethanol 3.0 10.05
Water 2.7 9.05

Preparing Stock Solutions

The following data is based on the product molecular weight 298.42 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Cai G, Wang Y, Houda T, Yang C, Wang L, Gu M, Mueck A, Croteau S, Ruan X, Hardy P. MicroRNA-181a suppresses norethisterone-promoted tumorigenesis of breast epithelial MCF10A cells through the PGRMC1/EGFR-PI3K/Akt/mTOR signaling pathway. Transl Oncol. 2021 Jun;14(6):101068. doi: 10.1016/j.tranon.2021.101068. Epub 2021 Mar 14. PMID: 33730679; PMCID: PMC7974027. 2. Brosnan JF, Sheppard BL, Kelly LA, O'Leary JJ, Norris LA. Norethisterone acetate alters coagulation gene expression in vitro in human cell culture. Thromb Res. 2013 Jan;131(1):72-7. doi: 10.1016/j.thromres.2012.09.006. Epub 2012 Sep 19. PMID: 22999413. 3. Cheng DC, Wolfe BM. Norethindrone acetate inhibition of triglyceride synthesis and release by rat hepatocytes. Atherosclerosis. 1983 Jan;46(1):41-8. doi: 10.1016/0021-9150(83)90162-4. PMID: 6838693.
In vitro protocol: 1. Cai G, Wang Y, Houda T, Yang C, Wang L, Gu M, Mueck A, Croteau S, Ruan X, Hardy P. MicroRNA-181a suppresses norethisterone-promoted tumorigenesis of breast epithelial MCF10A cells through the PGRMC1/EGFR-PI3K/Akt/mTOR signaling pathway. Transl Oncol. 2021 Jun;14(6):101068. doi: 10.1016/j.tranon.2021.101068. Epub 2021 Mar 14. PMID: 33730679; PMCID: PMC7974027. 2. Brosnan JF, Sheppard BL, Kelly LA, O'Leary JJ, Norris LA. Norethisterone acetate alters coagulation gene expression in vitro in human cell culture. Thromb Res. 2013 Jan;131(1):72-7. doi: 10.1016/j.thromres.2012.09.006. Epub 2012 Sep 19. PMID: 22999413.
In vivo protocol: 1. Cheng DC, Wolfe BM. Norethindrone acetate inhibition of triglyceride synthesis and release by rat hepatocytes. Atherosclerosis. 1983 Jan;46(1):41-8. doi: 10.1016/0021-9150(83)90162-4. PMID: 6838693.

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1: Chwalisz K, Surrey E, Stanczyk FZ. The hormonal profile of norethindrone acetate: rationale for add-back therapy with gonadotropin-releasing hormone agonists in women with endometriosis. Reprod Sci. 2012 Jun;19(6):563-71. doi: 10.1177/1933719112438061. Epub 2012 Mar 27. Review. PubMed PMID: 22457429.

2: Casey CL, Murray CA. HT update: spotlight on estradiol/norethindrone acetate combination therapy. Clin Interv Aging. 2008;3(1):9-16. Review. PubMed PMID: 18488874; PubMed Central PMCID: PMC2544373.

3: Maier WE, Herman JR. Pharmacology and toxicology of ethinyl estradiol and norethindrone acetate in experimental animals. Regul Toxicol Pharmacol. 2001 Aug;34(1):53-61. Review. PubMed PMID: 11502156.

4: Taitel HF, Kafrissen ME. Norethindrone--a review of therapeutic applications. Int J Fertil Menopausal Stud. 1995 Jul-Aug;40(4):207-23. Review. PubMed PMID: 8520623.

5: Stanczyk FZ, Roy S. Metabolism of levonorgestrel, norethindrone, and structurally related contraceptive steroids. Contraception. 1990 Jul;42(1):67-96. Review. PubMed PMID: 2143719.

6: Rajput R, Dhuan J, Agarwal S, Gahlaut PS. Central venous sinus thrombosis in a young woman taking norethindrone acetate for dysfunctional uterine bleeding: case report and review of literature. J Obstet Gynaecol Can. 2008 Aug;30(8):680-3. Review. PubMed PMID: 18786290.