
An estrogen conjugate is a
conjugate of an
endogenous
Endogeny, in biology, refers to the property of originating or developing from within an organism, tissue, or cell.
For example, ''endogenous substances'', and ''endogenous processes'' are those that originate within a living system (e.g. an ...
estrogen
Estrogen (also spelled oestrogen in British English; see spelling differences) is a category of sex hormone responsible for the development and regulation of the female reproductive system and secondary sex characteristics. There are three ...
. They occur
naturally in the body as
metabolite
In biochemistry, a metabolite is an intermediate or end product of metabolism.
The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, c ...
s of estrogens and can be reconverted back into estrogens. They serve as a circulating reservoir for estrogen, particularly in the case of
orally administered
Oral administration is a route of administration whereby a substance is taken through the mouth, swallowed, and then processed via the digestive system. This is a common route of administration for many medications.
Oral administration can be ...
pharmaceutical
Medication (also called medicament, medicine, pharmaceutical drug, medicinal product, medicinal drug or simply drug) is a drug used to diagnose, cure, treat, or prevent disease. Drug therapy ( pharmacotherapy) is an important part of the ...
estradiol
Estradiol (E2), also called oestrogen, oestradiol, is an estrogen steroid hormone and the major female sex hormone. It is involved in the regulation of female reproductive cycles such as estrous and menstrual cycles. Estradiol is responsible ...
. Estrogen conjugates include
sulfate
The sulfate or sulphate ion is a polyatomic anion with the empirical formula . Salts, acid derivatives, and peroxides of sulfate are widely used in industry. Sulfates occur widely in everyday life. Sulfates are salts of sulfuric acid and many ...
and/or
glucuronide
A glucuronide, also known as glucuronoside, is any substance produced by linking glucuronic acid to another substance via a glycosidic bond. The glucuronides belong to the glycosides.
Glucuronidation, the conversion of chemical compounds to glucu ...
conjugates of
estradiol
Estradiol (E2), also called oestrogen, oestradiol, is an estrogen steroid hormone and the major female sex hormone. It is involved in the regulation of female reproductive cycles such as estrous and menstrual cycles. Estradiol is responsible ...
,
estrone
Estrone (E1), also spelled oestrone, is a steroid, a weak estrogen, and a minor female sex hormone. It is one of three major endogenous estrogens, the others being estradiol and estriol. Estrone, as well as the other estrogens, are synthesized ...
, and
estriol
Estriol (E3), also spelled oestriol, is a steroid, a weak estrogen, and a minor female sex hormone. It is one of three major endogenous estrogens, the others being estradiol and estrone. Levels of estriol in women who are not pregnant are almost ...
:
* Sulfated:
**
Estrone 3-sulfate
Estrone sulfate, also known as E1S, E1SO4 and estrone 3-sulfate, is a natural, endogenous steroid and an estrogen ester and conjugate.
In addition to its role as a natural hormone, estrone sulfate is used as a medication, for instance in meno ...
(E1S)
**
Estradiol 3-sulfate (E2S, E2-3S) and
estradiol 17β-sulfate (E2-17S)
**
Estriol 3-sulfate
Estriol sulfate, or estriol 3-sulfate, is a conjugated metabolite of estriol that is present in high quantities during pregnancy. It is formed from estriol in the liver and is eventually excreted in the urine by the kidneys. It has much higher wa ...
(E3S)
**
Estradiol 3,17β-disulfate (E2DS)
* Glucuronidated:
**
Estrone 3-glucuronide (E1-G)
**
Estradiol 3-glucuronide
Estradiol 3-glucuronide (E2-3G), also known as 17β-estradiol 3-(β-D-glucuronide), is a naturally occurring and endogenous estrogen conjugate. It is specifically the C3 glucuronide conjugate of estradiol, the major estrogen in the body. It is fo ...
(E2-3G) and
estradiol 17β-glucuronide
Estradiol glucuronide, or estradiol 17β-D-glucuronide, is a conjugated metabolite of estradiol. It is formed from estradiol in the liver by UDP-glucuronyltransferase via attachment of glucuronic acid and is eventually excreted in the urine by ...
