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Encyclopedia > Estradiol
Estradiol
Systematic (IUPAC) name
(8S,9S,13S,14S,17S)-13-methyl-
6,7,8,9,11,12,14,15,16,17-decahydro
cyclopenta[a]phenanthrene-3,17-diol
Identifiers
CAS number 50-28-2
ATC code G03CA03
PubChem 5757
Chemical data
Formula C18H24O2 
Mol. mass 272.39
Pharmacokinetic data
Bioavailability 97-99% is bound
Metabolism Liver
Half life ~ 13 hours
Excretion Urine
Therapeutic considerations
Pregnancy cat.

X (USA) Image File history File links Download high-resolution version (1100x704, 39 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Estrogen Estradiol Estramustine ... Image File history File links Download high-resolution version (1100x765, 185 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Estradiol ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... The molecular mass (abbreviated MM) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of medication that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... The liver is an organ in some animals, including vertebrates (and therefore humans). ... It has been suggested that Effective half-life be merged into this article or section. ... Excretion is the process of eliminating waste products of metabolism and other materials that are of no use. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ...

Legal status

S4 (Au), POM (UK), ℞-only (U.S.) The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ...

Routes Oral, transdermal

Estradiol (17β-estradiol) (also oestradiol) is a sex hormone. Labelled the "female" hormone but 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. In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... Sex hormones are hormones that affect the reproductive system. ... Estriol. ...

Contents

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. Androstenedione is either converted to testosterone which in turn undergoes aromatization to estradiol, or, alternatively, androstenedione is aromatized to estrone which is converted to estradiol. Wikipedia does not have an article with this exact name. ... Wikipedia does not have an article with this exact name. ... Steroid skeleton of lanosterol. ... Cholesterol is a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues, and transported in the blood plasma of all animals. ... The term Side chain can have different meanings depending on the context: In chemistry and biochemistry a side chain is a part of a molecule attached to a core structure. ... Androstenedione (also known as 4-androstenedione) is a 19-carbon steroid hormone produced in the adrenal glands and the gonads as an intermediate step in the biochemical pathway that produces the androgen testosterone and the estrogens estrone and estradiol. ... Androstenedione (also known as 4-androstenedione) is a 19-carbon steroid hormone produced in the adrenal glands and the gonads as an intermediate step in the biochemical pathway that produces the androgen testosterone and the estrogens estrone and estradiol. ... Testosterone is a steroid hormone from the androgen group. ... Aromatase belongs to the group of cytochrome P450 enzymes (EC 1. ... Androstenedione (also known as 4-androstenedione) is a 19-carbon steroid hormone produced in the adrenal glands and the gonads as an intermediate step in the biochemical pathway that produces the androgen testosterone and the estrogens estrone and estradiol. ... Estrone (also oestrone) is an estrogenic hormone secreted by the ovary. ...


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. A granulosa cell is a supporting cell for the developing female gamete in the ovary of mammals. ... For ovary as part of plants see ovary (plants) Ovaries are egg-producing reproductive organs found in female organisms. ... The theca folliculi comprise a layer of the ovarian follicles. ... Estrone (also oestrone) is an estrogenic hormone secreted by the ovary. ... Layers of cortex. ... Human male anatomy The testicles, known medically as testes (singular testis), are the male generative glands in animals. ...


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 thus also produced in the brain and in arterial walls. Aromaticity is a chemical property in which a conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibit a stabilization stronger than would be expected by the stabilization of conjugation alone. ... It has been suggested that Subcutaneous fat be merged into this article or section. ... Section of an artery For other uses, see Artery (disambiguation). ...


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. In biochemistry, a receptor is a protein on the cell membrane or within the cytoplasm that binds to a specific factor (a ligand), such as a neurotransmitter, hormone, or other substance, and initiates the cellular response to the ligand. ... The estrogen receptor is a receptor for estradiol (the main endogenous estrogen); it is located intracellularly, in parallel with other steroid hormone receptors. ... In chemistry, a ligand is an atom, ion, or molecule (see also: functional group) that generally donates one or more of its electrons through a coordinate covalent bond to, or shares its electrons through a covalent bond with, one or more central atoms or ions (these ligands act as a... The eukaryotic cell nucleus. ... In genetics, transcription is the first of the two-step protein biosynthesis process. ... The life cycle of an mRNA in a eukaryotic cell. ... Figure 1: Ribosome structure indicating small subunit (A) and large subunit (B). ...


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. Selective estrogen receptor modulators (SERMs) is a class of medication that acts on the estrogen receptor. ...


