Nomegestrol | CAS#58691-88-6 | progestin

MedKoo Cat#: 561649 | Name: Nomegestrol

Featured

Description:

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

Nomegestrol is a progestin, or a synthetic progestogen, which was first introduced in the mid-1980s and is used in the treatment of gynecological disorders, in menopausal hormone therapy for the treatment of menopausal symptoms, and in hormonal contraceptives.

Chemical Structure

Nomegestrol

CAS#58691-88-6

Theoretical Analysis

MedKoo Cat#: 561649

Name: Nomegestrol

CAS#: 58691-88-6

Chemical Formula: C21H28O3

Exact Mass: 328.2038

Molecular Weight: 328.45

Elemental Analysis: C, 76.79; H, 8.59; O, 14.61

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 430.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

Nomegestrol;

IUPAC/Chemical Name

17-Hydroxy-6-methyl-19-norpregna-4,6-diene-3,20-dione

InChi Key

KZUIYQJTUIACIG-YBZCJVABSA-N

InChi Code

InChI=1S/C21H28O3/c1-12-10-18-16(15-5-4-14(23)11-17(12)15)6-8-20(3)19(18)7-9-21(20,24)13(2)22/h10-11,15-16,18-19,24H,4-9H2,1-3H3/t15-,16-,18-,19+,20+,21+/m1/s1

SMILES Code

CC([C@@]1(O)CC[C@@]2([H])[C@]3([H])C=C(C)C4=CC(CC[C@]4([H])[C@@]3([H])CC[C@]12C)=O)=O

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

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:

Nomegestrol is a potent and orally available progestin, acts as a selective full progesterone receptor agonist, with a Kd of 5.44 nM for rat uterine progesterone receptor.

In vitro activity:

The aim of this work was to evaluate the effect of NMGA on MRP2 activity in HepG2 and Caco-2 cells as models of human hepatocytes and enterocytes, respectively. NMGA (5, 50 and 500 nM; 48 h) decreased MRP2-mediated transport of 2,4-dinitrophenyl-S-glutathione in HepG2 cells, with no effect on MRP2 protein expression. Reference: Eur J Pharm Sci. 2018 Sep 15;122:205-213. https://pubmed.ncbi.nlm.nih.gov/29981893/

In vivo activity:

NOMAc (nomegestrol acetate) (2.5, 5 mg/kg) and MA (10 mg/kg) were able to significantly ameliorate the loss of body weight in the cisplatin-induced cachectic rats. NOMAc significantly reduced the serum levels of TNF-α at 10 mg/kg. Morphologically, iWAT atrophy, with a remarkable reduction in adipocyte volume, was observed in the cisplatin-induced cachectic rats, but the effects were reversed by administering 5, 10 mg/kg NOMAc or 10 mg/kg MA. Reference: Exp Ther Med. 2022 Nov 23;25(1):24. https://pubmed.ncbi.nlm.nih.gov/36561625/

Preparing Stock Solutions

The following data is based on the product molecular weight 328.45 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.

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. Tocchetti GN, Domínguez CJ, Zecchinati F, Arana MR, Ruiz ML, Villanueva SSM, Mottino AD, Weiss J, Rigalli JP. Inhibition of multidrug resistance-associated protein 2 (MRP2) activity by the contraceptive nomegestrol acetate in HepG2 and Caco-2 cells. Eur J Pharm Sci. 2018 Sep 15;122:205-213. doi: 10.1016/j.ejps.2018.07.017. Epub 2018 Jul 6. PMID: 29981893. 2. Ma AY, Xie SW, Zhou JY, Zhu Y. Nomegestrol Acetate Suppresses Human Endometrial Cancer RL95-2 Cells Proliferation In Vitro and In Vivo Possibly Related to Upregulating Expression of SUFU and Wnt7a. Int J Mol Sci. 2017 Jun 22;18(7):1337. doi: 10.3390/ijms18071337. PMID: 28640224; PMCID: PMC5535830. 3. Zhong R, Yang W, Li G, Xie S, Guo X, Zhou J, Ren B, Zhu Y. Nomegestrol acetate ameliorated adipose atrophy in a rat model of cisplatin‑induced cachexia. Exp Ther Med. 2022 Nov 23;25(1):24. doi: 10.3892/etm.2022.11723. PMID: 36561625; PMCID: PMC9748651. 4. van Diepen HA, Lam TW, Kuil CW. Nomegestrol acetate: steroid receptor transactivation profile in Chinese hamster ovary cells and ovulation inhibition in rat and monkey. Contraception. 2011 Aug;84(2):199-204. doi: 10.1016/j.contraception.2010.11.017. Epub 2011 Jan 20. PMID: 21757063.

