Estrone

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Estrone
Estron.svg
Estrona3D.png
Clinical data
ATC code G03CA07 (WHO) G03CC04 (WHO)
Legal status
Legal status
Pharmacokinetic data
Protein binding >95%[citation needed]
Biological half-life 19 hours[citation needed]
Identifiers
CAS Number 53-16-7 YesY
PubChem (CID) 5870
IUPHAR/BPS 2818
DrugBank DB00655 N
ChemSpider 5660 YesY
UNII 2DI9HA706A YesY
KEGG D00067 N
ChEBI CHEBI:17263 N
ChEMBL CHEMBL1405 N
ECHA InfoCard 100.000.150
Chemical and physical data
Formula C18H22O2
Molar mass 270.366 g/mol
3D model (Jmol) Interactive image
Melting point 254.5 °C (490.1 °F)
 NYesY (what is this?)  (verify)

Estrone (American English) (abbreviated as E1), or oestrone (British English), also known as estra-1,3,5(10)-trien-3-ol-17-one, is an estrogenic hormone secreted by the ovary as well as adipose tissue It is one of several natural estrogens, which also include estriol and estradiol. Estrone is the least abundant of the three hormones;[citation needed] estradiol is present almost always in the reproductive female body, and estriol is abundant primarily during pregnancy.

Estrone was discovered and isolated by German chemist Adolf Butenandt. It was formerly marketed under the brand name Theelin in the United States for intramuscular injection, but this formulation is no longer available.[1]

Biosynthesis[edit]

Estrone is synthesized via aromatase from 4-androstenedione. The conversion consists of the demethylation of the C19 position and the aromatization of the A ring. This reaction is similar to the conversion of testosterone to estradiol via aromatase. Estrone is also reversibly produced from estradiol via 17β-hydroxysteroid dehydrogenase.

Chemistry[edit]

Estrone has the chemical name 3-hydroxyestra-1,3,5(10)-triene-17-one or estra-1,3,5(10)-triene-3-ol-17-one and the chemical formula C18H22O2.[2] It is an odorless, solid crystalline powder, white in color with a melting point of 254.5 °C (490 °F) and a specific gravity of 1.23.[2][3][4] At high temperatures estrone is combustible and the products of combusting estrone are carbon monoxide (CO) and carbon dioxide (CO2).[3]

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, crystogen, oestrin, 1,3,5(10)-estratrien-3-ol-17-one, 1,3,5(10)-oestratrien-3-ol-17-one, and oestrone.[2][3]

Environmental exposure[edit]

Estrone is known to be a carcinogen for human females[citation needed] as well as a cause of breast tenderness or pain, nausea, headache, hypertension, and leg cramps in the context of non-endogenous exposure.[3][5] In men, estrone has been known to cause anorexia, nausea, vomiting, and erectile dysfunction.[2] 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.[6]

The use of estrone in norsteroid, a derivative of steroids, and in medications can cause its release into the environment through waste streams.[5]

Women[edit]

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.[2][3] Estrone can be found in the urine of pregnant women and can also be excreted in feces.[5] Estrone is commonly produced in large quantities of the livers of transgender women who take oral estradiol. This is a result of first pass metabolism converting estradiol to estrone.

Men[edit]

Exposure to estrone can cause anorexia, nausea, vomiting, edema, feminization including gynecomastia and erectile dysfunction in men.[2]

Eyes[edit]

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.[2]

Skin[edit]

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.[2]

Inhalation[edit]

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.[2]

Ingestion[edit]

If estrone is ingested, vomiting should not be induced. Medical attention may be necessary.[2]

Additional images[edit]

References[edit]

  1. ^ http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?fuseaction=Search.Set_Current_Drug&ApplNo=003977&DrugName=THEELIN&ActiveIngred=ESTRONE&SponsorApplicant=PARKEDALE&ProductMktStatus=3&goto=Search.DrugDetails
  2. ^ a b c d e f g h i j "Estrone". OSHA. Retrieved 21 February 2013. 
  3. ^ a b c d e "Material Safety Data Sheet Estrone" (PDF). ScienceLab.com. Retrieved 21 February 2013. 
  4. ^ "Estrone -PubChem". National Center for Biotechnology Information. Retrieved 2009-09-06. 
  5. ^ a b c "Estrone-Compound Summary". PubChem.com. Retrieved 21 February 2013. 
  6. ^ Helen Varney, Jan M. Kriebs, Carolyn L. Gegor. Varney's midwifery, Fourth Edition. Jones and Bartlett Publishers, 2004, p. 340.
  7. ^ Häggström, Mikael; Richfield, David (2014). "Diagram of the pathways of human steroidogenesis". WikiJournal of Medicine. 1 (1). doi:10.15347/wjm/2014.005. ISSN 2002-4436.