progesterone

from Wikipedia, the free encyclopedia
Structural formula
Structural formula of progesterone
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
CAS number 57-83-0
EC number 200-350-6
ECHA InfoCard 100,000,318
PubChem 5994
DrugBank DB00396
Wikidata Q26963
Drug information
ATC code

G03 DA04

Drug class

Progestin

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
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
08 - Dangerous to health

Caution

H and P phrases H: 351
P: 281
Toxicological data

327 mg kg −1 ( LD 50mouseip )

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

Volume model of progesterone

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

Schematic representation of the biosynthesis of steroid hormones

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

Monopreparations

  • 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

  1. a b c d e Entry on progesterone. In: Römpp Online . Georg Thieme Verlag, accessed on December 9, 2014.
  2. ^ The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, p. 1337, ISBN 978-0-911910-00-1 .
  3. a b Data sheet for progesterone ≥ 99% from Sigma-Aldrich , accessed on April 22, 2011 ( PDF ).
  4. ^ Entry on progesterone in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  5. 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 .
  6. 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 .
  7. 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 .
  8. ^ 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 .
  9. ^ Allen WM: Progesterone: how did the name originate? . In: South. Med. J. . 63, No. 10, 1970, pp. 1151-5. PMID 4922128 .
  10. 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.
  11. 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 .