ノルゲストレル
WordNet
- synthetic progestin used in oral contraceptives
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/03/31 16:26:00」(JST)
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Norgestrel
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| Systematic (IUPAC) name |
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(8R/S,9S/R,10R/S,13S/R,14S/R,17S/R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
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| Clinical data |
| AHFS/Drugs.com |
Micromedex Detailed Consumer Information |
| MedlinePlus |
a602008 |
| Legal status |
| Legal status |
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| Pharmacokinetic data |
| Biological half-life |
5–14 hours |
| Identifiers |
| CAS Number |
6533-00-2 Y |
| ATC code |
G03AA06 (WHO) G03FA10 G03FB01 (only combinations with estrogens) |
| PubChem |
CID 16051930 |
| ChemSpider |
10481953 Y |
| UNII |
3J8Q1747Z2 Y |
| KEGG |
D00954 Y |
| ChEBI |
CHEBI:7630 N |
| Chemical data |
| Formula |
C21H28O2 |
| Molar mass |
312.446 g/mol |
SMILES
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O=C\1CC[C@H]4C(=C/1)/CC[C@@H]3[C@@H]4CC[C@@]2(CC)[C@H]3CCC2(O)C#C
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InChI
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InChI=1S/C21H28O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23H,3,5-12H2,1H3/t16-,17+,18+,19-,20-,21?/m0/s1 Y
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Key:WWYNJERNGUHSAO-CULCCENASA-N Y
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| NY (what is this?) (verify) |
Norgestrel (INN, USAN, BAN, JAN) (brand names Logynon, Nordette, Eugynon, Microgynon, Ovran, Ovranette, Trinordiol, numerous others) is a steroidal progestin that has been used in hormonal contraceptives. It is a mixture of two stereoisomers, dextronorgestrel (CAS# 797-64-8 ) and levonorgestrel (CAS# 797-63-7 ).[1] Only levonorgestrel is biologically active.[2] Therefore, while some medications may contain dextronorgestrel, they are often labeled in terms of their levonorgestrel content only, ignoring the inert isomer.[citation needed]
Norgestrel has also been used as an emergency contraceptive in the Yuzpe regimen.[3]
See also
- Elsimar M. Coutinho
- Herchel Smith
References
- ^ Mutschler, Ernst; Schäfer-Korting, Monika (2001). Arzneimittelwirkungen (in German) (8 ed.). Stuttgart: Wissenschaftliche Verlagsgesellschaft. pp. 442f. ISBN 3-8047-1763-2.
- ^ Benagiano, G; Carrara, S; Filippi, V (2009). "Safety, efficacy and patient satisfaction with continuous daily administration of levonorgestrel/ethinylestradiol oral contraceptives". Patient preference and adherence 3: 131–43. PMC 2778424. PMID 19936155.
- ^ Yuzpe, A. A.; Smith, R. P.; Rademaker, A. W. (1982). "A multicenter clinical investigation employing ethinyl estradiol combined with dl-norgestrel as postcoital contraceptive agent". Fertility and Sterility 37 (4): 508–13. PMID 7040117.
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Progestogens and antiprogestogens
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| Progestogens |
| Retroprogesterone |
- Dydrogesterone
- Trengestone
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| 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)
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| 19-Norprogesterone |
- Demegestone
- Gestonorone caproate
- Nestorone
- Nomegestrol acetate
- Norgestomet
- Promegestone
- Trimegestone
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| 17α-Ethynyltestosterone |
- Dimethisterone
- Ethisterone
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| 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
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| 17α-Spirolactone |
- Canrenone
- Drospirenone
- Potassium canrenoate
- Spironolactone
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| Others |
- Non-steroidal: Tanaproget§
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SPRMs /
antiprogestogens |
- Aglepristone
- Asoprisnil†
- Mifepristone
- Telapristone§
- Ulipristal acetate
- Valproic acid
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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Androgenics
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Receptor
(ligands) |
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AR
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Agonists
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Mixed (SARMs)
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- AC-262,356
- Andarine
- BMS-564,929
- Enobosarm (ostarine)
- LGD-2226
- LGD-3303
- LGD-4033
- RAD140
- S-23
- S-40503
- TFM-4AS-1
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Antagonists
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- 3α-Hydroxytibolone
- 3β-Hydroxytibolone
- Abiraterone
- Abiraterone acetate
- Apalutamide
- AZD-3514
- Bisphenols (e.g., BADGE, BFDGE, bisphenol A, bisphenol F, bisphenol S)
- Benorterone
- Bicalutamide
- BMS-641,988
- BOMT
- Canrenoic acid
- Canrenone
- Chlormadinone acetate
- Cimetidine
- Cioteronel
- Clometerone
- Cyproterone
- Cyproterone acetate
- Delanterone
- DDT (via metabolite p,p’-DDE)
- Dieldrin
- Dienogest
- Drospirenone
- Endosulfan
- Enzalutamide
- EPI-001
- Epitestosterone
- Fenarimol
- Flutamide
- Galeterone
- Guggulsterone
- Hydroxyflutamide
- Inocoterone
- Ketoconazole
- Lavender oil
- Linuron
- Megestrol acetate
- Mespirenone
- Methiocarb
- Metogest
- Mifepristone
- Nilutamide
- Nomegestrol
- Nordinone
- Norgestimate
- ODM-201
- ONC1-13B
- ORM-15341
- Osaterone
- Oxendolone
- PF-998425
- Potassium canrenoate
- Prochloraz
- Procymidone
- R-2956
- Rosterolone
- RU-58642
- RU-58841
- Spironolactone
- Topilutamide (fluridil)
- Topterone
- Valproic acid
- Vinclozolin
- VT-464
- Zanoterone
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| Enzyme |
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Modulators
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- See here instead (modulators of 20,22-desmolase, 17α-hydroxylase/17,20-lyase, 3β-HSD, 17β-HSD, 5α-reductase, and aromatase).
