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Estradiol sulfamate

Index Estradiol sulfamate

Estradiol sulfamate (E2MATE; developmental code names J995, PGL-2, PGL-2001, ZK-190628), or estradiol-3-O-sulfamate, is a synthetic estrogen and steroid sulfatase (STS) inhibitor which is under development for the treatment of endometriosis.http://adisinsight.springer.com/drugs/800026648 It is the 3-sulfamate ester of estradiol, and in terms of its estrogenic activity, acts as a prodrug of estradiol. The drug shows profoundly reduced susceptibility to first-pass metabolism relative to estradiol, and was the first "potent" estradiol prodrug to be discovered. As of 2017, E2MATE is in phase II clinical trials for endometriosis. The drug has also been clinically investigated for potential use in hormone replacement therapy. Unlike estradiol and other estradiol esters, due to its unique sulfamate ester, E2MATE is not hydrolyzed during first-pass metabolism, and is instead cleaved into estradiol systemically. E2MATE itself shows no affinity for the estrogen receptor or estrogenic activity in vitro, requiring hydrolysis into estradiol for its estrogenicity. In accordance, the systemic potency of oral E2MATE is increased approximately 100-fold relative to that of oral estradiol, whereas its hepatotropic activity is increased only marginally, by about 2- to 3-fold. As such, E2MATE has virtually absent effects on estrogen-modulated liver functions with oral administration at typical dosages equivalent to those of estradiol and behaves much like parenterally or transdermally administered estradiol, thereby combining the advantages of transdermal estradiol with the convenience of oral administration. Unfortunately, it has been found that E2MATE, without being hydrolyzed first, can be converted by 17β-hydroxysteroid dehydrogenase into estrone sulfamate (EMATE), analogously to conversion of estradiol into estrone. Moreover, EMATE is the dominant fraction found in circulation, and EMATE is hydrolyzed into estrone, which is a far less potent estrogen than estradiol. In relation to these findings, according to Elger et al., "In spite of high levels of and EMATE in the circulation, only insignificant levels and no estrogenic effects were generated in humans (W. Elger, unpublished data)." As such, E2MATE and EMATE are actually not clinically effective as estrogens, and the researchers have subsequently developed new 17-sulfonamide ester estradiol prodrugs, such as EC508, that are not STS inhibitors and that cannot be transformed into the corresponding estrone variants. In addition to its estrogenic activity, E2MATE has been found to act as a potent and irreversible inhibitor of STS. This enzyme is responsible for the transformation of hormonally inactive steroid sulfates into their hormonally active forms, for instance hydrolysis of estrone sulfate into estrone. Inhibition of STS appears to be the basis for E2MATE's clinical development for endometriosis, as STS is expressed in the endometrium and the severity of endometriosis has been found to correlate with STS expression. In a clinical study, E2MATE was found to inhibit endometrial STS activity by 91% in premenopausal women, while circulating levels of estradiol were not affected, implying potential tissue-selective antiestrogenic effects of E2MATE in the endometrium. [1]

35 relations: Antiestrogen, Biotransformation, Bond cleavage, Clinical trial, EC508, Endometriosis, Endometrium, Enzyme, Enzyme inhibitor, Ester, Estradiol, Estrogen, Estrogen receptor, Estrone sulfamate, Estrone sulfate, First pass effect, Hormone replacement therapy, Hydrolysis, In vitro, Ligand (biochemistry), Liver, Menopause, Oral administration, Organic compound, Potency (pharmacology), Prodrug, Route of administration, Steroid, Steroid sulfatase, Sulfamic acid, Sulfate, Sulfonamide, Tissue selectivity, Transdermal, 17β-Hydroxysteroid dehydrogenase.


Antiestrogens, also known as estrogen antagonists or estrogen blockers, are a class of drugs which prevent estrogens like estradiol from mediating their biological effects in the body.

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Biotransformation is the chemical modification (or modifications) made by an organism on a chemical compound.

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Bond cleavage

Bond cleavage, or scission, is the splitting of chemical bonds.

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Clinical trial

Clinical trials are experiments or observations done in clinical research.

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EC508, also known as estradiol 17β-(1-(4-(aminosulfonyl)benzoyl)--proline), is an estrogen which is under development by Evestra for use in menopausal hormone therapy and as a hormonal contraceptive for the prevention of pregnancy in women.

