estrone

エストロン E1 　

WordNet

1. a naturally occurring weak estrogenic hormone secreted by the mammalian ovary; synthesized (trade name Estronol) and used to treat estrogen deficiency (同)oestrone, theelin, Estronol

PrepTutorEJDIC

1. ミネストローネ(肉・野菜・パスタなどを入れて煮たスープ)

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/06/17 21:05:40」(JST)

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Estrone

Systematic (IUPAC) name
(8R,9S,13S,14S)-3-hydroxy-13-methyl- 6,7,8,9,11,12,13,14,15,16- decahydrocyclopenta[a]phenanthren- 17- one
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Protein binding	>95%
Biological half-life	19 hours
Identifiers
CAS Number	53-16-7 Y
ATC code	G03CA07 (WHO) G03CC04 (WHO)
PubChem	CID 5870
IUPHAR/BPS	2818
DrugBank	DB00655 N
ChemSpider	5660 Y
UNII	2DI9HA706A Y
KEGG	D00067 N
ChEBI	CHEBI:17263 N
ChEMBL	CHEMBL1405 N
Chemical data
Formula	C18H22O2
Molar mass	270.366 g/mol
SMILES O=C4[C@]3(CC[C@@H]2c1ccc(O)cc1CC[C@H]2[C@@H]3CC4)C
InChI InChI=1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19H,2,4,6-9H2,1H3/t14-,15-,16+,18+/m1/s1 N Key:DNXHEGUUPJUMQT-CBZIJGRNSA-N N
Physical data
Melting point	254.5 °C (490.1 °F)
NY (what is this?)  (verify)

Estrone (E1, and also oestrone) is an estrogenic hormone secreted by the ovary as well as adipose tissue with the chemical name of 3-hydroxyestra-1,3,5(10)-triene-17-one and the chemical formula C₁₈H₂₂O₂. Estrone is an odorless, solid crystalline powder, white in color with a melting point of 254.5 °C and a specific gravity of 1.23. Estrone is one of several natural estrogens, which also include estriol and estradiol. Estrone is the least abundant of the three hormones; estradiol is present almost always in the reproductive female body, and estriol is abundant primarily during pregnancy.

Estrone is known to be a carcinogen for human females as well as a cause of breast tenderness or pain, nausea, headache, hypertension, and leg cramps in the context of non-endogenous exposure. In men, estrone has been known to cause anorexia, nausea, vomiting, and erectile dysfunction. Estrone is relevant to health and disease states because of its conversion to estrone sulfate, a long-lived derivative. Estrone sulfate acts as a reservoir that can be converted as needed to the more active estradiol. It is the predominant estrogen in postmenopausal women.

Estrone was discovered and isolated by German chemist Adolf Butenandt.

Nomenclature

The official chemical name of estrone is 3-hydroxyestra-1,3,5(10)-triene-17-one with the chemical formula C₁₈H₂₂O₂.

Estrone is also named aquacrine, bestrone, crinovaryl, folliculin, 1,3,5-estratriene-3-ol-17-one, estro-a, estronol, erystogen, 3-hydroxyestra-1,3,5(10)-trien-17-one, kestrone 5, propagon-s, menagen, theelin, theogen, destrone, aquacrine, crystogen, oestrin, 1,3,5(10)-estratrien-3-ol-17-one, 1,3,5(10)-oestratrien-3-ol-17-one, and oestrone.

Biosynthesis

Estrone is synthesized via aromatase from androstenedione, a derivative of progesterone. The conversion consists of the de-methylation of C-19 and the aromaticity of the 'A' ring. This reaction is similar to the conversion of testosterone to estradiol.

Physical and chemical properties

Estrone is a white, solid crystalline powder that is odorless. It has a melting point of 254.5 °C (490 °F) and has a specific gravity of 1.23. At high temperatures estrone is combustible and the products of combusting estrone are carbon monoxide (CO) and carbon dioxide (CO₂).

Exposure to estrone

Women

Estrone has been proven to be a known carcinogen for human females. The Occupational Safety and Health Administration (OSHA) classifies estrone as an OSHA Select carcinogen. Exposure to estrone can cause breast tenderness or pain, cervical hyper secretion, menstrual disorders including menorrhagia and metrorrhagia, nausea, headache, hypertension, leg cramps, vision disturbances, and endometriosis pain in women. Mothers lactating can also experience a decrease in the production of breast milk. Estrone can be found in the urine of pregnant women and can also be excreted in feces.

Men

Exposure to estrone can cause anorexia, nausea, vomiting, edema, feminization including gynecomastia and erectile dysfunction in men.

Eyes

If exposure of estrone to the eyes occurs, contacts should be removed and rinsed with water for 15 minutes. If any irritation occurs medical attention may be necessary. Exposure of estrone to the eyes can be prevented through the use of safety goggles.

Skin

If exposure of estrone to the skin occurs, the effected area should be washed with soap and water and then covered with an emollient or moisturizer. Medical attention may be necessary if irritation persists. Exposure of estrone can be prevented through the use protective gloves, the wearing of pants, shirts that cover the entire upper body, and lab coat.

