Norgestimate

Norgestimate
Systematic (IUPAC) name

(13-ethyl-17-ethynyl-3-hydroxyimino- 1,2,6,7,8,9,10,11,12,14,15,16- dodecahydrocyclopenta[a] phenanthren-17-yl) acetate
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a601050
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Biological half-life	12–30 hours
Identifiers
CAS Number	35189-28-7^Y
ATC code	G03AA11 (WHO) G03FA13 (only combinations with estrogens)
PubChem	CID 6540478
IUPHAR/BPS	7091
DrugBank	DB00957^Y
ChemSpider	5022837^Y
UNII	C291HFX4DY^Y
KEGG	D05209^Y
ChEBI	CHEBI:50815^Y
ChEMBL	CHEMBL1200934^N
Chemical data
Formula	C₂₃H₃₁NO₃
Molar mass	369.497 g/mol
SMILES O=C(O[C@@]2(C#C)CC[C@H]1[C@H]4[C@H](CC[C@@]12CC)[C@@H]3/C(=C\C(=N\O)CC3)CC4)C
InChI InChI=1S/C23H31NO3/c1-4-22-12-10-19-18-9-7-17(24-26)14-16(18)6-8-20(19)21(22)11-13-23(22,5-2)27-15(3)25/h2,14,18-21,26H,4,6-13H2,1,3H3/b24-17+/t18-,19+,20+,21-,22-,23-/m0/s1^Y Key:KIQQMECNKUGGKA-NMYWJIRASA-N^Y
^NY (what is this?) (verify)

Not to be confused with norgestomet.

Norgestimate (INN, USAN, BAN) is an acetylated progestin used as an oral contraceptive.^[1] It acts as a prodrug to norelgestromin (17-deacetylnorgestimate or levonorgestrel 3-oxime), the primary active metabolite, and levonorgestrel (deacetylation of norgestimate occurs in the intestines and the liver).^[1] Unlike levonorgestrel, norgestimate shows high selectivity for the progesterone receptor and low androgenic action due to a large drug-induced elevation in the level of sex hormone-binding globulin (SHBG) (which preferentially binds androgens and thus inhibits their action).^[1]^[2] In accordance, clinical trials have observed minimal androgenic side effects.^[2] Norgestimate and its metabolites themselves, unlike many other progestins, do not bind to SHBG.^[1] Norgestimate is used in combination with ethinyl estradiol as an oral contraceptive.^[3]

References

1 2 3 4 Thomas L. Lemke; David A. Williams (2008). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 1316–. ISBN 978-0-7817-6879-5.
1 2 Chapdelaine A, Desmarais JL, Derman RJ (1989). "Clinical evidence of the minimal androgenic activity of norgestimate". Int. J. Fertil. 34 (5): 347–52. PMID 2571595.
↑ Consumer Drug Information: Ortho Tri-Cyclen

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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