Nomegestrol

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Nomegestrol
Nomegestrol.svg
Clinical data
Other names19-Normegestrol; 6-Methyl-17α-hydroxy-δ6-19-norprogesterone; 17α-Hydroxy-6-methyl-19-norpregna-4,6-diene-3,20-dione
ATC code
Identifiers
  • (17α)-17-acetyl-17-hydroxy-6-methylestra-4,6-dien-3-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
Chemical and physical data
Formula C21H28O3
Molar mass 328.452 g·mol−1
3D model (JSmol)
  • O=C4\C=C3\C(=C/[C@@H]1[C@H](CC[C@@]2([C@@](O)(C(=O)C)CC[C@@H]12)C)[C@H]3CC4)C
  • 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
  • Key:KZUIYQJTUIACIG-YBZCJVABSA-N

Nomegestrol (INN), also known as 19-normegestrol, is a steroidal progestin which was patented in 1975 but was never marketed. [1] [2] It is the parent compound of nomegestrol acetate, which is marketed as a progestin. [1] [2]

Nomegestrol shows relatively low affinity for the progesterone receptor, only about 4% of that of progesterone and about 1.6% of that of nomegestrol acetate in one assay. [3]

See also

Related Research Articles

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<span class="mw-page-title-main">Norgestimate</span> Chemical compound

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<span class="mw-page-title-main">Chlormadinone acetate</span> Chemical compound

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<span class="mw-page-title-main">Melengestrol acetate</span> Chemical compound

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<span class="mw-page-title-main">Allylestrenol</span> Chemical compound

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<span class="mw-page-title-main">Nomegestrol acetate</span> Chemical compound

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<span class="mw-page-title-main">Quingestanol acetate</span> Chemical compound

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<span class="mw-page-title-main">Delmadinone acetate</span> Chemical compound

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<span class="mw-page-title-main">19-Norprogesterone</span> Chemical compound

19-Norprogesterone, also known as 19-norpregn-4-ene-3,20-dione, is a steroidal progestin and close analogue of the sex hormone progesterone, lacking only the C19 methyl group of that molecule. It was first synthesized in 1944 in the form of a mixture that also included unnatural stereoisomers of progesterone, and this mixture was found to be at least equivalent to progesterone in terms of progestogenic activity. Subsequent investigations revealed that 17-isoprogesterone and 14-iso-17-isoprogesterone are devoid of progestogenic activity. 19-Norprogesterone was resynthesized in 1951 with an improved method, and was confirmed to be the component of the mixture synthesized in 1944 that was responsible for its progestogenic activity. In 1953, a paper was published showing that 19-norprogesterone possessed 4- to 8-fold the activity of progesterone in the Clauberg assay in rabbits, and at the time of this discovery, 19-norprogesterone was the most potent progestogen known.

<span class="mw-page-title-main">Hydroxyprogesterone acetate</span> Chemical compound

Hydroxyprogesterone acetate (OHPA), sold under the brand name Prodox, is an orally active progestin related to hydroxyprogesterone caproate (OHPC) which has been used in clinical and veterinary medicine. It has reportedly also been used in birth control pills.

<span class="mw-page-title-main">Haloprogesterone</span> Chemical compound

Haloprogesterone, sold under the brand name Prohalone, is a progestin medication which was previously marketed by Ayerst but is now no longer available.

<span class="mw-page-title-main">Norgestomet</span> Chemical compound

Norgestomet, or norgestamet, sold under the brand name Syncro-Mate B and Crestar, is a progestin medication which is used in veterinary medicine to control estrus and ovulation in cattle.

<span class="mw-page-title-main">Anagestone acetate</span> Chemical compound

Anagestone acetate, sold under the brand names Anatropin and Neo-Novum, is a progestin medication which was withdrawn from medical use due to carcinogenicity observed in animal studies.

<span class="mw-page-title-main">Dimepregnen</span> Chemical compound

Dimepregnen, or 6α,16α-dimethylpregn-4-en-3β-ol-20-one, is a pregnene steroid described as an antiestrogen that was synthesized in 1968 and was never marketed. It is similar in structure to the progestins and progesterone derivatives melengestrol and anagestone.

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Gestronol (BAN), also known as gestonorone, as well as 17α-hydroxy-19-norprogesterone or 17α-hydroxy-19-norpregn-4-ene-3,20-dione, is a progestin of the 19-norprogesterone and 17α-hydroxyprogesterone groups which was never marketed. The C17α caproate ester of gestronol, gestonorone caproate, in contrast, has been marketed.

<span class="mw-page-title-main">Progestogen ester</span> Drug class

A progestogen ester is an ester of a progestogen or progestin. The prototypical progestogen is progesterone, an endogenous sex hormone. Esterification is frequently employed to improve the pharmacokinetics of steroids, including oral bioavailability, lipophilicity, and elimination half-life. In addition, with intramuscular injection, steroid esters are often absorbed more slowly into the body, allowing for less frequent administration. Many steroid esters function as prodrugs.

<span class="mw-page-title-main">Gestadienol acetate</span> Chemical compound

Gestadienol acetate an orally active progestin which was described in the literature in 1967 and was never marketed. It has no androgenic or estrogenic effects. The effects of gestadienol acetate on the endometrium and its general pharmacology were studied in a clinical trial in women. It has also been studied in a clinical trial for benign prostatic hyperplasia in men, but was ineffective.

<span class="mw-page-title-main">17α-Allyl-19-nortestosterone</span> Chemical compound

17α-Allyl-19-nortestosterone, also known as 3-ketoallylestrenol or as 17α-allylestr-4-en-17β-ol-3-one, is a progestin which was never marketed. It is a combined derivative of the anabolic–androgenic steroid and progestogen nandrolone (19-nortestosterone) and the antiandrogen allyltestosterone (17α-allyltestosterone). The drug is a major active metabolite of allylestrenol, which is thought to be a prodrug of 17α-allyl-19-nortestosterone.

References

  1. 1 2 J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 883–. ISBN   978-1-4757-2085-3.
  2. 1 2 Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 747–. ISBN   978-3-88763-075-1.
  3. Botella J, Duc I, Delansorne R, Paris J, Lahlou B (December 1990). "Structure-activity and structure-affinity relationships of 19-nor-progesterone derivatives in rat uterus". J. Endocrinol. Invest. 13 (11): 905–10. doi:10.1007/BF03349652. PMID   2090671. S2CID   37429648.