Inhalation

If inhalation of estrone occurs, one should move into the fresh air. If breathing ceases, artificial respiration should be administered. For difficult breathing, oxygen should be given. Medical attention may be necessary if breathing continues to be difficult. Inhalation of estrone can be prevented through the use of a dust respirator.

Ingestion

If estrone is ingested, vomiting should not be induced. Medical attention may be necessary.

Environmental effects

The use of estrone in norsteroid, a derivative of steroids, and in medications can cause its release into the environment through waste streams.

Additional images

• Androstenedione converting to estrone.

• Steroidogenesis

References

UpToDate Contents

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• 1. 閉経期のホルモン療法で用いる製剤 preparations for menopausal hormone therapy
• 2. 副腎アンドロゲンの測定 measurement of adrenal androgens
• 3. 女性化乳房の疫学、病態生理、および原因 epidemiology pathophysiology and causes of gynecomastia
• 4. 多嚢胞性卵巣症候群におけるステロイドホルモン代謝 steroid hormone metabolism in polycystic ovary syndrome
• 5. 膣萎縮症の治療 treatment of vaginal atrophy

English Journal

• Application of radio-immunoassays to assess the fate of estrogen EDCs in full scale wastewater treatment plants.

• Surujlal-Naicker S, Bux F.Sourcea Institute for Water and Wastewater Technology, Durban University of Technology , South Africa.
• Journal of environmental science and health. Part A, Toxic/hazardous substances & environmental engineering.J Environ Sci Health A Tox Hazard Subst Environ Eng.2013;48(1):37-47. doi: 10.1080/10934529.2012.707832.
• Wastewater effluents have been documented as major contributors of hormone endocrine disrupting compounds (EDCs) in to the aquatic ecosystem. The need for rapid, simple and cost effective methods to detect these EDCs has increased. The use of Radio-immunoassays (RIA) were assessed to determine the f
• PMID 23030386

• Body Size in Relation to Urinary Estrogens and Estrogen Metabolites (EM) Among Premenopausal Women during the Luteal Phase.

• Xie J, Eliassen AH, Xu X, Matthews CE, Hankinson SE, Ziegler RG, Tworoger SS.SourceChanning Division of Network Medicine, Department of Medicine, Brigham and Women's Hospital and Harvard Medical School, 181 Longwood Avenue, Boston, MA, 02115, USA.
• Hormones & cancer.Horm Cancer.2012 Dec;3(5-6):249-60. doi: 10.1007/s12672-012-0120-z. Epub 2012 Aug 4.
• Estrogen metabolism profiles may play an important role in the relationship between body size and breast carcinogenesis. Previously, we observed inverse associations between current body mass index (BMI) and plasma levels of parent estrogens (estrone and estradiol) among premenopausal women during b
• PMID 23011724

Japanese Journal

• Comparative Cytotoxic Activities of the Propanamide and Spiro-γ-lactone Derivatives of Δ-17α- and 17β-Estradiol Stereoisomers against Human Cancer Cell Lines

• TAMEGAI Hideyuki,OGAWA Shoujiro,KONISHI Hiroaki 他
• 日本大学文理学部自然科学研究所研究紀要 (47), 497-501, 2012-00-00
• NAID 40019303161

• Estrogenic Activity Profiles of River Water in Kobe, Japan Assessed by <I>In Vitro</I> Bioassay and Chemical Analysis

• YAMAGUCHI Takako,INOUE Naoki,YAMAZAKI Hiroyasu
• Journal of Water and Environment Technology 10(3), 289-301, 2012
• … Estrone (E1) was found at sites A-2, A-3 and ESTP, while E2 was found at site A-3 and ESTP. …
• NAID 130001907917

• Involvement of Specific Transport System on Uptake of Lactone Form of SN-38 in Human Intestinal Epithelial Cell Line Caco-2

• Ueno Yusuke,Matsuda Hiroko,Mizutani Hideki,Iwamoto Takuya,Okuda Masahiro
• Biological and Pharmaceutical Bulletin 35(1), 54-58, 2012
• … In contrast, concomitant sulfobromophthalein, taurocholate and estrone 3-sulfate significantly increased SN-38L uptake. …
• NAID 130001872342

Related Links

• Estrone | definition of estrone by Medical dictionary

estrone [es´trōn] an estrogen isolated from pregnancy urine, the human placenta, and palm kernel oil, and also prepared synthetically; used in estrogen replacement therapy for hypogonadism, ovariectomy, primary ovarian failure, atrophic vaginitis ...

• Estrone | Definition of Estrone by Merriam-Webster

:a natural estrogenic hormone that is a ketone C 18 H 22 O 2 found in the body chiefly as a metabolite of estradiol, that is also secreted especially by the ovaries ... Seen and Heard What made you want to look up estrone? Please ...

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estrone, E1, EO

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oestronum

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• 多嚢胞性卵巣症候群

参考

• 1. [charged] Steroid hormone metabolism in polycystic ovary syndrome - uptodate [1]

「EO」

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• 妊娠高血圧症候群の早発型(early onset type, EO)

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