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14-September-2008 18:02:46 - Estradiol Estradiol Systematic IUPAC name 8R,9S,13S,14S,17S-13-methyl- 6,7,8,9,11,12,14,15,16,17-decahydro cyclopentaaphenanthrene-3,17-diol Identifiers CAS number 50-28-2 ATC code G03CA03 PubChem 5757 Chemical data Formula C18H24O2 Mol. mass 272.39 SMILES eMolecules PubChem Pharmacokinetic data Bioavailability 97-99% is bound Metabolism Liver Half life ~ 13 hours Excretion Urine Therapeutic considerations Pregnancy cat. X USA Legal status S4 Au, POM UK, â„ž-only U.S. Routes Oral, transdermal Estradiol 17β-estradiol also oestradiol is a sex hormone. Mislabelled the female hormone, it is also present in males; it represents the major estrogen in humans. Estradiol has not only a critical impact on reproductive and sexual functioning, but also affects other organs including bone structure. Contents 1 Synthesis 2 Production 3 Mechanism of action 4 Metabolism 5 Measurement 6 Effects 6.1 Female reproduction 6.2 Sexual development 6.3 Male reproduction 6.4 Bone 6.5 Liver 6.6 Brain 6.7 Oncogene 6.8 Pregnancy 7 Role in sex differentiation of the brain 8 Estradiol medication 9 Therapy 9.1 Hormone replacement therapy 9.2 Estrogen and Mood 9.3 Blocking estrogens 9.4 Hormonal contraception 9.5 List of estradiol medications 10 Contraindications 11 Side effects 12 References 13 See also 14 Additional images Synthesis Conversion of testosterone to estradiol Conversion of testosterone to estradiol Estradiol, like other steroids, is derived from cholesterol. After side chain cleavage and utilizing the delta-5 pathway or the delta-4 pathway androstenedione is the key intermediary. A fraction of the androstenedione is converted to testosterone, which in turn undergoes conversion to estradiol by an enzyme called aromatase. Alternatively, androstenedione is aromatized to estrone, which is subsequently converted to estradiol. Production During the reproductive years, most estradiol in women is produced by the granulosa cells of the ovaries by the aromatization of androstenedione produced in the theca folliculi cells to estrone, followed by conversion of estrone to estradiol by 17β-hydroxysteroid reductase. Smaller amounts of estradiol are also produced by the adrenal cortex, and in men, by the testes. Estradiol is not only produced in the gonads: in both sexes, precursor hormones, specifically testosterone, are converted by aromatization to estradiol. In particular, fat cells are active to convert precursors to estradiol, and will continue to do so even after menopause. Estradiol is also produced in the brain and in arterial walls. Mechanism of action Estradiol enters cells freely and interacts with a cytoplasmic target cell receptor. When the estrogen receptor has bound its ligand it can enter the nucleus of the target cell, and regulate gene transcription which leads to formation of messenger RNA. The mRNA interacts with ribosomes to produce specific proteins that express the effect of estradiol upon the target cell. Estradiol binds well to both estrogen receptors, ERα and ERβ, in contrast to certain other estrogens, notably medications that preferentially act on one of these receptors. These medications are called selective estrogen receptor modulators, or SERMs. Estradiol is the most potent naturally-occurring estrogen. Recently there has been speculation about a membrane estrogen receptor, ERX. Metabolism In plasma, estradiol is largely bound to sex hormone binding globulin, also to albumin, -only a fraction is free and biologically active. Deactivation includes conversion to less active estrogens such as estrone and estriol. Estriol is the major urinary metabolite. Estradiol is conjugated in the liver by sulfate and glucuronide formation and as such excreted via the kidneys. Some of the watersoluble conjugates are excreted via the bile duct, and partly reabsorbed after hydrolysis from the intestinal tract. This enterohepatic circulation contributes to maintaining estradiol levels. Measurement Serum estradiol measurement in women reflects primarily the activity of the ovaries. As such they are useful in the detection of baseline estrogen in women with amenorrhea or menstrual dysfunction and to detect the state of hypoestrogenicity and menopause. Furthermore, estrogen monitoring during fertility therapy assesses follicular growth and is useful in