17 α- Hydroxyprogesterone

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Structural formula
Structure of 17α-hydroxyprogesterone
General
Non-proprietary name Hydroxyprogesterone
other names
  • 17-OH progesterone
  • 17 OHP
  • 17-hydroxypregn-4-en-3,20-dione
Molecular formula C 21 H 30 O 3
External identifiers / databases
CAS number 68-96-2
EC number 200-699-4
ECHA InfoCard 100,000,636
PubChem 6238
ChemSpider 6002
DrugBank DB14570
Wikidata Q175901
Drug information
ATC code

G03 DA03

Drug class

Progestin

properties
Molar mass 330.45 g mol −1
Physical state

firmly

Melting point

222–223 ° C with fast heating, 276 ° C with slow heating

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

danger

H and P phrases H: 360
P: 201-308 + 313
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

17 α -hydroxyprogesterone ( 17 OHP ) is a natural progestin (C 21 - Steroid ). It is both the precursor of 11-deoxycortisol ( glucocorticoids ) and of androstenedione ( androgens and estrogens ).

biosynthesis

The biosynthesis of 17 α -hydroxyprogesterone takes place primarily in the adrenal glands via the hydroxylation of progesterone by means of the enzyme 17 α -hydroxylase . In urine is found as a metabolic intermediate of the 17 α -OHP pregnanetriol. To a certain extent, it is also produced in the gonad , especially in the corpus luteum in the ovary .

Serum concentration

The 17-OHP serum concentration increases during the menstrual cycle along with that of the luteinizing hormone and, together with this, reaches its peak at ovulation . The normal 17-OHP level for children is 3–90 ng / dl, in women before ovulation it is 15–70 ng / dl and during the luteal phase it is 35–290 ng / dl. An increased concentration of 17-OHP is a sign of adrenogenital syndrome of type 5, an impaired hormone production in the adrenal gland.

application

Hydroxyprogesterone is used as a caproic acid ester (depot active ingredient for intramuscular administration) to delay premature births . The drug is still available in Germany out of distribution, in Austria, France and Italy.

Individual evidence

  1. ↑ Entry on hydroxyprogesterone. In: Römpp Online . Georg Thieme Verlag, accessed on December 28, 2014.
  2. ↑ a b Data sheet 17α-Hydroxyprogesterone from Sigma-Aldrich , accessed on March 17, 2011 ( PDF ).
  3. ↑ ABDA database (as of December 6, 2009).