(E2-17G)
**
Estriol 3-glucuronide
Estriol 3-glucuronide, or oestriol 3-glucuronide, also known as estriol 3-β-D-glucosiduronic acid, is a natural, steroidal estrogen and a glucuronic acid (β-D-glucopyranuronic acid) conjugate of estriol. It is found in the urine of women as a ...
(E3-3G),
estriol 16α-glucuronide
Estriol glucuronide (E3G), or oestriol glucuronide, also known as estriol monoglucuronide, as well as estriol 16α-β-D-glucosiduronic acid, is a natural, steroidal estrogen and the glucuronic acid (β-D-glucopyranuronic acid) conjugate of estri ...
(E3-16G)
* Mixed:
**
Estradiol 3-glucuronide 17β-sulfate
Estradiol 3-glucuronide 17β-sulfate (E2-3G-17S) is an endogenous estrogen conjugate and metabolite of estradiol. It is related to estradiol 3-sulfate and estradiol 17β-glucuronide. Estradiol 3-glucuronide 17β-sulfate has 0.0001% of the relati ...
(E2-3G-17βS)
**
Estradiol 3-sulfate 17β-glucuronide
Estradiol (E2), also called oestrogen, oestradiol, is an estrogen steroid hormone and the major female sex hormone. It is involved in the regulation of female reproductive cycles such as estrous and menstrual cycles. Estradiol is responsible fo ...
(E2-3S-17βG)
**
Estriol 3-sulfate 16α-glucuronide
Estriol sulfate glucuronide, or estriol 3-sulfate 16α-glucuronide, is an endogenous, natural product, naturally occurring conjugation (biochemistry), diconjugated metabolite of estriol. It is generated in the liver from estriol sulfate by UDP-glu ...
(E3-3S-16G)
Estrogen conjugates are conjugated at the C3, C16α, and/or C17β positions, where
hydroxyl group
In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...
s are available.
Estrogen conjugates have been used as
pharmaceutical
Medication (also called medicament, medicine, pharmaceutical drug, medicinal product, medicinal drug or simply drug) is a drug used to diagnose, cure, treat, or prevent disease. Drug therapy ( pharmacotherapy) is an important part of the ...
estrogens, as in estrone sulfate as
estropipate
Estropipate, also known as piperazine estrone sulfate and sold under the brand names Harmogen, Improvera, Ogen, Ortho-Est, and Sulestrex among others, is an estrogen medication which is used mainly in menopausal hormone therapy in the treatment ...
(piperazine estrone sulfate) and in
conjugated estrogens
Conjugated estrogens (CEs), or conjugated equine estrogens (CEEs), sold under the brand name Premarin among others, is an estrogen medication which is used in menopausal hormone therapy and for various other indications. It is a mixture of th ...
(Premarin) and
conjugated estriol
Conjugated estriol, sold under the brand names Progynon and Emmenin, is an estrogen medication which was previously used for estrogen-type indications such as the treatment of menopausal symptoms in women. The term specifically refers to formula ...
(Progynon, Emmenin).
See also
*
Catechol estrogen
A catechol estrogen is a steroidal estrogen that contains catechol (1,2-dihydroxybenzene) within its structure. The catechol estrogens are endogenous metabolites of estradiol and estrone and include the following compounds:
* 2-Hydroxylated:
** ...
*
Lipoidal estradiol
Lipoidal estradiol (LE2) is the variety of endogenous C17β long-chain fatty acid esters of estradiol which are formed as metabolites of estradiol. Important examples of these esters include estradiol arachidonate, estradiol lineolate, estradi ...
*
Steroid sulfate
Steroid sulfates are endogenous sulfate esters of steroids. They are formed by steroid sulfotransferases via sulfation of endogenous steroids like cholesterol and steroid hormones. Although steroid sulfates do not bind to steroid hormone receptor ...
References
{{Estrogen receptor modulators
Estranes
Estrogens
Human metabolites
Steroid hormones