Norgesterone

Norgesterone
Systematic (IUPAC) name

(17α)-17-Hydroxy-19-norpregna-5(10),20-dien-3-one
Identifiers
PubChem	CID 65606
ChemSpider	59047
Synonyms	Vinilestrenolone
Chemical data
Formula	C₂₀H₂₈O₂
Molar mass	300.43512 g/mol
SMILES CC12CCC3C(C1CCC2(C=C)O)CCC4=C3CCC(=O)C4
InChI InChI=1S/C20H28O2/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/h3,16-18,22H,1,4-12H2,2H3/t16-,17-,18+,19+,20+/m1/s1 Key:YPVUHOBTCWJYNQ-SLHNCBLASA-N

Norgesterone (INN), also known as norvinodrel, vinylestrenolone, and vinyl-noretynodrel,^[1] is a steroidal progestin of the 19-nortestosterone group.^[2] Combined with ethinyl estradiol as Vestalin, it is used as a hormonal contraceptive.^[3]^[4]^[5]

References

↑ J.P. Lavery; J.S. Sanfilippo (6 December 2012). Pediatric and Adolescent Obstetrics and Gynecology. Springer Science & Business Media. pp. 236–. ISBN 978-1-4612-5064-7.
↑ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 887–. ISBN 978-1-4757-2085-3.
↑ Wassef SA, Sami G, Hamid EA (1970). "Effect of switching with oral contraceptives". Egypt Popul Fam Plann Rev 3 (1): 77–93. PMID 12254511.
↑ Lars Philip Bengtsson; M. Tausk (September 1972). Pharmacology of the endocrine system and related drugs: progesterone, progestational drugs and antifertility agents. Pergamon Press.
↑ Cynthia A. Challener (1 December 2001). Chiral Drugs. Wiley. ISBN 978-0-566-08411-9.

Progestogens and antiprogestogens

Progestogens

Retroprogesterone	Dydrogesterone Trengestone

17α-Hydroxyprogesterone	Algestone Algestone acetophenide Chlormadinone acetate Cyproterone acetate Delmadinone acetate Hydroxyprogesterone acetate Hydroxyprogesterone caproate Hydroxyprogesterone heptanoate Medroxyprogesterone Medroxyprogesterone acetate^# Megestrol acetate Melengestrol acetate Other substitutions: Haloprogesterone (17α-bromo) Medrogestone (17α-methyl) Proligestone (14α,17α-propylidenedioxy)

19-Norprogesterone	Demegestone Gestonorone caproate Nestorone Nomegestrol acetate Norgestomet Promegestone Trimegestone

17α-Ethynyltestosterone	Dimethisterone Ethisterone

19-Nortestosterone	Allylestrenol Altrenogest Desogestrel Dienogest Etonogestrel Etynodiol diacetate Gestodene Gestrinone Levonorgestrel^# Lynestrenol Norelgestromine Norethandrolone Norethisterone (norethindrone)^# Norethisterone acetate Norethisterone enanthate Noretynodrel Norgesterone Norgestimate Norgestrel Norgestrienone Normethandrone (methylestrenolone) Norvinisterone Quingestanol acetate Tibolone Trenbolone

17α-Spirolactone	Canrenone Drospirenone Potassium canrenoate Spironolactone

Others	Progesterone Non-steroidal: Tanaproget^§

SPRMs /
antiprogestogens

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Progestogenics

Receptor
(ligands)

Agonists	3,8-Dihydrodiligustilide 5α-Dihydroprogesterone 20α-Dihydroprogesterone 11-Dehydroprogesterone 11-Deoxycorticosterone 17α-Hydroxyprogesterone 19-Norprogesterone Δ^4-Tibolone Algestone Algestone acetonide Algestone acetophenide Allylestrenol Altrenogest Amadinone Amadinone acetate Anagestone Anagestone acetate Canrenoic acid Canrenone Chlormadinone Chlormadinone acetate Cingestol Cismadinone Cismadinone acetate Clogestone Clogestone acetate Clomegestone Clometerone Cyproterone acetate Danazol Delmadinone Delmadinone acetate Demegestone Desogestrel Dienogest Dimethisterone Diosgenin Drospirenone Dydrogesterone Edogesterone Ethisterone Ethynerone Etonogestrel Etynodiol Etynodiol diacetate Flugestone Flugestone acetate Gestaclone Gestadienol Gestodene Gestonorone Gestonorone caproate Gestovister Gestrinone Gestronol Guggulsterone Haloprogesterone Hydromadinone Hydroxyprogesterone acetate Hydroxyprogesterone caproate Hydroxyprogesterone heptanoate Hydroxyprogesterone hexanoate Levonorgestrel Lutenyl Lynestrenol Medrogestone Medroxyprogesterone Medroxyprogesterone acetate Megestrol Megestrol acetate Melengestrol Melengestrol acetate Mespirenone Methylestrenolone Methynodiol Methynodiol diacetate Mometasone furoate Nandrolone Nestorone Nomegestrol Nomegestrol acetate Norelgestromin Norethisterone (norethindrone) Norethisterone acetate Norethisterone acetate oxime Norethisterone enanthate Noretynodrel Norgesterone Norgestimate Norgestomet Norgestrel Norgestrienone Norvinisterone Org-2058 Oxogestone Oxogestone phenpropionate Pentagestrone Potassium canrenoate Progesterone Proligestone Promegestone Retroprogesterone Riligustilide Quingestanol Quingestanol acetate Quingestrone Segesterone Spironenone Spironolactone Tanaproget Tetrahydrogestrinone Tibolone Tigestol Tosagestin Trengestone Trimegestone ZM-182,345

Mixed (SPRMs)	Apigenin Asoprisnil Asoprisnil ecamate Kaempferol J1042 LG-120,838 Naringenin Syringic acid Telapristone Antagonistic: Mifepristone Org-31710 Org-33628 Ulipristal acetate ZK-137,316

Antagonists	3α-Hydroxytibolone 3β-Hydroxytibolone Aglepristone Lilopristone Lonaprisan Onapristone Toripristone Valproic acid Vilaprisan ZM-150,271 ZM-172,406

Enzyme

Modulators	See here instead (modulators of 20,22-desmolase, 17α-hydroxylase/17,20-lyase, 3β-HSD, and 21-hydroxylase).

Others

Precursors/prohormones	Cholesterol 22R-Hydroxycholesterol 20α,22R-Dihydroxycholesterol Pregnenolone Pregnenolone sulfate 17-Hydroxypregnenolone

Indirect	Antigonadotropins (e.g., estrogens, progestogens, prolactin) GnRH agonists (e,g, GnRH, leuprorelin) GnRH antagonists (e.g., cetrorelix) Gonadotropins (e.g., FSH, hCG, LH) Kisspeptin Plasma proteins (ABP, albumin, SHBG)

See also: Androgenics • Estrogenics • Glucocorticoids • Mineralocorticoids

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