monitoring the treatment. Estrogen-producing tumors will demonstrate persistent high levels of estradiol and other estrogens. In precocious puberty estradiol levels are inappropriately increased. Estradiol levels blue line during the menstrual cycle Estradiol levels blue line during the menstrual cycle In the normal menstrual cycle estradiol levels measure typically 50 ng/ml at menstruation, rise with follicular development, drop briefly at ovulation, and rise again during the luteal phase for a second peak. At the end of the luteal phase estradiol levels drop to their menstrual levels unless there is a pregnancy. During pregnancy estrogen levels including estradiol rise steadily towards term. The source of these estrogens is the placenta that aromatizes prohormones produced in the fetal adrenal gland. Effects Female reproduction In the female, estradiol acts as a growth hormone for tissue of the reproductive organs, supporting the lining of the vagina, the cervical glands, the endometrium and the lining of the fallopian tubes. It enhances growth of the myometrium. Estradiol appears necessary to maintain oocytes in the ovary. During the menstrual cycle, estradiol that is produced by the growing follicle triggers, via a positive feedback system, the hypothalamic-pituitary events that lead to the luteinizing hormone surge, inducing ovulation. In the luteal phase estradiol, in conjunction with progesterone, prepares the endometrium for implantation. During pregnancy estradiol increases due to placental production. In baboons, blocking of estrogen production leads to pregnancy loss suggesting that estradiol has a role in the maintenance of pregnancy. Research is investigating the role of estrogens in the process of initiation of labor. Sexual development The development of secondary sex characteristics in women is driven by estrogens, specifically estradiol. These changes are initiated at the time of puberty, most enhanced during the reproductive years, and become less pronounced with declining estradiol support after the menopause. Thus, estradiol enhances breast development, and is responsible for changes in the body shape affecting bones, joints, fat deposition. Fat structure and skin composition are modified by estradiol. Male reproduction The effect of estradiol and estrogens upon male reproduction is complex. Estradiol is produced in the Sertoli cells of the testes. There is evidence that estradiol is to prevent apoptosis of male germ cells. 1 Several studies have noted that sperm counts have been declining in many parts of the world and it has been postulated that this may be related to estrogen exposure in the environment.2 Suppression of estradiol production in a subpopulation of subfertile men may improve the semen analysis.3 Males with sex chromosome genetic conditions such as Klinefelters Syndrome will have a higher level of estradiol. Bone There is ample evidence that estradiol has a profound effect on bone. Individuals without estradiol or other estrogens will become tall and eunuchoid as epiphysieal closure is delayed or may not take place. Bone structure is affected resulting in early osteopenia and osteoporosis. 4 Also, women past menopause experience an accelerated loss of bone mass due to a relative estrogen deficiency. Liver Estradiol has complex effects on the liver. It can lead to cholestasis. It affects the production of multiple proteins including lipoproteins, binding proteins, and proteins responsible for blood clotting. Brain Estrogens can be produced in the brain from steroid precursors. As antioxidants, they have been found to have neuroprotective function.5 The positive and negative feedback loop of the menstrual cycle involve ovarian estradiol as the link to the hypothalamic-pituitary system to regulate gonadotropins. Estrogen is considered to play a significant role in women's mental health. A conceptual model of how estrogen affects mood was suggested by Douma et al 2005 based on their extensive literature review relating activity of endogenous, bio-identical and synthetic estrogen with mood and well-being. They concluded that the sudden estrogen withdrawal, fluctuating estrogen, and periods of sustained estrogen low levels correlated with significant mood lowering. Clinical recovery from depression postpartum, perimenopause, and postmenopause was shown to be effective after levels of