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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2016/03/14 13:44:08」(JST)
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This article is about a non-clinically used progestin compound. For the pharmaceutical drug, see nomegestrol acetate.
Nomegestrol
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Systematic (IUPAC) name |
(17α)-17-acetyl-17-hydroxy-6-methylestra-4,6-dien-3-one
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Identifiers |
CAS Number |
58691-88-6 |
ATC code |
G03DB04 (WHO) |
PubChem |
CID 68783 |
ChemSpider |
62024 |
Chemical data |
Formula |
C21H28O3 |
Molar mass |
328.445 g/mol |
SMILES
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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
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InChI
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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
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Key:KZUIYQJTUIACIG-YBZCJVABSA-N
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Nomegestrol (INN) is a steroidal progestin which was never marketed.[1] It is the parent drug of nomegestrol acetate, a widely used progestogen and hormonal contraceptive.[1]
See also
- Nomegestrol acetate
- Megestrol
- Progestin
References
- ^ a b F.. Macdonald (1997). Dictionary of Pharmacological Agents. CRC Press. p. 1445. ISBN 978-0-412-46630-4. Retrieved 12 May 2012.
Androgenics
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Receptor
(ligands) |
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 |
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 |
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) |
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 |
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 |
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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English Journal
- Nomegestrol acetate/estradiol hormonal oral contraceptive and breast cancer risk.
- Pup LD, Berretta M, Di Francia R, Cavaliere C, Di Napoli M, Facchini G, Fiorica F, Mileto M, Schindler AE.Author information aDivision of Gynecological Oncology bDepartment of Medical Oncology cDepartment of Breast Surgery dHematology-Oncology and Stem Cell Transplantation Unit, National Cancer Institute, Aviano (PN), Italy eUro-Gynecological Oncology Unit, Istituto Nazionale per lo Studio e la Cura dei Tumori 'Fondazione Giovanni Pascale', IRCCS, Napoli fDivision of Radiotherapy, Arcispedale S. Anna, Ferrara, Italy gInstitute for Medical Research and Education, University of Hessen, Essen, Germany.AbstractCombined hormonal contraceptives (CHCs) contain estrogen and progestin, which can stimulate estrogen-sensitive and/or progesterone-sensitive breast cancer growth. Until recently, ethinylestradiol had been almost the only estrogen used for decades, and its dose has been greatly reduced over time. The first generations of birth control pills contained approximately five times more estrogen and four times more progestin than the latest contraceptives. Newer CHCs also contain steroids that more closely mimic the physiological estradiol (E2) and progesterone effects. The newer CHC formulations are thus expected to have less influence on the breast, although it is very difficult to demonstrate any difference among the recent available preparations in human studies. Recently, nomegestrol acetate (NOMAC), a neutral, nonandrogenic, progesterone-like profile progestin, has become available in combination with the 'natural' estrogen, E2. According to the literature, NOMAC/E2 is expected to have either a lesser stimulating effect or a neutral effect on estrogen-sensitive breast cancers. We performed an analysis of the available studies and a bibliographical review. The endocrine and metabolic effects of NOMAC/E2 formulation might lead to a lesser breast tissue stimulation. The data reported, confirmed through clinical studies, should be considered when choosing a hormonal contraceptive, especially when breast stimulation is a concern.
- Anti-cancer drugs.Anticancer Drugs.2013 Dec 16. [Epub ahead of print]
- Combined hormonal contraceptives (CHCs) contain estrogen and progestin, which can stimulate estrogen-sensitive and/or progesterone-sensitive breast cancer growth. Until recently, ethinylestradiol had been almost the only estrogen used for decades, and its dose has been greatly reduced over time. The
- PMID 24346139
- The "newer" progestogens and postmenopausal hormone therapy (HRT).
- Schindler AE.Author information Institute for Medical Research and Education, University Clinic, Essen, Germany. Electronic address: adolf.schindler@uni-due.de.AbstractAfter a worldwide breakdown of hormone therapy [HT] following the publications of the Women's Health Initiative trial and Million Women's Study in 2002-2003, there is now a trend to turn attention again to HT and to explore particular progestogens, which have been discredited with respect to their side effects. The progestogens to be considered should control undue proliferation of the endometrium and should not interfere negatively with the positive effects of estradiol, regarding carbohydrate and lipid metabolism as well as hemostasis. In the present review, three "newer progestogens" are scrutinized regarding their various actions, in combination with estradiol; the progestogens include dienogest, drospirenone and nomegestrol acetate. This article is part of a special issue entitled Menopause.
- The Journal of steroid biochemistry and molecular biology.J Steroid Biochem Mol Biol.2013 Dec 12. pii: S0960-0760(13)00275-6. doi: 10.1016/j.jsbmb.2013.12.003. [Epub ahead of print]
- After a worldwide breakdown of hormone therapy [HT] following the publications of the Women's Health Initiative trial and Million Women's Study in 2002-2003, there is now a trend to turn attention again to HT and to explore particular progestogens, which have been discredited with respect to their s
- PMID 24333799
- Possible role of PGRMC1 in breast cancer development.
- Neubauer H, Ma Q, Zhou J, Yu Q, Ruan X, Seeger H, Fehm T, Mueck AO.Author information University Women's Hospital , Düsseldorf , Germany.AbstractHormone therapy may increase the risk of breast cancer. Thus, especially the addition of synthetic progestins may play a decisive role according to the results of clinical studies. Overexpression of a special receptor, i.e. the progesterone receptor membrane component-1 (PGRMC1), may offer a potential new pathway to explain the observed increase in breast cancer risk in the combined arm of the Women's Health Initiative. PGRMC1 is expressed in breast cancer tissue and may be important in tumorigenesis. The expression of PGRMC1 in breast cancer tissue is significantly different from that in normal mammary glands. Certain synthetic progestins can increase the proliferation of PGRMC1-overexpressing breast cancer cells and may thus be involved in tumorigenesis, while progesterone and certain synthetic progestins such as nomegestrol or chlormadinone acetate react neutrally. Our investigations point towards an important role of estrogen receptor-α in the signaling cascade, resulting in the proliferative effect induced by progestins. Thus, activation of PGRMC1 may explain the increased breast cancer risk observed during treatment with certain progestins. Very recently, PGRMC1 was investigated in serum samples of lung cancer patients and matched healthy patients; significantly higher concentrations were shown in the cancer patients. Therefore, PGRMC1 might be a predictor for other cancers as well but, according to clinical trials, its importance for a possible screening tool, particularly for breast cancer risk during hormone therapy, seems of interest.
- Climacteric : the journal of the International Menopause Society.Climacteric.2013 Oct;16(5):509-13. doi: 10.3109/13697137.2013.800038. Epub 2013 Jun 12.
- Hormone therapy may increase the risk of breast cancer. Thus, especially the addition of synthetic progestins may play a decisive role according to the results of clinical studies. Overexpression of a special receptor, i.e. the progesterone receptor membrane component-1 (PGRMC1), may offer a potenti
- PMID 23758160
Japanese Journal
- Effect of nomegestrol acetate on spinability, ferning and mesh dimension of midcycle cervical mucus
Related Links
- 1. Drugs. 2010 Mar 26;70(5):541-59. doi: 10.2165/11532130-000000000-00000. Nomegestrol acetate: pharmacology, safety profile and therapeutic efficacy. Lello S. This review summarizes the pharmacology, safety and clinical ...
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