Estrone

Estrone: Estrone

Systematic (IUPAC) name

3-hydroxy-13-methyl- 6,7,8,9,11,12,13,14,15,16- decahydrocyclopenta[a]phenanthren- 17- one

Clinical data

Pregnancy cat. ?

Legal status ?

Pharmacokinetic data

Protein binding >95%

Half-life 19 hours

Identifiers

CAS number 53-16-7^Y

ATC code G03CA07 G03CC04

PubChem CID 5870

DrugBank DB00655

ChemSpider 5660^Y

UNII 2DI9HA706A^Y

KEGG D00067^N

ChEBI CHEBI:17263^N

ChEMBL CHEMBL1405^N

Chemical data

Formula C₁₈H₂₂O₂

Mol. mass 270.366 g/mol

SMILES eMolecules & PubChem

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

Melt. point 254.5 °C (490 °F)

N(what is this?) (verify)

Estrone (E1, and also oestrone) is an estrogenic hormone secreted by the ovary as well as adipose tissue.^[1]

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 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.

Estrone is the predominant estrogen in postmenopausal women.^[2]

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.

Additional images

Androstenedione converting to estrone.

Steroidogenesis

References

^ "Estrone -PubChem". National Center for Biotechnology Information. http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5870&loc=ec_rcs. Retrieved 2009-09-06.

^ Helen Varney, Jan M. Kriebs, Carolyn L. Gegor. Varney's midwifery, Fourth Edition. Jones and Bartlett Publishers, 2004, p. 340.

v · d · eEstrogens and progestogens (G03C-D, L02)

Progestogens/
progestins
(progesterone)

Agonist

1st

Norpregnene (Norethisterone^#/Norethisterone acetate • Ethynodiol diacetate)

2nd

Norpregnene (Levonorgestrel^#/Norgestrel/Norelgestromin)

3rd

19-nortestosterone (Desogestrel/Etonogestrel • Gestodene • Norgestimate)

4th

Androstene (Drospirenone) • 19-norprogesterone (Nomegestrol • Promegestone • Trimegestone) • 19-nortestosterone (Dienogest)

17-OH

Chlormadinone • Cyproterone • Medroxyprogesterone/Medroxyprogesterone 17-acetate^# • Megestrol

Other/
ungrouped

Pregnenedione (Gestonorone) • Pregnene (Ethisterone) • Pregnadiene (Medrogestone • Melengestrol) • Norpregnane (Norgestrienone) • Lynestrenol • Norethynodrel • Tibolone • Dydrogesterone • Quingestanol

Antiprogestin/
SPRM

antagonist: Mifepristone

Asoprisnil • CDB-4124 • Ulipristal acetate

Estrogens

Agonist

Steroidal

Diosgenin • Estradiol (Ethinylestradiol^#/Mestranol • Estradiol 17 beta-cypionate^# • Polyestradiol phosphate) • Estrone (Estrone sulfate) • Estriol • Promestriene • Equilenin • Equilin

Nonsteroidal

Chlorotrianisene • Dienestrol • Fosfestrol • Diethylstilbestrol • Zeranol

Antiestrogen/
SERM

Afimoxifene • Arzoxifene • Bazedoxifene • Cyclofenil • Lasofoxifene • Ormeloxifene • Raloxifene • Tamoxifen • Toremifene

Clomifene^# • Mepitiostane • Nafoxidine

pure antagonist: Fulvestrant

Aromatase inhibitors

nonselective: Aminoglutethimide • Testolactone
selective: Anastrozole • Atamestane • Exemestane • Fadrozole • Formestane • Letrozole • Vorozole

^#WHO-EM. ^‡Withdrawn from market. Clinical trials: ^†Phase III. ^§Never to phase III

M: ♀ FRS

anat/phys/devp

noco/cong/npls, sysi/epon

proc/asst, drug (G1/G2B/G3CD)

v · d · eCholesterol and steroid metabolic intermediates

Mevalonate pathway

to HMG-CoA

Acetyl-CoA · Acetoacetyl-CoA · HMG-CoA

Ketone bodies

Acetone · Acetoacetic acid · beta-Hydroxybutyric acid

to DMAPP

Mevalonic acid · Phosphomevalonic acid · 5-Diphosphomevalonic acid · Isopentenyl pyrophosphate · Dimethylallyl pyrophosphate

Geranyl-

Geranyl pyrophosphate · Geranylgeranyl pyrophosphate

Carotenoid

Prephytoene diphosphate · Phytoene

Non-mevalonate pathway

DOXP · MEP · CDP-ME · CDP-MEP · MEcPP · HMB-PP · IPP · DMAPP

To Cholesterol

Farnesyl pyrophosphate · Squalene · 2,3-Oxidosqualene · Lanosterol

Lanosterol · Lathosterol · 7-Dehydrocholesterol · Cholesterol
Lanosterol · Zymosterol · 7-Dehydrodesmosterol · Desmosterol · Cholesterol