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. Sex hormone binding globulin (SHBG) is a glycoprotein that binds to sex hormones, specifically testosterone and estradiol. ... Estrone (also oestrone) is an estrogenic hormone secreted by the ovary. ... Chemical structure of estriol Estriol (also oestriol) is one of the three main estrogens produced by the human body. ... Hydrolysis is a chemical reaction or process in which a chemical compound reacts with water. ... Enterohepatic circulation, is the excretion of a drug (or a metabolite of it) through the bile to be re-absorbed in the gut and sent again to the liver along the portal vein, so the excretion-reabsortion cycle can start again. ...


Measurement

Serum estradiol measurement in women reflect primarily the activity of the ovaries. As such they are useful the detect baseline estrogen in women with amenorrhea or menstrual dysfunction and to detect state of hypoestrogenicity and menopause. Furthermore estrogen monitoring during fertility therapy assesses follicular growth and useful to monitor the treatment. Estrogen-producing tumors will demonstrate persistent high levels of estradiol and other estrogens. In precocious puberty estradiol levels are inappropriately increased. Amenorrhoea (BE) or amenorrhea (AmE) is the absence of a menstrual period in a woman of reproductive age. ... Menopause is the physiological cessation of menstrual cycles associated with advancing age in women. ... Precocious puberty means early puberty. ...

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. Image File history File links Estradiol. ... Image File history File links Estradiol. ... Menstrual cycle The menstrual cycle is a recurring cycle of physiological changes in the females of some animal species that is associated with reproductive fertility. ...


During pregnancy estrogen levels including estradiol rise steadily towards term. The source of these estrogens is the placenta that aromatizes prehormones produced in the fetal adrenal gland. A pregnant woman near the end of her term Pregnancy is the carrying of one or more embryos or fetuses by female mammals, including humans, inside their bodies. ... The placenta is an ephemeral (temporary) organ present in female placental vertebrates during gestation (pregnancy), but a placenta has evolved independently also in other animals as well, for instance scorpions and velvet worms. ...


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. The vagina, (from Latin, literally sheath or scabbard ) is the tubular tract leading from the uterus to the exterior of the body in female placental mammals and marsupials, or to the cloaca in female birds, monotremes, and some reptiles. ... The endometrium is the inner membrane of the mammalian uterus. ... The myometrium is the middle layer of the uterine wall consisting of smooth muscle cells and supporting stromal and vascular tissue. ... An oocyte or ovocyte is a female gametocyte or germ cell involved in reproduction. ... For ovary as part of plants see ovary (plants) Ovaries are egg-producing reproductive organs found in female organisms. ... Menstrual cycle The menstrual cycle is a recurring cycle of physiological changes in the females of some animal species that is associated with reproductive fertility. ... Luteinizing hormone (LH) is a hormone synthesized and secreted by gonadotropes in the anterior lobe of the pituitary gland. ... Progesterone is a C-21 steroid hormone involved in the female menstrual cycle, pregnancy (supports gestation) and embryogenesis of humans and other species. ... Implantation occurs when a fertilized zygote attaches itself onto the lining of the uterus. ... A pregnant woman near the end of her term Pregnancy is the carrying of one or more embryos or fetuses by female mammals, including humans, inside their bodies. ... The placenta is an ephemeral (temporary) organ present in female placental vertebrates during gestation (pregnancy), but a placenta has evolved independently also in other animals as well, for instance scorpions and velvet worms. ...


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. Secondary sex characteristics are traits that distinguish the two sexes of a species, but that are not directly part of the reproductive system. ...


Male reproduction

The effect of estradiol (and estrogens) upon male reproduction is complex. Estradiol is produced in the Sertoli cell of the testes. There is evidence that estradiol is to prevent apoptosis of male germ cells.[1] A cell undergoing apoptosis. ...


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. XXY karyotype Klinefelters syndrome is a condition caused by a chromosome abnormality in males (specifically, a nondisjunction); sufferers have a pair of X sex chromosomes instead of just one. ...


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 affects 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. In medicine, cholestasis is a condition where bile cannot flow from the liver to the duodenum. ... A lipoprotein is a biochemical assembly that contains both proteins and lipids. ... Coagulation is the thickening or congealing of any liquid into solid clots. ...


Brain

Estrogens can be produced in the brain from steroid precursors. As an antioxidant, they have been found to have neuroprotective function.[5] Space-filling model of the antioxidant metabolite glutathione. ...