In vitro protocol:

In vivo protocol:

1. Zhong R, Yang W, Li G, Xie S, Guo X, Zhou J, Ren B, Zhu Y. Nomegestrol acetate ameliorated adipose atrophy in a rat model of cisplatin‑induced cachexia. Exp Ther Med. 2022 Nov 23;25(1):24. doi: 10.3892/etm.2022.11723. PMID: 36561625; PMCID: PMC9748651. 2. van Diepen HA, Lam TW, Kuil CW. Nomegestrol acetate: steroid receptor transactivation profile in Chinese hamster ovary cells and ovulation inhibition in rat and monkey. Contraception. 2011 Aug;84(2):199-204. doi: 10.1016/j.contraception.2010.11.017. Epub 2011 Jan 20. PMID: 21757063.

1: Farris M, Bastianelli C, Rosato E, Brosens I, Benagiano G. Pharmacodynamics of combined estrogen-progestin oral contraceptives: 2. effects on hemostasis. Expert Rev Clin Pharmacol. 2017 Oct;10(10):1129-1144. doi: 10.1080/17512433.2017.1356718. Epub 2017 Aug 7. Review. PubMed PMID: 28712325. 2: Bastianelli C, Farris M, Rosato E, Brosens I, Benagiano G. Pharmacodynamics of combined estrogen-progestin oral contraceptives: 1. Effects on metabolism. Expert Rev Clin Pharmacol. 2017 Mar;10(3):315-326. doi: 10.1080/17512433.2017.1271708. Epub 2017 Jan 11. Review. PubMed PMID: 27977304. 3: De Leo V, Musacchio MC, Cappelli V, Piomboni P, Morgante G. Hormonal contraceptives: pharmacology tailored to women's health. Hum Reprod Update. 2016 Sep;22(5):634-46. doi: 10.1093/humupd/dmw016. Epub 2016 Jun 15. Review. PubMed PMID: 27307386. 4: Grandi G, Napolitano A, Cagnacci A. Metabolic impact of combined hormonal contraceptives containing estradiol. Expert Opin Drug Metab Toxicol. 2016 Jul;12(7):779-87. doi: 10.1080/17425255.2016.1190832. Epub 2016 Jun 1. Review. PubMed PMID: 27187588. 5: Nelson AL. An update on new orally administered contraceptives for women. Expert Opin Pharmacother. 2015;16(18):2759-72. doi: 10.1517/14656566.2015.1100173. Epub 2015 Oct 29. Review. PubMed PMID: 26512437. 6: Lete I, Chabbert-Buffet N, Jamin C, Lello S, Lobo P, Nappi RE, Pintiaux A. Haemostatic and metabolic impact of estradiol pills and drospirenone-containing ethinylestradiol pills vs. levonorgestrel-containing ethinylestradiol pills: A literature review. Eur J Contracept Reprod Health Care. 2015;20(5):329-43. doi: 10.3109/13625187.2015.1050091. Epub 2015 May 26. Review. PubMed PMID: 26007631. 7: Zoely: a new combined oral contraceptive. Drug Ther Bull. 2014 Aug;52(8):90-3. doi: 10.1136/dtb.2014.8.0270. Epub 2014 Aug 7. Review. PubMed PMID: 25104773. 8: Ferrari S, Piacenti I, Napolitano A, Cagnacci A. [Pharmacological, metabolic and clinical aspects of new oral contraceptive associations containing natural estrogens]. Minerva Ginecol. 2014 Feb;66(1):91-102. Review. Italian. PubMed PMID: 24569408. 