エストラジオール 化学特性,用途語,生産方法
外観
白色～わずかにうすい褐色, 結晶～粉末又は顆粒
定義
本品は、卵胞ホルモンであり、次の化学式で表される。
溶解性
1,4-ジオキサンに易溶, アセトンにやや易溶, エタノールにやや難溶, 水にほとんど不溶。
解説
エストラジオール，白色の結晶または結晶性粉末．融点173～179 ℃．[α]D20"＋76～＋83°(ジオキサン)．水にほとんど難溶，ジオキサンに可溶．アセトンにやや易溶，エタノールにやや難溶，ごま油に難溶．代表的な発情ホルモンであり，プロゲステロンとともに子宮内膜を増殖させて周期的な変化を誘発し，妊卵の着床，妊娠の成立に重要な役割を果たしている．無月経，不妊症，更年期障害などの治療に用いられる．エストラジオールのエステル誘導体には17-ベンゾイルエストラジオール3-ベンゾエートなどが知られている．
森北出版「化学辞典（第2版）
用途
生体内代謝経路の研究、種々の癌に及ぼす性ホルモンの影響などの研究用。
用途
卵胞ホルモン剤です。
用途
卵胞ホルモン剤です。
化粧品の成分用途
皮膚コンディショニング剤
効能
月経障害治療薬, エストロゲン受容体作動薬
製造
発情ホルモンの一つ．妊婦尿，ヒト胎盤，ウマの睾丸，馬尿などから抽出される．人体に存在するおもな発情ホルモンのうちで，もっとも生物学的活性が強い．エストロンの還元またはジオスゲニン，コレステロール，スチグマステロールなどから誘導されるデヒドロエピアンドロステロンより部分合成により得られるエストラジオール．
商品名
エストラーナ (久光製薬); ジュリナ (バイエル薬品); ディビゲル (ポーラファルマ); ル・エストロジェル (資生堂)
使用上の注意
吸湿性あり
化学的特性
White or almost white, crystalline powder or colourless crystals.
使用
17β-Estradiol is the major estrogen secreted by the premenopausal ovary.This compound is a contaminant of emerging concern (CECs). Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA), environmental, and food contaminants.
定義
ChEBI: The 17beta-isomer of estradiol.
主な応用
β-Estradiol has been used:
for the in vitro maturation of bovine cumulus-oocyte complexes (COCs)
as a supplement in in vitro maturation medium (IVM), which is used as a control medium
in estrogen-induction assay
獲得抵抗性
Estradiol is the most potent endogenous estrogen, exhibiting high affinity for the ER and high potency when administered
parenterally. When administered orally, estradiol is promptly conjugated in the intestine and oxidatively metabolized by the liver,
resulting in its low oral bioavailability and therapeutic effectiveness.
一般的な説明
Estradiol, estra-1,3,5(10)-triene-3,17β-diol, is the most activeof the natural steroid estrogens. Although its 17β-OHgroup is vulnerable to bacterial and enzymatic oxidation toestrone, it can be temporarily protected as anester at C3 or C17, or permanently protected by adding a17α-alkyl group (e.g., 17α-ethinyl estradiol, the most commonlyused estrogen in oral contraceptives). The increasedoil solubility of the 17β-esters (relative to estradiol) permitsthe esters to remain in oil at the IM injection site for extendedperiods. These derivatives illustrate the principles of steroidmodification. Transdermal estradiolproducts avoid first-pass metabolism, allowing estradiol tobe as effective as oral estrogens for treating menopausalsymptoms. A new transdermal spray, Evamist, was approvedin 2007. Estradiol itself is typically not very effective orallybecause of rapid metabolism, but an oral formulation of micronizedestradiol that allows more rapid absorption of thedrug is available (Estrace). In addition to the oral and transdermalproducts, estradiol is also available in gel, cream, andvaginal ring formulations. The commercially available estradiolesters are the following:
Estradiol 3-acetate, USP (oral; vaginal ring)
Estradiol 17-valerate, USP (IM injection)
Estradiol 17-cypionate, USP (IM injection).
危険性
A carcinogen (OSHA).
生物活性
Endogenous estrogen receptor (ER) agonist (K i values are 0.12 and 0.13 nM for ER α and ER β respectively). Also high affinity ligand at membrane estrogen GPR30 receptors.
接触アレルゲン
Natural estradiol, used in transdermal systems for hormonal
substitution, can induce allergic contact dermatitis,
with the risk of systemic contact dermatitis after
oral reintroduction.
作用機序
The
most potent naturally occurring estrogen in mammals. It is synthesized
primarily in the ovary, and also in the testis, adrenal
gland and placenta, and to a limited extent by peripheral tissues
(e.g., liver, fat, and skeletal muscle) from androstenedione and
testosterone. It is responsible for the development of secondary
sex characteristics in the female at puberty (i.e., growth and
development of the vagina, uterus and fallopian tubes, enlargement
of the breasts, and growth and maturation of long bones).
安全性プロファイル
Confirmed carcinogen
with experimental carcinogenic,
neoplastigenic, tumorigenic, and
teratogenic data. A promoter. Human
reproductive effects by ingestion: ferthty
effects. Experimental reproductive effects.
Human mutation data reported. A steroid
hormone much used in medicine. When
heated to decomposition it emits acrid
smoke and irritating fumes.
職業ばく露
The working environment may be
contaminated during sex hormone manufacture, especially
during the extraction and purification of natural steroid hormones; grinding of raw materials; handling of powdered
products and recrystallization. Airborne particles of sex
hormones may be absorbed through the skin, ingested or
inhaled. Enteric absorption results in quick inactivation of
sex hormones in the liver. The rate of inactivation is
decreased for the oral, alkylated steroid hormones (methyl
testosterone, anabolic steroids, etc.). Sex hormones may
accumulate and reach relatively high levels even if their
absorption is intermittent. Consequently, repeated absorption of small amounts may be detrimental to health.
Intoxication by sex hormones may occur in almost all the
exposed workers if preventive measures are not taken. The
effect in the industrial sector is more successful than
the agricultural one (chemical caponizing of cockerels by
stilbestrol implants and incorporation of estrogens in feed
for body weight gain promotion in beef cattle), where measures taken are summary and the number of cases of intoxication is consequently bigger
輸送方法
UN3249 Medicine, solid, toxic, n.o.s., Hazard
Class: 6.1; Labels: 6.1-Poisonous materials
純化方法
17-Estradiol (previously known as -estradiol) is purified by chromatography on SiO2 (toluene/EtOAc 4:1) and recrystallised from CHCl3/hexane or 80% EtOH. It is stable in air, is insoluble in H2O, and is precipitated by digitonin. The UV has max at 225 and 280 nm. The diacetate [3434-88-6] has m 97-98o and forms leaflets from aqueous EtOH. The 3-benzoate crystallises from aqueous MeOH withm 193o and [] D 25 +58o to 63o (c 1, dioxane). [Meischer & Scholz Helv Chim Acta 20 263, 1237 1937, Biochem J 32 1273 1938, Oppolzer & Roberts Helv Chim Acta 63 1703 1980, Inhoffen & Zühlsdorff Chem Ber 7 4 1914 1941, Beilstein 6 IV 6611.]
エストラジオール 上流と下流の製品情報
原材料
準備製品