norethynodrel

Norethynodrel
Systematic (IUPAC) name
	(8S,9S,13S,14S,17S)-17-ethynyl-17-hydroxy-13-methyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
Identifiers
CAS Registry Number	68-23-5
ATC code	G03FA09
PubChem	CID: 6231
ChemSpider	5995
UNII	88181ACA0M
ChEMBL	CHEMBL1387
Synonyms	Noretynodrel; (17β)-17-ethynyl-17-hydroxyestr-5(10)-en-3-one
Chemical data
Formula	C20H26O2
Molecular mass	298.419 g/mol
	SMILES O=C4CCC\1=C(\CC[C@@H]2[C@@H]/1CC[C@]3([C@H]2CC[C@]3(C#C)O)C)C4 ;
	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/h1,16-18,22H,4-12H2,2H3/t16-,17-,18+,19+,20+/m1/s1 ; Key:ICTXHFFSOAJUMG-SLHNCBLASA-N ;
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WordNet

a progesterone derivative used in oral contraceptives and in the control of menstruation and the treatment of abnormal uterine bleeding

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/08/19 08:09:38」(JST)

Norethynodrel is a steroidal progestin which was formerly used in Enovid, the first oral contraceptive.^[1]^[2]

^ Edgren, R. A. (1994). "Early oral contraceptive history: Norethynodrel is not a prohormone". Steroids 59 (1): 58–59. doi:10.1016/0039-128x(94)90047-7. PMID 8140604. edit
^ "FDA Approved Drug Products". FDA.

This drug article relating to the genito-urinary system is a stub. You can help Wikipedia by expanding it.

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Penning TM1, Chen M2, Jin Y2.
The Journal of steroid biochemistry and molecular biology.J Steroid Biochem Mol Biol.2015 Jul;151:93-101. doi: 10.1016/j.jsbmb.2014.12.003. Epub 2014 Dec 10.
Many steroid hormones contain a Δ(4)-3-ketosteroid functionality that undergoes sequential reduction by 5α- or 5β- steroid reductases to produce 5α- or 5β-dihydrosteroids; and a subsequent 3-keto-reduction to produce a series of isomeric tetrahydrosteroids. Apart from steroid 5α-reductase all
PMID 25500069

Differential effects of synthetic progestagens on neuron survival and estrogen neuroprotection in cultured neurons.

Jayaraman A1, Pike CJ2.
Molecular and cellular endocrinology.Mol Cell Endocrinol.2014 Mar 25;384(1-2):52-60. doi: 10.1016/j.mce.2014.01.003. Epub 2014 Jan 11.
Progesterone and other progestagens are used in combination with estrogens for clinical purposes, including contraception and postmenopausal hormone therapy. Progesterone and estrogens have interactive effects in brain, however interactions between synthetic progestagens and 17β-estradiol (E2) in n
PMID 24424444

Bimodal binding and free energy of the progesterone receptor in the induction of female sexual receptivity by progesterone and synthetic progestins.

Kubli-Garfias C1, González-Flores O, Gómora-Arrati P, González-Mariscal G, Vázquez-Ramírez R, Beyer C.
The Journal of steroid biochemistry and molecular biology.J Steroid Biochem Mol Biol.2013 Jan;133:43-50. doi: 10.1016/j.jsbmb.2012.08.010. Epub 2012 Aug 31.
Synthetic progestins (SPs) are used for regulation of fertility, contraception and hormone replacement therapy. The acetylated medroxyprogesterone (MPA), megestrol (MGA) and chlormadinone (CLA) are related to progesterone (P). Other SPs are 19-nortestosterone derivatives such as: norethisterone (NET
PMID 22960752

p-Toluenesulfonyl isocyanate as a novel derivatization reagent to enhance the electrospray ionization and its application in the determination of two stereo isomers of 3-hydroxyl-7-methyl-norethynodrel in plasma

ZUO Ming,GAO Ming-jie,LIU Zhen,CAI Lei,DUAN Geng-Li
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 814(2), 331-337, 2005-01-25
NAID 10018273062

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
… 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

藤上文隆
関西医科大学雑誌 47(1-2), 20-28, 1995
… かった.<BR>3)合成型のプレグナン系プロゲスチンであるMedroxyprogesterone,Megestrolacetate投与では成熟非妊娠ラットplasmaPAF-AH活性は有意に上昇した.<BR>4)エストラン系プロゲスチンであるNorethindrone acetate, Norethynodrel投与では成熟非妊娠ラットplasmaPAF-AH活性は有意に低下した.<BR>5)PAF投与実験より,成熟非妊娠ラットのPAFの致死量はほぼ20nmol/kgと思われる.<BR>6)17a-Ethynylestradiol,Norethindroneacetate前処理にてPAF-AH活性が低 …
NAID 130004701379