Noretynodrel

Noretynodrel
Clinical data
Trade namesEnovid (with mestranol), others
Other namesNorethynodrel; Noretinodrel Norethinodrel; NYD; SC-4642; NSC-15432; 5(10)-Norethisterone; 17α-Ethinyl-19-nor-5(10)-testosterone; 17α-Ethynyl-δ5(10)-19-nortestosterone; 17α-Ethynylestr-5(10)-en-17β-ol-3-one; 19-Nor-17α-pregn-5(10)-en-20-yn-17β-ol-3-one
Routes of
administration		By mouth
Drug classProgestogen; Progestin; Estrogen
ATC code
Pharmacokinetic data
Protein bindingNoretynodrel: to albumin and not to SHBGTooltip sex hormone-binding globulin or CBGTooltip corticosteroid-binding globulin[1]
MetabolismLiver, intestines (hydroxylation, isomerization, conjugation)[1][3]
Metabolites• 3α-Hydroxynoretynodrel[2]
• 3β-Hydroxynoretynodrel[2]
• Norethisterone[2][1][3]
• Ethinylestradiol[3][4]• Conjugates[3]
Elimination half-lifeVery short (< 30 minutes)[5]
ExcretionBreast milk: 1%[6]
Identifiers
IUPAC name
  • (8R,9S,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.620
Chemical and physical data
FormulaC20H26O2
Molar mass298.426 g·mol−1
3D model (JSmol)
SMILES
  • O=C4CCC\1=C(\CC[C@@H]2[C@@H]/1CC[C@]3([C@H]2CC[C@]3(C#C)O)C)C4
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/h1,16-18,22H,4-12H2,2H3/t16-,17-,18+,19+,20+/m1/s1 Y
  • Key:ICTXHFFSOAJUMG-SLHNCBLASA-N Y
  (verify)

Noretynodrel, or norethynodrel, sold under the brand name Enovid among others, is a progestin medication which was previously used in birth control pills and in the treatment of gynecological disorders but is now no longer marketed.[3][6][7][8] It was available both alone and in combination with an estrogen.[7][8][9] The medication is taken by mouth.[7]

Noretynodrel 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 is a relatively weak progestogen.[10] The medication has weak estrogenic activity, no or only very weak androgenic activity, and no other important hormonal activity.[3][8][11][12] It is a prodrug of various active metabolites in the body, such as norethisterone among others.[3][13]

Noretynodrel was introduced for medical use in 1957.[8] It was specifically approved at this time in combination with mestranol for the treatment of gynecological and menstrual disorders.[8] Subsequently, in 1960, this formulation was approved for use as a birth control pill.[8][14] It was the first birth control pill to be introduced, and was followed by birth control pills containing norethisterone and other progestins shortly thereafter.[8][14][15] Due to its nature as a relatively weak progestogen, noretynodrel is no longer used in medicine.[10] As such, it is no longer marketed.[6][16]

  1. ^ a b c Cite error: The named reference pmid2170822 was invoked but never defined (see the help page).
  2. ^ a b c Cite error: The named reference pmid22210085 was invoked but never defined (see the help page).
  3. ^ a b c d e f g h Kuhl H (2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration" (PDF). Climacteric. 8 (Suppl 1): 3–63. doi:10.1080/13697130500148875. PMID 16112947. S2CID 24616324.
  4. ^ Cite error: The named reference Kuhl2011 was invoked but never defined (see the help page).
  5. ^ Cite error: The named reference pmid2256526 was invoked but never defined (see the help page).
  6. ^ a b c Sweetman SC, ed. (2009). "Sex hormones and their modulators". Martindale: The Complete Drug Reference (36th ed.). London: Pharmaceutical Press. pp. 2120–2121. ISBN 978-0-85369-840-1.
  7. ^ a b c Jucker E, ed. (21 December 2013). Progress in Drug Research / Fortschritte der Arzneimittelforschung / Progrès des recherches pharmaceutiques. Birkhäuser. pp. 85–88. ISBN 978-3-0348-7065-8.
  8. ^ a b c d e f g Marks L (2010). Sexual Chemistry: A History of the Contraceptive Pill. Yale University Press. pp. 74–75. ISBN 978-0-300-16791-7.
  9. ^ Cite error: The named reference WHO1974 was invoked but never defined (see the help page).
  10. ^ a b Williams DA, Foye WO, Lemke TL (January 2002). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 700–. ISBN 978-0-683-30737-5.
  11. ^ Runnebaum BC, Rabe T, Kiesel L (6 December 2012). Female Contraception: Update and Trends. Springer Science & Business Media. pp. 36–. ISBN 978-3-642-73790-9.
  12. ^ Sloane E (2002). Biology of Women. Cengage Learning. pp. 426–. ISBN 978-0-7668-1142-3.
  13. ^ Cite error: The named reference pmid12215716 was invoked but never defined (see the help page).
  14. ^ a b Hollinger MA (19 October 2007). Introduction to Pharmacology, Third Edition. CRC Press. pp. 160–. ISBN 978-1-4200-4742-4.
  15. ^ Cite error: The named reference Ravina2011 was invoked but never defined (see the help page).
  16. ^ Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
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