- 関
- norethisterone
WordNet
- a salt or ester of acetic acid (同)ethanoate
PrepTutorEJDIC
- 酢酸(さくさん)塩;アセテート(酢酸人造絹糸)
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/04/08 16:17:27」(JST)
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Norethisterone acetate
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| Systematic (IUPAC) name |
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(8R,9S,10R,13S,14S,17S)-17-ethynyl-13-methyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate
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| Clinical data |
| AHFS/Drugs.com |
International Drug Names |
| MedlinePlus |
a604034 |
Routes of
administration |
Oral tablet |
| Legal status |
- AU: S4 (Prescription only)
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| Identifiers |
| CAS Number |
38673-38-0 Y |
| PubChem |
CID 63021 |
| ChemSpider |
5627 N |
| ChEBI |
CHEBI:7628 N |
| ChEMBL |
CHEMBL1201146 N |
| Chemical data |
| Formula |
C22H28O3 |
| Molar mass |
340.456 g/mol |
| NY (what is this?) (verify) |
Norethisterone acetate (INN, BAN), also known as norethindrone acetate (USAN), sold under brand names including Aygestin, Gestakadin, Milligynon, Monogest, Norlutate (Canada, USA distributed by ERFA Canada 2012 Inc.[1]), Primolut (Fr., Ger., Swed.), Sovel, Styptin, and others, is a steroidal progestin with additional antigonadotropic (and hence antiandrogen and antiestrogen)[2] effects that is used as a hormonal contraceptive.[3][4] It is an acetate ester of norethisterone.[5] Norethindrone acetate is indicated for abnormal uterine bleedings.[6]
Synthesis
Riglovic progestational component:
[7][8]
Reaction of norethindrone (1) with acetic anhydride in the presence of p-toluene sulfonic acid, affords norethindrone acetate (2).[7] This in turn affords, on reaction with exess cyclopentanol in the presence of excess phosphorus pentoxide, the 3-cyclopentyl enol ether (3),[8] the progestational component of Riglovic®.
See also
- Norethisterone
- Norethisterone enanthate
- Ethisterone
- Nomegestrol acetate
- Progestin
References
- ^ http://www.eci2012.net/
- ^ Garza-Flores J, Menjívar M, Cardenas M, Reynoso M, García GA, Pérez Palacios G (January 1991). "Further studies on the antigonadotropic mechanism of action of norethisterone". The Journal of Steroid Biochemistry and Molecular Biology 38 (1): 89–93. doi:10.1016/0960-0760(91)90406-U. PMID 1825472.
- ^ F.. Macdonald (1997). Dictionary of Pharmacological Agents. CRC Press. p. 1450. ISBN 978-0-412-46630-4. Retrieved 12 May 2012.
- ^ Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 750. ISBN 978-3-88763-075-1. Retrieved 30 May 2012.
- ^ Norethisterone Acetate @ Drugs.com
- ^ http://www.drugs.com/ppa/norethindrone-acetate.html
- ^ a b Iriarte, J.; Djerassi, C.; Ringold, H. J. (1959). "Steroids. CVII.1Δ5(6)-19-Nor Steroids, a New Class of Potent Anabolic Agents2". Journal of the American Chemical Society 81 (2): 436. doi:10.1021/ja01511a042.
- ^ a b Ercoli, A.; Gardi, R. (1960). "Δ4-3-Keto Steroidal Enol Ethers. Paradoxical Dependency of Their Effectiveness on the Administration Route". Journal of the American Chemical Society 82 (3): 746. doi:10.1021/ja01488a062.
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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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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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English Journal
- Continuous Norethisterone Acetate versus Cyclical Drospirenone 3 mg/Ethinyl Estradiol 20 μg for the Management of Primary Dysmenorrhea in Young Adult Women.
- Al-Jefout M1, Nawaiseh N2.
- Journal of pediatric and adolescent gynecology.J Pediatr Adolesc Gynecol.2016 Apr;29(2):143-7. doi: 10.1016/j.jpag.2015.08.009. Epub 2015 Sep 3.
- STUDY OBJECTIVE: To evaluate the efficacy of continuous norethisterone acetate (NET-A), 5 mg (group N) vs cyclical combined oral contraceptive pill (COC) consisting of drospirenone 3 mg/ethinyl estradiol 20 μg pills (group P) in treating dysmenorrhea in young adult women.DESIGN, SETTING, AND PAR
- PMID 26342733
- Probing the binding of two 19-nortestosterone derivatives to human serum albumin: insights into the interactions of steroid hormone drugs with functional biomacromolecule.
- He J1, Wang Q1, Ma X1, Yang H1, Li S1, Xu K1, Li H1.
- Journal of molecular recognition : JMR.J Mol Recognit.2016 Mar 4. doi: 10.1002/jmr.2540. [Epub ahead of print]
- Norethindrone acetate (NETA) is a fatty acid ester of norethindrone (NET) that can convert to its more active parent compound NET when orally administered. To study the interactions of NETA and NET with human serum albumin (HSA), we applied fluorescence spectroscopy, circular dichroism (CD), and mol
- PMID 26940023
- Norethindrone acetate or dienogest for the treatment of symptomatic endometriosis: a before and after study.
- Vercellini P1, Bracco B2, Mosconi P3, Roberto A3, Alberico D4, Dhouha D2, Somigliana E4.
- Fertility and sterility.Fertil Steril.2016 Mar;105(3):734-743.e3. doi: 10.1016/j.fertnstert.2015.11.016. Epub 2015 Dec 8.
- OBJECTIVE: To assess the proportion of patients satisfied with their treatment before and after a systematic change from norethindrone acetate to dienogest as the first-line progestin for symptomatic endometriosis.DESIGN: Before and after study.SETTING: Academic department.PATIENT(S): The last 90 ne
- PMID 26677792
Japanese Journal
- Bilateral Foot Acrocyanosis in an Interferon-β-treated MS Patient
- 閉経後女性を対象とした新規E_2/NETA配合パッチRPR106522と既存のホルモン補充療法の更年期障害に対する有効性と安全性の比較(第III相臨床試験)
- 日本更年期医学会雑誌 = The Journal of the Japan Menopause Society 16(2), 220-231, 2008-10-01
- NAID 10025755487
- プロゲストーゲンの種類による標的臓器に対する効果の質的・量的相違とその発現機構(<特集>第57回学術講演会シンポジウム: ホルモン補充療法-その基礎と臨床-)
★リンクテーブル★
[★]
- 英
- norethisterone、norethisterone acetate
- ラ
- norethisteronum
- 同
- ノルエチンドロン norethindrone
- 商
- オーソ777-21、オーソM-21、シンフェーズT28、ソフィアA配合、ソフィアC配合、ノアルテン、ビホープＡ、プリモルトN、メノエイドコンビ、ルナベル配合
- 関
[★]
- 英
- norethisterone acetate
- 関
- ノルエチステロン