estrogen were stabilized and/or restored.6 Oncogene Estrogen is suspected to activate certain oncogenes, as it supports certain cancers, notably breast cancer and cancer of the uterine lining. In addition there are several benign gynecologic conditions that are dependent on estrogen such as endometriosis, leiomyomata uteri, and uterine bleeding. Pregnancy The effect of estradiol, together with estrone and estriol, in pregnancy is less clear. They may promote uterine blood flow, myometrial growth, sitmulate breast growth and at term, promote cervical softening and expression of myometrial oxytocin receptors. Role in sex differentiation of the brain One of the fascinating twists to mammalian sex differentiation is that estradiol is one of the two active metabolites of testosterone in males the other being dihydrotestosterone, and since fetuses of both sexes are exposed to similarly high levels of maternal estradiol, this source cannot have a significant impact on prenatal sex differentiation. Estradiol cannot be transferred readily from the circulation into the brain, while testosterone can, thus sex differentiation can be caused by the testosterone in the brain of most male mammals, including humans, aromatizing in significant amounts into estradiol. There is also now evidence that the programming of adult male sexual behavior in animals is largely dependent on estradiol produced in the central nervous system during prenatal life and early infancy from testosterone. 7 However, it is not yet known whether this process plays a minimal or significant part in human sexual behaviors although evidence from other mammals tends to indicate that it does. 8 Recently, it was discovered that volumes of sexually dimorphic brain structures in phenotypical males changed to approximate those of typical female brain structures when exposed to estradiol over a period of months. 9 This would suggest that estradiol has a significant part to play in sex differentiation of the brain, both pre-natal and throughout life. Estradiol medication Estrogen is marketed in a number of ways to address issues of hypoestrogenism. Thus there are oral, transdermal, topical, injectable, and vaginal preparations. Furthermore, the estradiol molecule may be linked to an alkyl group at C3 position to facilitate the administration. Such modifications give rise to estradiol acetate oral and vaginal applications and to estradiol cyprionate injectable. Oral preparations are not necessarily predictably absorbed and subject to a first pass through the liver where they can be metabolized and also initiate unwanted side effects. Thus, alternative routes of administration have been developed that bypass the liver before primary target organs are hit. Transdermal and transvaginal routes are not subject to the initial liver passage. A more profound alteration is ethinylestradiol, the most common estrogen ingredient in combined oral contraceptive pills Therapy Hormone replacement therapy If severe side effects of low levels of estradiol in a woman's blood are experienced commonly at the beginning of menopause or after oophorectomy, hormone replacement therapy may be prescribed. Often such therapy is combined with a progestin. Estrogen therapy may be used in treatment of infertility in women when there is a need to develop sperm-friendly cervical mucus or an appropriate uterine lining. Estrogen therapy is also used to maintain female hormone levels in male-to-female transsexuals. Estrogen and Mood Estrogen is considered to play a significant role in women's mental health. A conceptual model of how estrogen affects mood was suggested by Douma et al 2005 based on their extensive literature review relating activity of endogenous, bio-identical and synthetic estrogen with mood and well-being. They concluded the sudden estrogen withdrawal, fluctuating estrogen, and periods of sustained estrogen low levels correlated with significant mood lowering. Clinical recovery from depression postpartum, perimenopause, and postmenopause was shown to be affective after levels of estrogen were stabilized and/or restored. Blocking estrogens Inducing a state of hypoestrogenism may be beneficial in certain situations where estrogens are contributing to unwanted effects, e.g, certain forms of breast cancer, gynecomastia, and premature closure of epiphyses. Estrogen levels can be reduced by