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| Others |
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Precursors/prohormones
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- Cholesterol
- 22R-Hydroxycholesterol
- 20α,22R-Dihydroxycholesterol
- Pregnenolone
- Pregnenolone sulfate
- 17-Hydroxypregnenolone
- Progesterone
- 17-Hydroxyprogesterone
- 11-Deoxycortisol (cortodoxone)
- DHEA
- DHEA sulfate
- Δ5-Androstenediol
- Δ4-Androstenedione
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Indirect
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- 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)
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See also: Estrogenics • Glucocorticoids • Mineralocorticoids • Progestogenics
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Progestogenics
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Receptor
(ligands) |
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PR
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Agonists
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Mixed (SPRMs)
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- Apigenin
- Asoprisnil
- Asoprisnil ecamate
- Kaempferol
- J1042
- LG-120,838
- Naringenin
- Syringic acid
- Telapristone
- Antagonistic: Mifepristone
- Org-31710
- Org-33628
- Ulipristal acetate
- ZK-137,316
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Antagonists
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- 3α-Hydroxytibolone
- 3β-Hydroxytibolone
- Aglepristone
- Lilopristone
- Lonaprisan
- Onapristone
- Toripristone
- Valproic acid
- Vilaprisan
- ZM-150,271
- ZM-172,406
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| Enzyme |
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Modulators
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- See here instead (modulators of 20,22-desmolase, 17α-hydroxylase/17,20-lyase, 3β-HSD, and 21-hydroxylase).
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| Others |
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Precursors/prohormones
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- Cholesterol
- 22R-Hydroxycholesterol
- 20α,22R-Dihydroxycholesterol
- Pregnenolone
- Pregnenolone sulfate
- 17-Hydroxypregnenolone
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Indirect
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- 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)
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See also: Androgenics • Estrogenics • Glucocorticoids • Mineralocorticoids
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UpToDate Contents
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Japanese Journal
- Enantiomeric separation of norgestrel by reversed phase high-performance liquid chromatography using eluents containing hydroxypropyl-beta-cyclodextrin in stereoselective skin permeation study
- YE Jincui,CHEN Guosheng,ZENG Su
- Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 843(2), 289-294, 2006-11-07
- NAID 10025788900
- ヒト胎盤中のandrogen binding componentsに関する研究
- 金杉 浩
- 日本産科婦人科學會雜誌 36(2), 211-220, 1984-02-01
- … A unbound相の成分はheat labileであった.5)100倍molar excessの種々のステロイドを使用したcompetitionの成績を見ると,andros tenedione,dehydroepiandrosterone,dehydroepiandrosterone sulfateではCon A unbound相により高親和性であり,d norgestrelではCon A bound相により高親和性を示し,両群に明らかなsteroid specificityの差が認められた.6)IEFでの各々のピークに対し施行したsucrose gradientsの成績では,Con A unbound相の2つの結合成分が何れも4Sであったのに比しCo …
- NAID 110002112193
- 混合剤SH1000(norgestrel 0.25mg+ethinyl estradiol 0.05mg)による経口避妊について
Related Links
- Easy to read patient leaflet for norgestrel/ethinyl estradiol. Includes indications, proper use, special instructions, precautions, and possible side effects. ... Before using norgestrel/ ethinyl estradiol: Some medical conditions may ...
- Consumer information about the medication NORGESTREL (CONTRACEPTIVE) - ORAL (Ovrette), includes side effects, drug interactions, recommended dosages, and storage information. Read more about the prescription drug ...
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