The positive and negative feedback loop of the menstrual cycle involve ovarian estradiol as the link to the hypothalamic-pituitary system to regulate gonadotropins. In cybernetics and control theory, feedback is a process whereby some proportion or in general, function, of the output signal of a system is passed (fed back) to the input. ... Menstrual cycle The menstrual cycle is a recurring cycle of physiological changes in the females of some animal species that is associated with reproductive fertility. ... Gonadotropins are protein hormones secreted by gonadotrope cells of the pituitary gland of vertebrates. ...


Blood vessels

Estrogen affects certain blood vessels. Improvement in arterial blood flow has been demonstrated in coronary arteries.[6] The coronary circulation consists of the blood vessels that supply blood to, and remove blood from, the heart. ...


Oncogene

Estrogen is considered an oncogene as its 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. An oncogene is a modified gene that increases the malignancy of a tumor cell. ... Breast cancer is cancer of breast tissue. ... The endometrium is the uterine membrane in mammals which is thickened in preparation for fertilization, and into which a fertilized egg is implanted upon its arrival into the uterus. ... A leiomyoma (plural is leiomyomata) is a benign smooth muscle neoplasm that is not premalignant. ...


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. A pregnant woman near the end of her term Pregnancy is the carrying of one or more embryos or fetuses by female mammals, including humans, inside their bodies. ...


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, we do not know yet 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] Sexual differentiation is the process of development of the differences between males and females from an undifferentiated zygote (fertilized egg). ... For other uses, see DHT (disambiguation). ...


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. Female (left) and male Common Pheasant, illustrating the dramatic difference in both color and size between the sexes Sexual dimorphism is the systematic difference in form between individuals of different sex in the same species. ...


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). Hypoestrogenism refers to a lower than normal level of estrogen. ... An alkyl is a univalent radical containing only carbon and hydrogen atoms arranged in a chain. ...


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 Ethinylestradiol, also ethinyl estradiol (EE), is a synthetic derivative of estradiol. ... The combined oral contraceptive pill, often referred to as the Pill, is a combination of an estrogen (oestrogen) and a progestin (progestogen), taken by mouth to inhibit normal fertility. ...


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. Menopause is the physiological cessation of menstrual cycles associated with advancing age in women. ... Oophorectomy is the surgical removal of the ovaries of a female animal. ... Hormone replacement therapy (HRT) is a system of medical treatment for perimenopausal and postmenopausal women, based on the assumption that it may prevent discomfort and health problems caused by diminished circulating estrogen hormones. ... A progestin is a synthetic progestagen. ...


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. Infertility is the inability to naturally conceive a child or to carry a pregnancy to full term. ... Schematic frontal view of female anatomy The cervix (from Latin neck) is the lower, narrow portion of the uterus where it joins with the top end of the vagina. ...


Estrogen therapy is also used to maintain female hormone levels in male-to-female transsexuals. Transwomen or trans-women are transsexual or transgender people who were assigned male at birth but believe that this is not an accurate or complete description of themselves and therefore usually identify and live as women. ...


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] Breast cancer is cancer of breast tissue. ... Gynecomastia (pronounced GUY-nuh-ko-MASS-tee-uh; IPA pronunciation: ) is the development of abnormally large mammary glands in males resulting in breast enlargement, which can sometimes cause secretion of milk. ... Bone age is a way of describing the degree of maturation of a childs bones. ... A GnRH agonist is a synthetic peptide that acts like the gonadotropin-releasing hormone (GnRH) but has a much longer biological half life. ... Aromatase inhibitors (AI) are a class of drugs used in the treatment of breast cancer in post- menopausal women. ... Tamoxifen is an oral selective estrogen receptor modulator which is used in breast cancer treatment, and is currently the worlds largest selling breast cancer treatment. ...


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. Ethinylestradiol, also ethinyl estradiol (EE), is a synthetic derivative of estradiol. ... Hormonal contraception refers to birth control methods that act on the hormonal system. ... Ethinylestradiol, also ethinyl estradiol (EE), is a synthetic derivative of estradiol. ... A progestin is a synthetic progestagen. ... Gonadotropin Releasing Hormone (GnRH) is a peptide hormone responsible for the release of FSH and LH from the anterior pituitary. ... Luteinizing hormone (LH) is a hormone released by gonadotropes in the anterior lobe of the pituitary gland. ... Follicle stimulating hormone (FSH) is a hormone produced by gonadotropes in the anterior pituitary gland. ... Hormone is also the NATO reporting name for the Soviet/Russian Kamov Ka-25 military helicopter. ... Birth control is a regimen of one or more actions, devices, or medications followed in order to deliberately prevent or reduce the likelihood of a woman becoming pregnant or giving birth. ... Progestagens (also spelled progestogens or gestagens) are hormones similar in effect to progesterone, the only natural progestagen. ... Ethinylestradiol, also ethinyl estradiol (EE), is a synthetic derivative of estradiol. ...