inhibiting production using gonadotropin- releasing factor agonists GnRH agonists or blocking the aromatase enzyme using an aromatase inhibitor, or estrogen effects can be reduced with estrogen antagonists such as tamoxifen. Flaxseed is known to reduce estradiol.10 Hormonal contraception A synthetic form of estradiol, called ethinylestradiol is a major component of hormonal contraceptive devices. Combined forms of hormonal contraception contain ethinylestradiol and a progestin, which both contribute to the inhibition of GnRH, LH, and FSH. The inhibition of these hormones accounts for the ability of these birth control methods to prevent ovulation and thus prevent pregnancy. Other types of hormonal birth control contain only progestins and no ethinylestradiol. List of estradiol medications The following are marketed versions of estradiol: Oral versions: Estrace, Activella also contains a progestin, estradiol acetate, Progynova, estrofem Transdermal preparation: Alora, Climara, Vivelle, Vivelle-Dot, Menostar, Estraderm TTS Ointments: Estrasorb Topical, Estrogel, Elestrin Injection: Estradiol cyprionate: Lunelle monthly injection, Estradiol valerate Vaginal ointment: Estrace Vaginal Cream, Premarin Cream Vaginal ring: Estring estradiol acetate, Femring Estradiol is also part of conjugated estrogen preparations, including Premarin but is not the major ingredient Premarin consists of hundreds of estrogen derivatives due to its natural source...pregnant mare urine. Contraindications Estradiol should not be given to women who are pregnant or are breastfeeding, women with unexplained uterine bleeding, certain forms of cancer, or prone to blood clotting disorders. The medication is to be kept away from children. Detailed prescription information is available 11 Side effects Side effects of estradiol therapy may include uterine bleeding, breast tenderness, nausea and vomiting, chloasma, cholestasis, and migraine headaches. References ^ Pentikäinen V, Erkkilä K, Suomalainen L, Parvinen M, Dunkel L. Estradiol Acts as a Germ Cell Survival Factor in the Human Testis in vitro. The Journal of Clinical Endocrinology Metabolism 2006;85:2057-67 PMID 10843196 ^ Sharpe RM, Skakkebaek NE. Are oestrogens involved in falling sperm counts and disorders of the male reproductive tract? Lancet. 1993 May 29;3418857:1392-5. PMID 8098802 ^ Raman JD, Schlegel PN. Aromatase Inhibitors for Male Infertility. Journal of Urology. 2002, 167: 624-629. PMID 11792932 ^ Carani C, Qin K, Simoni M, Faustini-Fustini M, Serpente S, Boyd J, Korach KS, Simpson ER. Effect of Testosterone and Estradiol in a Man with Aromatase Deficiency. New England Journal of Medicine Volume 337:91-95 July 10, 1997 PMID 9211678 ^ Behl C, Widmann M, Trapp T, Holsboer F. 17-beta estradiol protects neurons from oxidative stress-induced cell death in vitro. Biochem Biophys Res Commun. 1995 Nov 13;2162:473-82. PMID 7488136 ^ Douma SL, Husband C., O'Donnell, M.E., Barwin B.N., Woodend AK. Estrogen-related Mood Disorders Reproductive Life Cycle Factors.Advances in Nursing Science2005, 28: No. 4:147-160. refLasiuk GC,.The Effects of Estradiol on Central Serotonergic Systems and Its Relationship to Mood in Women. Biological Research for Nursing. 2007, 9: No. 2:364-375. DOI: 10.1177/1099500407605600/ref--~~~~ ===Blood vessels=== Estrogen affects certain blood vessels. Improvement in arterial blood flow has been demonstrated in coronary artery|coronary arteries.refCollins P, Rosano GM, Sarrel PM, Ulrich L, Adamopoulos S, Beale CM, McNeill JG, Poole-Wilson PA. 17 beta-Estradiol attenuates acetylcholine-induced coronary arterial constriction in women but not men with coronary heart disease. Circulation. 1995 Jul 1;921:24-30 PMID 7788912 /li li id=cite_note-6'''#cite_ref-6|^''' cite journal | last = Harding | first = Prof. Cheryl F. | title = Hormonal Modulation of Singing: Hormonal Modulation of the Songbird Brain and Singing Behavior | journal = Ann. N.Y. Acad. Sci. | volume = 1016 | pages = 524-539 | publisher = The New York Academy of Sciences | month = June | year = 2004 | url = http://www.annalsnyas.org/content/vol1016/issue1/index.dtl | doi = 10.1196/annals.1298.030 | accessdate = 2007-03-07/li li id=cite_note-7'''#cite_ref-7|^''' cite journal | last = Simerly | first = Richard B. | title = Wired for reproduction: organization and development of sexually dimorphic circuits in the mammalian