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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/04/17 23:03:04」(JST)

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Norethisterone (or norethindrone) (or 19-nor-17α-ethynyltestosterone) is a molecule used in some combined oral contraceptive pills, progestogen only pills and is also available as a stand-alone drug. It is a progestogen and can be used to treat premenstrual syndrome, painful periods, abnormal heavy bleeding, irregular periods, menopausal syndrome (in combination with oestrogen), or to postpone a period. It is also commonly used to help prevent uterine hemorrhage in complicated non-surgical or pre-surgical gynecologic cases. Norethindrone was the first orally highly active progestin to be synthesized. It was synthesized for the first time by chemists Luis Miramontes, Carl Djerassi, and George Rosenkranz at Syntex in Mexico City in 1951.^[1] It was the progestin used in one of the first three oral contraceptives. Its related ester, norethisterone acetate, is used for the same indications.

Chemistry

References

^ Djerassi, C.; Miramontes, L.; Rosenkranz, G.; Sondheimer, Franz (1954). "Steroids. LIV. Synthesis of 19-Nor-17α-ethynyltestosterone and 19-Nor-17α-methyltestosterone". J. Am. Chem. Soc. 76 (16): 4092–94. doi:10.1021/ja01645a010.

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1. 月経抑制のためのホルモン避妊法 hormonal contraception for suppression of menstruation
2. 慢性月経過多または無排卵性子宮出血 chronic menorrhagia or anovulatory uterine bleeding
3. 成人女性における原発性月経困難症の治療 treatment of primary dysmenorrhea in adult women
4. 避妊している女性におけるホルモン剤内服中の出血のマネージメント management of unscheduled bleeding in women using contraception
5. 避妊の概要 overview of contraception

English Journal

Ectopic pregnancy with use of progestin-only injectables and contraceptive implants: a systematic review.

Callahan R1, Yacobson I2, Halpern V2, Nanda K2.
Contraception.Contraception.2015 Dec;92(6):514-22. doi: 10.1016/j.contraception.2015.08.016. Epub 2015 Sep 10.
BACKGROUND: Use of contraception lowers a woman's risk of experiencing an ectopic pregnancy. In the case of method failure, however, progestin-only contraceptives may be more likely to result in ectopic pregnancies than some other methods such as combined hormonal and barrier contraceptives.OBJECTIV
PMID 26363431

Hormonal contraceptive use and women's risk of HIV acquisition: priorities emerging from recent data.

Ralph LJ1, Gollub EL, Jones HE.
Current opinion in obstetrics & gynecology.Curr Opin Obstet Gynecol.2015 Dec;27(6):487-95. doi: 10.1097/GCO.0000000000000228.
PURPOSE OF REVIEW: Understanding whether hormonal contraception increases women's risk of HIV acquisition is a public health priority. This review summarizes recent epidemiologic and biologic data, and considers the implications of new evidence on research and programmatic efforts.RECENT FINDINGS: T
PMID 26536211

The degradation behaviour of nine diverse contaminants in urban surface water and wastewater prior to water treatment.

Cormier G1, Barbeau B2, Arp HP3, Sauvé S1.
Environmental science. Processes & impacts.Environ Sci Process Impacts.2015 Dec 1;17(12):2051-65. doi: 10.1039/c5em00338e.
An increasing diversity of emerging contaminants are entering urban surface water and wastewater, posing unknown risks for the environment. One of the main contemporary challenges in ensuring water quality is to design efficient strategies for minimizing such risks. As a first step in such strategie
PMID 26565064

Japanese Journal

Bilateral Foot Acrocyanosis in an Interferon-β-treated MS Patient

Internal Medicine 55(3), 319-319, 2016
NAID 130005122602

子宮内膜症治療薬が原因と推測された横静脈洞血栓症の1 例

脳卒中 37(6), 423-427, 2015
NAID 130005110530

子宮内膜症治療薬が原因と推測された横静脈洞血栓症の1 例

脳卒中 advpub(0), 2015
NAID 130005101614

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★リンクテーブル★

リンク元	「ノルエチステロン」
拡張検索	「norethisterone acetate」

「ノルエチステロン」

Norethisterone
Systematic (IUPAC) name
	(17β)-17-ethynyl-17-hydroxyestr-4-en-3-one;; (8R,9S,10R,13S,14S,17S)-17-ethynyl-17-hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
Clinical data
AHFS/Drugs.com	International Drug Names
MedlinePlus	a604034
Pregnancy cat.	?
Legal status	?
Pharmacokinetic data
Bioavailability	64%
Protein binding	>95%
Half-life	7 hours
Identifiers
CAS number	68-22-4
ATC code	G03AC01 G03DC02
PubChem	CID 6230
DrugBank	DB00717
ChemSpider	5994
UNII	T18F433X4S
KEGG	D00182
ChEBI	CHEBI:7627
ChEMBL	CHEMBL1162
Chemical data
Formula	C20H26O2
Mol. mass	298.419 g/mol
	SMILES O=C4\C=C3/[C@@H]([C@H]2CC[C@]1([C@@H](CC[C@]1(C#C)O)[C@@H]2CC3)C)CC4;
	InChI InChI=1S/C20H26O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,12,15-18,22H,4-11H2,2H3/t15-,16+,17+,18-,19-,20-/m0/s1 ; Key:VIKNJXKGJWUCNN-XGXHKTLJSA-N ;
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