Nomegestrol acetate
| Clinical data | |
|---|---|
| Trade names | Alone: Lutenyl With E2: Naemis, Zoely |
| Other names | NOMAC; NOMAc; Nomegesterol acetate; TX-066; TX-525; ORG-10486-0; Uniplant; 19-Normegestrol acetate; 6-Methyl-17α-acetoxy-δ6-19-norprogesterone; 17α-Acetoxy-6-methyl-19-norpregna-4,6-diene-3,20-dione |
| License data | |
| Routes of administration | By mouth[1] |
| Drug class | Progestogen; Progestin; Progestogen ester; Steroidal antiandrogen |
| ATC code | |
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| Pharmacokinetic data | |
| Bioavailability | 63%[1] |
| Protein binding | 97.5–98.0% (to albumin)[1] |
| Metabolism | Liver (by hydroxylation via CYP3A3, CYP3A4, CYP2A6)[1] |
| Metabolites | Six main metabolites, all essentially inactive[1] |
| Elimination half-life | ~50 hours (range 30–80 hours)[1][2] |
| Excretion | Urine, feces[1] |
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| ECHA InfoCard | 100.055.781 |
| Chemical and physical data | |
| Formula | C23H30O4 |
| Molar mass | 370.489 g·mol−1 |
| 3D model (JSmol) | |
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Nomegestrol acetate (NOMAC), sold under the brand names Lutenyl and Zoely among others, is a progestin medication which is used in birth control pills, menopausal hormone therapy, and for the treatment of gynecological disorders.[3][1][4][5][6][7] It is available both alone and in combination with an estrogen.[8][9] NOMAC is taken by mouth.[3] A birth control implant for placement under the skin was also developed but ultimately was not marketed.[10][11][12][13]
Side effects of NOMAC include menstrual irregularities, headaches, nausea, breast tenderness, and others.[1][14] NOMAC is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.[3] It has some antiandrogenic activity and no other important hormonal activity.[3]
Nomegestrol, a related compound, was patented in 1975, and NOMAC was described in 1983.[15][16] NOMAC was first introduced for medical use, for the treatment of gynecological disorders and in menopausal hormone therapy, in Europe in 1986.[1][17][18] It was subsequently approved in Europe in 2011 as a component of birth control pills.[1][17][18] NOMAC is available widely throughout the world.[8][19] It is not available in the United States or Canada.[8][1][17][18]
- ^ a b c d e f g h i j k l Lello S (March 2010). "Nomegestrol acetate: pharmacology, safety profile and therapeutic efficacy". Drugs. 70 (5): 541–559. doi:10.2165/11532130-000000000-00000. PMID 20329803. S2CID 24780717.
- ^ Cite error: The named reference
RuanSeeger2012was invoked but never defined (see the help page). - ^ a b c d Kuhl H (August 2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric. 8 (Suppl 1): 3–63. doi:10.1080/13697130500148875. PMID 16112947. S2CID 24616324.
- ^ Lemke TL, Williams DA (24 January 2012). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 1403–. ISBN 978-1-60913-345-0.
- ^ Shields-Botella J, Chetrite G, Meschi S, Pasqualini JR (January 2005). "Effect of nomegestrol acetate on estrogen biosynthesis and transformation in MCF-7 and T47-D breast cancer cells". The Journal of Steroid Biochemistry and Molecular Biology. 93 (1): 1–13. doi:10.1016/j.jsbmb.2004.11.004. PMID 15748827. S2CID 25273633.
- ^ "Nomegestrol/estradiol assessment report" (PDF). European Medicines Agency. Archived from the original (PDF) on 2018-08-12. Retrieved 2018-08-12.
- ^ "Australian Public Assessment Report for Nomegestrol acetate/oestradiol" (PDF). October 2011.
- ^ a b c "Zoely: Uses, Side Effects, Benefits/Risks".
- ^ Cite error: The named reference
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RoyerJones2014was invoked but never defined (see the help page). - ^ Cite error: The named reference
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Elks2014was invoked but never defined (see the help page). - ^ Cite error: The named reference
pmid6683550was invoked but never defined (see the help page). - ^ a b c Yang LP, Plosker GL (October 2012). "Nomegestrol acetate/estradiol: in oral contraception". Drugs. 72 (14): 1917–1928. doi:10.2165/11208180-000000000-00000. PMID 22950535. S2CID 44335732.
- ^ a b c Burke A (2013). "Nomegestrol acetate-17b-estradiol for oral contraception". Patient Preference and Adherence. 7: 607–619. doi:10.2147/PPA.S39371. PMC 3702550. PMID 23836965.
- ^ Cite error: The named reference
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