9: Del Pup L, Berretta M, Di Francia R, Cavaliere C, Di Napoli M, Facchini G, Fiorica F, Mileto M, Schindler AE. Nomegestrol acetate/estradiol hormonal oral contraceptive and breast cancer risk. Anticancer Drugs. 2014 Aug;25(7):745-50. doi: 10.1097/CAD.0000000000000050. Review. PubMed PMID: 24346139. 10: Schindler AE. The "newer" progestogens and postmenopausal hormone therapy (HRT). J Steroid Biochem Mol Biol. 2014 Jul;142:48-51. doi: 10.1016/j.jsbmb.2013.12.003. Epub 2013 Dec 12. Review. PubMed PMID: 24333799. 11: Neubauer H, Ma Q, Zhou J, Yu Q, Ruan X, Seeger H, Fehm T, Mueck AO. Possible role of PGRMC1 in breast cancer development. Climacteric. 2013 Oct;16(5):509-13. doi: 10.3109/13697137.2013.800038. Epub 2013 Jun 12. Review. PubMed PMID: 23758160. 12: Shulman LP. Changing convention in combination oral contraceptives: estradiol and nomegestrol acetate in a monophasic 24/4 regimen. J Fam Plann Reprod Health Care. 2013 Jul;39(3):211-6. doi: 10.1136/jfprhc-2013-100605. Epub 2013 May 24. Review. PubMed PMID: 23709606. 13: Christin-Maitre S, Laroche E, Bricaire L. A new contraceptive pill containing 17β-estradiol and nomegestrol acetate. Womens Health (Lond). 2013 Jan;9(1):13-23. doi: 10.2217/whe.12.70. Review. PubMed PMID: 23241152. 14: van Diepen HA. Preclinical pharmacological profile of nomegestrol acetate, a synthetic 19-nor-progesterone derivative. Reprod Biol Endocrinol. 2012 Oct 8;10:85. doi: 10.1186/1477-7827-10-85. Review. PubMed PMID: 23043680; PubMed Central PMCID: PMC3571880. 15: Arowojolu AO, Gallo MF, Lopez LM, Grimes DA. Combined oral contraceptive pills for treatment of acne. Cochrane Database Syst Rev. 2012 Jul 11;(7):CD004425. doi: 10.1002/14651858.CD004425.pub6. Review. PubMed PMID: 22786490. 16: Arowojolu AO, Gallo MF, Lopez LM, Grimes DA. Combined oral contraceptive pills for treatment of acne. Cochrane Database Syst Rev. 2012 Jun 13;(6):CD004425. doi: 10.1002/14651858.CD004425.pub5. Review. Update in: Cochrane Database Syst Rev. 2012;(7):CD004425. PubMed PMID: 22696343. 17: Pintiaux A, Gaspard U, Nisolle M. [Zoely, a combined oral contraceptive, monophasic pill containing estradiol and nomegestrol acetate]. Rev Med Liege. 2012 Mar;67(3):152-6. Review. French. PubMed PMID: 22611833. 18: Ruan X, Seeger H, Mueck AO. The pharmacology of nomegestrol acetate. Maturitas. 2012 Apr;71(4):345-53. doi: 10.1016/j.maturitas.2012.01.007. Epub 2012 Feb 24. Review. PubMed PMID: 22364709. 19: Su Y, Lian QQ, Ge RS. Contraceptives with novel benefits. Expert Opin Investig Drugs. 2012 Jan;21(1):83-90. doi: 10.1517/13543784.2012.642368. Epub 2011 Dec 8. Review. PubMed PMID: 22149760. 20: Sitruk-Ware R, Nath A. Metabolic effects of contraceptive steroids. Rev Endocr Metab Disord. 2011 Jun;12(2):63-75. doi: 10.1007/s11154-011-9182-4. Review. PubMed PMID: 21538049.