WordNet
- a salt or ester of acetic acid (同)ethanoate
- a synthetic progestational hormone (trade name Norlutin) used in oral contraceptives and to treat endometriosis (同)norethindrone_acetate, norethandrolone, Norlutin
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- 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）』「2015/06/09 16:28:13」(JST)
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Norethisterone acetate
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| Systematic (IUPAC) name |
| (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 |
| Clinical data |
| AHFS/Drugs.com |
International Drug Names |
| MedlinePlus |
a604034 |
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Legal status
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- AU: Prescription Only (S4)
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Routes of
administration
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Oral tablet |
| Identifiers |
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CAS Registry Number
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38673-38-0 Y |
| PubChem |
CID: 63021 |
| ChemSpider |
5627 N |
| ChEBI |
CHEBI:7628 N |
| ChEMBL |
CHEMBL1201146 N |
| Chemical data |
| Formula |
C22H28O3 |
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Molecular mass
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340.456 g/mol |
| N (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. edit
- ^ 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. edit
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Progestogens and antiprogestogens
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| Agonists |
| 1st |
- Norpregnene
- Norethisterone#/Norethisterone acetate/Norethisterone enanthate
- Etynodiol diacetate
- Pregnene
- Norpregnane
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| 2nd |
- Norpregnene
- Levonorgestrel#/Norgestrel/Norelgestromin
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| 3rd |
- 19-Nortestosterone
- Desogestrel/Etonogestrel
- Gestodene
- Norgestimate
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| 4th |
- Androstene
- 19-Norprogesterone
- Demegestone
- Nestorone
- Nomegestrol acetate
- Promegestone
- Trimegestone
- 19-Nortestosterone
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| 17-OH |
- 17-Hydroxyprogesterone acetate
- 17-Hydroxyprogesterone caproate
- Chlormadinone acetate
- Cyproterone acetate
- Medroxyprogesterone
- Medroxyprogesterone acetate#
- Megestrol acetate
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Other/
ungrouped |
- Pregnadiene
- Pregnenedione
- Dydrogesterone
- Haloprogesterone
- Lynestrenol
- Norethynodrel
- Progesterone
- Proligestone
- Quingestanol acetate
- Tibolone
- Trengestone
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Antagonists /
SPRMs |
- Antagonists
- Aglepristone
- Mifepristone
- Gestrinone
- Telapristone
- Ulipristal acetate
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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Index of reproductive medicine
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| Description |
- Anatomy
- Physiology
- Development
- sex determination and differentiation
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| Disease |
- Infections
- Congenital
- Neoplasms and cancer
- male
- female
- gonadal
- germ cell
- Other
- Symptoms and signs
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| Treatment |
- Procedures
- Drugs
- benign prostatic hypertrophy
- erectile dysfunction and premature ejaculation
- sexual dysfunction
- infection
- hormones
- androgens
- estrogens
- progestogens
- GnRH
- prolactin
- Assisted reproduction
- Birth control
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Progestogenics
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| Receptor |
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| Enzyme |
- 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: 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)
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See also: Androgenics • Estrogenics • Glucocorticoidics • Mineralocorticoidics
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UpToDate Contents
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English Journal
- Hormonal Add-Back Therapy for Females Treated With Gonadotropin-Releasing Hormone Agonist for Endometriosis: A Randomized Controlled Trial.
- DiVasta AD1, Feldman HA, Sadler Gallagher J, Stokes NA, Laufer MR, Hornstein MD, Gordon CM.
- Obstetrics and gynecology.Obstet Gynecol.2015 Jul 15. [Epub ahead of print]
- OBJECTIVE: To assess whether add-back therapy with norethindrone acetate or norethindrone acetate plus conjugated equine estrogens is superior to maintain bone health in adolescents and young women using gonadotropin-releasing hormone agonists for endometriosis. Gonadotropin-releasing hormone agonis
- PMID 26181088
- Hypertriglyceridemic Pancreatitis Caused by the Oral Contraceptive Agent Estrostep.
- Abraham M1, Mitchell J1, Simsovits D1, Gasperino J2.
- Journal of intensive care medicine.J Intensive Care Med.2015 Jul;30(5):303-7. doi: 10.1177/0885066614528083. Epub 2014 Mar 26.
- Norethindrone acetate/ethinyl estradiol (Estrostep; Warner Chilcott, Rockaway, New Jersey) is an "estrophasic" type of oral contraceptive, which combines a continuous low progestin dose with a gradually increasing estrogen dose. In clinical trials, this medication failed to produce clinically signif
- PMID 24671004
Japanese Journal
- Gabapentin does not interact with a contraceptive regimen of norethindrone acetate and ethinyl estradiol
- ラット血漿Platelet-activating factor acetylhydrolase活性に対する各種プロゲスチン(剤)の効果の多様性
- 藤上 文隆,安田 勝彦,椹木 勇
- 日本産科婦人科學會雜誌 47(6), 539-546, 1995-06-01
- … 2) 合成型のプレグナン系プロゲスチンである Medroxyprogesterone, Megestrol acetate (50mg/kg, 3日間)投与では成熟非妊娠ラット血漿PAF-AH活性は有意に上昇した. … 3) エストラン系プロゲスチンである Norethindrone acetate, Norethynodrel (50mg/kg, 3日間)投与では成熟非妊娠ラット血漿PAF-AH活性は有意に低下した. …
- NAID 110002111325
Related Links
- Norethindrone Acetate tablets, USP contain the following inactive ingredients: anhydrous lactose, magnesium stearate, methylene chloride, and microcrystalline cellulose. The USP Dissolution Test is pending.
- Norethindrone comes as a tablet to take by mouth. Norethindrone is taken on different schedules that depend on the condition that is being treated and on how well norethindrone works to treat the conditions. When norethindrone is ...