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®, Menostar®, Estraderm TTS®
  • Ointments: Estrasorb Topical®, Estrogel®
  • Injection: Estradiol cyprionate: Lunelle® monthly injection, Estradiol valerate
  • Vaginal ointment: Estrace Vaginal Cream®, Premarin Cream®
  • Vaginal ring: Estring® (estradiol acetate)

Estradiol is also part of conjugated estrogen preparations, including Premarin®. Premarin is a mixture of estrogens isolated from mares urine (PREgnant MARes urINe) made by Wyeth Pharmaceuticals. ...


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. Melasma on adult females cheek. ...


References

  1. ^ 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
  2. ^ Sharpe RM, Skakkebaek NE. Are oestrogens involved in falling sperm counts and disorders of the male reproductive tract? Lancet. 1993 May 29;341(8857):1392-5. PMID 8098802
  3. ^ Raman JD, Schlegel PN. Aromatase Inhibitors for Male Infertility. Journal of Urology. (2002), 167: 624-629. PMID 11792932
  4. ^ 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
  5. ^ 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;216(2):473-82. PMID 7488136
  6. ^ Collins 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;92(1):24-30 PMID 7788912
  7. ^ Harding, Prof. Cheryl F. (June 2004). "Hormonal Modulation of Singing: Hormonal Modulation of the Songbird Brain and Singing Behavior". Ann. N.Y. Acad. Sci. 1016: 524-539. DOI:10.1196/annals.1298.030. Retrieved on 2007-03-07. 
  8. ^ Simerly, Richard B. (2002-03-27). "Wired for reproduction: organization and development of sexually dimorphic circuits in the mammalian forebrain" (pdf). Annual Rev. Neurosci. 25: 507-536. DOI:10.1146/annurev.neuro.25.112701.142745. PMID 12052919. Retrieved on 2007-03-07. 
  9. ^ Hulshoff, Cohen-Kettenis et. al. (July 2006). "Changing your sex changes your brain: influences of testosterone and estrogen on adult human brain structure". European Journal of Endocrinology (155): 107-114. DOI:10.1530/eje.1.02248. ISSN 0804-4643. 
  10. ^ Chevallier, Andrew (2000). in Gillian Emerson-Roberts: Encyclopedia of Herbal Medicine: The Definitive Home Reference Guide to 550 Key Herbs with all their Uses as Remedies for Common Ailments. DK Publishing. ISBN 0-7894-6783-6. 
  11. ^ Estrace/Estradiol patient information leaflet - Warner Chilcott (manufacturer)

A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the Anno Domini (common) era. ... March 7 is the 66th day of the year in the Gregorian calendar (67th in leap years). ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the Anno Domini (common) era. ... March 7 is the 66th day of the year in the Gregorian calendar (67th in leap years). ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... ISSN, or International Standard Serial Number, is the unique eight-digit number applied to a periodical publication including electronic serials. ...

See also

The estrogen insensitivity syndrome (EIS) is a form of congenital estrogen deficiency and refers to a condition in which the estrogen receptor (ER) is defective. ... Hormone replacement therapy (HRT) is a system of medical treatment for perimenopausal and postmenopausal women, based on the assumption that it may prevent discomfort and health problems caused by diminished circulating estrogen hormones. ... Gender often refers to the distinctions between males and females in common usage. ... Androgen is the generic term for any natural or synthetic compound, usually a steroid hormone, that stimulates or controls the development and maintenance of masculine characteristics in vertebrates by binding to androgen receptors. ... Oral contraceptives come in a variety of formulations. ...

Additional images

  • Links to external chemical sources

  Results from FactBites:
 
Estradiol - Wikipedia, the free encyclopedia (733 words)
Androstendione is either converted to testosterone which in turn undergoes aromatization to estradiol, or, alternatively, androstendione is aromatized to estrone which is converted to estradiol.
During the reproductive years most estradiol in women is produced by the granulosa cells of the ovaries by aromatization of testosterone from the theca cells, or conversion of estrone to estradiol.
One of the fascinating twists to mammalian sexual differentiation is that estradiol is one of the two active metabolites of testosterone in males (the other being dihydrotestosterone).
  More results at FactBites »

 
 

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