forebrain | journal = Annual Rev. Neurosci. | volume = 25 | pages =507-536 | date = 2002-03-27 | url = http://www.healthsystem.virginia.edu/internet/neuroscience/BehavioralNeuroscience/Simerley-EFR-1-4.pdf | doi = 10.1146/annurev.neuro.25.112701.142745 | pmid = 12052919 | format = pdf | accessdate = 2007-03-07/li li id=cite_note-eje-utrecht-8'''#cite_ref-eje-utrecht_8-0|^''' cite journal| author = Hulshoff, Cohen-Kettenis et al. | year = 2006 | month = July | title = Changing your sex changes your brain: influences of testosterone and estrogen on adult human brain structure | url = http://www.eje-online.org/cgi/content/abstract/155/suppl_1/S107 | journal = European Journal of Endocrinology | issue = 155 | pages = 107-114 | doi = 10.1530/eje.1.02248 | id = ISSN|0804-4643 | | volume = 155/li li id=cite_note-9'''#cite_ref-9|^''' cite book | first=Andrew | last= Chevallier | year= 2000 | title=Encyclopedia of Herbal Medicine: The Definitive Home Reference Guide to 550 Key Herbs with all their Uses as Remedies for Common Ailments | chapter= | or=Gillian Emerson-Roberts | others= | pages= | publisher= DK Publishing | id=ISBN 0-7894-6783-6 | url= | authorlink= /li li id=cite_note-10'''#cite_ref-10|^''' http://warnerchilcott.com/pdfs/pi/pi_estrace_wc_imprint.pdf Estrace/Estradiol patient information leaflet - Warner Chilcott manufacturer/li/ol/ref See also estrogen insensitivity syndrome hormone replacement therapy gender androgen Oral contraceptive formulations Additional images Steroidogenesis v d e Endocrine system: hormones/endocrine glands Peptide hormones, Steroid hormones Hypothalamic-pituitary Hypothalamus: TRH, CRH , GnRH, GHRH, somatostatin, dopamine - Posterior pituitary: vasopressin, oxytocin - Anterior pituitary: α FSH, LH, TSH, GH, prolactin, POMC ACTH, MSH, endorphins, lipotropin Adrenal axis Adrenal medulla: epinephrine, norepinephrine - Adrenal cortex: aldosterone, cortisol, DHEA Thyroid axis Thyroid: thyroid hormone T3 and T4 - calcitonin - Parathyroid: PTH Gonadal axis Testis: testosterone, AMH, inhibin - Ovary: estradiol, progesterone, inhibin/activin, relaxin pregnancy Other end. glands Pancreas: glucagon, insulin, somatostatin - Pineal gland: melatonin Non-end. glands Placenta: hCG, HPL, estrogen, progesterone - Kidney: renin, EPO, calcitriol, prostaglandin - Heart atrium: ANP - Stomach: gastrin, ghrelin - Duodenum: CCK, GIP, secretin, motilin, VIP - Ileum: enteroglucagon - Adipose tissue: leptin, adiponectin, resistin - Thymus: Thymosin - Thymopoietin - Thymulin - Skeleton: Osteocalcin - Liver/other: Insulin-like growth factor IGF-1, IGF-2 Target-derived NGF, BDNF, NT-3 v d e Sex hormones and related agents primarily G03, also L02, H01C - human endogenous in CAPS Progestogens: receptor Agonist PROGESTERONE, Dienogest, Desogestrel, Drospirenone, Dydrogesterone, Ethisterone, Etonogestrel, Ethynodiol diacetate, Gestodene, Gestonorone, Levonorgestrel, Lynestrenol, Medroxyprogesterone, Megestrol, Norelgestromin, Norethisterone, Norethynodrel, Norgestimate, Norgestrel, Norgestrienone, Tibolone SPRM Asoprisnil, CDB-4124 Antiprogestogen Mifepristone Androgens: receptor Agonist TESTOSTERONE, Androstanolone, Fluoxymesterone, Mesterolone, Methyltestosterone, see also anabolic steroids Antiandrogen Bicalutamide, Cyproterone, Dienogest, Flutamide, Nilutamide, Spironolactone Estrogens: receptor Agonist ESTRADIOL, ESTRIOL, ESTRONE, Chlorotrianisene, Dienestrol, Diethylstilbestrol, Ethinylestradiol, Fosfestrol, Mestranol, Polyestradiol phosphate SERM Afimoxifene, Arzoxifene, Bazedoxifene, Clomifene, Fulvestrant, Lasofoxifene, Raloxifene, Tamoxifen, Toremifene AI Aminoglutethimide, Anastrozole, Atamestane, Exemestane, Fadrozole, Formestane, Letrozole, Vorozole Antiestrogen Mepitiostane Gonadotropins: FSHR/LHCGR ovulation stim. Clomifene, Urofollitropin Antigonadotropin Danazol, Gestrinone GnRH: receptor Agonist Buserelin, Goserelin, Histrelin, Leuprorelin, Nafarelin, Triptorelin Antagonist Abarelix, Cetrorelix, Ganirelix Retrieved from http://en..org/wiki/Estradiol Categories: Estrogens | Phenols Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages БългарÑ?ки ÄŒesky Deutsch Þ‹Þ¨ÞˆÞ¬Þ€Þ¨Þ„Þ¦Þ?Þ° Eesti Español Ù?ارسی Français עברית Magyar Nederlands 日本語 Occitan Polski Português РуÑ?Ñ?кий Suomi Svenska This page was last modified on 11 September 2008, at 17:06
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