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a naturally occurring estrogenic hormone; a synthetic form is used to treat estrogen deficiency (同)oestriol

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/07/07 13:15:21」(JST)

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Estriol (also oestriol or E3) is one of the three main estrogens produced by the human body.

Biosynthesis[edit]

Human steroidogenesis, showing estriol at bottom right. In essence, it follows the pathway from dehydroepiandrosterone or DHEA (at left), but with a modified DHEA with an additional OH-group.

Estriol is only produced in significant amounts during pregnancy as it is made by the placenta from 16-hydroxydehydroepiandrosterone sulfate (16-OH DHEAS),^[1] an androgen steroid made in the fetal liver and adrenal glands.

The human placenta produces pregnenolone and progesterone from circulating cholesterol. Pregnenolone is converted in the fetal adrenal gland into dehydroepiandrosterone (DHEA), a C19 steroid, then subsequently sulfonated to dehydroepiandrosterone sulfate (DHEAS). DHEAS is converted to 16-OH DHEAS in the fetal liver. The placenta converts 16-OH DHEAS to estriol, and is the predominant site of estriol synthesis.

Levels[edit]

Levels of estriol in non-pregnant women do not change much after menopause, and levels are not significantly different from levels in men.

Therapeutic use[edit]

In pregnant women with multiple sclerosis, estriol reduces the disease's symptoms noticeably,^[2] according to researchers at UCLA's Geffen Medical School.

Estriol can be a weak or strong estrogen depending on if it is given acutely or chronically when given to immature animals, but is an antagonist when given in combination with estradiol.^[3] Estriol may play a role in the development of breast cancer, but based on in vitro research does appear to act as an antagonist to the G-protein coupled estrogen receptor.^[4] Though estriol is used as part of the primarily North American phenomenon of bioidentical hormone replacement therapy, it is not approved for use by the FDA or Health Canada. Though initial research in the 1970s suggested it could be used therapeutically as an estrogen, subsequent research failed to confirm this hypothesis.^[5]^[6]

Use in screening[edit]

Estriol can be measured in maternal blood or urine and can be used as a marker of fetal health and wellbeing. DHEA-S is produced by the adrenal cortex of the fetus. This is converted to estriol by the placenta.

If levels of "unconjugated estriol" are abnormally low in a pregnant woman, this may indicate chromosomal or congenital anomalies like Down syndrome or Edward's syndrome. It is included as part of the triple test & quadruple test for antenatal screening for fetal anomalies.

Because many pathological conditions in a pregnant woman can cause deviations in estriol levels, these screenings are often seen as less definitive of fetal-placental health than non-stress testing. Conditions which can create false positives and false negatives in estriol testing for fetal distress include preeclampsia, anemia, and impaired kidney function.^[7]

References[edit]

^ Raju U, Bradlow HL, Levitz M (1990). "Estriol-3-sulfate in human breast cyst fluid. Concentrations, possible origin, and physiologic implications". Ann. N. Y. Acad. Sci. 586: 83–7. doi:10.1111/j.1749-6632.1990.tb17793.x. PMID 2141460.
^ Sicotte NL, Liva SM, Klutch R, Pfeiffer P, Bouvier S, Odesa S, Wu TC, Voskuhl RR (October 2002). "Treatment of multiple sclerosis with the pregnancy hormone estriol". Ann. Neurol. 52 (4): 421–8. doi:10.1002/ana.10301. PMID 12325070.
^ Melamed M, Castaño E, Notides AC, Sasson S (November 1997). "Molecular and kinetic basis for the mixed agonist/antagonist activity of estriol". Mol. Endocrinol. 11 (12): 1868–78. doi:10.1210/me.11.12.1868. PMID 9369454.
^ Lappano R, Rosano C, De Marco P, De Francesco EM, Pezzi V, Maggiolini M (May 2010). "Estriol acts as a GPR30 antagonist in estrogen receptor-negative breast cancer cells". Mol. Cell. Endocrinol. 320 (1–2): 162–70. doi:10.1016/j.mce.2010.02.006. PMID 20138962.
^ Sites CK (March 2008). "Bioidentical hormones for menopausal therapy". Women's Health (Lond Engl) 4 (2): 163–71. doi:10.2217/17455057.4.2.163. PMID 19072518. (free subscription required)
^ Derzko, C (2009). "Bioidentical Hormone Therapy at Menopause" (pdf). Endocrinology Rounds 9 (6): 1–6.
^ Pagana TJ, Pagana KD (2009). Mosby's Manual of Diagnostic and Laboratory Tests. St. Louis: Mosby. p. 240. ISBN 0-323-05747-0.

