progesterone
Structural formula | |||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
General | |||||||||||||||||||
Non-proprietary name | progesterone | ||||||||||||||||||
other names |
Pregn-4-en-3,20-dione |
||||||||||||||||||
Molecular formula | C 21 H 30 O 2 | ||||||||||||||||||
Brief description |
colorless crystals |
||||||||||||||||||
External identifiers / databases | |||||||||||||||||||
|
|||||||||||||||||||
Drug information | |||||||||||||||||||
ATC code | |||||||||||||||||||
Drug class | |||||||||||||||||||
properties | |||||||||||||||||||
Molar mass | 314.47 g · mol -1 | ||||||||||||||||||
Physical state |
firmly |
||||||||||||||||||
Melting point |
127–131 ° C (α-form) or 121 ° C (β-form) |
||||||||||||||||||
solubility |
|
||||||||||||||||||
safety instructions | |||||||||||||||||||
|
|||||||||||||||||||
Toxicological data | |||||||||||||||||||
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . |
The C 21 - steroid hormone progesterone is the most important representative of progestogens (luteal hormone). The compound belongs to the group of sex hormones . It is the basic structure of progestins , the synthetic progestin analogues.
In women, progesterone is mainly produced by the corpus luteum (corpus luteum) in the second phase of the menstrual cycle and in significantly higher amounts by the placenta during pregnancy . In men, the Leydig cells in the testes make up the majority. Small amounts of progesterone are also synthesized by the adrenal cortex in women and men . In the human organism, progesterone is synthesized from cholesterol .
Progesterone stimulates the growth of the uterine lining and prepares it for the embedding of a fertilized egg cell . If the egg cell is fertilized, progesterone prevents further follicle maturation ; If, on the other hand, there is no conception, progesterone production decreases again and the lining of the uterus is shed and excreted.
discovery
Progesterone was discovered independently by four working groups.
Willard Myron Allen discovered progesterone with his anatomy professor George Washington Corner at the University of Rochester Medical School in 1933 and determined the first melting point, molecular mass and partial structure. He gave the compound the name Progesterone derived from Proge stational Ster oidal Ket on . In 1928, Corner and Allen developed a test to determine progesterone activity on the rabbit endometrium.
properties
Progesterone is a crystalline solid. The compound occurs in three polymorphic crystal forms, which can be distinguished by their melting point. The thermodynamically stable form I (α-form) melts at 129 ° C (Δ f H = 26.17 kJ / mol). The other two forms - form II or β-form (m.p. 122 ° C, Δ f H = 21.42 kJ / mol) and form III (m.p. 104 ° C, Δ f H = 16.13 kJ / mol) - are metastable and are monotropic to form I.
physiology
Progesterone is synthesized and released mainly in the corpus luteum by the granulosa cells and in the placenta, and in smaller quantities also by other tissues. The synthesis starts from the pregnenolone and requires the enzyme 3 β -hydroxysteroid dehydrogenase .
The release of the hormone is stimulated by LH . The release causes a modification of the proliferated endometrium that is required for nidation , especially its lamina functionalis , which is thereby gland-rich and well supplied with blood (then referred to as decidua ) and an adaptation of the uterine muscles to the growing embryo .
In some steroid-producing cells in the gonads , the progesterone acts as a starting material for the synthesis of androgens and estrogens .
Progesterone is metabolized to pregnanediol and excreted in the urine after glucuronidation .
Pathophysiology
In addition to pregnancy, increased progesterone levels occur primarily in ovarian tumors and in adrenogenital syndrome (AGS). With menstrual disorders and with so-called hypogonadism , an underdevelopment of the ovaries , the progesterone concentration is reduced.
use
Progesterone is used to treat endometriosis .
Manufacturing
Progesterone is technically obtained in large quantities by the oxidative breakdown of stigmasterol (contained in soybean oil), solanum alkaloids or from the sapogenin diosgenin , which is isolated from plantations grown yams (Dioscoreaceae).
Trade names
- Arefam ( A )
- Crinone ( D , CH )
- Progestogel (D, CH)
- Prolutex ( D , CH )
- Utrogest (D, CH)
- Utrogestan (A, F )
- Generic (CH)
See also
literature
- Lois Jovanovic, Genell J. Subak-Sharpe: Hormones. The medical manual for women. (Original edition: Hormones. The Woman's Answerbook. Atheneum, New York 1987) From the American by Margaret Auer, Kabel, Hamburg 1989, ISBN 3-8225-0100-X , pp. 34, 88-92, 148 f., 204 ff ., 384 and more.
Individual evidence
- ↑ a b c d e Entry on progesterone. In: Römpp Online . Georg Thieme Verlag, accessed on December 9, 2014.
- ^ The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, p. 1337, ISBN 978-0-911910-00-1 .
- ↑ a b Data sheet for progesterone ≥ 99% from Sigma-Aldrich , accessed on April 22, 2011 ( PDF ).
- ^ Entry on progesterone in the ChemIDplus database of the United States National Library of Medicine (NLM) .
- ↑ Butenandt A, Westphal U: For the isolation and characterization of the corpus luteum hormone . In: Reports of the German Chemical Society . 67, 1934, pp. 1440-1442. doi : 10.1002 / cber.19340670831 .
- ↑ Hartmann M, Wettstein A: A crystallized hormone from the corpus luteum . In: Helvetica Chimica Acta . 17, 1934, pp. 878-882. doi : 10.1002 / hlca.193401701111 .
- ↑ Slotta KH, Ruschig H, Fels E: Pure representation of the hormones from the corpus luteum . In: Reports of the German Chemical Society . 67, 1934, pp. 1270-1273. doi : 10.1002 / cber.19340670729 .
- ^ Allen WM: The isolation of crystalline progestin . In: Science . 82, No. 2118, 1935, pp. 89-93. doi : 10.1126 / science.82.2118.89 . PMID 17747122 .
- ^ Allen WM: Progesterone: how did the name originate? . In: South. Med. J. . 63, No. 10, 1970, pp. 1151-5. PMID 4922128 .
- ↑ Hans Heinz Simmer and Jochen Süss: The Corner Allen Test. The development of a specific semi-quantitative biological detection method for the corpus luteum hormone (progesterone). In: Würzburger medical history reports 17, 1998, pp. 291–313, especially pp. 304–308.
- ↑ B. Legendre, Y. Feutelais, G. Defossemont: "Importance of heat capacity determination in homogeneous nucleation: application to progesterone," in Thermochim. Acta , 2003 , 400 , pp. 213-219; doi : 10.1016 / S0040-6031 (02) 00492-6 .
This text is based in whole or in part on the entry progesterone in Flexikon , a wiki of the DocCheck company . The takeover took place on July 10, 2004 under the then valid GNU license for free documentation . |