Nomegestrol acetate

Nomegestrol acetate
Clinical data
Trade namesAlone: Lutenyl
With E2: Naemis, Zoely
Other namesNOMAC; 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 classProgestogen; Progestin; Progestogen ester; Steroidal antiandrogen
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability63%[1]
Protein binding97.5–98.0% (to albumin)[1]
MetabolismLiver (by hydroxylation via CYP3A3, CYP3A4, CYP2A6)[1]
MetabolitesSix main metabolites, all essentially inactive[1]
Elimination half-life~50 hours (range 30–80 hours)[1][2]
ExcretionUrine, feces[1]
Identifiers
  • [(8S,9S,10R,13S,14S,17R)-17-acetyl-6,13-dimethyl-3-oxo-1,2,8,9,10,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl] acetate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.055.781 Edit this at Wikidata
Chemical and physical data
FormulaC23H30O4
Molar mass370.489 g·mol−1
3D model (JSmol)
  • CC1=CC2C(CCC3(C2CCC3(C(=O)C)OC(=O)C)C)C4C1=CC(=O)CC4
  • InChI=1S/C23H30O4/c1-13-11-20-18(17-6-5-16(26)12-19(13)17)7-9-22(4)21(20)8-10-23(22,14(2)24)27-15(3)25/h11-12,17-18,20-21H,5-10H2,1-4H3/t17-,18-,20-,21+,22+,23+/m1/s1
  • Key:IIVBFTNIGYRNQY-YQLZSBIMSA-N

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]

  1. ^ 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.
  2. ^ Cite error: The named reference RuanSeeger2012 was invoked but never defined (see the help page).
  3. ^ 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.
  4. ^ Lemke TL, Williams DA (24 January 2012). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 1403–. ISBN 978-1-60913-345-0.
  5. ^ 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.
  6. ^ "Nomegestrol/estradiol assessment report" (PDF). European Medicines Agency. Archived from the original (PDF) on 2018-08-12. Retrieved 2018-08-12.
  7. ^ "Australian Public Assessment Report for Nomegestrol acetate/oestradiol" (PDF). October 2011.
  8. ^ a b c "Zoely: Uses, Side Effects, Benefits/Risks".
  9. ^ Cite error: The named reference EMA-Zoely was invoked but never defined (see the help page).
  10. ^ Cite error: The named reference BracheFaundes2002 was invoked but never defined (see the help page).
  11. ^ Cite error: The named reference ErkkolaLandgren2005 was invoked but never defined (see the help page).
  12. ^ Cite error: The named reference Shoupe2011 was invoked but never defined (see the help page).
  13. ^ Cite error: The named reference RoyerJones2014 was invoked but never defined (see the help page).
  14. ^ Cite error: The named reference Lutenyl-Label was invoked but never defined (see the help page).
  15. ^ Cite error: The named reference Elks2014 was invoked but never defined (see the help page).
  16. ^ Cite error: The named reference pmid6683550 was invoked but never defined (see the help page).
  17. ^ 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.
  18. ^ 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.
  19. ^ Cite error: The named reference IndexNominum2000 was invoked but never defined (see the help page).