Noretynodrel

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. It was available both alone and in combination with an estrogen. The medication is taken by mouth.

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
MetabolismLiver, intestines (hydroxylation, isomerization, conjugation)
Metabolites• 3α-Hydroxynoretynodrel
• 3β-Hydroxynoretynodrel
• Norethisterone
• Ethinylestradiol• Conjugates
Elimination half-lifeVery short (< 30 minutes)
ExcretionBreast milk: 1%
Identifiers
  • (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)
  • O=C4CCC\1=C(\CC[C@@H]2[C@@H]/1CC[C@]3([C@H]2CC[C@]3(C#C)O)C)C4
  • 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 is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. It is a relatively weak progestogen. The medication has weak estrogenic activity, no or only very weak androgenic activity, and no other important hormonal activity. It is a prodrug of various active metabolites in the body, such as norethisterone among others.

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

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