UpToDate Contents

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1. Treatment of genitourinary syndrome of menopause (vulvovaginal atrophy)
2. まれな先天性副腎過形成 uncommon congenital adrenal hyperplasias
3. ダウン症の母体血清スクリーニングに関する臨床検査の問題 laboratory issues related to maternal serum screening for down syndrome
4. ダウン症候群およびトリソミー18のスクリーニングのための、妊娠初期のcombined testおよびintegrated test first trimester combined test and integrated tests for screening for down syndrome and trisomy 18
5. Management of hereditary hemorrhagic telangiectasia

English Journal

Determination of two progestin metabolites (17α-hydroxypregnanolone and pregnanediol) and different classes of steroids (androgens, estrogens, corticosteroids, progestins) in rivers and wastewaters by high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS).

Zhang K1, Fent K2.
The Science of the total environment.Sci Total Environ.2018 Jan 1;610-611:1164-1172. doi: 10.1016/j.scitotenv.2017.08.114. Epub 2017 Aug 30.
PMID 28847137

Expression of a new laccase from Moniliophthora roreri at high levels in Pichia pastoris and its potential application in micropollutant degradation.

Bronikowski A1,2, Hagedoorn PL3, Koschorreck K1,2, Urlacher VB4,5.
AMB Express.AMB Express.2017 Dec;7(1):73. doi: 10.1186/s13568-017-0368-3. Epub 2017 Mar 29.
PMID 28357784

Sensitive detection of estriol hormone in creek water using a sensor platform based on carbon black and silver nanoparticles.

Raymundo-Pereira PA1, Campos AM2, Vicentini FC3, Janegitz BC4, Mendonça CD2, Furini LN5, Boas NV2, Calegaro ML2, Constantino CJL5, Machado SAS2, Oliveira ON Jr6.
Talanta.Talanta.2017 Nov 1;174:652-659. doi: 10.1016/j.talanta.2017.06.058. Epub 2017 Jun 27.
PMID 28738637

Japanese Journal

Differences in Apoptotic Status in the Bovine Placentome between Spontaneous and Induced Parturition

HIRAYAMA Hiroki,USHIZAWA Koichi,TAKAHASHI Toru [他],SAWAI Ken,MORIYASU Satoru,KAGEYAMA Soichi,MIURA Ryotaro,MATSUI Motozumi,FUKUDA Shigeo,NAITO Akira,FUJII Takashi,MINAMIHASHI Akira
The Journal of reproduction and development 58(5), 585-591, 2012-10-01
… Cows delivered i) after the administration of dexamethasone followed by prostaglandin F2α and estriol, ii) after the administration of prostaglandin F2α and estriol or iii) spontaneously. …
NAID 10031123304

Sonophotolytic Degradation of Estriol at Various Ultraviolet Wavelength in Aqueous Solution

Na Seungmin,Park Beomguk,Cho Eunju [他],Koda Shinobu,Khim Jeehyeong
Jpn J Appl Phys 51(7), 07GD11-07GD11-4, 2012-07-25
… This study investigated degradation of the hormone estriol by sonolysis, photolysis and sonophotolysis at various UV wavelengths. … The dominant reaction mechanism of estriol in sonolysis was estimated as hydroxyl radical reaction by the addition of tert-butanol (t-BuOH), which is a common hydroxyl radical scavenger. …
NAID 150000104372

2Pb4-7 超音波と光の併用によるエリストールの分解に対する紫外線波長の効果(ポスターセッション)

Na Seungmin,Cai Jinhua,Park Beomguk,Khim Jeehyeong
超音波エレクトロニクスの基礎と応用に関するシンポジウム講演論文集 (32), 245-246, 2011-11-08
NAID 110008913396

Related Pictures

★リンクテーブル★

国試過去問	「082A044」
リンク元	「エストリオール」「ET」「E3」
拡張検索	「estriol tripropionate」「estriol benzoate diacetate」

「082A044」

Estriol
Identifiers
CAS number	50-27-1
PubChem	5756
ChemSpider	5553
UNII	FB33469R8E
DrugBank	DB04573
KEGG	C05141
MeSH	Estriol
ChEBI	CHEBI:27974
ChEMBL	CHEMBL193482
ATC code	G03CA04,G03CC06
Jmol-3D images	Image 1
	SMILES Oc1cc3c(cc1)[C@H]2CC[C@@]4([C@@H](O)[C@H](O)C[C@H]4[C@@H]2CC3)C ;
	InChI InChI=1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,17+,18+/m1/s1 ; Key: PROQIPRRNZUXQM-ZXXIGWHRSA-N InChI=1/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,17+,18+/m1/s1; Key: PROQIPRRNZUXQM-ZXXIGWHRBN ;
Properties
Molecular formula	C18H24O3
Molar mass	288.38 g mol−1
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references