Steroid

Corticosteroids
(C21 pregnane)

Mineralocorticoids

Pregnenolone · Progesterone · Cortodoxone · Corticosterone · Aldosterone

Glucocorticoids

Pregnenolone · 17-Hydroxypregnenolone · 17-Hydroxyprogesterone · Cortisol
Cortisol · Cortisone

Sex steroids

Androgens
(C19 androstane)

DHEA · Androstenedione/5-Androstenediol · Testosterone · Dihydrotestosterone
DHEA sulfate · Epitestosterone

Estrogens
(C18 estrane)

Estrone · Estradiol · Estriol

Nonhuman

Phytosterols

Stigmasterol · Brassicasterol

Ergosterols

Ergosterol · Ergocalciferol

M: MET

mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m

k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon

m(A16/C10),i(k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)

M: END

anat/phys/devp/horm

noco(d)/cong/tumr, sysi/epon

proc, drug (A10/H1/H2/H3/H5)

biochemical families: prot · nucl · carb (glpr, alco, glys) · lipd (fata/i, phld, strd, gllp, eico) · amac/i · ncbs/i · ttpy/i

Categories:
Estrogens
Biochemistry stubs

Estrone


Systematic (IUPAC) name
3-hydroxy-13-methyl- 6,7,8,9,11,12,13,14,15,16- decahydrocyclopenta[a]phenanthren- 17- one
Clinical data
Pregnancy cat.	?
Legal status	?
Pharmacokinetic data
Protein binding	>95%
Half-life	19 hours
Identifiers
CAS number	53-16-7^Y
ATC code	G03CA07 G03CC04
PubChem	CID 5870
DrugBank	DB00655
ChemSpider	5660^Y
UNII	2DI9HA706A^Y
KEGG	D00067^N
ChEBI	CHEBI:17263^N
ChEMBL	CHEMBL1405^N
Chemical data
Formula	C₁₈H₂₂O₂
Mol. mass	270.366 g/mol
SMILES	eMolecules & PubChem
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
Melt. point	254.5 °C (490 °F)
N(what is this?) (verify)

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Look at other dictionaries:

Estrone — structure de l estrone Général No CAS … Wikipédia en Français
estrone — [es′trōn΄] n. [ ESTR(US) + ONE] a female sex hormone, C18H22O2 … English World dictionary
estrone — œstrone [ ɛstrɔn ] n. f. VAR. estrone • v. 1921; de œstrus ♦ Physiol. Nom chimique de la folliculine, l une des hormones œstrogènes sécrétées par l ovaire et le placenta. ● œstrone ou estrone nom féminin Synonyme de folliculine. ● œstrone ou… … Encyclopédie Universelle
estrone — A metabolite of 17β estradiol, commonly found in urine, ovaries, and placenta; has considerably less biologic activity than the parent hormone. SYN: follicular hormone, folliculin, ketohydroxyestrin, oestrone. * * * es·trone es .trōn … Medical dictionary
estrone — estronas statusas T sritis chemija apibrėžtis Estrogenas. formulė (CH₃)C₁₇H₁₈(=O)OH atitikmenys: angl. estrone rus. фолликулин; эстрон ryšiai: sinonimas – folikulinas … Chemijos terminų aiškinamasis žodynas
estrone — noun a naturally occurring weak estrogenic hormone secreted by the mammalian ovary; synthesized (trade name Estronol) and used to treat estrogen deficiency • Syn: ↑oestrone, ↑theelin, ↑Estronol • Usage Domain: ↑trade name (for: ↑Estronol) … Useful english dictionary
Estrone sulfotransferase — In enzymology, an estrone sulfotransferase (EC number|2.8.2.4) is an enzyme that catalyzes the chemical reaction:3 phosphoadenylyl sulfate + estrone ightleftharpoons adenosine 3 ,5 bisphosphate + estrone 3 sulfateThus, the two substrates of this… … Wikipedia
estrone — noun Etymology: estrane Date: 1933 a natural estrogenic hormone that is a ketone C18H22O2 found in the body chiefly as a metabolite of estradiol, that is also secreted especially by the ovaries, and that is used to treat various conditions (as… … New Collegiate Dictionary
estrone — /es trohn/, n. 1. Biochem. an estrogenic hormone, C18H22O2, produced by the ovarian follicles and found during pregnancy in urine and placental tissue. 2. Pharm. a commercial form of this compound, obtained from the urine of pregnant women or… … Universalium
estrone — noun An estrogenic hormone excreted by the ovaries; sometimes manufactured synthetically for use in cases of estrogen deficiency. Syn: theelin … Wiktionary

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Estrone

Biosynthesis

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References

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Estrone

Biosynthesis

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References

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