Gestrinone
Encyclopedia
Gestrinone is a synthetic steroid
hormone
that acts as an anti-progestin
and also has some androgen
ic activity. It is marketed under the names Dimetriose, Dimetrose, and Nemestran, as a treatment for endometriosis
. Gestrinone is available in many countries, but not in the USA. As it has anabolic effects, its use in competition has been banned by the International Olympic Committee
.
s. Gestrinone also interacts with the endometrium
, inhibiting its growth. The inhibition is the result of gestrinone's interaction with the androgen receptor
; this is also the reason for androgenic side effects. Gestrinone has been shown to interact with the estrogen receptor
, the androgen receptor
, and the progesterone receptor
.
, during lactation
, and in patients with severe cardiac, renal or hepatic insufficiency. It is also contraindicated in patients who experienced metabolic and/or vascular disorders during previous estrogen or progestogen therapy, or who are allergic to the medication. The drug is contraindicated in children.
Side effects include vaginal spotting, and, in susceptible individuals, signs of increased androgen activity such as acne, oily skin, fluid retention, weight gain, hirsutism, voice change, or hair loss.
. It also has been used to shrink uterine fibroids and to reduce menorrhagia
Its androgenic properties are more exploited in a "designer steroid", the derivative tetrahydrogestrinone
. THG was banned by the Food and Drug Administration
(FDA) in 2003.
Steroid
A steroid is a type of organic compound that contains a characteristic arrangement of four cycloalkane rings that are joined to each other. Examples of steroids include the dietary fat cholesterol, the sex hormones estradiol and testosterone, and the anti-inflammatory drug dexamethasone.The core...
hormone
Hormone
A hormone is a chemical released by a cell or a gland in one part of the body that sends out messages that affect cells in other parts of the organism. Only a small amount of hormone is required to alter cell metabolism. In essence, it is a chemical messenger that transports a signal from one...
that acts as an anti-progestin
Progestin
A progestin is a synthetic progestogen that has progestinic effects similar to progesterone. The two most common uses of progestins are for hormonal contraception , and to prevent endometrial hyperplasia from unopposed estrogen in hormone replacement therapy...
and also has some androgen
Androgen
Androgen, also called androgenic hormone or testoid, is the generic term for any natural or synthetic compound, usually a steroid hormone, that stimulates or controls the development and maintenance of male characteristics in vertebrates by binding to androgen receptors...
ic activity. It is marketed under the names Dimetriose, Dimetrose, and Nemestran, as a treatment for endometriosis
Endometriosis
Endometriosis is a gynecological medical condition in which cells from the lining of the uterus appear and flourish outside the uterine cavity, most commonly on the ovaries. The uterine cavity is lined by endometrial cells, which are under the influence of female hormones...
. Gestrinone is available in many countries, but not in the USA. As it has anabolic effects, its use in competition has been banned by the International Olympic Committee
International Olympic Committee
The International Olympic Committee is an international corporation based in Lausanne, Switzerland, created by Pierre de Coubertin on 23 June 1894 with Demetrios Vikelas as its first president...
.
Method of action
Its mechanism of action consists of suppression of the release of pituitary gonadotropinGonadotropin
Gonadotropins are protein hormones secreted by gonadotrope cells of the pituitary gland of vertebrates. This is a family of proteins, which include the mammalian hormones follitropin , lutropin , placental chorionic gonadotropins hCG and eCG and chorionic gonadotropin , as well as at least two...
s. Gestrinone also interacts with the endometrium
Endometrium
-Function:The endometrium is the innermost glandular layer and functions as a lining for the uterus, preventing adhesions between the opposed walls of the myometrium, thereby maintaining the patency of the uterine cavity. During the menstrual cycle or estrous cycle, the endometrium grows to a...
, inhibiting its growth. The inhibition is the result of gestrinone's interaction with the androgen receptor
Androgen receptor
The androgen receptor , also known as NR3C4 , is a type of nuclear receptor that is activated by binding of either of the androgenic hormones testosterone or dihydrotestosterone in the cytoplasm and then translocating into the nucleus...
; this is also the reason for androgenic side effects. Gestrinone has been shown to interact with the estrogen receptor
Estrogen receptor
Estrogen receptor refers to a group of receptors that are activated by the hormone 17β-estradiol . Two types of estrogen receptor exist: ER, which is a member of the nuclear hormone family of intracellular receptors, and the estrogen G protein-coupled receptor GPR30 , which is a G protein-coupled...
, the androgen receptor
Androgen receptor
The androgen receptor , also known as NR3C4 , is a type of nuclear receptor that is activated by binding of either of the androgenic hormones testosterone or dihydrotestosterone in the cytoplasm and then translocating into the nucleus...
, and the progesterone receptor
Progesterone receptor
The progesterone receptor also known as NR3C3 , is an intracellular steroid receptor that specifically binds progesterone...
.
Metabolism
The drug is well absorbed via the oral route, passed through the liver, and has a half-life of about 24 hours. It is metabolized by the liver and excreted by urine and feces.Contraindications and side effects
The drug is contraindicated in pregnancyPregnancy
Pregnancy refers to the fertilization and development of one or more offspring, known as a fetus or embryo, in a woman's uterus. In a pregnancy, there can be multiple gestations, as in the case of twins or triplets...
, during lactation
Lactation
Lactation describes the secretion of milk from the mammary glands and the period of time that a mother lactates to feed her young. The process occurs in all female mammals, however it predates mammals. In humans the process of feeding milk is called breastfeeding or nursing...
, and in patients with severe cardiac, renal or hepatic insufficiency. It is also contraindicated in patients who experienced metabolic and/or vascular disorders during previous estrogen or progestogen therapy, or who are allergic to the medication. The drug is contraindicated in children.
Side effects include vaginal spotting, and, in susceptible individuals, signs of increased androgen activity such as acne, oily skin, fluid retention, weight gain, hirsutism, voice change, or hair loss.
Other uses
The drug has also been investigated for use as a prospective contraceptive agent and as a postcoital contraceptiveEmergency contraception
Emergency contraception , or emergency postcoital contraception, refers to birth control measures that, if taken after sexual intercourse, may prevent pregnancy.Forms of EC include:...
. It also has been used to shrink uterine fibroids and to reduce menorrhagia
Menorrhagia
Menorrhagia is an abnormally heavy and prolonged menstrual period at regular intervals. Causes may be due to abnormal blood clotting, disruption of normal hormonal regulation of periods or disorders of the endometrial lining of the uterus...
Its androgenic properties are more exploited in a "designer steroid", the derivative tetrahydrogestrinone
Tetrahydrogestrinone
Tetrahydrogestrinone is an anabolic steroid developed by Patrick Arnold. It has affinity to the androgen receptor and the progesterone receptor, but not to the estrogen receptor...
. THG was banned by the Food and Drug Administration
Food and Drug Administration
The Food and Drug Administration is an agency of the United States Department of Health and Human Services, one of the United States federal executive departments...
(FDA) in 2003.