　　[★]

急速遂娩の適応となるのはどれか

(1) accelerationの出現一過性頻脈
(2) NST nonreactive
(3) late decelerationの出現遅発一過性徐脈
(4) 胎児末梢血のpH7.10
(5) 母体尿中estriol値10mg/day

a. (1)(2)
b. (1)(5)
c. (2)(3)
d. (3)(4)
e. (4)(5)

[正答]

「エストリオール」

　　[★]

英: estriol, E3, ET
ラ: oestriolum
商: エストリール、ホーリン、メリストラーク
関: 生殖器官用剤

図：NGY.47(グラフ)

概念

女性で産生されるホルモン
子宮内膜に対する作用はほとんど無く、主に腟上皮や頚管に作用することから、膣炎、子宮頚管炎、および子宮膣部びらんの治療に用いられる。(参考1 QB.Q-229)

妊娠中の検査としての意義

NGY.111

最近は胎児胎盤機能検査としては使われなくなっている(代わりにNST,BPS,超音波ドプラ、CSTを使用)

胎児内分泌機能、胎盤機能、母体-胎盤-胎児血液循環能

尿中エストリオール

概念：

。妊娠末期に向かって増加していくが、低値で胎児・胎盤系の機能不全が示唆される。　→　潜在性胎児仮死

解釈：(妊娠末期)正常:40mg/day, 注意:≦20mg/day, 危険≦10mg/day

ex. 082A044

高値

多胎妊娠

低値

胞状奇胎、無脳児妊娠、子宮内胎児死亡、胎児赤芽球症、子宮内胎児発育遅延、胎児胎盤機能不全、胎盤サルファターゼ欠損症、胎盤アロマターゼ欠損症、重症妊娠高血圧症候群

産生

(母体)コレステロール　→　(胎盤)プレグネノロン　→　(胎児副腎)デヒドロエピアンドロステロンサルフェート(DHEA-S)　→　(胎児肝臓)16α-OH-DHEA-S　→　(胎盤)エストリオール

適応

ホーリンＶ腟用錠1mg

腟炎(老人，小児及び非特異性)，子宮頸管炎並びに子宮腟部びらん

参考

ホーリンＶ腟用錠1mg - 添付文書

http://www.info.pmda.go.jp/go/pack/2529701H2046_1_04/2529701H2046_1_04

「ET」

　　[★]

「E3」

　　[★]

エストリオール estriol

「estriol tripropionate」

　　[★]

トリプロピオン酸エストリオール

関: estriol、estriol benzoate diacetate

「estriol benzoate diacetate」

　　[★]

安息香酸・酸エストリオール

関: estriol、estriol tripropionate

[pmid2141460-1] Raju U, Bradlow HL, Levitz M (1990). "Estriol-3-sulfate in human breast cyst fluid. Concentrations, possible origin, and physiologic implications". Ann. N. Y. Acad. Sci. 586: 83–7. doi:10.1111/j.1749-6632.1990.tb17793.x. PMID 2141460.

[pmid12325070-2] Sicotte NL, Liva SM, Klutch R, Pfeiffer P, Bouvier S, Odesa S, Wu TC, Voskuhl RR (October 2002). "Treatment of multiple sclerosis with the pregnancy hormone estriol". Ann. Neurol. 52 (4): 421–8. doi:10.1002/ana.10301. PMID 12325070.

[pmid9369454-3] Melamed M, Castaño E, Notides AC, Sasson S (November 1997). "Molecular and kinetic basis for the mixed agonist/antagonist activity of estriol". Mol. Endocrinol. 11 (12): 1868–78. doi:10.1210/me.11.12.1868. PMID 9369454.

[pmid20138962-4] Lappano R, Rosano C, De Marco P, De Francesco EM, Pezzi V, Maggiolini M (May 2010). "Estriol acts as a GPR30 antagonist in estrogen receptor-negative breast cancer cells". Mol. Cell. Endocrinol. 320 (1–2): 162–70. doi:10.1016/j.mce.2010.02.006. PMID 20138962.

[Sites-5] Sites CK (March 2008). "Bioidentical hormones for menopausal therapy". Women's Health (Lond Engl) 4 (2): 163–71. doi:10.2217/17455057.4.2.163. PMID 19072518. (free subscription required)

[Derzko-6] Derzko, C (2009). "Bioidentical Hormone Therapy at Menopause" (pdf). Endocrinology Rounds 9 (6): 1–6.

[isbn0-323-05747-0-7] Pagana TJ, Pagana KD (2009). Mosby's Manual of Diagnostic and Laboratory Tests. St. Louis: Mosby. p. 240. ISBN 0-323-05747-0.

匿名

検索

案内

案内

estriol