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Endometriosis is a condition in which the endometrium, the layer of tissue that normally covers the inside of the uterus, grows outside of it.

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The endometrium is the inner epithelial layer, along with its mucous membrane, of the mammalian uterus.

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Enzymes are macromolecular biological catalysts.

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Enzyme inhibitor

4QI9) An enzyme inhibitor is a molecule that binds to an enzyme and decreases its activity.

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In chemistry, an ester is a chemical compound derived from an acid (organic or inorganic) in which at least one –OH (hydroxyl) group is replaced by an –O–alkyl (alkoxy) group.

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Estradiol (E2), also spelled oestradiol, is an estrogen steroid hormone and the major female sex hormone.

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Estrogen, or oestrogen, is the primary female sex hormone.

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Estrogen receptor

Estrogen receptors (ERs) are a group of proteins found inside cells.

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Estrone sulfamate

Estrone sulfamate (EMATE), or estrone-3-O-sulfamate, is a highly potent, irreversible inhibitor of steroid sulfatase (STS) with additional estrogenic activity which is used in scientific research.

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Estrone sulfate

Estrone sulfate (E1S), or estrone 3-sulfate, is a natural, endogenous steroid and an estrogen ester and conjugate.

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First pass effect

The first pass effect (also known as first-pass metabolism or presystemic metabolism) is a phenomenon of drug metabolism whereby the concentration of a drug is greatly reduced before it reaches the systemic circulation.

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Hormone replacement therapy

Hormone replacement therapy (HRT) is any form of hormone therapy wherein the patient, in the course of medical treatment, receives hormones, either to supplement a lack of naturally occurring hormones or to substitute other hormones for naturally occurring hormones.

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Hydrolysis is a term used for both an electro-chemical process and a biological one.

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In vitro

In vitro (meaning: in the glass) studies are performed with microorganisms, cells, or biological molecules outside their normal biological context.

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Ligand (biochemistry)

In biochemistry and pharmacology, a ligand is a substance that forms a complex with a biomolecule to serve a biological purpose.

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The liver, an organ only found in vertebrates, detoxifies various metabolites, synthesizes proteins, and produces biochemicals necessary for digestion.

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Menopause, also known as the climacteric, is the time in most women's lives when menstrual periods stop permanently, and they are no longer able to bear children.

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Oral administration

| name.

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Organic compound

In chemistry, an organic compound is generally any chemical compound that contains carbon.

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Potency (pharmacology)

In the field of pharmacology, potency is a measure of drug activity expressed in terms of the amount required to produce an effect of given intensity.

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A prodrug is a medication or compound that, after administration, is metabolized (i.e., converted within the body) into a pharmacologically active drug.

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Route of administration

A route of administration in pharmacology and toxicology is the path by which a drug, fluid, poison, or other substance is taken into the body.

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A steroid is a biologically active organic compound with four rings arranged in a specific molecular configuration.

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Steroid sulfatase

Steroid sulfatase (STS), or steryl-sulfatase, formerly known as arylsulfatase C, is a sulfatase enzyme involved in the metabolism of steroids.

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Sulfamic acid

Sulfamic acid, also known as amidosulfonic acid, amidosulfuric acid, aminosulfonic acid, and sulfamidic acid, is a molecular compound with the formula H3NSO3.

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The sulfate or sulphate (see spelling differences) ion is a polyatomic anion with the empirical formula.

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In chemistry, the sulfonamide functional group (also spelled sulphonamide) is -S(.

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Tissue selectivity

Tissue selectivity is a topic in distribution (pharmacology) and a property of some drugs.

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Transdermal is a route of administration wherein active ingredients are delivered across the skin for systemic distribution.

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17β-Hydroxysteroid dehydrogenase

17β-Hydroxysteroid dehydrogenases (17β-HSD, HSD17B), also 17-ketosteroid reductases (17-KSR), are a group of alcohol oxidoreductases which catalyze the reduction of 17-ketosteroids and the dehydrogenation of 17β-hydroxysteroids in steroidogenesis and steroid metabolism.

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Redirects here:

E2MATE, Estradiol sulphamate, Estradiol-3-O-sulphamate, J 995, J-995, J995, PGL 2, PGL 2001, PGL-2, PGL-2001, PGL2001, ZK 190,628, ZK 190628, ZK-190,628, ZK-190628, ZK190628.


[1] https://en.wikipedia.org/wiki/Estradiol_sulfamate

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